27 Actually 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.

Now that the dreary days of winter are behind us, let's look forward to the season that Chicagoans do best and deserve most: summer. Chicago has got some of the best lakeside beaches, street fairs, live music festivals, and events to keep your head spinning. And if that wasn’t enough, the city has one of the finest culinary scenes in the nation—which you can now enjoy al fresco. The parks are green, the patios are open, and everyone seems to be walking around with a sunshine-induced serotonin high, so it's safe to say: “It’s summertime, baby.” From sailing out on the lake to rocking out at a street festival, here are some of the best 2022 summertime things to do.

The 606
The 606

Whether you're walking, running, biking, rollerblading, or sitting, the 606 is the destination when you're looking for a break from street-level life. The once-abandoned train route now serves as a 2.7 mile elevated pedestrian pathway connecting Bucktown, Wicker Park, Logan Square, and Humboldt Park, and is overflowing with blooming native flowers, shrubs, and trees alongside rotating and embedded artwork installed by local artists.

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-to's 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.

Lollapalooza
Lollapalooza | Photo by Greg Noire - Photographer

Whether you're looking to subtly sway back and forth, taking in the melodic tones of an indie rock band, or dance until you drop at a glow stick waving rave, when it comes to music festivals, Chicago has it all. This year the lineup is top-notch with acts like Wiz Khalifa and Post Malone at Lyrical Lemonade Summer Smash Festival; Doja Cat and J. Cole at Lollapalooza; Busta Rhymes and Lupe Fiasco at Hyde Park Summer Fest; and Phil Lesh and Friends and Black Pumas at Sacred Rose Festival. But wait, there’s more! Out of Space at Canal Shores, North Coast Music Festival, ARC Festival, Pitchfork Music Festival, Spring Awakening, Sueños Music Festival, Windy City Smokeout, or Riot Fest, are bound to get your head bopping. 

Chicago Park District
Chicago Park District

Pack a picnic and head to a public park

You don’t have to go far to enjoy some grassy legroom. Chicago’s public parks encompass 8,800 acres of green space and are the perfect places to stretch out on a blanket or grill out with some friends. Touristy downtown parks like Grant Park and Maggie Daley Park offer magnificent views of the city’s skyline, while Garfield Park and Humboldt Park set inside Chicago's westside neighborhoods are filled with locals playing dominos and practicing yoga. Find more parks at the Chicago Public Park District’s website.

Anita Tijoux
Anita Tijoux

Every Monday and Thursday from June 20 through August 18th, Jay Pritzker Pavilion is hosting a free, yes FREE, music series featuring emerging and established artists from all over the world. Kicking off the series is 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 Gospel Music Festival on June 4, Chicago Blues Festival from June 9 through the 12, and Chicago Jazz Festival from September 1 through 4.

Old Town Merchants and Residents Association
Old Town Merchants and Residents Association

Let loose at a street festival

If there's one thing Chicago is good at, it’s throwing a party. All summer long, street festivals will be popping off, featuring live music, hosting dance classes, and selling beer, food, wine, and artwork. Check out some local and global art at Wells Street Art Festival, 57th Street Art Fair, Bucktown Art Fest, and Old Town Art Fair, grab a partner and learn how to dance at the outdoor Chicago Summer Dance series, and listen to local bands, eat, drink, and party at Mole de Mayo Festival, May Fest, Do Division Street Festival, Lincoln Park Greek Fest, Taste of Chicago, Logan Square Art Festival, and more.

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, and no worries if you’re wheeless—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’s 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.

The Gwen, A Luxury Collection Hotel

Because drinking is always better with a view. Cindy’s Rooftop atop the Chicago Athletic Association is always a great place to enjoy the sips and sights, with tasty food and drinks plus spectacular panoramas of Millennium Park. Chic and lively outpost Cabra offers stellar views of the West Loop, whilst serving up yummy drinks and shareable Peruvian plates, like empanadas and ceviche. If you’re looking for other summertime roofless venues, Celeste is prime for outdoor garden vibes, Lonesome Rose serves up a damn good Margarita, Z Bar is date night 101, and Cerise Rooftop brings the party with regular DJs and events.

Chicago Red Stars
Chicago Red Stars

The Cubs, White Sox, Chicago Fire, and Red Stars are ramping it up for their spring and summer season, and this year, it’s going to be good. 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.

Maplewood Brewery & Distillery
Maplewood Brewery & Distillery

Yeah, we know—every city claims to have a “great beer scene, bro.” Chicago may be the Windy City, but such claims around these parts are far from hot air. We may not be on par with, say, Denver or Portland in terms of breweries per capita, but Chicago’s compelling craft scene continues to expand its ever-growing beer belly with no signs of drying up. From up and coming breweries and brewpubs reinventing themselves to classic beer bars and local scene staples, you won’t have to wander too far to cop a warming stout or hop-heavy IPA on a beautiful summer day.

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. 

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—aka 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.

The Press Room Chicago
The Press Room Chicago

There’s a reason why the speakeasy never goes out of style. Sometimes you just need to hide out in a dark hole and drink cocktails like it’s illegal. Whether or not our own ‘20s turn out to mirror the Roaring ones of yore, Chicago still offers plenty of options to unleash your inner Capone. Here’s our full roundup of local speakeasies and secret bars, since you asked. Shh.

