I I t’s no secret that Chicago summers dominate every other summer on the face of the earth. But just in case you need a little extra motivation, we took it upon ourselves to create a comprehensive city guide that’s got you covered in all facets of local life, from food and drink to road trips and culture. If you’re bored during summer in Chicago, it’s now entirely your own fault.
Michael J/Flickr


1.The best burger in town. If there is any argument, it’s between Kuma’s and Au Cheval. But really, there’s no argument.

2. Pizza, not just deep dish. Chicago may be known for its deep dish, but that doesn’t mean there isn’t some kick-ass thin crust around the city.

3. Chicago Hot Dog Fest. Local hot dog institutions from Fatso’s Last Stand to Bryon’s compete to bring you the craziest, most amped-up dogs imaginable.

4. Italian beef. You aren’t a true Chicagoan until you’ve experienced the soggy delight that is Italian beef. You decide your favorite, but our money’s still on Johnnie’s.

5. Lakeview Taco Fest. Mexican wrestling and tacos go together like, well, Mexican wrestling and tacos.

6. Donuts. Chicago likes its donuts. Like, really likes its donuts. It’s kind of a problem for swimsuit season, but whatever.

7. It may have taken a while, but Chicago food trucks can now legally cook on site. It was worth the wait.

8. Chicago is the biggest Polish city this side of Warsaw. Your summer needs some zapiekanka. (Don’t ask, just order.)

9. Puerto Rican cuisine is one of Chicago’s most delicious secrets. Long live the steak jibarito.

10. Hit up Chinatown. Because sometimes it’s good to be freaked out by your food.

Parson's Chicken & Fish


11. In a secret speakeasy. Because only tourists use doors.

12. At a tiki bar. Bamboo makes everything better.

13. Hit up a classic dive. You haven’t experienced Chicago until you’ve sung karaoke at 4am.

14. So you've tried outdoor bars, dive bars, old bars, new bars. But have you acquainted yourself with Chicago's most important bars

15. Take in the view from a rooftop bar. The elevator ride up is what Chicagoans consider summer hiking.

16. Check out one of Chicago’s top beer bars. Because beer is a love only surpassed in Chicago by Italian beef.

17. Chicago’s local brew scene is the best in the Midwest (that’s right, Grand Rapids).

18. Go to some achingly cool bars and loudly proclaim that you totally knew all these places before they made it.

19. Take your bestest buddy, and your favorite humans, to a dog-friendly bar. Humans aren’t the only ones thirsty for the outdoors this summer.

20. Recline with a drink anywhere near the water. Any body of water.



21. Did you know camping is a thing around Chicago? Well, cabin camping at least. Hey, some of these cabins even come with their own alpacas. Which is nice.

22. Take a trip out of the city to explore the Land of Lincoln’s weirder side. If you’re into giant Superman statues, that is. Which, let’s be honest, who isn’t?

23. Quick! Name 3 cities outside of metro Chicago that aren’t Springfield, Peoria, and Champaign-Urbana. You can’t do it, can you? Maybe this will help.

24. Vacation the Midwest like a total boss.

25. Road trip to awesome little diners around the state. Because what the hell else is Route 66 good for?

26. Take a pizza road trip. Yes, this is now a thing.

27. Check out Chicago's best drinking destinations. Which are definitely as cool as they sound.

28. Discover your new favorite Midwest town that isn’t Madison or Milwaukee.

29. Fling pieces of hardened cow dung. For fun.

30. Fall in love with our neighbor to the north. There’s more to Wisconsin than cheese. Not that we have anything against cheese.



31. Millennium Park is always cool, but it amps up for summer so you may as well just camp there. 

32. Dig up the most obscure festival you can find. Because there’s only about a BILLION to choose from.

33. Watch a movie, outside. Sticky movie theatre floors not included.

34. Hit up one of Chicago’s craziest parties. Warning: power sanders may be included.

35. Ride a fly board over Lake Michigan. Because only tourists traverse waterways via boat.

36. Cross a ton off your bucket list. Okay, you’ve already done the closing a 4am bar one.

37. Get weird at a free full moon fire jam. Because only suckers pay for that.

38. Explore the city west of Western. Yes, there is cool stuff that isn’t Logan Square here. Blocks of it.

39. Immerse yourself in a sensory-deprivation flotation tank while you ponder how many things on this list you still have to do. What’s the worst that would happen?

40. Take a date on a little-known nature escape.



41. Check out an outdoor concert. Wilco in Millennium Park? Pearl Jam at Wrigley? Yes, please.

42. Take a date somewhere actually cool. Like, somewhere that is definitely NOT Navy Pier.

43. Stay in a hipster crash pad after indulging in affordable Michelin-starred cuisine.

44. Get a taste of Chicago’s up-and-coming burlesque scene.

45. Tour highly underrated neighborhoods in Chicago. Wrigleyville is not one of them.

46. Check out the most awesomely weird bike beer fest in all the land.

47. Get your metal fix at Chicago’s coolest new music festival.

48. Roll Cubanos and party with a white tiger.

49. Dance like nobody’s watching. All summer long. For free.

50. Pimp up your car and enter it into a lowrider festival.

Jay Gentile is a Thrillist contributor and he only plays ping pong in flower shops, out of general principle. Follow @innerviewmag.


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