Best Things To Do In Chicago

Chicago is one of the largest cities in the United States and its cultural influence is significant throughout the Midwest. I invite you to get to know it under the recommendations I have prepared for you of the most interesting places in this great American metropolis.
Best Things To Do In Chicago

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    Are you going to travel to the United States soon and Chicago is going to be one of the stops on your tourist itinerary? Well let me assure you that this is going to be one of the best experiences of your life, as this great city of over 9 million people is one of the tourist epicentres of all of North America.

    With these attractions and activities that I have highlighted for you, you will be able to enjoy a pretty comprehensive look at this beautiful community and at the same time give you the opportunity to keep yourself entertained from the first moments of your trip, until that last moment when you find yourself leaving your hotel on a transfer to the Chicago airport.

    1. Participate in a guided tour of the city centre

    people walking in the garden| ©RockledgeGardens
    people walking in the garden| ©RockledgeGardens

    Being such a large city with so much history, it is predictable that there are plenty of alternative tours of Chicago for those interested in learning about this community in a more personalised and conventional tourist mode.

    Most of these guided tours will take you to the most important sites in the downtown area and this is convenient as this is the area with the most tourist traffic. So having an itinerary that fits in with the experts' knowledge can save you a couple of detours and a lot of time.

    At the same time, you have to understand that the modalities offered by these tours are very different and there is a huge repertoire for tourists with all kinds of interests. For example, the mobster and gangster tours are some of the most entertaining of the local offer, as it is a tour that takes you to the corners that became crime scenes during the times when the mafia took over this city.

    Some tours are in tour buses and others in minibuses, but you also have the option of going to see the city from the heights with the spectacular helicopter tours of Chicago.

    Details of interest:

    • Prices: prices are another favourable aspect of these guided tours, as on average they cost between 25 and 40 euros per person, although helicopter flights tend to have higher prices.
    • Duration: It all depends on the chosen itinerary, but they vary between 3 and 5 hours, although this is only an approximation.

    Book the best tours of Chicago

    2. Take a cruise along the shores of Lake Michigan and the banks of the Chicago River

    people on a boat on Lake Michigan| ©Thomas Shockey
    people on a boat on Lake Michigan| ©Thomas Shockey

    Chicago is located right on the southern end of Lake Michigan, one of the five bodies of water that make up the Great Lakes system that straddle the border of Canada and the United States. The city's skyline has grown along this shoreline, so it's a good idea to spend some time during your visit touring some of the sites that this community has created to enjoy the waters of one of the world's largest lakes.

    North Avenue Beach is a favourite if you're looking for beach fun on a summer's day, while The Concrete Beach is an extension of that promenade, but with less vegetation that can be an ideal place for a bike ride.

    Navy Pier is another stop you can't miss if you want to tour the Lake Michigan shoreline on your visit to Chicago. This pier was one of the longest in the world for many years and today has several attractions such as the Chicago Children's Museum which joins a lot of shops and public parks with free admission.

    As for the Chicago River you should know that this is one of the most interesting waterways on the planet. In the 19th century, its waters were redirected thanks to a major civil engineering project that allowed it to flow in a southerly direction, thus preventing the pollution of Lake Michigan.

    Riverwalk is the path that has been conditioned so that pedestrians can enjoy the banks of the river in a good part of its passage through downtown and the recommendation I can make is that you walk it from the bridge section of N Columbus Dr. to the Franklin-Orleans Street Bridge.

    But there are also cruises that tell you the history of Downtown, while highlighting the relevance of each of the skyscrapers and elevated bridges in the area. While cruises with tours of Lake Michigan are other highly recommended entertainment alternatives after a morning of sightseeing in the urban heart of the city.

    • Read more... If you want to know more about water cruises in Chicago, check out this article on Lake Michigan cruises.

    Book a cruise on Lake Michigan

    3. Experience an afternoon full of art at the Chicago Art Institute

    man posing in colourful mural| ©Chait Goli
    man posing in colourful mural| ©Chait Goli

    Right next to Millennium Park is the Art Institute of Chicago. This is an important institution in the global art world, both for the breadth of its repertoire of works and also for the relevance that some have within the interpretative currents to which they belong.

    American Gothic by Grant Wood, Afternoon on the Island of Grande Jette by Seurat and Van Gogh's self-portrait are just some of the great protagonists of this museum. It has the highest number of visitors of any museum in the city, reaching an impressive 1.5 million admissions annually.

    The collection spans several branches of art history ranging from American art to a strong display of Byzantine works, as well as African art and contemporary and modernist works.

    Other iconic buildings such as the Chicago Symphony Orchestra are on the perimeter near this museum. It is certainly not a bad idea to get your tickets through some of Chicago' s tourist attraction passes and enjoy the best museums in Chicago.

    One of these tourist passes, the Chicago Explorer Pass, includes, for example, tickets to the Museum of Contemporary Art Chicago, and also access to Chicago's 360 Observation Deck, two of the city's must-see attractions.

    Book a visit to the Art Institute of Chicago

    4. See the city from the heights at the Willis Tower

    buildings under the blue sky| ©Otto Rascon
    buildings under the blue sky| ©Otto Rascon

    The Willis Tower is a place that is automatically associated with Chicago's architectural identity, as this 110-storey skyscraper was the tallest building in the world for a couple of years. To this day it remains the king of the skies in this city and even though it is no longer called the Sears Tower and is now officially known as the Willis Tower, it has remained an important landmark for this community.

    You have the opportunity to get to know this building in a very particular way, because on the 103rd floor there is a viewpoint that allows you to stand on glass cubes that will literally leave you standing on a panorama of the city.

    The viewpoint is known as Skydeck and the glass cornices are called The Ledge. On a day with favourable weather you will have the opportunity to see absolutely the entire city in a panoramic way and your visibility will extend all the way to the well-known suburbs of the Chicago Metropolitan Area.

    Details of interest:

    • Prices: Ticket prices for the Willis Tower Skydeck are usually around 30 euros per adult and 20 to 25 euros per child. I advise you to buy your tickets in advance if you want to guarantee a space for the times you have available for this activity in your day.
    • Opening times: It is open every day of the week and its opening hours extend until 9:00 pm. Which is logical knowing that enjoying this beautiful view is one of the best things to do in Chicago at night if you're talking about a plan with a family focus.

    Book a visit to the Chicago Skydeck at Willis Tower

    5. Take a guided tour of Chicago by Segway

    people on segway| ©ivecanski
    people on segway| ©ivecanski

    If you want to admire Chicago's Museum Campus and Lake Chicago, this guided Segway tour is a great option. You don't have to walk, you just ride an electric skateboard, but with this comfortable vehicle you enjoy the same sights as when you're on foot.

    An expert guide will tell you stories and interesting facts about the city and the places you pass through. You will have a 7 or 8 mile Segway tour to visit various sites such as Soldier Field, the home of the Chicago Bears.

    Book a guided segway tour of Chicago

    6. Fly over Chicago in a private helicopter

    Chicago from the air| ©Karl Solano
    Chicago from the air| ©Karl Solano

    Taking a helicopter tour of Chicago's skyline is a must-do if you're visiting the modern city. This tour lasts 45 minutes, which is more than enough time to take some epic photos.

    Also, please note that the tour includes noise-reducing headphones and commentary from a guide. Also, please note that this tour is a good option for 3 passengers, so you can go with your family or friends.

    • Read more... If you want to know more about this type of activity, check out this article on the best helicopter tours.

    Book a helicopter tour in Chicago

    7. Buy the Chicago CityPASS and get into a variety of amazing sites

    Chicago CityPASS| ©Jeff Keenan
    Chicago CityPASS| ©Jeff Keenan

    In case you didn't know, the Chicago CityPASS offers admission to various tourist sites in the city. For example, Skydeck Chicago, Shedd Aquarium, Field Museum and other sites. The aim of this pass is to save up to 50% on entrance fees to some of the most popular sites.

    Other sites you can visit with this pass are Chicago 360 Observatory and Art Institute of Chicago. You even have the option to visit the Adler Planetarium, one of the most recommended sites for the whole family, including the kids.

    Buy Chicago CityPASS

    8. Take a minibus tour of Chicago

    two white minibuses| ©Paul Hills
    two white minibuses| ©Paul Hills

    If you want to see the sights of Chicago on a minibus, this might be the best option for you. It's a small-group tour with stops at tourist highlights. Bring your camera or drone to take exciting photos and videos.

    Among the sites you'll see are: The Rookery skyscraper, Millennium Park, Museum Campus, Buckingham Fountain, Magnificent Mile, Chicago River, Lincoln Park and Gold Coast. You will definitely have a great time with a local guide who will tell you interesting facts about the city.

    Book a minibus tour of Chicago

    9. The Field Museum is another of the city's great wonders

    Skeleton of the Museum| ©tagbuzzard
    Skeleton of the Museum| ©tagbuzzard

    Continuing the idea that the Museum Campus area is an ideal place for a sightseeing itinerary in this beautiful city, the Field Museum of Natural History in Chicago stands out. It is known for the fact that the largest Tyrannosaurus Rex ever unearthed is exhibited inside, making it an unmissable stop for lovers of the curiosities of our planet earth.

