Chicago City Guide

59 Best Things to Do in Chicago

by: Mara Ganz
Last Updated on July 29, 2022 | 0 Comments
things to do in chicago
Last Updated on July 29, 2022 | 0 Comments

Planning a trip to the midwest and looking for things to do in Chicago? Look no further! 

Chicago is a great city that has a huge offering of tourist attractions, museums, restaurants and bars. But if you’re not familiar with the city or are planning a visit, figuring out what to do, what to see and what to eat can easily feel a little overwhelming. But have no fear: This guide to things to do in Chicago will help you plan the perfect trip if you’re visiting or the perfect day if you’re exploring your own city.             


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Foodie Things to Do in Chicago

1. Cooking Classes in Chicago

Looking to enhance your cooking skills while you’re in the Windy City? Then add cooking classes in Chicago to your things to do in Chicago list. Thanks to the renowned chefs who run these classes, your world will be opened up to all sorts of cuisine, flavors and cultures. There is also a whole variety of online cooking classes you can choose from that will start your journey to being a master ramen maker, an authentic ravioli chef and an expert sushi roller. Start browsing all cooking classes near you to get started.

cooking classes are a fun thing to do in chicago
via Cozymeal

2. Private Chef Experiences

If you’re more into the idea of having a private chef do the heavy lifting, take a look at these private chefs in Chicago. Their talent knows no bounds as they cook up gourmet Latin food, classic French cuisine and sophisticated Southern-style dishes. Private chefs near you handle all of the shopping, cooking, service and clean-up and make for an enjoyable thing to do in Chicago. 

3. Food Tours

Who wouldn’t love getting their daily steps in while chowing down on some of a city’s greatest food offerings? If this sounds like an ideal way to spend your day, check out the food tours in Chicago. Not only do food tours near you leave your taste buds satisfied, but they are an amazing way to explore the best foods of Chicago from a fresh perspective. Chicago pizza tours, for example, will help you find the best deep dish in town!

enjoying a hot dog on a food tour
via Cozymeal

4. Winery Tours and Tastings           

Another great thing to do in Chicago as a way to explore the city is to tour a few wineries. By the end of the day you’ll have a new favorite wine and consider yourself a bit of a sommelier. 

5. Brewery Tours and Tastings

If beer is your preferred drink of choice, hit up some of the city’s best watering holes on a brewery tour as a fun thing to do in Chicago. Sample and taste all sorts of beers — IPAs, stouts, lagers — while learning about the history of different Chicago bars. 

brewery tours are a fun thing to do in chicago
via Canva

6. A 1940s Drive-In Restaurant

Traveling back in time to the 1940s at Superdawg Drive-In is a great thing to do in Chicago. While they’re known for their hot dogs, they’ve got all kinds of fast food that will come straight to your car thanks to a uniformed server. There's a reason Superdawg makes our list of best restaurants in Chicago.

7. Classic Chicago Food

If you’re looking to taste a classic Chicago food, visit Al’s #1 Italian Beef for the Italian beef sandwich. The restaurant has been in business since 1938 and any and all meat lovers should add having a meal here to their things to do in Chicago list.  

Al's Number 1 Italian Beef
via Al's #1 Italian Beef

Things for Couples to Do in Chicago

8. Sign Up for Some Virtual Experiences

If you and your partner are more into the idea of hunkering down than exploring, have no fear as there is a wide variety of live virtual experiences that are available to you. If you guys feel like learning how to make the hottest new cocktail, online mixology classes might be for you. Want to expand your knowledge on whiskey or coffee? Check out virtual whiskey tastings and online coffee classes. And if wine is your beverage of choice, there is a selection of virtual wine tastings to choose from, too.     

