How to Take Your Chicago Summer to the Next Level

Dove's Luncheonette
Kailey Lindman Photography

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.Eat the new hot dogs at Wrigley. Is it wrong to be as excited about the food as the action on the field? We think not.

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.Hit up the Windy City Smokeout. Featuring some of the finest BBQ pitmasters in the land, including local standouts Smoque and Lillie’s Q. Pack extra napkins.

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

7. Got to the Logan Square Food Truck Social. Yes, food truck socials are now a thing. A very delicious thing.

8. Banh mi. It’s what’s for lunch. And dinner.

9.Try these top hangover-killing foods. It’s time to fight fire with fire.

10.Brunch like a boss. Go beyond the eggs and mimosas with chicken-fried biscuits or bacon-infused bourbon.

The J. Parker
The J. Parker

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

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

13. On a boat. Some call them booze cruises. We call them moments of pure happiness.

14. Kick back with a cocktail at a Chicago beach bar. Is there anything better?

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

16. Order a drink from someone who actually knows what the hell they’re doing. Like any of these lovely ladies.

17.Explore Chicago’s rapidly growing craft beer scene. Best in the Midwest (take that, Grand Rapids).

18. Drink like a real Chicagoan -- in a Chicago slashie.

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.

Candlewood Cabins
Courtesy of Candlewood Cabins

21.Rent a cabin with your bros (or significant other). Some even come with their own alpacas.

22.Explore the most beautiful places in Illinois you had no idea existed. If you didn’t know, there are bison here.

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.Bust out the tent at kick-ass Midwest campsites. You don’t need to be in Colorado to fall in love with nature.

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

27. Check out the Midwest’s finest drinking pilgrimages. Because it’s good to have goals in life.

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

Courtesy of Shea Flynn

31. Explore the 606. Luckily, it comes with plenty of stops for food and booze along the way.

32.Sneak into a hotel pool. We won’t say anything.

33. Watch a movie outside. Because picnic blankets are way better than sticky theater floors.

34.Take a day trip to an actually decent Chicago suburb. Yes, there are a bunch.

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

36.Cross a ton off your bucket list. You’ve probably done the closing a 4am bar one, but there’s a lot more!

37.Bike one of the country’s finest trail systems. Not that the Divvy route from your place to the liquor store isn’t arduous.

38.Go hiking around Chicago. Bar crawls don’t count as outdoorsy.

39.Do some actually cool touristy stuff when your friends come to visit. Not that the inside of your apartment isn’t dope.

40. Enjoy some personal time at a little-known nature escape.

Outdoor concerts chicago
f11photo /

41. Check out an outdoor concert. This summer we got Kings of Leon in Tinley Park, Pretty Lights at Northerly Island, and Green Day at Wrigley, among many others.

42. Tour the local underground comedy scene. Second City isn’t the only game in town, kid.

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

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

47. Rock out with your you-know-what out at Chicago’s best music festival.

48. Roll Cubanos and party with a white tiger.

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

50.Tour a Chicago music landmark. No, Joe’s on Weed Street doesn’t count.

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