50 Things to Do in Chicago this Weekend

50 Things to Do in Chicago this Weekend

Chicago has been one of my favorite cities for nearly a decade. Although I don’t miss living in the states – particularly as of late – I do find myself longing for a bit of normalcy from time to time. Sometimes I miss the Windy City so much it actually hurts. I think it’s normal, though. After all, Chicago was my first love.

The older I get, the more I realize how absolutely fortunate I am to have called this city my home for as long as I did. Even more so, I’m insanely blessed to be able to deem Chicago as my “college town,” as well as to have met everyone I did along the way. One of the reasons this city was so fun throughout college was the fact that we always had something to do. Seriously – there will never be a shortage of things to do in Chicago this weekend or any weekend in the future.

Whether you’re lucky enough to call this gorgeous city your current or lifetime home or you’re headed there for a getaway, here’s a list of 50 things to do in Chicago this weekend. I made sure all of the options are available year-round and not weather dependent/seasonal. Enjoy!


#Traveling to #Chicago but not sure what to do? I want to make this the least overwhelming experience for you. Attached are some of my favorite activities and sights. It's a given that there will be something for everyone's interest. Check it out! www.willfulandwildhearted.com


50 things to do in Chicago this weekend


1. Tour the city by boat via the famous architecture tour hosted by The Chicago Architecture Foundation

2. Sip on some top-secret cocktails at Chicago’s own Safe House

3. Travel back in time and catch some jazz tunes at Al Capone’s former hangout, The Green Mill

4. Devour a slice of deep dish at Pequod’s in Lincoln Park

5. Take a stroll through the Museum Campus in the Loop

6. Catch a comedy show at The Second City, one of the world’s most iconic comedy clubs

7. Head up to the top of the Chicago Skydeck. On a clear day, you can see four states: Illinois, Indiana, Wisconsin, and Michigan.

8. Take the el over to Garfield Park and tour the magnificent conservatory. Admission is free!

9. Party in style at one of Chicago’s best modern speakeasy bars

10. Pack a picnic and nosh on the lawn of the Pritzker Pavilion

things to do in chicago this weekend www.willfulandwildhearted.com

11. Play some pinball with your friends at one of the city’s arcade bars

12. Eat some of the best sandwiches of your life within the Chicago French Market

13. Order a chocolate shake at The Weiner Circle. It’s not what you think it is.

14. Watch an indie film at The Music Box Theater

15. Stop by Jeni’s ice cream for some of the most delicious scoops of your LIFE

16. Pick up some of the world’s rarest vintage blues, jazz and global vinyl at the iconic Dusty Groove

17. Indulge in some European pastries at the Polish-owned Alliance Bakery

18. Take a trip out of the city into Evanston to view the ornate Bahá’í House of Worship

19. Drink your way through the beer list – and brave the firecracker fries – at The Bad Apple

20. Hop on a Divvy bike and ride the 606 trail

21. Sort through antiques and vintage delights at the Randolph Street Market

22. Try a Chicago-style hotdog at Superdawgs

23. Get cultured at the Art Institute of Chicago

24. Peruse the streets of Pilsen and take in the vibrant street art

25. Pop into Pilsen’s famed pub Simone’s for a truly unique experience

26. Wolf down a massive Obatzda Pretzel at Laschet’s Inn

27. Answer the Tamale Man’s beckoning call. Never turn down the Tamale Man.

28. Consume what is allegedly the world’s largest ice cream sundae at Margie’s

29. Share some curries or saris on Devon Avenue, one of North America’s largest Pakistani, Indian and Bangladeshi communities