9. Visit the Museum of Contemporary Art, Chicago 

Are you and your significant other into the art scene? Then a romantic thing to do in Chicago for the two of you is to visit the Museum of Contemporary Art. This museum displays a variety of art such as large scale installations, video installations, music and photography. Check out exhibits from up and coming artists as well as more established artists. The museum also features regular talks with all sorts of writers and creators and it should definitely be added to your list of things to do in Chicago.   

visit the museum of contemporary art for a fun thing to do in chicago
via Museum of Contemporary Art

10. Listen to Jazz

If you’re a Chicago resident or visiting over a Labor Day weekend, definitely add the four-day Jazz Festival in Millennium Park to your list of things to do in Chicago.

11. Walk Hand in Hand Through Garfield Park Conservatory

While this is not your typical date night excursion, it could certainly be a fun date idea in Chicago. The Garfield Park Conservatory has eight indoor display gardens that, together, feature more than 100,000 plants. In fact, one of the gardens features the largest range of succulents and cacti in the Midwest. And, thanks to the indoor gardens, this makes for a great thing to do in Chicago all year-round.

Garfield Park Conservatory
via Garfield Park Conservatory

12. Catch a Show at the Chicago Theatre

The Chicago Theatre first opened in 1921 and some famous names such as Duke Ellington, Diana Ross and Lewis Black have found their way onto its marquee over the years. Today, it’s a spot to catch a comedy show, some great theatre and live music, making a visit there a great thing to do in Chicago. 

13. Go Indoor Skydiving

A less scarier date night option than actual skydiving is indoor skydiving, which you can do at iFLY Chicago. No jumping out of a plane is required, but you’ll still get pumped up just enough. 

visit ifly for a fun thing to do in chicago
via iFly

14. Take a Boat Cruise

Do you and your significant other like dinner? Do you also like cruises? Then sign up for a dinner boat cruise (or a brunch cruise or a lunch cruise!) as a unique thing to do in Chicago. The options are endless —choose to catch the sunset, listen to live music or watch some fireworks.

15. Root for a Sports Team

There’s no shortage of sports in the city of Chicago. You’ve got the White Sox, Cubs, Bears and Bulls to name just a few. There’s a sport for everyone, which makes taking in a game the perfect thing to do in Chicago.

wrigley field stadium
via Canva

16. Soak in an Ancient Bath

A very romantic thing to do in Chicago is to have a date night at AIRE Ancient Baths where there are multiple different ancient bath pools and plenty of massage options to choose from.  

17. Catch a Flick

A great thing for couples to do in Chicago is to see a movie at The Music Box Theatre, which happens to be Chicago’s premiere arthouse theatre. It’s also notorious for being one of the world’s most beautiful cinemas. They show arthouse movies, documentaries and foreign language films, making it easy for you and your partner to agree on something.

catch a movie at the music box theater for a fun thing to do in chicago
via The Music Box Theatre

18. Watch a Movie at the Drive-in

Nothing says romance quite like a drive-in movie, not to mention that Rock Island Public House screens their movies for free on the weekends. All you have to do is drive up, pay for snacks and enjoy the film, which sounds like the perfect thing to do in Chicago to us.  

Free Things to Do in Chicago

19. Take in a Public Art Show

Art on theMART is a public platform for artists (both local and international) to display their moving image work. It runs 2.5 acres, which makes it the world’s current largest digital art projection and an item that should definitely be added to your things to do in Chicago list.

art on the mart
via Art on theMART

20. Ice Skate

If you happen to be visiting Chicago in the winter (or if you’re a resident) a fun and free thing to do in Chicago is to go ice skating at the McCormick Tribune Ice Rink in Millennium Park. While skating you’ll have a view of the famous “Bean” and the lights of Michigan Avenue. Reservations are required so make sure you book in advance so that you don’t miss this fun thing to do in Chicago!

