Your 2019 Chicago Summer Bucket List

June 21 may be the official first day of summer, but we’ve been planning our perfect June, July and August for weeks. From art fairs to oysters, we’ve got 23 must-do activities to fill your calendar.

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1. Drink on Chicago’s best patios

When someone asks “Where do you summer?” don’t roll your eyes. Just tell them you summeron the patio of your favorite neighborhood restaurant. We’ve got the master list.

2. Catch outdoor music at an iconic festival

Pack a picnic and head to the North Shore for Ravinia. The decades-old outdoor music festival isin full swing until September 15. We can’t wait to see Jennifer Hudson.

3. Get out on the water

Those kayaking lessons on the Chicago River are totally worth the cost, but you can also pay just $10 to paddle if you volunteer with Friends of the Chicago River at one of its monthly river cleanups. Just sayin’.

heidi harris
Heidi Harris/Our Labor of Love

4. Spend a day strolling the Riverwalk

This summer, we’re inventing the Riverwalk crawl: Start with a bite at River Roast, stroll to City Winery for a glass of rosé and end your evening by walking all the way east to the new OffShore rooftop bar at Navy Pier. [[link?]]

5. Hit up a farmers market

Buy your week’s groceries at one of Chicago’s many outdoor farmers markets. It’s good for the local economy, good for the earth and (most important?) good for your fantasies of living that European lifestyle.

6. See free concerts in Millennium Park

Head to Millennium Park on Monday and Thursday nights at 6:30 p.m. for free concerts from the likes of singer-songwriter Natalie Prass and New Orleans brass band Cha Wa.

7. Bike all over town

Summer makes simple things like riding a bike downright blissful. Pick up a used bike from Working Bikes (you’ll be supporting a good cause), but not before you learn about bike safety.

marcin cymmer
Marcin Cymmer

8. Have a French happy hour

We probably won’t make it to France this summer, so we’ll go to the newly opened Café Cancale. Paul Kahan and One Off Hospitality are serving up oysters and cocktails in a spot named for a seaside town in Brittany.

9. Watch fireworks (and not just on the 4th)

Catch the free fireworks off Navy Pier every Wednesday and Saturday night. Trust us, that’s all you need for a magical summer evening.

10. Cool off with Taiwanese treats

Take a break from your gelato routine with a trip to Meet Fresh in Chinatown. The mountains of flavored ice, jellies and mochi are best split with a friend, but don’t be surprised if you want them all to yourself.

liz lauren
Liz Lauren

11. Get cultured with some theater

Summer may not seem like prime time for theater—until you’re watching The Comedy of Errors in your neighborhood park…for free. More of a musical gal? The Music Man opens at the Goodman on June 29.

12. Hang out on a boat

If boat ownership is out of reach, live the dream for an afternoon with Chicago Electric Boat Company. Or the Water Taxi always has its charms.

13. Take a trip to space

Chances are, you’ll need a break from the heat. So spend a day getting lost in the (air-conditioned) Museum of Science + Industry. Highlights include a film in the Giant Dome Theater showing new footage of the Apollo 11 landing, plus summer camps for kids.

14. Head to wine country

Fun fact: Nine wineries surround St. Joseph, Michigan, just a 90-minute drive from Chicago. Road trip, anyone?

15. Hop on a scooter

The Bird has landed. We’re referring of course to the scooters you now see across the city. Grab your helmet and take a joy ride with a friend.

16. Browse wares from local artists

Don’t kill us for bringing up the end of summer right now, but the Lakeview East Festival of the Arts (September 14 and 15) is the best way to celebrate it.


17. Check out a legendary designer’s newest project

Apparently, an exhibit at the MCA isn’t good enough. Virgil Abloh has also teamed up with Nike to design a community space right next to the Nike Store on Michigan Avenue. Stop in for workshops and giveback programs now through July 28.

18. Lace up your running shoes for a good cause

Every summer you say you’ll enjoy a run on the Lakefront Trail. Well, here’s some incentive: On July 20 and 21, you can run the Humana Rock ’n’ Roll 5K, half marathon or marathon and raise money to benefit the literacy nonprofit Open Books.

19. Celebrate Pride

Partake in Chicago’s Pride Fest fun: From live music and general revelry to the parade on June 30, there’s a little something for everyone.

20. Join a water-based workout class

Work your core, lengthen your limbs and above all do something pretty badass with a standup paddleboard yoga class at North Avenue Beach. Full moon, sunrise and sunset class times only make the occasion that much cooler.

anthony tahlier
Anthony Tahlier

21. Check out the city’s coolest new hotel

No Soho House membership? No problem. The Hoxton Hotel in West Loop has a gorgeous lobby and rooftop pool that are every bit as cool (and open to the public).

22. Upgrade your standard ballpark eats

What do you get when a James Beard Award–winning chef and a legendary Cubs manager team up? Maddon’s Post, the brainchild of Tony Mantuano and Joe Maddon, is a modern all-day Italian- and Polish-inspired restaurant just steps from Wrigley Field.

23. Have an elevated beach day

Next time you’re planning a day at North Avenue Beach, do yourself a favor and go to nearby Shore Club instead. You’ll eat better food and leave with less sand…everywhere.

amanda nyren
Amanda Nyren

Writer, yogi, mom to about a dozen houseplants

A lifelong Chicago resident, Amanda started covering the local scene for PureWow in 2016. She's a freelance writer and content strategist.
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