Chicago's Top Ten Summer Musts

by Nina Kokotas Hahn
When the temperatures rise, the Windy City hits the water. Photo courtesy Chicago Sailing.

Summertime is when Chicago comes alive. Local girl and travel writer Nina Kokotas Hahn finds the best things to do under the hot summer sun.

CHICAGO – Many locals (like me) will tell you that summer is the main reason — the only reason — we stick it out through Chicago's long and brutal winters. Under the summer sun, the City by the Lake literally sings and sparkles all the hot day long, almost never sleeps at night, and makes it hard to want to be anywhere else.

And, let's be real, summers in Chicago are all too short to waste on gimmicky, tourist attractions. Instead, here's my locally vetted, totally repeatable bucket list for more authentic Chicago love. Warning: You may never want to leave.

1. Get on a Boat

Nothing beats the thrill or intimacy of seeing the Chicago skyline across Lake Michigan from a sailboat (try Chicago Sailing). If sailing is not your bag, there's kayaking, windsurfing, stand-up paddle boarding or any number of architectural cruises that start on the Chicago River.

2. Run, Walk, or Bike the Lakefront Trail

Yeah, the 18-mile trail gets thick and hairy with tourists and locals pretty much anytime the sun is shinning. But you can avoid the worst of it early in the morning or closer to sunset. No matter the hour, you'll feel high on all that energy, scenery, and people-watching so good it almost feels wrong.

Summer festival

Photo: Ashley Garmon / Courtesy of Lollapalooza

3. Find a Neighborhood Summerfest

Hit any number of big and small neighborhood festivals happening all summer long for the chance to taste local brews and food while hearing great bands. My favorites include Taste of Randolph Street, Wicker Park Fest, Chicago Pride Parade, Square Roots, and the motherload of Chicago music festivals, Lollapalooza.

Radisson Blu Aqua

4. Stay at a Fresh, Summery Hotel

New hotels keep popping up all over Chicago, with many wisely keeping summer top of mind. There's Hotel Lincoln, with its J. Parker rooftop bar, pedicab service, and a location right across from Lincoln Park Zoo. Radisson Blu Aqua smokes the pool-going competition with a huge, beautiful outdoor pool deck and garden smack in the center of Lakeshore East.

5. Spend a Rainy Day at the Art Institute of Chicago

There are fantastic museums all over the city, but the Art Institute is a favorite for grown-ups (though not so much for kids). You'll see little-known and wildly popular masterpieces, remarkable photography exhibits, and a gorgeous Modern Wing. Definitely splurge on an audio tour, dine at Terzo Piano, and shop the Modern Wing store.

6. Stroll Millennium Park

A massive outdoor architectural wonderland, Millennium Park sits right next door to the Art Institute just off Michigan Avenue. I especially like it at night for the video screens at Crown Fountain and free concerts in the pavilion, though my kids love the giant reflective Bean and splashing in the fountain by day.

Trump Terrace

7. Cocktail by Rooftop

Call it a mood, but lately I can't stand to slum it inside or at street level in a city with so many amazing rooftop bars. There's the new Drumbar with its beautifully crafted cocktails, Lincoln Park's J. Parker with panoramic Lake views, and Trump's Terrace with landmark architecture and river views. Of course, rooftop cocktails cost a small fortune, but the open sky and warm breezes make it well worth it.

8. Be a Savvy Shopper

Michigan Avenue is a tourist trap, and you'll find far better shopping in neighborhoods just beyond downtown. Tried and true local favorites include the trendy boutiques on Armitage and Halstead in Lincoln Park (Art Effect and Lori's Designer Shoes), the high-end but still personal Oak Street beauties in the Gold Coast (Prada and Barneys New York), and the artsy cool shops on Milwaukee in Wicker Park (Saint Alfred and RSVP Gallery). 


Nellcôte, courtesy of Potluck Creative

9. Eat! Mostly on Randolph Street

Chicago has no shortage of diverse and incredible eateries, but the hottest cluster is found on Randolph Street in the West Loop. Girl and the Goat, g.e.b., Au Cheval, Haymarket, Vivo, De Cereo — seriously, each block reads like a checklist of must-eat Chicago restaurants of the moment. Of special note: Nellcôte, for its light and summery fare, its beautiful sidewalk setup, and the just-opened RM Champagne salon in the back.

10. See a Chicago Cubs Game

Doesn't matter if you are a Cubs fan or even a baseball fan: The gritty and sweet Americana magic in the Friendly Confines of Wrigley Field are hard to resist. No matter how lousy the Cubbies may be playing.


Brunch at Publican and Big Star

Photos of Radisson Blu Aqua, Trump Terrace, and Au Cheval by Nina Hahn.

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