21. Explore Grant Park

If you’re looking for things to do in Chicago that lets you spend time outside, look no further. Grant Park spans 313 acres and has gardens full of flowers, baseball diamonds and multiple walking paths. It starts at the Loop and ends in Chicago’s South Side. It also houses Buckingham Fountain, which is one of the world’s largest fountains that has 133 jets. The fountain performs choreographed shows during which water is shot 150 feet into the air. The night shows are accompanied by lights and music, which makes this a fun thing to do in Chicago at night.

explore grant park for a fun thing to do in chicago
via Canva

22. Visit an Impressive Library

While a library may not sound all that exciting to some, the Stony Island Arts Bank is just the opposite and a visit to the building is definitely a fun thing to do in Chicago. Not only that, but this former bank offers free tours every Sunday, free dance classes and free live music performances.

23. Visit the Zoo

If you visit the Lincoln Park Zoo you’ll have the opportunity to see about 200 different species of animals. There are zebras, sloths, hippos and a big display of large mammals. This is a great thing to do in Chicago, especially if you have kids.   

lincoln park zoo
via Lincoln Park Zoo

24. Stroll Magnificent Mile

Sure, the shopping on Magnificent Mile isn’t free, but that doesn’t mean a nice walk around the area isn’t a great thing to do in Chicago. You’ll get a nice look at the Chicago Water Tower, the Wrigley Building and Tribune Tower. And if the temptation of Bloomingdale’s, Macy’s and Nordstrom is too much and you find yourself wandering in, that’s okay, too. 

25. Pose for Pictures at the Bean

While it has certainly become a trendy sight, a visit to the Bean, at 42 feet wide and 66 feet long, is also certainly a cool thing to do in Chicago. 

take pictures at the bean for a fun thing to do in chicago
via Canva

26. Walk the 606

Did you know Chicago has its own version of New York City’s Highline? The windy city refers to it as The Bloomingdale Trail and the 606 and it’s located on the North Side of Chicago. A walk, run or bike ride along the three mile stretch is a lovely thing to do in Chicago. You can also enjoy the trail’s art installations along the way.

27. Spend a Day at the Beach

If you’re looking for a fun day in the sun, hit up North Avenue Beach. There’s space for lounging in between volleyball courts and a slew of restaurants for when you get hungry, making a day here an ideal thing to do in Chicago. 

north avenue beach
via North Avenue Beach

28. Check out the Hubbard Street Murals

Art fans will definitely want to add this to their things to do in Chicago list. The Hubbard Street Murals go back to 1971 when they were started by a group of students and they are still alive today thanks to a group of local artists. Taking the time to check out the five blocks worth of murals is definitely a cool thing to do in Chicago.  

29. Bike Along the Chicago Lakefront Trail

Another outdoorsy thing to do in Chicago is to hop on a bike and pedal away on this 18-mile long trail that overlooks Lake Michigan.

biking along the lakefront is a fun thing to do in chicago
via Canva

30. Explore Promontory Point

Much like the Bean, Promontory Point is a current hot spot for Instagram photos. However, it’s also a great place to spend the day walking around and checking out the public art that’s on display.

31. Walk Around Chinatown

Whether you want to shop, eat some incredible dumplings or just take a walk, Chicago’s Chinatown is a great neighborhood to explore and definitely a solid thing to do in Chicago.

people enjoying dim sum
via Canva

Things to Do in Chicago at Night

32. Travel to Paris at Bordel

Yes, this is a thing to do in Chicago, but you’ll feel like you’re in Paris while visiting this Parisian style cocktail bar. Not only are there all sorts of unique cocktails at Bordel, but there is also live entertainment, such as a show from the city’s one and only burlesque dancer who happens to swallow swords.   

33. Listen to Live Music at the Green Mill

This bar used to be buzzing with 1920s gangsters like Al Capone. Now it’s a great spot to listen to and enjoy live jazz performed by Chicago locals. 

the green mill bar
via Green Mill

34. See a Breathtaking View of the Skyline

If views are what you’re looking for, you will definitely want to add the 360 CHICAGO Observation Deck (which used to be called the John Hancock Observatory) to your list of things to do in Chicago. The observation deck goes 1,000 feet above ground and even has a room that tilts. Needless to say, a visit at night is sure to leave you pretty blown away.