    It really is one of the largest museums in the world in terms of the breadth of its exhibits and the type of approach taken by the curators. There you will learn about the different ecosystems that make up life on the planet, while also accessing the occasional exhibition of articles from the history of ancient and modern societies.

    Details of interest:

    • Prices: If you are interested in buying tickets to the Field Museum of Natural History in Chicago, you have to know that the rates are around 30 euros per adult for a general admission and 36 or 38 euros for an access that allows you to simultaneously enjoy the 3D cinema that is in this facility. Children between the ages of 5 and 18 get an approximate 10% discount.

    • Opening hours: Open daily from 9 am to 5 pm. Keep in mind that it will take you approximately 4 hours to go through all the exhibits.

    • Read more... If you want to know more about this activity, read the article Field Museum of Natural History tickets.

    Book a visit to the Field Museum of Natural History

    10. Enjoy an authentic gastronomic tour of the city

    pizzas on display| ©Annija Mieze
    pizzas on display| ©Annija Mieze

    Every city begins to develop a rather unique gastronomic universe as the years go by. They also do so according to the historical and cultural events that mark the growth of society as a community. In the case of Chicago something quite interesting happens, as it is a very authentic and unique blend of Italian, American and Irish cuisine that came about as a consequence of the mix of these populations in this beautiful city.

    Eating Chicago style pizza, tasting Hot Dogs under the locals' interpretation and sitting in a bar drinking an authentic Irish beer are some of the activities that could be part of these gastronomic tours of the city. These can come in a variety of forms to suit all types of tourists.

    For example, there are some tours that focus exclusively on the best doughnut shops in the city, while others combine a sightseeing cycling route with stops at the most iconic restaurants in the area. As long as they are dedicated to preparing these meals that have been enhanced with Chicago's gastronomic flair.

    Keep in mind that most of Chicago' s best food tours tend to occur in the early morning or after noon, as well as prices vary depending on the type of activity being undertaken. Clearly, tours that include a bike rental along with a couple of food stops tend to have higher rates than a walking tour that only focuses on a two or three kilometre perimeter.

    Details of interest:

    • Prices: It all depends on the type of tour chosen, but on average they can vary between 20 and 60 euros depending on the number of stops and whether or not they include the meals advertised in the itinerary.

    • Duration: It is not common for a gastronomic tour to last more than three hours, but it is also unusual for them to last less than one hour.

    • Read more... If you want to know more about the best food in the city, check out this article on food tours in Chicago.

    Book a food tour of Chicago

    11. Admire the city's architecture while strolling along the Chicago River

    boats on the river with a view of the buildings| ©Victor Silas
    boats on the river with a view of the buildings| ©Victor Silas

    A ride on the mighty Chicago River will allow you to admire the urban architecture from a natural setting with your family, including children, who will also be fascinated by the natural environment and beautiful views. Plus, on this tour you'll enjoy commentary from an architectural expert, so you'll learn about the historical aspects of the site.

    Some of the imposing buildings you will see include Willis Tower, Tribune Tower and John Hancock Center. In other words, you'll see 100-storey skyscrapers for you to take unforgettable photos and post on Instagram and other social media. Keep in mind that this tour lasts 1 hour and 15 minutes, so you'll be able to go to other tourist sites on the same day.

    Book a Chicago river tour

    12. Stop at Union Station

    train station| ©Luis Leon
    train station| ©Luis Leon

    If you love historic buildings and have a passion for all things railroad related then you must visit Union Station. It is the most important station in the US public rail system for the Midwest region and its internal car storage configuration is so large that it extends underground for 9 city streets.

    The structure of the building is quite iconic and for this simple reason it is already an interesting destination in your tourist planning. The marble floors, wide staircases and neo-classical finishes of its architecture also make it one of the last spaces that adequately preserves the beauty of the American railway stations of the last century.

    In turn, if you are travelling in the month of December, this is a very suitable place to include in your plans to see and do in Chicago during Christmas. This is due to the fact that it is a space that is decorated in all the splendour of Christmas aesthetics and this makes it an ideal place for a first class photo shoot.

    13. Take a nighttime ride on a BIGBUS around Chicago

    bigbus at night| ©Matt Taylor
    bigbus at night| ©Matt Taylor

    The BIGBUS has a roofless second deck, so you can get a better view of the city at night and enjoy the lights of the shops and impressive skyscrapers. Note that the BIGBUS passes by the Campus Museum, from where you can see Chicago's illuminated skyline.

    One of the stops is the Tribune Tower for beautiful views at dusk. Another site on the tour is The Magnificent Mile, one of the largest avenues in the United States. In addition, the bus has audio commentary in English.

    Book a ticket for Chicago's Big Bus

    14. Cruise Lake Michigan on a speedboat

    speedboat on the lake| ©West Osee
    speedboat on the lake| ©West Osee

    I invite you to take a 2,000 horsepower speedboat ride on the wide and beautiful Lake Michigan. This is an activity that mixes natural scenery and incredible urban views of the city of Chicago.

    Also, a guide will give you entertaining descriptions of Chicago as you speed along in the boat. This speedboat ride lasts 30 minutes and allows you to see The Magnificent Mile, Buckingham Fountain, Navy Pier, among other sites.

    Book a speedboat tour of Lake Michigan

    15. Drink delicious Chicago craft beers

    people with beer in hand| ©Oleksandr Pidvalnyi
    people with beer in hand| ©Oleksandr Pidvalnyi

    This is one of my favourite tours in Chicago, as I love the taste of craft beer. Thanks to this tour you can visit the most outstanding breweries in Chicago. Among them, I can mention a craft beer production company, so you can see how this delicious beverage is brewed.

    In total, this tour offers a visit to 3 popular breweries in the windy city. In addition, the package includes 45 to 55 ounces of craft beer and a bus shaped like a keg of beer. Do you like beer? In Chicago you'll taste great local brews.

    Book a Chicago Craft Beer Tour

    16. Visit "The Loop" and hear incredible stories of ghosts and mobsters

    The Loop| ©Ken Yuel
    The Loop| ©Ken Yuel

    Chicago's Loop district is steeped in history, with a number of local mobsters who have left their mark on the city. You'll learn stories and anecdotes of gangsters and ghosts, two subjects at a low cost.

    A guide will also tell you spooky stories of the district and show you various haunted sites that you will never forget. This is definitely an activity you can enjoy at any time of the year.

    Book a ghost tour of The Loop

    17. Root for your Chicago White Sox team

    Aerial view of the ballpark| ©|=_=|
    Aerial view of the ballpark| ©|=_=|

    Attend a Major League Baseball game with perhaps your favourite team, the Chicago White Sox. Clap and yell in support of your MLB team; the excitement amidst thousands of baseball fans is breathtaking.

    All games take place at Guaranteed Rate Field, the home stadium of the Chicago White Sox. Not only will you get to see your team play, but also their MLB rivals, depending on the ticket you buy. What are you waiting for? Buy Chicago White Sox tickets in advance to see this MLB team playing in their home city.

    Book Chicago baseball tickets

    18. Visit Millennium Park and see the world famous Cloud Gate

    metal structure under the blue sky| ©Adam Bernstein
    metal structure under the blue sky| ©Adam Bernstein

    Chicago is a city that is internationally known for the vastness of its green spaces and the modernity that characterises these public parks. Millennium Park is one of the most iconic of them all and its proximity to the financial and tourist epicentre of the city makes it a main stop on your first days of your trip.

    It was inaugurated in 2004 and since then its 10 hectares full of modern and abstract sculptures are presented as an entrance to what has become the Downtown of the city.

    There you will find all kinds of iconic elements of architecture and art, leaving as a great protagonist of the place the concert pavilion that was designed by the talented architect Frank Gehry. If you're lucky, you're likely to catch a band playing live music, simply because this public space tries to remain an interesting place for tourists and locals alike.

    However, the attraction that undoubtedly steals the show here is the Cloud Gate sculpture, which was designed by Anish Kapoor and is now known as The Bean for its curious structure that resembles a giant, reflective metallic bean.

    Keep in mind that admission to this beautiful corner of the city is completely free. In addition, its proximity to the urban epicentre of this metropolis makes it an excellent plan to do in the morning and continue a tour of the Chicago River skyscraper area.

    As this park is located right on the axis of public spaces that extend for several kilometres along the shores of Monroe Harbour, it is also advisable to take part in the best Segway tours in Chicago.

    These state-of-the-art scooters can take you from Millennium Park to Buckingham Fountain or Grant Park, both of which are other beautiful sites worth a morning's walk in the fresh air.

    Book a Chicago Segway Tour

    19. Stop by the Adler Planetarium

    Adler Planetarium| ©Logan Selinski
    Adler Planetarium| ©Logan Selinski

    The Adler Planetarium is another one of the most important institutions in the country and, interestingly, the oldest planetarium in the United States. It was opened in 1930 and today combines technological shows about outer space with permanent exhibitions of antique astronomy instruments and all kinds of books on this interesting branch of science.

