15 Cool Things to Do in Chicago This Summer

Now is the time for street fairs, live music festivals, beach days, and boat tours in the Windy City.

If you didn’t get to sneak away on a vacation this summer, fret not, there’s still time to squeeze out the last bit of sunny fun here in Chicago. To stave off your end-of-summer nervous breakdown, we’ve rounded up a list of events and activities, from outdoor live music performances, dance festivals, sports games, boat tours, and more—some going on long past Labor Day. So just ignore the premature pumpkins stocking up at Mariano’s, and keep doing summer while it lasts. Here are some fun summer activities and events you should know about right now.

The Salt Shed
The Salt Shed

The highly anticipated venue, The Salt Shed, opened in early August and has already had quite an impressive lineup for its debut season. The now open outdoor venue is built on Chicago's historic Morton Salt Factory complex, while the indoor venue is set to open in 2023. Kicking off its outdoor season were iconic bands like Fleet Foxes, Sharon Van Etten, and Andrew Bird, with veteran indie rock band Deathcab for Cutie closing out the year September 24. With a great selection of local food and drink vendors, superb acoustics, a sophisticated lineup, and a great view of Chicago's skyline, the venue checks all the boxes. Check the website for the rest of the season’s lineup and get your tickets.

Get groovy at Millenium Park’s free music and dance festivals

The Chicago Jazz Festival is a Chicago Labor Day tradition with headlining performances taking place both at Chicago Cultural Center and Millennium Park from September 1 through 4. A host of local neighborhood events will also be in full swing throughout the city from August 20 - 31, so be sure to check the full festival schedule.

Other festivals like the Chicago House Music Festival will also be held at the park September 15 - 18 and the Chicago Summer Dance series, which will host a full day of live performances and social dancing on its final day Saturday, September 17.

Chicago Botanic Garden
Chicago Botanic Garden

Find tranquility at a nearby nature conservatory or botanic garden

Sometimes spending a peaceful hour or two inside a nature-filled haven tucked inside the city is just what the doctor ordered. Nature conservatories and botanic gardens are accessible ways to enjoy the natural beauty of the season without having to drive very far. Chicago Botanic Garden, Garfield Park Conservatory, Lincoln Park Conservatory, and Oak Park Conservatory are great destinations to press pause and recharge.

Yes, the “air” portion of the Air and Water Show might be a smidge loud, but most of us can agree that watching the daredevil pilots of the US Navy Blue Angels nose-diving and flipping their jets in unison above Lake Michigan is pretty darn cool. The Chicago Air and Water Show is a yearly tradition that has been wowing Chicagoans since 1959 and is the biggest of its kind in the United States. This year the spectacle will take place on August 20 and 21 from 10 am - 2 pm and you'll be able to view it anywhere on the lakefront. The “water” portion, which includes water-skiing and boat-jumping, can be viewed best from North Avenue Beach.

Urban Kayaks
Urban Kayaks

The city sure looks beautiful shoreside, but the best way to capture Chicago’s impressive architecture is from a kayak, jetski, sailboat, or yacht. Companies like Waterriders, Urban Kayaks, and Kayak Chicago are your go-tos if you’re looking to leisurely float down Chicago's waterways from a kayak, while Chicago Water Sport Rentals at 31st Street Harbor, Jet Ski Chicago, and Next Wave Watersports are your high-speed jet ski providers. You won’t need any excuse to round up some buddies and rent a private sailboat from Chicago Sailboat Charters or Come Sailing Inc, or a motorboat from Chicago Yachting—and if you’re willing to splurge a little, rent yourself a yacht from Meridian Private Yacht, Free Spirit Yacht Cruises, or Anita Dee Yacht Charters. Still haven't found what you're looking for? Scroll through an endless list of boats and yachts being rented by private owners at Boatsetter and Get My Boat—kind of like Airbnb, but for boats.

Big Joe/Shutterstock
Osterman Beach | Big Joe/Shutterstock

Lake Michigan might be the city's most lively destination in the summertime. Grab a towel, your sun hat, some SPF, and head to one of Chicago’s glorious beaches, and whatever you do, don’t forget to stuff a few dollars in your pocket to buy a cold, tasty paleta or other frozen beach snacks. If you're thirsty or hungry, bars and restaurants dot the lakeside’s edge like Cafe Olivia off of Ohio beach, Theater on the Lake off of Fullerton beach, or Castaways off of North Avenue beach. Get sandy playing volleyball with old and new friends, or stay sandless and set off on a rented paddleboard—there are no boundaries at the lake.

Anita Tijoux
Anita Tijoux

Every Monday and Thursday through August 18, Jay Pritzker Pavilion is hosting a free music series featuring emerging and established artists from all over the world. The series kicked off with the iconic and adored Femi Kuti & The Positive Force followed by other impressive acts like Jeff Tweedy, Ana Tijoux, and DakhaBrakha. Get there early to snag a seat, and pack a picnic and spread out on the expansive lawn. To boot, the pavilion will also be hosting the Chicago Jazz Festival from September 1 through 4.