35. Take an Architecture Tour on a Boat

If you’re looking for fun things to do in Chicago for adults, the Architecture River Tour is a great option. You’ll learn a ton about various buildings from trained docents while rolling down the Chicago River as the sun sets.

taking an architecture tour is a fun thing to do in chicago
via Chicago Architecture Center

36. Scout for Up and Coming Comedy Talent

Seeing a comedy show at The Groundlings or The Second City is a fun thing to do in Chicago for adults that will leave you in stitches. There’s a chance you could also see the next Bill Murray, Tina Fey, Steve Carell or Amy Poehler in action.

37. Get the Blues at Buddy Guy’s Legends

This bar, which is owned by Buddy Guy, a Grammy-winning Blues musician, has live blues music performances every day of the week as well as delicious New Orleans-style food. 

buddy guy's
via Buddy Guy's Legends

38. Get in the Holiday Spirit

A thing to do in Chicago around the holidays is to spend a night at Light Up the Lake at Navy Pier. In addition to a big light show, there’s a skating rink, train rides for kids and a beer garden for adults.   

39. See a Show at the Chicago Theatre

This thing to do in Chicago allows you to see some live theatre and, if you sign up for an organized tour, you can also see the theatre’s rehearsal space and learn all about the venue’s history.

see a show at the chicago theater for a fun thing to do in chicago
via Chicago Theatre

40. Play Trivia at the Hideout

Once a month, historian Paul Durica hosts a trivia night at the Hideout. A lot of other events go on at the bar as well such as dance parties, variety shows and live DJ performances, which means that no matter what day of the week it is, a hang here is an entertaining thing to do in Chicago.

Unique Things to Do in Chicago

41. Kayak Along the Chicago River

Thanks to Urban Kayaks, you can add kayak along both the Chicago River or Chicago lakefront to your things to do Chicago list. Soak in some great views of the city while enjoying a day out on the water!  

kayaks on the chicago river
via Urban Kayaks

42. Visit the American Writers Museum

If you’re a writer or a fan of good writing, a visit to the American Writers Museum could be the perfect thing to do in Chicago. This museum features visits from various writers as well as the actual typewriters used by famous writers such as Orson Welles, Truman Capote and Ernest Hemingway. After a visit you may just be inspired to sit down and write the next great American novel. 

43. Get Sky High in a Helicopter

Feeling fancy? Then add this unique thing to do in Chicago to your to-do list: a Legacy Helicopter Tour of Downtown Chicago. Wave hi to buildings and sites such as the Navy Pier, Willis Tower and Soldier Field from many, many feet off the ground. You will not be disappointed if you add this thing to do in Chicago to your list! 

a helicopter ride is a fun thing to do in chicago
via Canva

44. Go on a Gangster Tour

If you’re a crime junkie, you definitely will want to secure your seat on a gangster and crime tour, which is a very unique and fun thing to do in Chicago. Learn all about the Chicago mob while seeing the spots where gangsters like Al Capone used to hang out.

45. Tour Frank Lloyd Wright’s Old Stomping Grounds 

Frank Lloyd Wright became known for his architecture while living in Chicago, so it should come as no surprise that there are plenty of buildings around the city that are designed by him. If you want to see more as a thing to do in Chicago, you can head to Oak Park for a tour of his home and studio.

touring Frank Lloyd Wright architecture for a fun thing to do in chicago
via Frank Lloyd Wright Trust

46. Pick Up Some Vinyl Records

If you’re looking to add to your vinyl collection, add a visit to Dusty Groove to your list of cool things to do in Chicago. Their collection is quite impressive to say the least. 

47. Ice Skate With Van Gogh

While ice skating itself isn’t super unique, the Maggie Daley Ice Skating Ribbon (which is open from November to March) has taken the sport to another level by decorating their rink with renderings of Van Gogh’s work. So lace up your skates and have yourself a “Starry Night."

