Actually Cool Things to Do in Chicago this Summer

Summertime sadness? Not this year.

Summer in Chicago is always looked upon with a fever pitch of anticipation. It’s no secret that Chicagoans are always ready for summer, but this year, we’re really, really, really ready for summer. From beach bars, rooftops, and patios to museums, boats, and music venues, here’s your guide to packing two years worth of warm weather debauchery into a single three-month span. Here’s everything fun you can get into in Chicago this summer. Get after it, but keep the mask on as needed—this thing ain’t over yet.

Hit up Chicago’s glorious beach bars, rooftops, and patios

Make up for lost time after having missed last year’s beach season by hitting up each and every one of the city’s top sandy shores this summer. What could be better than listening to the crashing waves while staring at skyscrapers above? Doing so with a cocktail in hand, of course. Get the job done by paying a visit to the civic treasures that are Chicago’s beach bars, and you may as well hit a rooftop bar while you’re at it. If patios are what you seek, it’s high time to explore the new Parson’s locations in Lincoln Park and West Town (or pay homage to the OG in Logan Square). No matter how you slice it, you’ve got options.

Catch a concert on the lawn at Ravinia

As everyone who has lived through the past year can attest, summer just isn’t summer without a show at Ravinia. Thankfully, outdoor concerts will be gracing the legendary Highland Park stage once again from early July through late September. The schedule is still TBD, but it doesn’t really matter all that much who you’re coming to see, now does it? Just smuggle some of your favorite hooch onto the Metra, grab a spot on the lush lawn, and take it all in. Summer is back, baby.

Check out the city’s newest hotspots

Chicago’s dining scene is always evolving, and not even a pandemic can stop cool new joints from popping up all over the city. Peep the newest offering from Bridgeport brewing overlords Marz at Bucktown’s Life on Marz Community Club and get amped for the upcoming opening of chic new apres ski-inspired farm-to-table restaurant Chalet in the former Farmhouse space in River North. While not exactly “new,” recently unveiled Pilsen Yards continues to keep its game tight and live music fans can choose between a pair of hot new venues: Golden Dagger, stashed in the former Tonic Room space in Lincoln Park, and mind-bogglingly epic Epiphany Center for the Arts, located in a stunningly gorgeous renovated church.


Whether it’s more hours of sunlight or the sight of new budding greenery, there’s just something about spring that makes you want to get back out there. With allergy relief from ZYRTEC®, your allergies don’t have to get in the way of your plans, either. ZYRTEC® starts working at hour one, and works twice as hard when you take it the next day, so whether you’re planning on biking a city park or escaping to a nearby trail, you’ll be ready for wherever the season takes you.  
© J&JCI 2021

Visit a Chicago museum & see some superheroes

With most of Chicago’s museums back in operation, there’s no shortage of reasons to go full Ferris Bueller ogling the Monets at the Art Institute or spend some time hanging out with Sue at the Field Museum. But one of Chicago’s most in-demand exhibits this summer is the Museum of Science & Industry’s new Marvel: Universe of SuperHeroes, running now through October. With more than 300 artifacts including costumes, comics, and interactive displays, this 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 rundown. Did someone say there’s an entire museum dedicated to leather and bondage? Sure did.

Pay a visit to a speakeasy—all the cool kids are doing it

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 at stylish new outposts like Dead Plants at Press Room and Grand Cabaret After Dark at Porkchop. Here’s our full roundup of local speakeasies and secret bars, since you asked. Shh.

Embark on a classic summer road trip

While air travel is finally starting to return to its pre-pandemic form, it’s clear that the Great American road trip is continuing to make quite the comeback. Luckily, you don’t have to travel too far to check out some amazing destinations near Chicago, from idyllic mainstays like Lake Geneva to new favorites like Elkhart Lake. Looking to stay in Illinois? No problem. Need an Airbnb? We’ve got you covered.

Eat in the street during Dine Out Broadway

Last year’s pandemic-fueled Dine Out Broadway was so successful that it’s being brought back for a second season, running two weekends per month from May through September. Dig into seasonal bests from 25+ local purveyors along Broadway from Belmont to Wellington, with additional restaurants on Sheffield north of Broadway. 

Attend a summer music festival… maybe?

