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36 Awesome Things to Do in Chicago

Chicago is an incredible city with plenty of things to do to keep you busy and having a blast! It's got culture, history, fun and games indoors and out, quality live theater and museums, iconic architecture, and unique delicious foods! Here are 36 awesome things to do in Chicago!

May 14, 202319 min read

Anecia Ascalon
Anecia Ascalon
Team Building Expert

Chicago is an incredible city with plenty of things to do to keep you busy and having a blast! It's got culture, history, fun and games indoors and out, quality live theater and museums, iconic architecture, and unique delicious foods!

Though there's plenty more to do than what we list here, these 36 awesome things to do in Chicago are a good place to start!

1. Skydeck

The Ledge at Skydeck

For the best views of Chicago, head to Skydeck on the 103rd Floor of the Willis Tower, the third tallest building in the Western Hemisphere! You can see for up to 50 miles and four states on a clear day. The views are simply jaw-dropping. For the ultimate thrill, step out onto ‘The Ledge’, a glass box that juts out from the building giving you a view of the street 1,450 feet below.

2. The Escape Game Chicago

people playing an escape game

Have an adventure day or night at The Escape Game Chicago, where you’ll put your detective hats on to find a way out of a ‘locked’ room. Each of their five games has multiple rooms to explore and puzzles that fit the game’s theme. Stop a global catastrophe by apprehending evil forces hiding in a mysterious night market. Break out of a 1950s prison cell or recover a stolen Monet painting from an art thief. Whatever game you choose, you’ll have lots of ‘wow’ moments and a fantastic time!

3. Second City Comedy Club

Chicago’s comedy scene is one of the best in the country its alumni include many Saturday Night Live cast members like Tina Fey, Bill Murray, Dan Aykroyd, and John Belushi Other comedy clubs worth a visit are the iO Theater, which produced Amy Poehler, Chris Farley, and Bill Hader. The laid-back Lincoln Lodge hosts both stand-up comedy and variety shows in an intimate setting, while the Comedy Clubhouse hosts shows in a homey setting with very affordable tickets. See here for a list of Chicago comedy clubs.

4. Chicago’s sports teams

wrigley field

For an authentic Chicago experience, see the Chicago Cubs play baseball at Wrigley Field, one of the oldest ballparks in America! There’s also the White Sox at Guaranteed Rate Field. You can also catch the legendary NBA team the Chicago Bulls or the WNBA team, the Chicago Sky. From August through December, see a Chicago Bears football game at Soldier Field. Find out more about Chicago’s amazing sports teams! If you are looking for great work party ideas in Chicago, seeing a game is one of the best options!

5. Magnificent Mile

Magnificent Mile is a lively stretch of Michigan Avenue lined with examples of Chicago’s marvelous architecture and historic landmarks. With 275 restaurants in this area, you’ll have no trouble finding something to eat! Plus, there are theaters, comedy clubs, and other entertainment. For other evening ideas, see our article on things to do at night in Chicago!

6. Art Institute of Chicago

Monet at the Chicago Art Institute

The Art Institute of Chicago is one of the most respected art museums in the world. Make time to see its fantastic collection of Impressionist paintings, the largest outside the Louvre Museum in Paris. There’s so much more to the Art Institute though. The collection has 300,000 pieces of art from around the world, some as old as 5,000 years! See works from the ancient world to modern-day gems.

7. Free Chicago Walking Tours

Get to know Chicago close-up and personal! Let a knowledgeable guide show you the town and tell you all about its history, famous figures, and current-day happenings! Free Tours By Foot offers several tours that will teach you a lot about the city and keep you entertained! Their tours include the Loop and Downtown Chicago, a Riverwalk Architecture tour, a Lincoln Park & Blues tour, a Haunted History of Chicago tour, and more.