Maggie Daley Ice Skating Ribbon
via Maggie Daley Ice Skating Ribbon

48. Check Out the Museum of Science and Industry

There’s plenty to see at this museum, including a 700-ton German submarine from World War II, a vintage Boeing 727 and a steam locomotive. Needless to say, this is a great thing to do in Chicago for any history buff. 

49. Pick Up Your New Favorite Book

Bookstores are not dead and Pilsen Community Books can prove it. They have new and used books and anything you purchase will help support their small local business. So not only is shopping here a great thing to do in Chicago, but you’re helping out the community at the same time. 

visit Pilsen Community Books for a fun thing to do in chicago
via Pilsen Community Books

50. Go Antiquing

Wooly Mammoth is quite popular among the antiquing crowd. If you’re looking for a unique experience, this store should be added to your list of things to do in Chicago. They have a one-of-a-kind selection of taxidermy items, skull bones, skeletons and military gear. 

51. Experience the Museum of Illusions

As noted on their website, this museum invites its guests to “truly experience the impossible.” They call themselves an “edutainment destination” and they offer over 80 exhibits that include immersive experiences and optical illusions. Magic and illusion fans will definitely want this added to their list of unique things to do in Chicago. 

Museum of Illusions
via Museum of Illusions

Family-Friendly Things to Do in Chicago

52. Hit up Navy Pier

A visit to Chicago’s Navy Pier will keep the whole family busy and is a great thing to do in Chicago. There’s a 196-foot tall ferris wheel, a swing-seat ride, a carousel and an 18-hole miniature golf course. For a little bit more of a cultural experience, there’s the Chicago Children’s Museum. There’s plenty to do without kids, too. You can see a show at the Chicago Shakespeare Theatre, sip a beer at the Miller Lite Beer Garden or see a concert. Depending on the time of year, the pier is sometimes open until midnight, which makes it a great thing to do in Chicago at night. 

53. Take a Segway Tour

With the help of a knowledgeable tour guide, the whole family can learn something and have fun on a Segway tour, making it a fun and educational thing to do in Chicago. There are even haunted Segway tours if being spooked is your thing. 

a segway tour is a fun thing to do in chicago
via Canva

54. Brush Up on Your History at the Field Museum of Natural History

If you’re looking for a place for you and your family to learn about 4.6 billion years of natural history, this is the spot. In fact, because this museum houses over 40 million artifacts, it’s considered by some to be the greatest natural history museum in the world. 

55. Star Gaze at the Adler Planetarium

Any kids who are into space and astronomy are sure to have a good time at the Adler Planetarium. Not only are the exhibits here very impressive, but they also have live stargazing shows — prepare to be wowed with this immersive thing to do in Chicago.

Adler Planetarium
via Adler Planetarium

56. Play at LEGOLAND Discovery Center

Yes, this is slightly outside of Chicago’s city center, but it’s a great thing to do in Chicago and well worth the approximate 30-minute trip. There are rides, Legos to build and a 4D cinema. 

57. Swim With the Fishes

With about 32,000 different kinds of underwater animals such as penguins, sharks and whales, Shedd Aquarium is definitely a fun thing to do in Chicago for adults and kids alike.

visit the Shedd Aquarium for a fun thing to do in chicago
via Shedd Aquarium

58. Visit a Designer Toy Store

Thanks to their collection of designer toys, Rotofugi is fun for kids and adults and a visit there is a unique thing to do in Chicago. In addition to loads of toys, the store also has an art gallery that offers free shows.  

59. Head to the Skydeck

Another thing to do in Chicago for the whole family is to head straight to Chicago’s Skydeck to check out the city from 103 floors up. If you want to feel like you’re hanging over the city, use one of the Skydeck’s glass balconies for even better views.  

tourists on the chicago skydeck
via Skydeck

While there is of course more to see, do and eat, these are some of the best things to do in Chicago. Whether you’re visiting the Windy City or live there, it’s a place anyone and everyone can appreciate.

For even more things to do in Chicago, check out other experiences happening on Cozymeal.

by: Mara Ganz
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