James Andrews1/Shutterstock

Chicago is an incredibly bike-friendly city, with countless bike lanes and paved mixed-use routes winding through diverse neighborhoods. But nothing beats biking along the lake with a nice summer breeze running through your hair. Grab your helmet and hop on your trusty steed, but no worries if you don’t have one—the folks over at Divvy have you covered with an easy pay-as-you-go ride. If you’re looking for a more specialized bike, Bike and Roll stocks tandem bikes, kids’ bikes, bike wagons, quadricycles, electric bikes, and fitness bikes to accommodate any of your cycling needs. Along the 18-mile stretch, you’ll not only take in spectacular views of the skyline, but also pass by some pretty amazing parks and scenic areas, like Buckingham Fountain, Navy Pier, Northerly Island, Maggie Daley Park, and Lincoln Park Zoo.

Chicago's First Lady Cruises
Chicago's First Lady Cruises

For those who don’t like to dive head first into Lake Michigan, there are plenty of opportunities to ride atop it. And now that summer temps have arrived, there's no shortage of enticing boat tours hitting Chicago’s waters. Snag a seat aboard Chicago's First Lady, Wendella Tours & Cruises, Shoreline Sightseeing, or Chicago River Boat Architecture Tours for a rip-roaring good time amid the panoramic skyline. And if you time it right, you can also scope out ART on the Mart—the dazzling digital art performance along the RiverWalk.

Chicago Red Stars
Chicago Red Stars

The Cubs, White Sox, Chicago Fire, and Red Stars are all well into their seasons, and if you haven’t been to a single game, you’re missing out. Whether your MLB loyalty lies on the northside or the South Side, the Cubs and Sox each have plenty of games on the docket (finally), but make sure to grab your tickets early and often (or just post up in an outstanding local sports bar for the ultimate game day festivities). Hit up the Chicago Fire’s full schedule to see when the MLS will be taking over Soldier Field, and visit the SeatGeek Stadium for our beloved Chicago Red Stars.

Babygold Barbeque
Babygold Barbeque | PHOTO BY DTKINDLER PHOTOGRAPHY

It ain’t quite KC or Memphis, but Chicago’s barbecue landscape has certainly come a long way, baby. From iconic haunts like Lem’s and Earl’s to more modern outposts like Lillie’s Q and Smoque, BBQ is enjoying something of a renaissance, as newer spots like Babygold continue to push the envelope. Don’t be shy and pick up a full spread from one of Chicago’s top smoker specialists. 

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Photo courtesy of Tito’s Handmade Vodka

Festival season is finally upon us, so join Tito’s Handmade Vodka at a few amazing local events in Chicago. Whether you’re checking out awesome acts at Lollapalooza or Mas Flow, or tasting some of the city’s best BBQ at Windy City Smokeout, there are so many great options. Cheers to good music, great food, and tasty Tito’s cocktails!

Old Town Ale House
Old Town Ale House | Photo by JIM VONDRUSKA for THRILLIST

Fancy new rooftop bars are cool and all, but once summer revs up, it’s time for Chicago’s rich civic treasure—a.k.a. dive bars—to really shine (metaphorically, of course). With warmer air bringing out the shut-ins, it’s time to hole up in your favorite old man bar and drink until fall rolls around (or 4 am, whichever comes first). Quality options run rampant in this city, but no one’s ever regretted a late-night foray into Old Town Ale House. And if a “slashie” (half bar/half liquor store) is more your style, may we humbly suggest Rite Liquors?

Field Museum
Field Museum

With museums back in operation, you can once again go full Ferris Bueller ogling the Monets at the Art Institute or spend some time hanging out with Sue at the Field Museum, where over 300 artifacts, including costumes, comics, and interactive displays, should tide you over until C2E2 returns. For more offbeat options, including the perennially creepy International Museum of Surgical Sciences, check out our full museum guide. Did someone say there’s an entire museum dedicated to leather and bondage? Sure did.

Beechwood Cottage | Courtesy of Airbnb

While air travel has mostly returned to its pre-pandemic form, it’s clear that the Great American Road Trip isn’t going out of style anytime soon. Luckily, you don’t have to venture too far to get in on some amazing destinations near Chicago, from exploring forested trails to indulging in some summertime R&R at a luxurious cabin or resort. Looking for a staycation? No problem. Need an Airbnb? We’ve got you covered.

Chef Brian Jupiter
Chef Brian Jupiter | Photo COURTESY OF HILARY HIGGINS

Whatever else you do this season, be sure to continue to do your part in making the community we live in a better place for every Chicagoan. Aid in the fight for racial justice and social equity taking place across the city by supporting Chicago’s Black community via everything from BIPOC-focused nonprofits and community organizations to Black-owned restaurants and bookstores. Here's how to get started.

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Elanor Bock is a contributor for Thrillist.
Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile