The 50 best things to do in Chicago right now

What is it? One of Chicago's most iconic—and beautiful—parks.

Why go? Millennium Park may be a popular stop for tourists when Chicago's weather warms up, but it should also be on your list of places to visit during peak fall. The 20-plus–acre beauty on the north end of Grant Park is home to elms, hawthorns and maples that show off their colors before winter arrives.

Don't miss: Stroll through Lurie Garden, a 2.5-acre landscape just south of the Pritzker Pavilion's Great Lawn that turns into an autumn-hued prairie come autumn. 

What is it? A full slate of fall-themed events at Lincoln Park Zoo.

Why go? Throughout the monthlong festival, you can snag a photo with a giant pumpkin, watch master carvers at work, enjoy live music and see all kinds of animals. The festival also includes several ticketed experiences such as carousel rides, a bounce house, harvest maze, a slide and more. 

Don't miss: Just outside the zoo's entrance is Alfred Caldwell Lily Pool, an oasis that recently reopened to the public after a two-year closure.

What is it? Avondale, a Northwest Side gem next door to buzzy hipster enclave Logan Square 

Why go? Earlier this year, Time Out named Avondale the fifth coolest neighborhood in the world, and with good reason: Avondale houses an eclectic mix of charming two-flats and bungalows, vibrant street art, repurposed warehouses and lively stretches of Polish and Latin American storefronts.

Don't miss: Choose anything from this itinerary created by an Avondale resident of ten years, and you can't go wrong.

What is it? The Chicago Architecture Center's annual free festival providing behind-the-scenes access to hundreds of typically off-limits buildings throughout the city and suburbs. 

Why go? Open House Chicago will feature approximately 210 locations across 25 Chicago neighborhoods, including more than 30 new additions—check out the full list here. In addition to the open sites, OHC will host more than 40 programs and activations throughout the weekend.

Don't miss: If you’re feeling especially competitive, enter the OHC Photo Competition, during which attendees can submit photos taken at Open House Chicago sites. Selected entrants will have their photography printed and displayed at the Chicago Architecture Center’s November 2025 exhibition “Framed Views: OHC Photography.”

What is it? The breeziest way to survey the city's famed architecture.

Why go? An architectural tour is a must for any visit to Chicago, and the Chicago Architecture Foundation employs certified volunteer docents who narrate the history behind more than 50 downtown buildings for the duration of a 90-minute cruise along the Chicago River.

Don’t miss: An evening version of the tour that allows you to take in the twinkling city lights from the river.

What is it? A 25-story-tall video installation projected on the south side of THE MART.

Why go? ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. Currently on display is City Circle Heart—a collaboration with local nonprofit Arts of Life, which is celebrating 25 years of supporting artists with intellectual and developmental disabilities.

Don't miss: Pregame the night's projections with a stop at Island Party Hut's Fall Fest on The Riverwalk.

What is it? An acclaimed Italian restaurant helmed by Carbone-trained chef Matt Eckfeld.

Why go? A highly anticipated venture from Cornerstone Restaurant Group (Urbanbelly, Michael Jordan’s Steakhouse), Dimmi Dimmi offers Italian-American fare from a Chicago perspective in its intimate Lincoln Park digs. 

Don't miss: Believe the hype around Dimmi Dimmi's mozzarella sticks—dunked in a healthy amount of sauce, each bite is followed by a tiny cascade of bread crumbs. 

What is it? Night of 1,000 Jack-o’-Lanterns, the Chicago Botanic Garden's annual spooky season celebration.

Why go? The event brings together more than 1,000 real pumpkins—some weighing up to 150 pounds—which are LED-lit and staged along the garden's pathway where other entertaining characters and activations await visitors.

Don't miss: The pumpkin-lined route features live gourd carving demonstrations, costumed entertainers and seasonal bites and beverages available for purchase.

What is it? Nearby destinations full of autumn festivities.

Why go? Nothing says fall like a pumpkin patch, where you pick out your own gourd, go on a hayride and play with animals in a petting zoo. 

Don't miss: If you’re looking for even more seasonal activities, make a whole day out of it by checking out the best places to see fall foliage outside of Chicago.

What is it? The city’s lush green spaces, from Chicago parks to sprawling botanical gardens.

Why go? Get away from the bustle of the city and reconnect with nature by visiting one of these (mostly) free gardens. You’ll find stunning Japanese gardens, serene lily ponds, rose gardens, conservatories filled with thousands of plants, and much more.

Don't miss: If you're looking for some under-the-radar destinations, check out one of Chicago's many secret parks and gardens.

What is it? A European-style vintage market curated by the folks behind the wildly popular Randolph Street Market.

