52 Coolest Things to Do in Chicago

There are so many cool things to do in Chicago, I’ve been twice and I’d totally go back for the hat trick.

This big, beautiful, lakeside city in the state of Illinois deserves a whole lot of cheesy love because it’s one of the quirkiest around. Home to dozens of museums, deep dish pizza and the Obamas, Jennifer Hudson and Bill Murray, it’s just that bit cooler than New York IMHO. 

I love the fact there’s a beach, the views from the high points are amazing, and once you’re done with the bright lights of the city centre, you can go and explore the unique personalities of the 77 Chicago neighbourhoods.

Coolest Things to Do in Chicago

Visit The Bean in Chicago

1. Let’s start with the most famous Chicago activity of them all, getting a photo by the Cloud Gate – better known as The Bean. 

2. Enjoy a park with a difference by walking along the 606. It’s an abandoned railway come recreational space 2.7-miles long complete with art installations, plants and great views.

3. See the dinosaurs at the Field Museum of Natural History.

4. Put a life jacket on to kayak the various Chicago river trails. Probably an activity best done in the summer to be honest. 

5. Become a little starry eyed with a trip to the Adler Planeterium. Check out their website for details of the late night openings.  

6. Learn what it took to create the Chicago skyline with the Chicago Architecture Foundation River Cruise. I have it on good authority that this is one of the coolest things to do in Chicago. 

7. Step back in time with a drink and some jazz at the legendary Green Mill cocktail lounge.

8. Tick a baseball game off your all-American bucket list with a visit to Wrigley Field. And you’ve only really been to the baseball when you have a hot dog in the stalls. 

Chicago skyline

9. Watch an outdoor movie at Millennium Park. There are often concerts and special events here so make sure to check the listings for your dates.

10. Explore the shops, restaurants and gardens of Navy Pier. You’ll find Harry Caray’s here, a big ferris wheel and that great American staple, Bubba Gumps. 

11. Take a tour underground in the city’s freight tunnels.

12. Enjoy one of the best cups of Joe at Heritage Bicycles, part bike shop, part coffee house.

13. Check out the world’s largest stained glass Tiffany dome at the Chicago Cultural Center. There’s also an impressive one at Macy’s. 

14. Live out your Grey’s Anatomy fantasies at the International Museum of Surgical Science.

15. Say hello to the animals at the Lincoln Park Zoo – it’s free! 

16. Then do your downward dog beside some of the coolest cats with a free class of outdoor yoga, pilates or zumba inside the Zoo. There’s a special area for the yoga, looking out to the Chicago skyline. 

17. Garfield Park Conservatory is one of the country’s biggest greenhouses with over 600 species of plants and trees for you to have a gander at. It’s also nice and warm. Just thinking of anyone visiting Chicago in winter – this is a good shout. 

Coolest things to do in chicago

18. Freak out as you look down from 103rd floor of the Willis Tower on the Skydeck. Honestly, it’s amazing the trick it plays on your mind. 

19. Unleash your inner art critic at The Art Institute of Chicago. There are some incredible originals from well-known artists here – one of the best collections in the world in fact. 

20. Enjoy a lazy Sunday with a bit of bargain hunting at the Maxwell Street Market. Around since 1984, it has some of the city’s finest Mexican food as well as vintage items.

21. Walk the Magnificent Mile and do some window shopping, or if you wanna splash some cash, step right up. 

22. See otters, octopuses, dolphins and penguins at the Shedd Aquarium.

23. Time travel back to the 90s at The Wormhole Coffee where Nintendo and Back to the Future rule.

24. Prepare to wait in line for two hours as you queue for the best tacos and margaritas in town at Big Star.

25. See an old movie or watch a talk with a film director at the Music Box Theatre. If you can catch it on a good day it’s definitely one of the coolest things to do in Chicago.

26. Explore the world of the Wizard of Oz fans at Oz Park where statues of the characters are dotted about the greenery. Get your selfie on with the Tin Man. 

View of Chicago skyline

27. Stock up on your spy supplies at Wicker Park Secret Agent Supply Co. and feel good about it because profits go to tutoring kids.

28. From there, keep ticking items off the shopping list with a trip to Woolly Mammoth Antiques and Oddities, which sells objects bought back to life. Apparently the aim of the shop is to help us all feel a bit better about death.

29. Pay your respects to all things pooch poop at the Shit Fountain which serves as a reminder for dog owners to poop and scoop.

30. Feel like you’ve actually achieved something by rock climbing at the Maggie Daley Park climbing wall.

31. Pick up a good read at Myopic Books. Then go and sit at one of the city’s many, many coffee shops to read through. 

32. Or, spend an afternoon with your new book on the urban Ohio Street Beach.

33. Lean 1,000 feet over Chicago’s Michigan Avenue at 360 Chicago with the Tilt experience.

34. Feel a little creepy standing in the exact spot the Obamas are thought to have locked lips for the first time at the Obamas Kissing Rock on 53rd Street and Dorchester Avenue. Do we believe it? 

35. Celebrate the invention of one of the best baked goods, the brownie, at the Palmer House Hilton.

36. Live out your mad scientist dreams at the Museum of Science and Industry.

Chicago Lou Mitchells

37. Get a huge breakfast at Lou Mitchell’s to set you up for the day. It’s the start of Route 66, so get your kicks! 

38. Unwind with a bit of music and comedy at the Phyllis’ Musical Inn.

39. Learn about all things deep crust and cheesy and greasy at the U.S. Pizza Museum. One of the most calorific and coolest things to do in Chicago. 

40. Afterwards, check out Giordano’s for authentic deep dish Chicago pizza. Or Malnati’s – you need to weigh in and decide on your favourite of the two for future reference. Eating is seriously one of the most important things to do in Chicago. There are so many iconic dishes to work your way through. Take a look at this guide to Chicago specialities by thesavvyglobetrotter for starters.

41. Listen to some of the best live blues and jazz at the oldest blues house in the city, Kingston Mines.

42. In the summer months, try stand up paddleboarding on Lake Michigan.

43. Buy an umbrella hat from Chicago radio DJ Carl Bonafede, apparently you can’t go home without one.

44. Head to Big Joe’s bar on a Friday night to watch a real-life turtle race (it’s a thing).

45. Take your clothes to be cleaned at Pert Cleaners and wander the Antique Fabricare Museum at the back while you wait.

46. Enjoy a mid afternoon sugar rush at Stan’s Donuts, or, if you’re up by Lincoln Park, try Firecakes Donuts. They’ve won awards for their sugary delights and I popped in for a try.

Coolest things to do in chicago

47. See where the likes of Tina Fey and Bill Murray started out with a trip to the Second City comedy complex.

48. Continue your showbiz education at the Museum of Broadcast Communications.

49. Have a drink in a boat come bar looking out at the lake at North Avenue Beach House.

50. Fill yourself up for the day with brunch at the The J. Parker rooftop restaurant.

51. Burn it off by renting a bike and cycling the 18-mile stretch around the lakefront. This is definitely one of the coolest things to do in Chicago as you get a good look around the city. 

52. Find yourself some wheels and visit the Superdawg drive in for one of the city’s best hot dogs.


I was in Chicago, Illinois thanks to Enjoy Illinois, the Illinois Office of Tourism. I received visits to most of the above in return for a review and a mention in my travel blog. If you’d like to find out more about Illinois, just click this link.


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