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.

Carlos Yudica/Shutterstock

Park it at a local drive-in (or, gasp, see a movie in an actual theater)

One positive byproduct of this annoyingly resilient pandemic has been the re-emergence of the drive-in theater, with al fresco flicks screening on a regular basis at ChiTown Movies in Pilsen. And if you’re masked and vaxxed, local movie emporiums like the historic Music Box Theatre should never be overlooked. Ever.

Lighthouse ArtSpace Chicago
Lighthouse ArtSpace Chicago

The stateside premier of this international project continues to wow crowds at Chicago’s Germania Club Building with an immersive experience featuring moving images illustrating the works of Vincent Van Gogh. The 600,000-cubic-foot experience includes bright flashing lights set to soundtracks in a historic Gold Coast building. And, ahem, date night packages are available to anyone looking to woo a special art-lover in their lives.

James Andrews1/Shutterstock

The Chicago Lakefront Trail is always a popular choice, but it’s not the only place to ingest some crisp summer air. Did you know the entire Chicagoland area is surrounded by a 210-mile nature trail complete with campsites and lakes? How about a 2.7-mile urban hiking trail along a former railway corridor? How about one of America’s newest national parks, perched just across the border in Indiana? Any more brain busters? Right this way.

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.

City Winery Chicago
City Winery Chicago

Music venues around town have reopened for live events, with heavy hitters City Winery, Carol’s Pub, Martyrs’, Rosa’s, Reggie’s, Green Mill, Montrose Saloon, Uncommon Ground, FitzGerald’s, Kingston Mines, and Empty Bottle leading the charge. So what the hell are you waiting for? If you’re looking for something with a more romantic vibe, check out the Fever’s candlelight concert series to catch classical music in unique outposts like Stan Mansion and Salvage One. Pretty hard to screw up that date night.

Zanies Comedy Club Chicago
Zanies Comedy Club Chicago

If Netflix reruns of The Office aren’t quite as funny as you remember, turn to the experts for your giggle fix. Comedy clubs across the city are doing their best to keep you laughing through America’s somehow-still-not-over pandemic, including live stand-up shows at Zanies and, of course, the world-famous improv-sters at Second City. In the meantime, head over to Lincoln Lodge to bask in the oddball glory of the nation’s longest running independent comedy showcase, recently back from hiatus. For even more options, check out this handy rundown.

The Forge: Lemont Quarries
The Forge: Lemont Quarries

From archer battles, and ax throwing to laser tag and escape rooms, The Forge: Lemont Quarries certainly isn’t lacking when it comes to summer-centric entertainment. If that’s not enough, you can also fill up on cheffy post-adrenaline rush cuisine at Forgefire Adventure Dining. Suddenly, a trip to the ’burbs doesn’t sound like such a terrible idea, after all.

Cruise Chicago’s Emerald Necklace

A scenic drive around the city is never a bad idea, especially now that summer is here. Yes, you could certainly parade down Lake Shore Drive—and by all means, you should. But for a lesser-known option that allows you to see the actual beating heart of the city instead of a few stretches of concrete, head to Chicago’s Emerald Necklace, a 26-mile network of interior city streets and wide boulevards. Linking together some of the city's most grandiose green spaces like Humboldt, Garfield, Washington, and Jackson Parks, this is the way Chicago was meant to be seen—with the added bonus of being excellent quarantine-era therapy.

Dispensary 33
Dispensary 33

Who knew that just a few months after Illinois became the 11th state to legalize recreational marijuana, a full-blown public health emergency would bring our society to its knees? And, furthermore, can you imagine dealing with the past two years without a little green? We don’t even want to think about it, and you don’t have to either. Deemed essential businesses with more than $1 billion in sales in 2020, legal weed is clearly here to stay in Illinois. Check out our full dispensary guide for all the hairy details.

Pizzeria Portofino
Courtesy of Pizzeria Portofino

Chicago’s world-renown pizza bonafides grew even stronger during the pandemic, with a wave of new pie-centric eateries opening up throughout this comfort food-crazed city. Recent-ish headliners include Pizza Friendly Pizza next to Empty Bottle, Pizza Lobo in Logan Square, PB&J in the West Loop, Pizzeria Portofino from Lettuce Entertain You, Pazza Pizza for pizza by-the-slice in Old Town, Detroit-style pies from Five Squared, and new deep-dish entry Ruth’s Panmade Pizza from the folks behind Roots Handmade Pizza, among others. Throw in offerings from Honey Butter and Hot Doug’s at Piece and there’s never been a better time to carbo-load in Chicago.

The University of Chicago, Hyde Park neighborhood | STLJB/Shutterstock

Don’t make a rookie mistake and behave like some bewildered out-of-towner by thinking all of Chicago can be experienced downtown. Sure, the Loop is great and all but, as any self-respecting Chicagoan knows, the real heart of the city lies within its spectacularly diverse 77 neighborhoods. From the laid-back residential enclave of Norwood Park to the historic sights of Bronzeville, there’s always something to discover. Bundle up, snag a mask, and get out there and pound the pavement.

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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