Why go? Look as chic as your fashion icons, but at a better price. From the folks behind the Randolph Street Market, this one-day pop-up showcases a curated collection of apparel, home decor, furniture and more. Style mavens can shop vintage wares spanning eras and price points by high-end designers such as Chanel, Pucci and Hermès. 

Don't miss: After you're done racking up thrift scores, stroll along Ravenswood Avenue—otherwise known as “Malt Row”—for a boozy libation.

What is it? Terrifying immersive attractions filled with monsters, clowns and other terrors that go bump in the night.

Why go? If you love to be scared, there’s no better time than fall. Plan a trip to the top haunted houses around Chicago and steel your nerves as grotesque horrors await in every room and dark corner. 

Don’t miss: Certain dates offer special experiences, like blackout nights or nights of isolation (i.e., no actors are present).

What is it? An annual Halloween parade routed through in Chicago's landmark LGBTQ Northalsted neighborhood.

Why go? You'll find drag queens, kids, parents and pets marching in this procession, which typically features impressive group costumes and dancers performing all the moves to Michael Jackson's "Thriller."

Don't miss: Stick around after the parade wraps up—an awards show commences at Halsted and Brompton at 8:30pm.

What is it? A museum dedicated to astronomy and all things outer space.

Why go? You'll escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. The Doane Observatory is also home to the largest public telescope in the area, and gathers 7,000 times more light than the human eye.

Don't miss: Make the most out of your trek down to Museum Campus by visiting the Adler's neighbors: the Field Museum and Shedd Aquarium. 

What is it? Kayak Chicago sends you paddling along the Chicago River from a dock located just north of Goose Island.

Why go? After a few quick lessons, you'll be ready to set out on a self-guided river tour in a kayak. You can rent your boat by the hour or pay a flat fee to take it out for the entire day and check out changing leaves along the water.

Don't miss: A handful of guided excursions that highlight Chicago architecture or simply allow you to navigate the river at night.

What is it? Plucking fruit straight from the source.

Why go? With over 10 nearby apple orchards to choose from, there's no shortage of day trip and quick picking opportunities this fall. If you're craving caramel apples and a good maze, visit All Seasons Orchard. For a wealth of activities—like a petting zoo and corn maze—to go with your apple-picking adventure, hop over to Indiana's County Line Orchard.

Don't miss: Enjoy a variety of fall activities—like corn mazes, haunted houses, and drive-in movies—featured in our Fall 2025 Things to Do guide.

What is it? Every year, Chicago's trees burst into stunning shades of yellow, orange and crimson as fall descends upon the city for a few short weeks. 

Why go? You'll see fall foliage whether you're looking for it or not—with trees scattered throughout the city, it's pretty hard to miss—but we prefer checking out some tried-and-true spots for maximizing gorgeous views. And between graceful weeping willows in Graceland Cemetery's arboretum, dense forest preserves and fiery red Japanese maples at the Chicago Botanic Garden, you're not short on options. 

Don't miss: Peak fall color, thanks to this useful map that predicts when local foliage will achieve maximum splendor. 

What is it? A world-renowned orchestra.

Why go? Considered one of the leading orchestras in the United States, the CSO plays a variety of enthralling music and hosts touring soloists and small ensembles as well. During fall to spring, Symphony Center is home to the CSO. 

Don't miss: Watch your favorite flicks like never before—with a spellbinding live score—during the “CSO at the Movies” series.

What is it? A weekly 75-minute yoga class held in the Judy Istock Butterfly Haven, a greenhouse brimming with tropical plants and over 75 species of exotic butterflies and stunning birds.

Why go? Experience nature like never before with a beginner-friendly yoga class in one of Chicago's hidden gems. Find your flow surrounded by over a thousand butterflies and birds flying around (and sometimes on) you. After class, wander through lush flora and tropical trees that will make Chicago feel half a world away—if only for a little while.

Don't miss: Stick around until 2pm for the museum's daily “First Flight Butterfly Release.” 

What is it? The Newberry Library, founded in 1887, is an independent research library located right in the heart of the Gold Coast.

Why go? From illuminated medieval manuscripts to the personal papers of local authors, the Newberry is home to an impressive collection of work that is free to access. The library hosts exhibitions, theatrical performances, lectures, seminars, workshops and more. 

Don't miss: Sign up for a free tour of the Newberry's current exhibition, “Winging It: A Brief History of Humanity’s Relationship with Birds,” which chronicles avian history through a cultural lens.

What is it? Intricately designed labyrinths set in large fields.

Why go? Whether it’s themed after Jurassic Park or Super Mario Bros., a corn maze offers excitement for both children and adults alike. Wander through acres of corn stalks, with mystery awaiting around every turn. 

Don't miss: If you're hoping to dial up the spookiness, check out Heap’s Haunted Corn Maze—a nighttime-only walkthrough dotted with ghouls and goblins whose only goal is to scare the living daylights out of you.