    There are also exhibitions about the Apollo 11 moon landing and if you wish, you can go back to the beginning of the last century to see what the Chicago sky looked like before the excess of light pollution that characterises modern metropolis.

    Clearly, it is one of the best activities to see or do in Chicago with children because of the educational potential of an experience like this. It is also fun for the whole family.

    Its location on the shores of Lake Michigan is also privileged, as it is in the same area of public parks where the Shedd Aquarium and the Field Museum of Natural History are located. These are other family entertainment alternatives that you can visit on other days of your trip, or even visit on the same date if you organise yourself so that one is behind the other in your tourist planning.

    Details of interest:

    • Prices: prices range from 20 to 35 euros per adult depending on the number of audiovisual shows to which you have access. The cheapest ticket only includes admission to the planetarium museum.
    • Opening hours: open every day of the week from 9 am to 9 pm except Wednesdays, when it is open until 10 pm. There are special opening hours during peak tourist seasons.

    20. Marvel at the beauty of the Chicago Theatre

    View of the Chicago Theatre| ©Antonio Intini
    View of the Chicago Theatre| ©Antonio Intini

    If you've done a little research on theatres that are influential in popular culture, you've probably come across a couple of images of the Chicago Theater. Its recognisable vertical sign with the city's name on it stands 20 feet tall and over the decades has become an emblem of the identity of this beautiful metropolis.

    It is over 100 years old and at the time of its creation it functioned as a cinema for showing silent films. With the passing of time it has become a more complete space and today it is used for the staging of theatrical projects as well as live concerts.

    You can get to know it with some of the guided tours that are given every afternoon, which is a good opportunity to learn first-hand about the secrets that have been kept in this building since the times when artists such as Frank Sinatra performed in massive shows inside.

    You also have the option of experiencing a live show. Also, conveniently, the theatre's official website announces its schedule of events several months in advance. At the same time, the perfect air-conditioning of this incredible establishment also makes seeing a show one of the best things to do in Chicago during the winter if you're escaping the cold temperatures of the Windy City.

    21. Book a bus with free stops around Chicago

    Tour People| ©Dan Gaken
    Tour People| ©Dan Gaken

    A hop-on hop-off bus tour should not be missing from your Chicago bucket list, as it gives you the opportunity to visit the sites you want to see, such as the Chicago River, Willis Tower, Adler Planetarium and Cloud Gate. It's up to you whether you buy a Deluxe, Premium or Classic ticket, each option has its advantages.

    Also, note that you can stop at Millennium Park, Skydeck Chicago, Water Tower and Magnificent Mile, so this is a pretty complete tour of Chicago.

    Book a Chicago sightseeing bus tour with free stops

    22. Catch a Chicago Cubs game

    Chicago cubs ticket| ©Shutter Runner
    Chicago cubs ticket| ©Shutter Runner

    When you go to Chicago don't forget to visit the major league baseball stadium Wrigley Field, especially if you'd like to see a Chicago Cubs game. This baseball stadium was built in 1914 and has a capacity of 41,160 for games and 41,847 for concerts.

    The Chicago Cubs play other MLB teams throughout the year, but you should check available dates and plan your visit accordingly. If you want to know more about Chicago Cubs tickets, check out the upcoming games.

    Book Chicago Cubs tickets

    23. See the city from a 360° observation deck

    people at the observatory| ©Mike Steele
    people at the observatory| ©Mike Steele

    In Chicago there is an amazing observation deck from where you can see much of the city in 360°. As such, it's a favourite activity for epic selfie lovers. By the way, the formal name of this place is the John Hancock Observatory.

    From the observatory you can enjoy beautiful views and take in the Chicago skyline. In addition, you can opt for an exemplary view of the city from a tilting platform (TILT). The latter option is 305 metres high.

    24. Dine on a dinner cruise and enjoy incredible views in Chicago

    people seated at the dinner cruise table| ©Kelly
    people seated at the dinner cruise table| ©Kelly

    This is a 3-course dinner on Lake Michigan. Plus, the dinner takes place on a beautiful Chicago cruise ship, so you can admire the architecture of the place while sharing a delicious meal with your loved ones.

    In addition to dinner, the package includes unlimited hot or iced tea, water and coffee. This way, you won't have to carry drinks with you to quench your thirst or warm up your body. In addition to that, I would like to inform you that the average duration of the cruise is 2.5 hours.

    Book the dinner cruise in Chicago

    25. Cycle through the city of Chicago on a bike tour

    two people cycling by the lake| ©Chait Goli
    two people cycling by the lake| ©Chait Goli

    With this tour you can cycle up to 22 km through the Windy City. The tour also includes stops at craft breweries and high-quality local food shops. In other words, in just 4 hours you'll be able to sample a variety of Chicago dishes and beers.

    Some of the places you'll visit include The Wiener's Circle, Murphy's Bleachers and Half Acre Bear Company. The package includes admission to these and other sites, so you won't have to spend extra money on different tickets. All you have to pay for is admission to Wrigley Field.

    Book a Chicago Bike Tour

    26. Experience the fascinating Art Deco Chicago

    two buildings with a view from below| ©Irina Hynes
    two buildings with a view from below| ©Irina Hynes

    Walk around the city in the company of a professional guide to see the incredible Art Deco buildings or skyscrapers. This is because Chicago is one of the few cities that promotes the Art Deco movement in the world.

    For example, you can enjoy the 1920's Jazz Deco and Modern Art buildings of Chicago. Also, the tour includes admission to the Chicago Architecture Center, where you can see various architectural galleries.

    Book an Art Deco tour of Chicago

    27. Have a BYOB Spray experience with The Studio W.I.P

    man painting a picture| ©Leon Keay
    man painting a picture| ©Leon Keay

    The Studio W.I.P. offers you a street painting experience that opens your mind and helps you to unleash all the creativity you have inside. The school provides you with a workshop with local artists in which you can create your own work.

    In this way, using aerosols or stencils you will create your BYOB painting together with a teacher or expert guide. At the end of the workshop you can take your artwork home. The workshop includes the materials to paint and the canvas to take home.

    Book a street art workshop in Chicago

    28. Learn about historical aspects of literature at the American Writers Museum.

    People looking at paintings on the wall| ©Rasande Tyskar
    People looking at paintings on the wall| ©Rasande Tyskar

    Learn about the history of poets and sports writers, as well as their places of origin. Also, see the houses affiliated with this museum at Writers Hall. And other things to explore include galleries such as Wintrust Chicago and The Mind of Writers.

    In the Wintrust Chicago gallery you'll find important facts about local writers and their literary style. Also, check out the Tools of the Trade gallery, where you'll find various tools used by famous writers.

    Reserve tickets for the American Writers Museum

    29. Sample Chicago's most delicious pizzas

    Entrance to the pizzeria| ©Matt
    Entrance to the pizzeria| ©Matt

    Are you really a pizza lover? Well, through this tour you will get to know different favourite pizzerias in Chicago. For example, Pizano's Pizza and Flo & Santo's, two legendary local pizzerias. Fun fact, the first one has been in business since 1943.

    Another pizzeria you can visit on this gastronomic tour is Pequod's, a pizza legend, thanks to the caramelised cheese topping. You can also check out Coalfire, a place that sells charcoal-baked pies.

    Book a pizza tour in Chicago

    30. Step into Chicago's world of crime

    people in a shop| ©Daniel Rangel
    people in a shop| ©Daniel Rangel

    Hear the stories of Al Capone and The Untouchables, as well as the Chicago mob. There are many crimes committed by Chicago mobsters and you will investigate them with a professional guide and chauffeur. In other words, you'll have live commentary on the bus.

    You can also take pictures from the bus at various crime scenes, which makes the activity much more complete. And if that wasn't enough, you'll enjoy a controlled temperature depending on the weather at the time.

    Book a Chicago Crime Tour

    31. Attend a hilarious Shakespeare play with a drunken professional actor

    group of people having drinks| ©joe valenzuela
    group of people having drinks| ©joe valenzuela

    Have you ever seen a drunken actor doing a Shakespeare play? Well, you've come to the ideal activity; in it a professional performer with 5 shots of whisky tries his hand at acting in a high-class play. Yes, a drunken actor, as you read it, how fun it sounds!

    The play takes place in "The Lounge" in The Loop district. On site you can drink craft cocktails, so the activity is limited to people aged 21 and over. Don't forget to book the performance via the button below.

    32. Go to a Chicago Bulls game

    kid in a red jersey| ©slevy15
    kid in a red jersey| ©slevy15

    Chicago Bulls is one of the best basketball teams in the NBA and plays several games in their hometown. In this regard, you can't miss a basketball game. Normally, basketball games in Chicago take place in the imposing multi-sport arena of the United Center.