8. Deep-dish pizza

deep dish pizza

Deep-dish pizza is a must-try when in the Windy City. Lou Malnati’s and Giordano's are two of the best places to try this iconic Chicago food. Lou Malnati’s is believed to be the first family to introduce deep-dish pizza to Chicago, and have been serving pies since the 1970s. Giordano’s opened in 1974. Its deep-dish pizza is based on a recipe from the family’s ancestors in Torino, Italy!

9. Chicago's street art

Who needs a museum when you can see captivating art outside in the streets? Chicago’s street murals are vibrant, dynamic and a sight to be seen. You can use this free, self-guided mural walk that takes you to off-the-beaten-track locations.

10. Chicago Theatre District

Chicago Theatre

Can't make it to New York City for a Broadway show? No need if you are in Chicago! The Chicago Theatre District has several theaters that put on excellent musicals and plays. See performances at gorgeous, historic theaters like the Chicago Theatre, James M. Nederlander Theatre, and the Cadillac Palace. Check here to see what’s on when you are in town.

11. Lincoln Park Zoo

This zoo was founded in 1868, making it one of the oldest zoos in North America. It’s small but packs a punch with over 200 species of animals, including big cats, polar bears, penguins, and birds of prey. It’s an especially family-friendly thing to do in Chicago, with its fun exhibits like the Kovler Seal Pool, the Pritzker Family Children's Zoo, and the Farm-in-the-Zoo exhibit.

12. The Bean

The Bean

A selfie with The Bean in Millennium Park is one of the best souvenirs of your time in Chicago. This iconic sculpture, whose real name is Cloud Gate, is recognized around the world and it’s incredibly Instagram-worthy! Millennium Park is open until 11 pm every night. In the warm months, the Jay Pritzker Pavilion in the park hosts free concerts.

13. Maggie Daley Park

Adjacent to Millennium Park is the whimsical Maggie Daley Park, one of the most family-friendly places to visit in Chicago. The park has six playgrounds, each designed for a specific age group. The Skating Ribbon is great for rollerblading. In the winter it becomes an ice-skating track! There are tennis courts, an 18-hole miniature golf course, and a rock climbing wall.

14. North Avenue Beach

North Avenue Beach

You may not think of Chicago as a ‘beach town’, but the city has 26 miles of shoreline along Lake Michigan. Choose from more than 20 public beaches each with its own atmosphere. North Avenue Beach is very popular as there are lots of fun things to do besides swimming and sunbathing. You can rent kayaks, play volleyball, or even take a yoga class! Plus, on those hot days in Chicago, a dip in the water will cool you off!

15. Lake Michigan cruises

Chicago skyline from Lake Michigan

Speaking of Lake Michigan, look into one of the many cruises available. Being out on the water is a pleasant way to spend a few hours, and the Chicago skyline views are wonderful. There are sightseeing cruises as well as lunch and dinner cruises. Take a party cruise for your Girls’ Night Out in Chicago!

16. Chicago Ghost and Gangster Tours

Chicago is home to some of the most haunted places in the country, and Chicago ghost tours will take right to them. From the legendary haunted Congress Plaza Hotel to the infamous H.H. Holmes Murder Castle, you'll hear stories that will make your hair stand on end. There’s a three-hour bus tour by Original Chicago Hauntings Ghost Tour. Mix in some mobsters with a two-hour Chicago Gangster and Ghost Tours walking tour where you’ll hear about famous gangster Al Capone in addition to the other spine-tingling tales. Given the scary nature of this activity, it may not be appropriate for families with young kids, but it is a wonderful thing to do in Chicago for adults!

17. Navy Pier

Centennial Wheel

Head to Chicago’s Navy Pier, for a fun day or night out. Take a walk along the boardwalk, do some shopping, and grab some food and drinks at one of several restaurants. Ride the famous Centennial Wheel that offers amazing views of the city and Lake Michigan from 200 feet up! Navy Pier hosts a variety of events throughout the year, including concerts and festivals. In the summer, there is a fireworks display every Wednesday and Saturday night.

