Actually Cool Things to Do in Chicago this Fall

From apple-picking trips to public art crawls, it’s time to get cute.

While summer hogs all the attention with its sun-soaked rooftops and bleary-eyed festivals, fall is quite probably the best time to be alive in the city of Chicago. There’s just something about the crunching leaves underfoot, games of pick-up football in the park, and cool breezes off the lake that makes this season unlike any other. Well, that and a whole truckload of parties and events.

From apple picking and art peeping to weed toking and pizza eating, here’s everything fun you can do in Chicago this fall.

Maplewood Brewery & Distillery
Maplewood Brewery & Distillery

Dive headfirst into Chicago’s booming craft beer scene

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. While we may not be on par with, say, Denver or Portland in terms of breweries per capita, Chicago’s massive 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 crispy cold one on a fine autumn day.

Chicago Thanksgiving Parade
Chicago Thanksgiving Parade

Hit up some of the season’s finest events

Event season certainly isn’t as predictable as it once was, but there are still a few fall classics you can count on. From the annual Halloween spectacle that is Arts in the Dark and the family-friendly Chicago Thanksgiving Parade to the cosplay-drenched C2E2 and the drunk-before-noon TBOX Christmas bar crawl, there’s something for every kind of reveler.

Green Street Smoked Meats
Green Street Smoked Meats

Slather yourself in Chicago’s BBQ scene

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.

Edwards Apple Orchard
Edwards Apple Orchard

Stupidly exclaim “How ‘bout them apples!” at an area orchard

There are few events as fall-centric as apple picking, which is why this is the season to actually make it happen if you’re ever gonna do it. Get out of the city and explore the picturesque surrounding farms in Illinois and Wisconsin for a fresh taste of what the season is all about. Remember, you can always DVR the Bears game. Chart a crunchy course with help from our lowdown.

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

Get lost in a dive bar… maybe even a slashie?

Fancy new rooftop bars are cool and all, but once summer winds down, it’s time for Chicago’s rich civic treasure—AKA dive bars—to really shine (metaphorically, of course.) With cooler air bringing out the shut-ins, it’s time to hole up in your favorite old man bar and drink until next summer (or 4 am). Options are far too many to mention, but no one ever regretted a late-night foray into Old Town Ale House. And if a “slashie” (half bar/half liquor store) is more your liking, may we humbly suggest Rite Liquors?

The Art Institute of Chicago
The Art Institute of Chicago

Visit a Chicago museum and catch sight of superheroes

With Chicago’s 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. But one of Chicago’s most in-demand exhibits continues to be the Museum of Science & Industry’s ongoing Marvel: Universe of SuperHeroes, running now through October 24. 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 guide. Did someone say there’s an entire museum dedicated to leather and bondage? Sure did.

The Press Room Chicago
The Press Room Chicago

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. Here’s our full roundup of local speakeasies and secret bars, since you asked. Shh.

U.S. Forest Service - Shawnee National Forest
U.S. Forest Service - Shawnee National Forest

Embark on a classic fall road trip

While air travel has clearly returned to its pre-pandemic form (with just a touch more rage), 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 check out some amazing fall destinations near Chicago, from laid-back whiskey tastings along the Michigan coast to raucous Big 10 college football stadiums. Looking to stay instate? No problem. Need an Airbnb? We’ve got you covered. Oh, and did someone say fall foliage? Naturally.

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

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 theatres like the historic Music Box Theatre should also not be overlooked. Ever.

Wendella boat
Courtesy of Wendella

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. But that doesn’t mean you still can’t get in on the action in fall. 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. For something a little different, try renting a charming little e-boat departing from Rockwell on the River near Metropolitan Brewing from Chicago Electric Boat Company, running through November 14.

Check out trippy paintings come to life at Immersive Van Gogh

The stateside premier of this international project continues to wow crowds at Chicago’s Germania Club Building for 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. For dessert, peep the Art of Banksy, the world’s largest traveling exhibit devoted to the legendary street artist, open now through Halloween.

Chicago Botanic Garden
Chicago Botanic Garden

Stretch your legs in the great outdoors

The Chicago Lakefront Trail is always a popular choice, but it’s not the only place to greedily ingest some fresh fall 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 peep its jaw-dropping assemblage of vibrant fall foliage. Need more outdoor ideas? Right this way.

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

Support Chicago’s Black Community

Whatever else you do this fall, 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 how to get get started.

Go see some live music (perhaps in a mansion)

Music venues around town have reopened for live events, with heavy hitters City Winery, Carol’s, 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 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 again

If Netflix reruns of The Office aren’t quite as funny as you remember, 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 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
Courtesy of The Forge: Lemont Quarries

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 fall-centric outdoor entertainment. If that’s not enough, you can also fill up on cheffy cuisine paired with scenic views at the Forgefire experience. Suddenly, a trip to the ’burbs isn’t such a terrible idea.

Rogers Park | MarinaP13 / Shutterstock

Go on the ultimate Chicago outdoor mural crawl

One thing the pandemic 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 works turn the neighborhood’s streets and alleys into an outdoor feast for the senses. Trackdown standouts 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 crawl with a trip up 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? 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 installations 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—continues its screenings on the south façade of the Merchandise Mart through November 25.

VIP Paints
VIP Paints

Cruise Chicago’s Emerald Necklace

A scenic drive around the city is never a bad idea, especially now that winter is just around the corner. 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 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 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-era 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 thing, you may not find 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. After you get your fill, amble over to some of the city’s best dive bars, conveniently located a mere stone's throw away.

Dispensary 33
Dispensary 33

Smoke some of Illinois’ most “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-and-a-half 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.

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.

Chef Bill Kim's Pizza & Parm Shop
Courtesy of Chef Bill Kim's Pizza & Parm Shop

Take part in Chicago’s ongoing pizza Renaissance

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. Check out recently opened 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 behind Roots Handmade Pizza. 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.

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