    Moreover, you can watch different NBA teams at the United Center in Chicago, so don't miss out on this opportunity. Best of all, you can buy tickets to a Chicago Bulls game throughout the year, so plan your visit to the Windy City accordingly.

    33. Explore the Museum of Contemporary Art, Chicago

    Man sitting and looking at art| ©Mary Warren
    Man sitting and looking at art| ©Mary Warren

    At this museum you can view contemporary art galleries at any time of the year. Admire the architecture of this sprawling museum, which opened in 1967. Inside, the museum hosts a variety of events for the general public. However, you must pay to attend some of them.

    Note that you can see various works by artists who are still alive, i.e. artists of our time. Likewise, the museum has a shop, restaurant and bar, so you can spend a different time eating among amazing art galleries or simply buy some souvenirs.

    34. Take a Chicago Street Art Tour

    Street Art| ©Daniel Lobo
    Street Art| ©Daniel Lobo

    While many overlook Chicago's street art, this walking tour will take you to the city's most artistic and iconic streets. Murals, small graffiti and contemporary street art will leave you open-mouthed with their colourful designs.

    Street artists' techniques can be seen on streets such as The 606 and Wicker Park, ideal places for mural and graffiti lovers. If you want to go to the toilet or grab a bite to eat and drink, don't worry, because you'll enjoy a stop at the Ipsento coffee shop.

    Book a Chicago street art tour

    35. Play and escape through a 60-minute experience in Chicago

    River North| ©Mitchell Joyce
    River North| ©Mitchell Joyce

    At River North you can enjoy a 60-minute escape game. There are several options to choose from, for example, the "Gold Rush" game, through which you must find gold to achieve victory. There is also a game called "Special Ops", where you become a secret agent and solve a complex case.

    Another game offered by this tour is "Prison Break", in which you must escape from prison as best you can. As if that wasn't enough, you have other options such as "The Heist", a game in which you must recover a stolen work of art.

    Book an escape room in Chicago

    36. Indulge your taste buds at the best places in Chinatown.

    entrance to the Chinese restaurant| ©edwardhblake
    entrance to the Chinese restaurant| ©edwardhblake

    Without a doubt, one of the neighbourhoods where you can find excellent gastronomy in Chicago is Chinatown. This Chinatown is one of the 9 Chinatowns in the United States. The Asian-style houses and shops will surprise you a lot, so take a good camera with you to take pictures.

    Of course, the Asian cuisine ranges from Chinese street-style fried rice to chop suey. Other dishes on the tour include Cantonese dim sum, Sichuan chicken and Mongolian stews. Note that the food tour will take you to different restaurants in Chinatown such as Lao Sze Chuan.

    37. Walk through the Medieval Torture Museum

    museum information board| ©Doss
    museum information board| ©Doss

    In this museum you can see different tools of torture, macabre interrogation and immobilisation of people. In addition, there are different waxen assassins with their bloody victims showing the atrocious tortures that existed at some point in history.

    Also, you will enjoy clear and informative audio about each torture device. This site is 6000 feet in size, so you will be able to see different aspects related to the tortures of medieval times.

    Book tickets for the Medieval Torture Museum

    38. Eat delicious doughnuts around Chicago

    donut with coffee| ©Thomas Hawk
    donut with coffee| ©Thomas Hawk

    Because there are many people like me who love donuts, I recommend the amazing Underground Donuts tour. Through this tour you'll enjoy a taste of delicious donuts at Chicago favourites like Dappeer Doughnuts, Firecakes, Do-Rite Donuts, Stans and Doughnut Vault.

    And, don't worry, vegan and gluten-free doughnuts are also available, as well as traditional doughnuts with all the fixings. You should let the tour organisers know in advance so they can accommodate your requirements.

    Book the Chicago doughnut tour

    39. Spend an enjoyable afternoon in the Navy Pier area

    Navi Pier seen from afar| ©Gio Mag
    Navi Pier seen from afar| ©Gio Mag

    The Navy Pier area (on the shores of Lake Michigan) provides a variety of entertainment options for an enjoyable afternoon with your family or friends. From mechanical rides for adults and children to live music.

    You can also shop for clothes and food at this place, thanks to its various fashion shops and restaurants. In addition, Navy Pier allows you to see free dance, theatre and other cultural events. There are even fireworks on occasion, so you'll have to wait for nightfall.

    40. Ride a Harley-Davidson in Chicago

    Harley-Davidson information sign| ©Robert John
    Harley-Davidson information sign| ©Robert John

    The streets and avenues of the Windy City are unparalleled for the Harley-Davidson, BMW and Indian Pursuit enthusiast to enjoy at your own pace on a motorbike. The good news is that you don't have to buy these motorbikes, you just have to rent them.

    At Rental Motor Bike you can choose the bike you like best. By the way, another of my favourite motorbikes to ride around Chicago is the Honda Goldwing 1800, of course, as well as models like the Harley-Davidson Pan America 1250. Do you feel like riding a motorbike around Chicago?

    41. Distract your eyes with Michelangelo's works in Chicago

    white structure| ©Oleksandr Pidvalnyi
    white structure| ©Oleksandr Pidvalnyi

    Chicago's Sintine Chapel Exhibit is home to an immersive Michelangelo photo gallery. The painter's works left a huge mark on the Vatican and now you can see high-resolution images of his epic paintings up close.

    The people in charge of this site have done exhibits on Star Trek and Titanic, so you can imagine the high quality of this activity. In fact, they have done exhibitions of Michael Jackson and Frida Kahlo. If you like painting, don't miss these kinds of exhibits in Chicago.

    42. Feed a giraffe at the Brookfield Zoo

    zoo information sign| ©Paula Longshore
    zoo information sign| ©Paula Longshore

    As well as feeding a giraffe you can enjoy other animals such as dolphins, butterflies, birds and much more. There are no limits at Brookfield Zoo as there is even a carousel for the whole family to enjoy. There is also the Hamill Family Play Zoo, ideal for adults and children.

    In fact, if you want, you can adopt an animal from the zoo and help take care of it, just go to their official website to learn more about it. And, of course, one of the zoo's favourite attractions is that you can feed a giraffe - yes, now your dream is possible.

    43. Kayak the Chicago River

    people kayaking on the Chicago River| ©Brian Kay
    people kayaking on the Chicago River| ©Brian Kay

    In a high quality kayak you can freely navigate the Chicago River. Stop for a moment if you want to admire the great architectural works of the city from the water. For example, Art Deco buildings and modern architecture, including incredible skyscrapers.

    You can rent a kayak in Chicago to enjoy nature and urban views at the same time. Kayak and safety accessories are included for this activity.

    44. Tune your senses to classical music by candlelight

    young people playing instruments on stage| ©Sun Valley Group of Schools
    young people playing instruments on stage| ©Sun Valley Group of Schools

    With the Candlelight Concerts experience you will hear everything from classical music to tributes from Beyoncé, Queen or Adele. All in a unique candlelit atmosphere that will relax your mind and sharpen your senses.

    Some of the venue's events have been tributes to Aretha Franklin, Juan Gabriel and Taylor Swift, so there is music for all tastes. I even recommend the anime-inspired concerts, as they offer a mix of feelings for anime fans.

    45. Get creative with your kids at LEGOLAND Discovery Center

    entrance to Legoland| ©swimfinfan
    entrance to Legoland| ©swimfinfan

    Unleash your ideas at the LEGOLAND Discovery Center in Chicago. There you will find millions of LEGO bricks and various masterpieces, for example, iconic city buildings in LEGO version.

    In Kingdom Quest you can destroy skeletons and in the movie theatre you can see your favourite LEGO characters. Without a doubt, this is a highly recommended activity for the whole family, as you probably love the LEGO world as much as your children do.

    46. Visit Frank Lloyd Wright's Home and Studio

    people outside at Frank Lloyd Wright's Studio| ©Joseph Hollick
    people outside at Frank Lloyd Wright's Studio| ©Joseph Hollick

    Learn about architecture in the home of the famous Frank Lloyd Wright. Inside you can see Wright's architectural works. Note that the Prairie style was created in this studio and you'll even see the first work of this incredible architectural style.

    What are you waiting for? Book a guided tour of Lloyd Wright's Home and Studio, which includes a tour of the surrounding area. Architecture lovers and students can immerse themselves in the world of Frank Lloyd Wright with this guided tour.

    47. Experience a skydiving simulation in Chicago

    Two skydivers flying in the wind tunnel.| ©Joseba Zubiaurre
    Two skydivers flying in the wind tunnel.| ©Joseba Zubiaurre

    Are you a little scared of jumping out of a plane? Don't worry, with this experience you can experience skydiving indoors, as there are several skydiving entertainment centres in Chicago. This is a safe air tunnel system with an expert guide who will explain how to position your body when falling from a plane (before releasing the parachute).

    Note that this activity can also be done by your children, so you will all enjoy it as a family. One of the companies that professionally perform this type of activity is iFLY, which is located in Lincoln Park. There are also other tour agencies that can offer this activity; check the following link for more information.