While most of Chicago’s big-name music festivals including Lollapalooza and Pitchfork Music Festival have yet to cement 2021 dates, a few festivals have been so bold as to put their 2021 dates in ink. North Coast Music Festival has been scheduled for Labor Day weekend, followed by Riot Fest September 17 through 19. Both festivals fully acknowledge the significant chance that the events might not actually go down as planned, but it never hurts to think positive, eh?

Watch the fireworks from the newly reopened Navy Pier

We know, we know. We’ve been known to make fun of Navy Pier as much as anyone else, but after the year we’ve had, seeing the weekly Saturday night summer fireworks show return to Navy Pier feels like a much-needed push toward normalcy. That, and tourists from Iowa wearing fanny packs and cell phone clips swarming the pretzel stand.

Celebrate Chicago Pride, eat BBQ in a parking lot, and see Jeff Tweedy at the drive-in

While most Chicago street festivals are maintaining a “wait and see” approach, Pride in the Park has been officially scheduled for June 26 to 27 and it seems nothing can stop this party. Additional large-scale events on the books thus far include Windy City Smokeout, slated for July 8 through 11 in the United Center parking lot,and Jeff Tweedy at SeatGeek Stadium's drive-in, currently scheduled for June 4. Finger’s crossed.

Stroll State Street (free from traffic) during Sundays on State

This summer, the Sundays on State series will close State Street to traffic from Lake to Madison to allow pedestrians to safely promenade down the iconic thoroughfare the way it was meant to be, er, promindaded down. Happening every Sunday starting July 11, the Chicago Loop Alliance promises “plenty of surprises” at this free “interactive block party.” Consider us psyched.

Hit a local drive-in (or see a movie in the park)

One positive byproduct of the pandemic has been the re-emergence of the drive-in theater, with drive-in flicks being shown on a regular basis at ChiTown Movies in Pilsen. In the meantime, local movie theatres like the historic Music Box Theatre have also started to reopen in recent weeks, so be sure to check their websites for the latest information. And in other most welcome news, you can catch a screening in any one of 100 city parks starting July 6—the Chicago Park District’s Night Out in the Parks program has officially announced it will be returning for 2021.

Get on a boat

If there’s one summer rite of passage in Chicago on par with passing out in a field at Lollapalooza, it’s boating season. Grab a few buds and set sail along the Chicago River or Lake Michigan with a drink in hand for an instant reminder as to why Chicago is the greatest city in the world. Wendella and Shoreline are always popular choices, but you can also check out our full listing of boozy cruises here. Touristy? Yes. One of the best things you’ll do all year? Also, yes.

Check out trippy paintings come to life at Immersive Van Gogh

The US premier of this international project lands in Chicago’s Germania Club Building for an immersive experience featuring moving images illustrating the works of Vincent Van Gogh now through September 6. The 600,000-cubic-foot experience includes bright flashing lights set to soundtracks in a historic Gold Coast building.

Get lost in some local nature

The Chicago Lakefront Trail is always a popular choice, but it’s not the only place to grab some beautiful summer day fresh air. Did you know the entire Chicago metro 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 just across the Indiana border? Also be sure to stop by Morton Arboretum to see their new Human+Nature outdoor art exhibition or wander amidst the seasonal blooms during “It’s Showtime” at the Chicago Botanic Garden. Need more outdoor ideas? Right this way.

Support Chicago’s Black Community

Whatever else you do this summer, be sure to continue to do your part in making the community we live in a better place for all its residents. 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 our guide to doing just that.

Go see some live music (maybe in a mansion)

Most of the music venues around town have recently reopened for live events including City WineryCarol’sMartyrs’, Rosa’sReggie’sGreen MillMontrose SaloonUncommon GroundFitzGerald’sKingston Mines, and GMan Tavern. What are you waiting for? If you’re looking for something with a more romantic vibe, check out the candlelight concert series from Fever and catch classical music in unique outposts like Stan Mansion and Salvage One. Pretty hard to screw up that date night.

Remember how to laugh

If Netflix reruns of The Office aren’t quite as funny as you remember them, you might need to turn to the experts for your comedy fix. Comedy clubs across the city are doing their best to keep you laughing through America’s still-not-over pandemic, including live stand-up shows at the recently reopened Zanies. 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.

