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!
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
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
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.
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!