30. Spook yourself on Chicago’s ghost tour

31. Hail a water taxi over to Chinatown to nibble on some bao and noodle dishes

32. Go on a mind trip at a Blue Man Group show

33. Tour a Chicago brewery – for free.

34. Take a trip back in time at the Redhead Piano Bar

35. Snap a selfie at the Cloud Gate sculpture, often referred to as The Bean

things to do in chicago this weekend www.willfulandwildhearted.com

36. Meander along the Chicago River Walk

37. Shoot a shot of Jeppson’s Malört at Simon’s Tavern

38. Throw back a few tacos and margaritas at Wicker Park’s Big Star. PROTIP: Get there early for prime outdoor seating.

39. Delight in the sights of the city’s skyline from my favorite nighttime secret spot

40. Feast at one of Chicago’s best brunch restaurants

41. Order a “Chicago Mix” from Garrett Popcorn

42. Taste test the lentil soup at Andersonville’s Taste of Lebanon

43. Stand the test of time and attempt to get the goods Doughnut Vault. The early bird gets the worm.

44. Stuff your face at the all-you-can-eat chocolate buffet at The Peninsula. It begins at 8 PM and costs $30 USD.

45. Cast some spells at the Occult Bookstore

46. Laugh your tush off at the Annoyance Theater, the bizarrely incredible staple in Chicago’s gay-friendly Boystown neighborhood

47. Peruse the National Museum of Mexican Art. Hunt down some nearby Mexican food afterward.

48. Take advantage of the plentiful eco-spaces within Chicago. (A few are open year-round!)

49. Dine within the city’s most famous home goods store, Restoration Hardware. No, seriously.

50. Participate in one of the city’s most extreme food eating challenges.

things to do in chicago this weekend www.willfulandwildhearted.com

Most importantly, relish in every beautiful moment the city hands you. Chicago is as beautiful as it is unique. It’s my second home, and it’s a place that will always feel like an all-encompassing, warm bear hug. I hope you feel the same when you travel there, too. Please let me know if you have any questions or suggestions in the comments below!



  1. October 17, 2017 / 11:10 am

    What a delightful and packed with information post, Laura! I haven’t made it to the Windy City yet, but I am more and more looking forward to visiting it, especially after reading these awesome tips!

    Thanks, pinned for later reading as I will need it.

    The Vocabulary Titan

  2. October 17, 2017 / 7:09 pm

    You had me at cocktails and ice cream! lol! But I love the variety you’ve included here. Definitely the Blue Man Group would be high on my list to see. While I’d love to say I would do all you can eat chocolate, I think I’d have to stay away!

    I haven’t been to Chicago partially because I just didn’t understand the appeal. Reading this makes me re-think that sediment and I would really like to visit…in the summer 🙂

  3. October 18, 2017 / 12:46 pm

    I’ve been to Chicago twice and both times, I had so much fun! On one trip, I planned my whole itinerary on an episode of “No Reservations” ha ha ha. I have only done a few of these but I would love to go back to Chicago one day. I had no idea that you can see four states: Illinois, Indiana, Wisconsin, and Michigan from the Chicago Skydeck.

  4. October 18, 2017 / 6:59 pm

    Wow! This is a huge list. The free tour a Chicago brewery jumped out at me immediately. I went to the site and I would love to go to Moody Tongue Brewing Co.. The interior is amazing and atmosphere looks amazing.

  5. October 18, 2017 / 11:10 pm

    Yay, there is so much fun to be had in Chicago. I especially love the pizza and the architecture boat tour 😉 I know I’ll be back for a visit very soon!

  6. October 19, 2017 / 2:19 am

    The weekend is really going to be something to write home about looking at the myriad options of activities in Chicago. I would love to take a boat cruise first and bask in the city skyline. Then I would like to gorge on a heavy brunch and possibly snap a selfie or two at the Bean.

  7. October 19, 2017 / 10:50 am

    Whoa! Was never aware that there’s so much to do and see in Chicago. But given a choice I would love to just explore the city and indulge in the brewery tour and sample some of them.
    Gazing at the skyline is also pretty high on my list as I am an avid fan of modern architecture.
    Hopefully I will make it to Chicago one day and this list would go a long way in preparing my days there.


  8. October 19, 2017 / 11:54 am

    Wow! I really didn’t know that there are so many things to do in Chicago!! I am not really a city person as I find it boring with not much to do. But, now that you have given so many things to do in Chicago, I doubt I will ever get bored!! Thanks for sharing and I’ve pinned it for later 🙂

  9. January 24, 2018 / 7:34 pm

    Wow! You got everything on here. Got the standard River Walk and food places and even some more specific things that I love like the Occult Bookstore. Love the post!

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