Swing from the trees at North America’s largest aerial adventure course

From outdoor adventure courses and trail-running to laser tag and escape rooms, The Forge: Lemont Quarries certainly isn’t lacking when it comes to the world of outdoor entertainment. If that’s not enough, you can also fill up on cheffy cuisine paired with scenic views at the Forgefire experience. What more do you need?

Go on the ultimate Chicago outdoor mural crawl

One thing Covid can’t stop is the city’s thriving street art scene, which can best be enjoyed IRL via an urban mural crawl. Start your excursion in Pilsen, where dozens of vibrant murals turn the neighborhood’s streets and alleys into an outdoor feast for the senses. Check out standout options like the Hector Duarte Studio at 1900 W. Cullerton before making your way to Logan Square to marvel at the famous Robin Williams mural outside Concord Music Hall and the nearby “Greetings From Chicago” mural at 2226 N. Milwaukee. Finish the mural crawl with a trip to Rogers Park, where you can see a mile-long stretch of wall art along the Red Line path as well as the brightly colored seawall of murals off the lake at Tobey Prinz Beach Park.

Check out the public art downtown 

Looking to get out of the house and stretch your legs a bit? Yes, you can go see The Bean, but don’t stop there. Swing by the Chicago Picasso, or Calder’s Flamingo, then head down to the southern end of Grant Park to walk among the giant, headless sculptures that make up Agora. Take a selfie with the Art Institute lions, and be sure to check out the new People in Your Neighborhood installation along the Chicago Riverwalk between Lake and Franklin. The concentration of world-class public art downtown is astounding and not to be missed. And, even better, Art on theMART—the world’s largest permanent digital art installation—has recently returned to the south façade of the Merchandise Mart.

Cruise Chicago’s Emerald Necklace

A scenic drive around the city is never a bad idea, especially now that winter is in the rear-view. Yes, you could certainly cruise 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 just highway, seek out Chicago’s Emerald Necklace, a 26-mile network of interior city streets and wide boulevards. Linking together some of the city's most grandiose parks 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 therapy.

Make a mental health pilgrimage to the Shit Fountain

If you’re in the Ukrainian Village area and looking to do the whole public art crawl thing, you may not have as dense of a concentration of murals as Pilsen or as many fine art sculptures as downtown. But you have one thing those other places can’t touch: the one and only Shit Fountain. The human feces-shaped sculpture is located on a residential front lawn just off Augusta and Wolcott, created by a Chicagoan fed up with dog poop. Cheers.

Smoke some of Illinois’ “essential” legal green

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 year 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 last year, legal weed is clearly here to stay in Illinois. Check out our full dispensary rundown for details.

Listen to a local podcast

If the sheer number of choices between new streaming services has left you overwhelmed, it might be time to catch up on that podcast you’ve always been meaning to listen to. Luckily, Chicago is rife with an array of interesting options. Get your politics fix with David Alexrod’s The Axe Files, nerd out on music with Greg Kot and Jim DeRogatis on Sound Opinions, learn about unique aspects of local city life with WBEZ’s Curious City, drink virtual beer while exploring the brewing industry with Good Beer Hunting, or give Hollywood a lesson or two via Chicago-based Please Make This. And that’s barely scratching the surface.

Take part in Chicago’s ongoing pizza Renaissance

Chicago’s world-renown bona fides in the department of pizza got even stronger during the pandemic, with a wave of new pizza-centric eateries opening up in a comfort food-craving city. Check out recently opened pizza hotspots like Pizza Friendly Pizza next to Empty Bottle, Pizza Lobo in Logan Square, PB&J in the West Loop, Bill’s Original Tavern Pizza and B Square Pizza from Lettuce Entertain You, Pazza Pizza for pizza by-the-slice in Old Town, Detroit-style pies from Chef Bill Kim’s Pizza & Parm Shop, and new deep dish entry Ruth’s Panmade Pizza from the folks at Roots Handmade Pizza. Throw in new offerings from Honey Butter and Hot Doug’s at Piece and never has there been a better time to be a pizza fanatic in Chicago.

Discover a new cool neighborhood

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. Get out there and pound the pavement.

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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
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