    Book a skydiving simulation experience in Chicago

    48. Let your kids play at the Chicago Children's Museum

    child playing with blue and red pieces| ©Paul_Henry_
    child playing with blue and red pieces| ©Paul_Henry_

    At the Chicago Children's Museum you will find a space where play and learning merge. This activity is specially designed for children, but parents can go in with them and play together. One of the attractions here is a tree house, which is sure to delight the kids.

    Another activity is Cloud Booster, where your kids get a workout as they go through a mesh tunnel that is quite fun and safe. Also, as most kids love the world of dinosaurs, here they can find an expedition of dinosaurs and skeletons of these amazing animals. In fact, there are dinosaurs recreated in Jurassic Park-style form, so to speak.

    49. Take pictures at Cloud Gate (The Bean)

    people around the Cloud Gate| ©austin02
    people around the Cloud Gate| ©austin02

    In 2004 the great artist Anish Kapoor created The Bean, one of the most impressive sculptures in the city of Chicago and it's totally free. That's right, you won't have to pay to see this piece in AT&T Plaza, which is part of Millennium Park. This is an activity that is best enjoyed during the day, but some tourists like me prefer to go at night, as you can see the buildings or skyscrapers illuminated, making it an ideal occasion to take some epic photos.

    However, if you go during the day or at night you can see how the Cloud Gate reflects the people on the site, thanks to its smooth and polished mirror-like surface. Don't forget to visit the surrounding area and have a delicious meal with your loved ones.

    This activity is included in several Chicago tours, but going on your own will allow you to take as much time as you want for photos and entertaining moments. Here is the exact address according to the Google map.

    50. Get your body wet at Whealan Pool Aquatic Center

    blue water park| ©curtis locke
    blue water park| ©curtis locke

    At the Whealan Pool Aquatic Center there is fun for the whole family. It's a large pool with slides for all ages and water rides designed for younger children.

    If you don't know how to swim, this place can be the perfect place to learn, thanks to swimming lessons of up to 30 minutes, which are conducted by expert swimmers. Also, you should know that there are places to rest and even a food shop. Don't you get hungry when you go to the pool? I am.

    51. Visit the historic home of Frederick C. Robie

    orange brick house| ©willie__
    orange brick house| ©willie__

    Another of Frank Lloyd Wright's creations is the imposing Robie House. This is one of the most important architectural works of the 20th century and was built between 1908 and 1910. You can enter the site from Monday to Friday, but you must book in advance.

    The Robie House is also Wright's last prairie-style work and is considered a historic landmark in the United States. It is also a UNESCO World Heritage Site. Incidentally, the building is approximately 18 x 55 metres in size, so it is quite large. And it is worth mentioning that there is a wheelchair inside for disabled people.

    52. Dance and drink with friends in Chicago's nightclubs

    people dancing in a bar| ©Daniel Rangel
    people dancing in a bar| ©Daniel Rangel

    Chicago has several nightclubs, some of which are gay-friendly. For example, there's Smart Bar, which offers drag shows, exotic dancers and a host of themed events such as Madonna, Prince and Björk. There are also 80s-themed activities.

    But if you're not too interested in a gay-friendly club, I recommend The Underground, which is a favourite among electronic music lovers. Of course, people of any sexual preference can enter this place, but they all have to respect an elegant dress code. And best of all, it has hosted some of the world's top DJs and you may even see a celebrity or two in the audience.

    On the other hand, there is the Smart Bar, which focuses on dance music, so dancing and drinking there will be quite a pleasant experience for lovers of this music genre. In fact, famous DJs from various parts of the world and, of course, the United States have played here.

    53. Stop by the Superdawg Drive-In and eat in your own car

    Superdawg Drive-In| ©Jim Hill
    Superdawg Drive-In| ©Jim Hill

    The legendary Superdawg Drive-In restaurant awaits you if you're in Chicago. Here you will mainly find delicious hot dogs and hamburgers.

    In addition, you can buy drinks and side items (e.g. fries). Luckily, you can do it all from your car, which is a great way to avoid paying for parking. The customer service staff will treat you very well and will answer your questions when you place your order. Simply go to the ticket office with your car, you don't even have to get out to pay.

    54. Learn history and see curiosities at the Chicago History Museum

    history museum sign| ©Alan Partridge
    history museum sign| ©Alan Partridge

    At the Chicago History Museum there are collections from a variety of designers who made fashion history. For example, Stephen Burrows, Patrick Kelly and Scotty Piper. However, you should check their website to find out which galleries or collections are available at the time of your visit.

    You'll also learn about historical aspects of Chicago and, if you want, you can hire a local, expert guide to learn about the city from a historical point of view. For Halloween, there are usually some haunted events that will entertain the whole family. In fact, in December, there are some very exciting Christmas activities, so there is high quality entertainment all year round.

    55. Learn about aspects of Latino culture at the National Museum of Mexican Art

    National Museum of Mexican Art| ©BORIS G
    National Museum of Mexican Art| ©BORIS G

    Latino art comes to Chicago through the National Museum of Mexican Art. The museum hosts a variety of activities throughout the year, including a Day of the Dead event. The museum also offers workshops, book readings and art festivals on various dates.

    In the same vein, there is a permanent collection of Mexican history and aspects of the border with the United States. In this collection you will see Mesoamerican objects, popular art and modern Mexican art. Relax and immerse yourself in Mexican culture and its evolution throughout history.

    56. Speed up on Lake Michigan

    person on a jet ski| ©fjsmalaga
    person on a jet ski| ©fjsmalaga

    Want to ride a Yamaha VX110 jet ski on Lake Michigan? Well, this activity is waiting for you, as it offers motorbikes in excellent condition and essential accessories such as life jackets and seat belts. This way, you can admire the Windy City from the water.

    Note that you can rent a jet ski from Jet Ski, and it is even possible to take a lesson with a professional from the company before you go out on your own. By the way, the jet skis have 110 horsepower, so you'll be going at a speed that won't bore you for a second.

    57. Get up close and personal with the animals at Lincoln Park Zoo

    Zoo entrance| ©Jack
    Zoo entrance| ©Jack

    At Lincoln Park Zoo you can view a variety of wild and exotic animals from a safe distance. Among the animals are rhinoceros, red panda, hippopotamus and Japanese macaque. Also, other animals such as the Jamaican iguana or the African penguin.

    In total, there are approximately 200 different species of animals, so it will be a nice experience to go as a couple or with the whole family. Likewise, you will find gardens with more than 1200 species, for example, the American elm and wild apple trees, which are very beautiful.

    58. Listen to great music at the Chicago Jazz Festival

    jazz band on stage| ©robert.fr.22
    jazz band on stage| ©robert.fr.22

    The Chicago Jazz Festival takes place every year and features local, national and international artists. This is an event that usually takes place annually around Labor Day. In addition, the festival lasts between 8 and 9 days.

    The jazz concerts are held at various venues throughout the city and tickets are free. Some of the usual live venues include The South Side Jazz Coalition, Constellation, Sleeping Village, Hungry Brain, Live the Spirit Residency and The Birdhouse Inc. However, check the full schedule before you travel.

    59. Get inebriated at Chicago's rooftop bars

    wine and drinks on the table| ©Timur Saglambilek
    wine and drinks on the table| ©Timur Saglambilek

    Cocktails and other drinks await you at Chicago's fabulous rooftop bars. I start by talking about Z Bar, but not because it is the best or the worst, as I really like the three options I recommend here. The Z Bar is very striking at first glance, so for photos or selfies of the city it is a spectacular place. High quality food and drinks are available.

    Another must-visit rooftop bar is the Cerise Rooftop, which offers live music with excellent local DJs and is close to your room if you decide to stay at Virgin Hotels Chicago.

    Finally, I recommend Tony's Rooftops Bar, where you can enjoy a delicious meal with wine and fine cocktails. Interestingly, this bar is named after Time Out founder Tony Elliott and has vintage Time Out London covers, as well as elegant wooden beams and twinkling lights that decorate the place nicely.

    60. Enter Ernest Hemingway's Birthplace Museum

    beige and green building| ©Irina Hynes
    beige and green building| ©Irina Hynes

    The Ernest Hemingway Birthplace Museum is located in Oak Park, west of Chicago. Ernest Hemingway was born on the first floor of this house and is one of the leading writers and novelists of the 20th century. The architecture of the house is in the Queen Anne style, so it is a popular site for tourists and students, due to its architectural significance.

    The house was built in 1890 and was the first to have electricity in Oak Park. If you enter the museum, you can admire both the interior design of the period and the antique furniture. And, of course, in this house you'll hear stories of this amazing American writer, who lived there in his youth.

    61. Explore the DuSable Museum of African American History

    Museum information sign| ©Smart Chicago Collaborative
    Museum information sign| ©Smart Chicago Collaborative

    The DuSable Museum of African American History honours African American figures who left their mark on the country. You'll also see stories about Africans who came to the United States during the slavery era.