18. The Original Rainbow Cone

One of the sweetest things to do in Chicago is to stop by Original Rainbow Cone for one of the greatest ice cream cones of all time! This South Side shop opened in 1926 and has been going strong ever since! The classic sugar cone is topped with five flavors of ice cream - chocolate, strawberry, Palmer House (a New York vanilla with cherries and walnuts), pistachio, and good old-fashioned orange sherbet. Then it’s topped with whipped cream and a bright red cherry. It can't get any better than that!

19. Clarence F. Buckingham Memorial Fountain

Buckingham Fountain

This majestic Beaux-Arts-style fountain in Grant Park was built in 1927. It’s not only beautiful, but it’s also a source of some playful entertainment. In the summer, the fountain's main jet, which shoots water up to 150 feet in the air, is accompanied by a state-of-the-art light and music show!

20. Field Museum of Natural History

T Rex at the Field Museum

The Field is one of the largest and most impressive natural history museums in the world. As soon as you step inside, you will be surrounded by an incredible array of exhibits that showcase the amazing diversity of life on Earth. From the towering skeletons of dinosaurs to the delicate wings of butterflies, you’ll learn about the fascinating stories of the creatures that have roamed our planet over millions of years. The Field has something for everyone and all ages!

21. Riverwalk


A stroll along Chicago’s 1.25-mile-long Riverwalk is a popular activity with locals and tourists alike. Along the river are places to stop for food or a glass of wine. There’s also public art on display and the amazing nightly light show, Art on The Mart, where artwork is projected onto the side of the massive Mart Building.

22. Architecture Cruises

chicago river cruises

These cruises are a unique and enjoyable way to experience Chicago’s rich architectural heritage. Tours are led by knowledgeable guides who share interesting anecdotes and facts about the buildings and other structures that line the river. You can admire the diverse range of architectural styles that Chicago is known for, from the Gothic Revival style of the Tribune Tower to the modernist design of the Willis Tower (formerly known as the Sears Tower). It’s also a nice way to spend time outdoors on a relaxing boat ride.

23. Seadog Speed Boat

For an entirely different kind of boat ride, try City Cruise’s Seadog! This jet-propelled boat ride on Lake Michigan travels at speeds of up to exhilarating speeds of up to 45 miles per hour. The Seadog takes you on 360-degree turns, sharp twists, and full-throttle slaloms. The Seadog is a Chicago activity that teens will surely love! Find out about more things to do with teens in Chicago!

24. Chicago-Style Hot Dogs at Portillo’s

Chicago Hot Dog

A Chicago hot dog is a unique spin on the frank. A Chicago hot dog starts with an all-beef frank tucked in a poppy seed bun. Then it’s slathered with yellow mustard, sweet pickle relish, pickled sport peppers, chopped white onions, tomato slices, a smidgen of celery salt then topped off with a dill pickle spear!

25. Lucky Strike

This modern take on the classic bowling alley is a total blast, with 18 state-of-the-art bowling lanes, ping pong tables, billiard tables, and over 100 arcade games. The atmosphere is fun, with vibrant neon lights and lively music. You can grab food and drinks at their on-site restaurant and bar. There’s so much here to keep you busy, it’s a great way to spend a rainy day in Chicago.

26. Walk The 606

The 606 walkway in Chicago

The 606 is a 2.7-mile elevated park and trail system that runs through four interesting neighborhoods in Chicago: Bucktown, Wicker Park, Logan Square, and Humboldt Park. This urban oasis was built on an old elevated railway line, and it's now a stunning example of urban renewal and repurposing. The 606 features beautiful landscaping, public art installations, and plenty of places to relax and enjoy the views.

27. Epiphany Center for the Arts

The Center for the Arts is a multi-disciplinary arts center that offers a wide range of programs and events that celebrate Chicagoans’ creativity and community. Here you’ll find visual arts, music, dance, theater, or literary arts all under one roof. Just about every day of the week, from 5 pm to 8 pm, you can see performers for free! Through its intimate performances, workshops, large-scale exhibitions, and festivals, the center fosters diversity and inclusivity. It’s an inspiring place that brings people together to enjoy the arts.