    You'll also find antique furniture that was and still is important to the history of African-American culture. And among its collections is a Charles C. Dawson watercolour painting. You'll even find a George Washington Carver painting in a laboratory.

    62. Experience a sunset boat ride

    yellow boat on the lake| ©Aaron Burden
    yellow boat on the lake| ©Aaron Burden

    Enjoy a romantic experience watching the sunset and the beautiful Chicago skyline from Lake Michigan. There are several boat tours available, so you can also choose from a variety of boats (sailboat, cruise ship, speedboat, etc.). This is definitely a special activity that you should experience with your partner. If you add to this a glass of wine or a delicious aperitif, it will be even more interesting.

    In the same vein, there are boats that include a ride to see the fireworks in the Navy Pier area. Even if you know how to sail or want a private sailboat, you can rent one; almost anything is possible in Chicago. Check out the various sunset boat tours here. This type of activity will leave couples with a beautiful memory of their visit to Chicago.

    63. Ice skating at Maggie Daley Park

    aerial view of ice skating rink| ©Brian Kay
    aerial view of ice skating rink| ©Brian Kay

    Maggie Daley Park has an ice skating rink which is usually open in winter. It is a large rink with side safety bars. You can skate there for free if you bring your own skates. However, to enjoy free skating you should check the opening times on the website, as free skating is not allowed at certain times of the day.

    Also, you can pay for skate rental if you don't have your own skates, so you can definitely have an ice skating experience at Maggie Daley Park. And another important thing to know about this activity is that the park has other attractions for the whole family, and there is even a food stall on site.

    64. Eat a delicious ice cream at Rainbow Cone

    girl eating ice cream| ©Parker Johnson
    girl eating ice cream| ©Parker Johnson

    There is one excellent locally sourced ice cream parlour in Chicago and that is Rainbow Cone. If you love ice cream, you must visit to try their unique and delicious flavours. One of my favourite ice creams is the Original Rainbow Cone, which has 5 flavours, Chocolate, Orange Sherbet, Palmer House, Pistachio, Strawberry. In other words, this ice cream is the main speciality of the house.

    In addition, at this local ice cream parlour you can enjoy mini donuts with coffee, a recent addition to their extensive menu. Another exquisite snack is the chocolate cake with the 5 rainbow flavours. Undoubtedly, you will feel like a kid eating candy at this ice cream parlour. By the way, you can go to Rainbow Cone with the whole family without any problem.

    65. Listen to blues bands at Buddy Guy's Legends

    man playing saxophone| ©Kris Long
    man playing saxophone| ©Kris Long

    Listening to live blues is one of the top activities for locals and visitors to Chicago. You should know that blues and jazz are two musical genres that are part of the city's culture. For this reason, at Buddy Guy's Legends there are many national and international blues and jazz concerts.

    And, as you would expect in a blues bar, there is food from New Orleans, the city where the blues is historically believed to have been born. This place is run by Buddy Guy, a blues legend who, if you're a fan of the genre, you're sure to have heard his music.

    On the other hand, you should know that the musicians who play in this bar are quite talented, for example, Ivy Ford, Paul Nelson, Joana Connor and Demetria Taylor, just to name a few. Also, there are top blues bands such as Liz Mandeville & Big Dez and The Nu Blu Band.

    66. Cheer on the Chicago Blackhawks hockey team

    Chicago Blackhawks games are held at the United Center. This team is a big deal for locals and visitors who want to see in person a real rink hockey game with professional NHL players.

    The official website offers group tickets, individual tickets and season tickets; don't forget to check the upcoming Chicago Blackhawks games before you travel. Also, please note that tickets are available for seniors and VIP members. Either way, go and cheer on the team at one of their games, which take place at various times throughout the year.

    67. Take advantage of the free Millennium Park Summer Music Series concerts

    band on stage| ©Pete
    band on stage| ©Pete

    Music is an intrinsic part of Millennium Park and if you want to enjoy free concerts, you can attend the Summer Music Series. These take place between June, July and August, but only on Mondays and Thursdays. Don't miss out on the musical activities if you're in Chicago during these months of the year.

    Well-known and emerging artists perform at the Jay Pritzker Pavilion, which is easily accessible from Randolph Street, Millennium Garage or Monroe Street. In addition, activities usually run from 6:30 pm to 9:00 pm.

    Some of the artists who have performed there are Abigail Washburn, Gabriel Garzón Montano, Brandi Clark, Samantha Crain, Chicago Immigrant Orchestra, Jeff Tweedy, Escuela Popular de Música and Ana Tijoux. Here you can find information about the Millennium Park Summer Music Series.

    68. Be amazed by the various acrobatics of the Chicago Air & Water Show

    group of aeroplanes doing aerobatics| ©didimouman
    group of aeroplanes doing aerobatics| ©didimouman

    This free event is put on by the City of Chicago and features a series of planes and expert pilots performing aerobatics over Lake Michigan and North Ave Beach. Also, you should know that this is the largest aerobatics activity in the United States.

    How much does it cost? Don't worry about the price as the activity is completely free and can be viewed from anywhere on the shores of Lake Michigan. When does it take place? It usually takes place in the summer (August), so you can see the acrobatics in clear skies. Bring an umbrella to protect you from the sun, as the show lasts 4 hours.

    For more information visit the Chicago Air & Water Show website.

    69. Admire the plants at the Garfield Park Conservatory

    Garfield Park Conservatory| ©Steve Kuenstler
    Garfield Park Conservatory| ©Steve Kuenstler

    Its 8 gardens behind glass will leave you open-mouthed with thousands of plants from all over the world. The most impressive thing is that the plants are behind glass, so that they are better preserved. This is known as landscape art under glass.

    In addition, there are several natural environments for children and a water lily pond in this botanical conservatory. There are also 10 acres of open gardens for the whole family. If you're inside the conservatory, you'll experience tropical temperatures, which is an added bonus for any visitor.

    Here's more information about the Garfield Park Conservatory.

    70. Laugh at the many faces of the Crown Fountain

    Crown Fountain| ©Igor Sorokin
    Crown Fountain| ©Igor Sorokin

    Going to the Crown Fountain in Millennium Park will allow you to enjoy incredible urban views and at the same time laugh at the funny faces in the video sculpture. This fountain was designed by Spanish artist Jaume Plensa and built by Krueck and Sexton Architects. Please note that the fountain was inaugurated in July 2004.

    The fountain has two towers or video sculptures at each end and a sheet of water on the ground. You can walk around, get your feet wet and admire up close the faces of people opening their mouths. By the way, this is the address of the Crown Fountain according to Google Maps. You don't have to pay to see the fountain, as it is public.

    71. See the Buckingham Fountain at night

    Buckingham Fountain at night| ©Snejana Iordanova
    Buckingham Fountain at night| ©Snejana Iordanova

    This incredible urban water fountain is located in Grant Park and is one of Chicago's most treasured landmarks. It was designed by British-American artist Edward H. Bennett. The monument is inspired by the Latona Fountain.

    It is worth noting that in this work you can see small statues in the shape of horses where the water comes out. By the way, although you can admire the imposing work during the day, I also recommend you do so at night, as it has a colourful and eye-catching light show. Don't wait any longer to go and see it and take a few photos in front of it.

    Check the address of Buckingham Fountain and plan a visit. Luckily, it's a public fountain, so there's no entrance fee or tax to pay.

    72. Marvel at a Broadway show in Chicago

    James M. Nederlander Theatre| ©League of Historic American Theatres
    James M. Nederlander Theatre| ©League of Historic American Theatres

    The James M. Nederlander Theatre is the official home of several Broadway shows in Chicago. The theatre opened in May 1926 and features period style architecture.

    The first "Broadway in Chicago" play to be performed in this theatre was Wicked, for 3 long years. Since 2019 it has been named after Broadway founder James M. Nederlander. Today it is still home to Broadway shows in the Windy City, so you can check out their page to properly schedule a visit to the theatre.

    Some of the events that have been performed there include "The Lion King", "Les Miserables" and "Disney's Aladdin". Do you like Broadway plays and musicals? In Chicago you can also see some shows.

    73. Sing and scream at Lollapalooza Festival

    people gathered on the concert field| © Danny Howe
    people gathered on the concert field| © Danny Howe

    If you like a variety of music festivals, I recommend Lollapalooza, which takes place every July in Chicago. The most popular music genres at this festival are rock, punk rock, metal and electronica. You should check the official Lollapalooza website for information about the next Lollapalooza.

    Internationally renowned artists and bands such as Metallica, Dua Lipa and Green Day have performed at this festival. By the way, Lollapalooza takes place in Grand Park, so you have several accommodation options nearby. Keep an eye on ticket sales to make sure you don't miss out, as tickets are hard to come by closer to the festival date.

    74. Tour the Museum of Science and Industry

    museum entrance| ©Paul_Henry_
    museum entrance| ©Paul_Henry_

    The Museum of Science and Industry offers a host of science experiments and amazing exhibits for you to learn more about the world of science and industry. You should also know that this museum has 400,000 square feet of exhibit space.

    One of the attractions in this museum is a 5-storey screen for the cinematic world. And, of course, my favourite attraction is the German U-505 submarine from World War II. This submarine makes your hair stand on end with its excellent design and the history that brought it to the United States. Interestingly, the U-505 is the only German submarine in the country.

    75. Be in awe at the Lyric Opera of Chicago

    view of the stage from the back seats| ©Timothy Neesam
    view of the stage from the back seats| ©Timothy Neesam

    Chicago has some excellent classical and contemporary opera, thanks to the Lyric Opera of Chicago's theatre, which features national and international opera artists and orchestra. In addition, this venue not only hosts a variety of opera events, but also musicals and other cultural activities.

    This theatre is acoustically very well designed for high-level musical performances, so no matter where you sit in the hall, you will always hear the music being played on stage clearly. By the way, at the Lyric Opera of Chicago there is not only live music, but also educational and innovative activities.

    76. Experience delicious and unforgettable dishes at Alinea

    people tasting food in the restaurant| ©Steve Jurvetson
    people tasting food in the restaurant| ©Steve Jurvetson

    Alinea Restaurant is one of the top 3 Michelin Star dining venues in the United States. So, if unique food prepared by national and international chefs is your thing, this is the ideal choice. Eating here is an unforgettable experience if you like modern flavours.

    Moreover, this restaurant has received several awards such as Best Restaurant in the USA by Gourmet and Business Insider and "Best Restaurant in the World" by Elite Traveler. Without a doubt, the dishes you will taste here are a culinary masterpiece. You can make a reservation on their official website, so don't wait any longer to eat at Alinea Restaurant!

    77. Give your children a unique play experience at Pirates' Cove theme park

    pirate ship at night| ©Jared Beaney
    pirate ship at night| ©Jared Beaney

    Children will have the time of their lives on the various attractions at Pirates' Cove Children's Theme Park. Among the attractions is an 18th century pirate ship, where your children can let their imagination and creativity run wild.

    On the top floor of the pirate ship you'll find a room for birthday parties. There is also a place called Cannonball Falls for picnics. In fact, this area is so large that it can accommodate 5 birthday parties at once. However, Cannonball Falls is available for full reservation on Thursdays, Saturdays and Sundays from 5:00 pm to 8:00 pm.

    78. Fill your stomach at the Taste of Chicago food festival

    person buying pizza| ©jorjeanna
    person buying pizza| ©jorjeanna

    If you're in Chicago in June or July, you can't miss the Taste of Chicago food festival. This festival takes place in different locations in Chicago such as Grant Park, so check out all the information on the website above.

    This is the perfect activity to fill your stomach with the best local restaurants. This festival only takes place on Saturdays, which you should be aware of before your visit to Chicago. Also, don't worry about parking your vehicle, as there are several options such as Grant Park North Garage, Millennium Park Garage or Grant Park South Garage.

    79. Enjoy a family experience at the Peggy Notebaert Nature Museum

    Green bird on a branch| ©tieulinhclc - Thanks for 2 million + views
    Green bird on a branch| ©tieulinhclc - Thanks for 2 million + views

    As part of the Chicago Academy of Sciences I recommend the Peggy Notebaert Nature Museum. This place is a plus for the whole family's workout, as it has children's attractions and butterfly gardens for people of different ages.

    This museum is open every day and also offers views of animals such as rodents and frogs. The museum also offers creative art classes, Critter Connections and outdoor explorations. Take your kids to this museum where they can learn while having fun.

    For more information about the museum, visit the official website.

    80. Walk inside Bloomingdale's and shop for a variety of products.

    Entrance to Bloomingdale's| ©Ryan
    Entrance to Bloomingdale's| ©Ryan

    At Bloomingdale's in Chicago you can find different departments such as jewellery and household goods. In addition, each department stores' offers unique products that are only available on site or are sold there for the first time. Likewise, Bloomingdale's offers different beauty and personal care services.

    On the other hand, while spending time there browsing their products you can stop for a bite to eat or drink at Forty Carrots. Here you can eat delicious yoghurt ice cream, smoothies and other snacks such as salads or sandwiches. In addition, inside Bloomingdale's there are plenty of clothing shops, such as Lafayette 148, David Yurman, Chloé and Canali 1934.

    81. Learn at the Richard H. Driehaus Museum

    Lit candelabra| ©Stephanie Barto
    Lit candelabra| ©Stephanie Barto

    The Richard H. Driehaus Museum features several historical attractions such as the Great Chicago Fire of 1871 or the incredible Tiffany stained glass windows, also known as The Tiffany Trail. Another interesting experience can be found in the Nickerson Mansion.

    Also, you should know that the museum offers an app for iOS and Android, which allows for self-guided tours on all 3 floors. It is recommended to go to the museum in person for a more immersive experience at the site. Your mobile device must have internet data, as you won't have free WiFi there.

    Other things I should warn you about are downloading the app before you go to the museum and bringing a headset or headphones with you. This is because the app offers excellent audio to guide you through the museum.

    82. Experience jazz in all its splendour at The Green Mill

    band playing| ©rebecca anne
    band playing| ©rebecca anne

    Enjoy an authentic jazz experience at The Green Mill, a bar that features the best local jazz bands and artists, but also foreign artists on various special occasions. The venue hosts performances every day, so if you're in Chicago, you're sure to be able to have a drink while listening to great music at the bar.

    The Green Mill also offers comedy and poetry events for those who don't listen to jazz. By the way, the sound of the place is wonderful, everyone can enjoy complex harmonies and syncopated drum rhythms in crystal-clear clarity.

    83. Get a relaxing massage at a Chicago spa

    woman getting a facial| ©Raphael Lovaski
    woman getting a facial| ©Raphael Lovaski

    As you might expect, there are plenty of luxurious, refreshing and relaxing spas in Chicago, so before you head home you should stop by one of them. For example, The Peninsula Spa is one of my favourites. There you will be attended by people who specialise in skin treatments and massages. Not for nothing is it known as Chicago's urban oasis.

    Relax your mind, body and spirit like never before at this wonderful luxury spa where you'll find yourself enveloped in Asian and Ayurvedic philosophy. Some of the experiences offered at the spa include natural stone massages, aromatic oils and the popular Marma massage.

    Other spas I recommend visiting include Allyu Spa, Spa Space Chicago and Chuan Spa at The Langham.

    84. Cheer on the NFL's Chicago Bears at an NFL game

    Another must-do Chicago activity is a Chicago Bears game. This American football team usually plays in their home city, specifically, at the Soldier Field multi-purpose stadium. Games are held on various dates each year, so check the official Chicago Bears website to keep up to date and buy tickets in advance.

    This monumental football stadium has also been home to many concerts by famous national and international artists. One of the most striking things for locals and visitors alike is the sheer size of Soldier Field and the adrenaline rush you feel as you cheer on your favourite team with thousands of people around you.

    85. Arrive early and have a delicious meal at Au Cheval

    chef preparing hamburger| ©Spanish Hipster
    chef preparing hamburger| ©Spanish Hipster

    Looking for a restaurant where you don't have to make reservations to visit? You've come to the right place, Au Cheval Restaurant doesn't require a reservation, it's first come, first served. There you can eat hamburgers with steak and smoked bacon.

    Likewise, at Au Cheval you must try the Bologna, which is one of the main ingredients in their recipes. And not only will you be able to eat delicious food in this restaurant, but there are also drinks of all kinds, so the experimentation will be much more enjoyable. Don't forget to arrive early to avoid queues.

    86. Head to Dusty Groove to buy vinyl

    Vinyl in order| ©Patrick Foisy
    Vinyl in order| ©Patrick Foisy

    This place is like paradise for CD and vinyl collectors, as here you will find original albums from various retro bands and artists, as well as from today's world. Rock, funk, soul and hip hop are just some of the genres of music in their stock. There are thousands of vinyls from all over the world, including rare or little-known albums.

    You can view the vinyl catalogue on the official Dusty Groove website, and it is even possible to buy online, as the company ships nationally and internationally. New vinyls are constantly being added to their library, so you might just find the vinyl you've been looking for everywhere.

    87. Try different specialty foods at Time Out Market.

    people sitting at the tables| ©Harry Carmichael
    people sitting at the tables| ©Harry Carmichael

    Sample food from various regions of the world or various well-known brands here at Chicago's Time Out Market. The site also features a 50,000 square foot hall where you'll not only eat, but also enjoy live music. There are also other activities for children and even yoga.

    This place also offers excellent services for work groups, birthdays or semi-private meetings with your friends. Of course, I can't end this review without mentioning some of the culinary options at Chicago's Time Out Market: fried chicken, burgers, hot dogs, desserts, salads and more.

    88. Surprise yourself with a concert by the Chicago Symphony Orchestra

    group of people playing violin| ©Samuel Sianipar
    group of people playing violin| ©Samuel Sianipar

    Do you like classical music? Then you can't miss a concert of the Chicago Symphony Orchestra, which has been active since 1891 and is one of the most important in the world. Also, you should know that the orchestra's conductor Riccardo Muti is giving his last season after 13 years of hard work.