28. Shedd Aquarium

Shedd Aquarium

Chicago’s Shedd Aquarium is home to over 32,000 aquatic animals, including dolphins, whales, sharks, penguins, sea turtles, and so many more! Its exhibits will introduce you to several marine environments like the Amazon River, the Great Lakes, and the Caribbean Reef. If you're looking for a truly unforgettable experience, be sure to check out the Shedd Aquarium's animal encounters. You can swim with the dolphins, get up close and personal with penguins, and even feed some of the animals!

29. Chicago Bus Tours

Whether you are a tourist or a local, Chicago bus tours are a fantastic way to experience the amazing sights and sounds of the Windy City, from the iconic skyscrapers of Downtown Chicago to the shoreline of Lake Michigan. You'll be led by knowledgeable and passionate tour guides who share fascinating facts and stories about Chicago's history, culture, and architecture. You'll learn about the city's famous jazz scene, the Great Chicago Fire, the World's Fair, and so much more.

30. Jazz and Blues

a saxaphone player

Chicago has a legendary blues and jazz scene and you can hear some of the best musicians of this genre in famous clubs. The Hideout, a Chicago institution, is an intimate venue with a bar up front and a stage in the back room with an eclectic line-up. The Green Mill Cocktail Lounge, a former speakeasy, opened in 1907! It’s the longest continuously-running jazz club in the United States. The storied and luxurious Chicago Theater, opened in 1921, hosts all kinds of performances Find out who’s playing when you are in town.

31. Chinatown

a chinese dragonpuppet

Chicago's Chinatown, with its streets lined with colorful banners, ornate archways, and traditional lanterns, will transport you to a different world. And it's where you’ll find some of the best Chinese restaurants in the city. Try dim sum, hot pot, or crispy Peking duck! If you're interested in history and culture, you can explore the Chinese-American Museum or visit the Nine Dragon Wall to admire the intricate artwork and architecture.

32. 360 Chicago

360 Chicago

Competing with Skydeck for the best place to get spectacular 360-degree views of Chicago, is 360 Chicago, on the 94th floor of the John Hancock Center. Besides the panoramic views, you can check out TILT - the thrilling attraction that lets you lean out over the city - safely of course!! If you are seeking ideas for a romantic date night in Chicago, you can have drinks with a view at the Signature Lounge!

33. Frank Lloyd Wright Home and Studio

Located in Oak Park just outside of Chicago, this visionary architect’s home and studio was built in 1889 and served as Wright's primary residence and workspace for over two decades. The building is a stunning example of Wright's signature Prairie Style, with its low-pitched rooflines, overhanging eaves, and emphasis on horizontal lines and organic materials. The inside is just as remarkable. For architecture aficionados, a visit here is an absolute must!

34. Adler Planetarium

people watching a space show

At this museum, dedicated to exploring the wonders of space and the universe through interactive exhibits, you can learn about the history of astronomy and space exploration, and marvel at the incredible telescopes and other instruments used by scientists to study the cosmos. The Adler also has a state-of-the-art digital dome theater, where you can watch shows about the universe that will make you feel like you are flying through space as you watch these stunning shows!

35. Chicago Children's Museum

Located at Navy Pier, the Chicago Children's Museum is an awesome place to bring the tots while in Chicago. There’s a Tinkering Lab where your children can get creative using age-appropriate materials. At the Dinosaur Expedition, kids can explore a real fossil pit! Ages ten and under will love this place!

36. Lincoln Park Conservatory

Lincoln Park Conservatory

This conservatory has manicured gardens and a Victorian Era glass house, built in 1895. There are four distinct sections with different flora and fauna: the Palm House, Orchid House, Fern Room, and Show House. The conservatory features a collection of exotic and rare plants from around the world, including palms, ferns, orchids, and cycads. It’s an oasis in the heart of the city!

After reading this list of great things to do in Chicago, you may feel overwhelmed about how to see so much during your visit.

For some guidance, check out our 2 day Chicago itinerary to get you off to a good start!