    In addition, to enjoy the best concerts you have several subscription options such as CSO Classical Thursday I, CSO Classical Saturday B, CSO Classical Saturday E, CSO Classical Saturday G, CSO Classical Saturday H, CSO Classical Sunday A and CSO Classical Tuesday B.

    Among the works presented are Prokofiev's Sixth, Rachmaninov's Symphony No. 2, Shostakovich's Eighth, Beethoven's Missa solemnis, Mozart's Symphony No. 40, among others. This does not mean that the works are repeated, as they vary. In other words, the orchestra presents new works throughout the year.

    Run and buy your ticket for the Chicago Symphony Orchestra and live a different experience that disconnects you from your daily routine.

    89. Learn about archaeological discoveries at the Oriental Institute of Chicago

    person viewing oriental art| ©Daniel & Kate
    person viewing oriental art| ©Daniel & Kate

    Another activity you should not miss is a visit to the Oriental Institute of Chicago. There you can see various archaeological discoveries such as tablets, photographs, Yelda Khorsabad Court, Edgar and Deborah Jannotta Mesopotamian Gallery, Henrietta Herbolsheimer MD Syro-Anatolian Gallery, Robert and Deborah Aliber Persian Gallery, Robert F. Picken Family Nubian Gallery, Joseph and Mary Grimshaw Egyptian Gallery, and so on.

    For example, in Joseph's gallery you will see 800 objects from the pre-dynastic period to the Byzantine period, a 17-foot high statue of King Tutankhamun which you will see at the entrance of the gallery. Likewise, in the court of Yelda Khorsabad the most incredible objects you will see are the 16-foot tall Human and the Winged Bull of the Head.

    90. Cheer on the Chicago Fire at Soldier Field

    Who doesn't love football? If you're a fan of the team then cheer on the Chicago Fire at Soldier Field, the 61,500 capacity multi-purpose stadium. As a fun fact, it was built as a tribute to the people who died in the First World War.

    Without a doubt, it will be an unforgettable experience to be in this stadium with the locals and support their team. To buy tickets for the matches here is the official website of the Chicago Fire Football Club.

    91. Ride the roller coasters at Six Flags Great America

    Red attraction| ©Jeremy Thompson
    Red attraction| ©Jeremy Thompson

    Feel like a kid enjoying the rides at Six Flags Great America, especially the 15 roller co asters and let out all the adrenaline inside you. Besides, you can live this experience in the company of your family, since in this site there are also 3 children's themed areas, spectacular shows and an incredible water park with 20 acres.

    There are also other activities that you can enjoy such as festivals and music concerts, so it is worth visiting this amusement park in Chicago. However, some of these events are only available in specific months, so here is more information about Six Flags Chicago.

    92. Have a drink at the Hard Rock Café in Chicago

    Hard Rock Cafe| ©Philippe Reichert
    Hard Rock Cafe| ©Philippe Reichert

    This iconic venue is located in the River North neighbourhood. Not only will you be able to have a few drinks there, but you will also see amazing pieces of music legends such as Jimi Hendrix, Billy Joel, Prince and Buddy Guy on the walls.

    Also, you have different dining options such as burgers, bruschettas, wings, classic nachos, sandwiches, salads, ribs, fajitas, hot fudge brownie, ice cream, cheesecake, as well as a kids menu.

    If you're interested in this place, I recommend buying a ticket to the Hard Rock Café Chicago online before you travel, as you should be sure of their availability before you get on the plane.

    93. Get a tan at Oak Street Beach

    aerial view of the beach| ©Jonathan J. Castellon
    aerial view of the beach| ©Jonathan J. Castellon

    On the shores of Lake Michigan lies a favourite beach for locals and tourists of all ages. This is Oak Street Beach, where you can tan your body and swim. However, you should make sure that the beach is open on the day of your visit to Chicago, as due to weather changes, maintenance and other reasons, sometimes the beach is not open.

    How attractive is this beach? Well, the beach itself is small, but it has spectacular views of the Chicago skyline, Lake Michigan and several incredible buildings or skyscrapers. Also, from the site you can see impressive sports boats, cruise ships and sailboats in motion. If you want an unforgettable photo for your social media, come to this beach and take a wonderful selfie.

    Here is the address of Oak Street Beach on Google Maps. Note that admission to this beach is free, but unfortunately, parking is not very easy to find nearby.

    94. Explore Chicago Park District Golf

    two guys playing golf| ©Kaleidoscope
    two guys playing golf| ©Kaleidoscope

    Golf in Chicago? Of course you can, Chicago is home to the Chicago Park District Golf, which is made up of a number of golf parks. There are even options to learn golf. The learning site I recommend is Diversey Practice Center.

    Another park in the district that you must visit is Jackson Park, which has 18 holes and a very striking course at first sight, thanks to its mature trees that invite you to be more precise with every shot. I also recommend Sydney R. Marovitz Park, which has beautiful views of Lake Michigan and the city's skyscrapers.

    Either way, go to the golf course of your choice, as the district has a wide variety, for example, I hadn't mentioned the South Shore Golf Course or the Robert A. Black Golf Course.

    95. Feed your mind at the Smart Museum of Art

    people at the smart museum| ©uchicagoalumniweekend
    people at the smart museum| ©uchicagoalumniweekend

    This museum is run by the University of Chicago, inspiring the study of art and its conservation. Its collection is quite extensive, with an average of 16,000 objects to admire. You should also know that it has worksfrom all over the world.

    Another aspect of the Smart Museum of Art that will impress you is its collection of landscape and environmental paintings. Visit the museum for some of its events or exhibitions, but first go to its website to find out about its activities in detail.

    96. Gamble at the Horseshoe Hammond Casino

    Horseshoe Casino| ©David Beasley
    Horseshoe Casino| ©David Beasley

    Gambling and gambling are attractive to people from all over the world, so if you're in Chicago, you must visit the Horseshoe Hammond Casino. This casino is located next to Lake Michigan, in Casino Center Dr Hammond.

    This casino is part of Caesars Entertainment, one of the best casino companies in the United States. In addition, inside there are several options such as table games and slots. Also, you can enjoy a restaurant for you to eat or drink if you wish.

    97. Walk through the Pullman National Monument

    Entrance to Pullman National Monument| ©Matthew Dillon
    Entrance to Pullman National Monument| ©Matthew Dillon

    The Pullman National Monument is a large historical site where you can find the Administration-Clock Tower Building, which has an architecture dating back to 1880, the year it was built.

    In addition, at the monument you will see the Pullman Exhibit Hall, which offers an introductory film, informative exhibits and artifacts. In addition, you should visit the National A. Phlip Randolph Pullman Porter Museum, where you'll enjoy permanent and multimedia exhibits.

    98. Stop by Chicago's skateboarding parks

    skateboarder in the air| ©Giovanna Gomes
    skateboarder in the air| ©Giovanna Gomes

    While interest in skateboarding isn't common among many people, it's a bit more popular in Chicago. The city has some excellent parks where amateurs and professionals alike practice the sport. One of the parks is the Audubon Skate Park, which has an indoor and outdoor area and is next to a field where young people can train baseball.

    Another place to check out is the Skate Park on Sacramento Ave If you're a skateboarder, practice there, as there are different rails, stairs and platforms for acrobatics. Also, I recommend spending some time at the Wilson Skate Park, one of the most visited skate parks by local athletes. Here you can see people doing stunts on their skateboards.

    Also, I can't leave out Fargo Skateboarding, a skateboarding shop with a skating rink and skating lessons. This shop is located approximately 2 hours from downtown Chicago (outside the city).

    99. Paddleboarding (SUP) in Chicago

    man paddleboarding| ©JGiacomino
    man paddleboarding| ©JGiacomino

    If you want to SUP (stand-up paddle) in calm waters, rent a board from Chicago Water Sport Rentals. Rentals include a life jacket, paddleboard and paddle, so you won't have to get these accessories on the side.

    SUP practice usually takes place on the calm Lake Michigan, a perfect place to learn this water sport. Also, the boards and paddle are of high quality, for example, the paddle is made of polycarbonate F2. Of course, this activity gives you the opportunity to admire the city of Chicago from the water, that is, you will have breathtaking views during your practice.

    100. Dance at the Spring Awakening Music Festival

    people at the night festival| ©Tamara Susa
    people at the night festival| ©Tamara Susa

    The Spring Awakening Music Festival is one of the most popular music festivals in the United States. Since 2008 it has brought many electronic music artists. The agency React Presents has been running this event for several years and has brought DJs from various parts of the world.

    Some of the DJs who have performed at this festival are: Armin van Buuren, Deadmau5, Martin Garrix and Steve Aoki. In other words, it is an excellent show with national and international artists of the highest level in the world of electronic music.

    If you want to know more about this great Chicago event (days, time, line-up and more), go to its official website.