What is it? A formerly abandoned stretch of elevated railway track named after the first three digits in every Chicago zip code. 

Why go? Looking for a convenient way to get between Logan Square, Humboldt Park, Wicker Park and Bucktown? This is it. The 2.7-mile path was spruced up by the city and turned into a functional attraction that delights locals and visitors.

Don’t miss: Local artist Jeff Zimmermann's colorful Conagra Mural (Urbs in Horto) just across the Milwaukee Avenue bridge, which acknowledges Chicago's agricultural legacy.

What is it? What people think of when they hear “Chicago theater.”

Why go? Steppenwolf is known for its all-star collection of ensemble talent (folks like Laurie Metcalf, John Malkovich, Carrie Coon and Tracy Letts number among its ranks).

Don't miss: Mr. Wolf, gut-wrenching story about a 15-year-old's return to her family of origin after being kidnapped as a child.

What is it? A bright and airy brewery specializing in saison-style beers.

Why go? Since staking their claim on Ravenswood’s flourishing “Malt Row,” Is/Was Brewing has emerged as an authority on saison-style beers. Their success has echoed far beyond Chicago, too—recently being crowned one of the top saison producers in the world by Craft Beer & Brewing.

Don't miss: Weekly Trivia Tuesdays with QuizzDaddy Trivia and Bingo Thursdays.

What is it? Expanded and updated in 2015, this riverside walkway hosts restaurants, bars, boating docks and plenty of spots to sit and admire the views.

Why go? Like everything else downtown, the Riverwalk can be pricey, but you can't beat the views when you snag a glass of vino at City Winery or enjoy some local grub at Chicago Brewhouse. Several boat tour also have launch points along the Riverwalk, if you prefer to get out on the water.

Don't miss: Post up at the Riverwalk nightly at 8:30pm and 9pm to catch Art on theMART, the 25-story light projection show across the water.

What is it? An 18-hole miniature golf course located in Maggie Daley Park.

Why go? There's a kitschy kind of charm to mini-golfing in the shadow of the Chicago skyline, especially since the course is decorated with replicas of famous Chicago attractions (like a six-foot-tall Willis Tower and a teeny version of the Picasso sculpture in Daley Plaza). 

Don’t miss: Snapping a photo next to the mini Chicago landmark of your choice.

What is it? A storied 5am dive with a killer jazz jukebox, no-nonsense attitude and the most conversation-inducing bar art in the city.

Why go? Knock back stiff drinks with a gloriously diverse cast of characters from grizzled old timers to tourists from nearby Second City at this late-night watering hole. It’s a favorite of many cultural icons, from the late Anthony Bourdain and actor Michael Shannon (he watched the Oscars here in 2018) to Chicago film critic Roger Ebert—and should be a fave of yours, too.

Don’t miss: The bar is decked out with nudie paintings of famous politicians like Sarah Palin and Rod Blagojevich by Bruce Elliott, the establishment’s longtime owner.

What is it? Home to pro basketball and hockey, as well as big-ticket pop acts. 

Why go? You can't see Michael Jordan play at the United Center anymore (though you can get a picture in front of his statue in the venue's public atrium), but this West Side arena still hosts plenty of stars. During basketball and hockey season, the venue serves as home turf for the Bulls and the Blackhawks—two of the city's biggest pro sports teams. It's also a destination for major pop and rock concerts, including acts like U2, Drake and Madonna.

Don’t miss: The arena has partnered with local restaurants like Honey Butter Fried Chicken and Lillie’s Q to provide dishes and drinks that handily outclass typical stadium fare.   

What is it? A pinball palace located in the Salt Shed's former boiler room (owned by none other than Jim Zespy of Logan Arcade).

Why go? Housing over 100 games, 8-bit purists, pinball wizards and casual gamers will all find fun ways to collect virtual prize tickets, which can be redeemed at a fully-stocked prize shop. Billed as an all-ages space by day and adult-centric playground—complete with jello shots—by night, there's something for everyone at Elston Electric.

Don't miss: Regular Pinball League Nights, where groups of four duke it out for concert tickets, game cards and more.

What is it? Guarded by an iconic pair of bronze lions, the Art Institute of Chicago houses a permanent collection of more than 300,000 artworks. 

Why go? The Art Institute of Chicago is filled with masterpieces from every era, from Georges Seurat’s iconic painting A Sunday on La Grande Jatte (notable for its appearance in Ferris Bueller’s Day Off) to Andy Warhol's print of actress Elizabeth Taylor. 

Don’t miss: Catch the new exhibit Gustave Caillebotte: Painting His World, which features a body of work by a titan of the Impressionist movement.

What is it? A gorgeous glass structure home to more than 100,000 plants. 

Why go? When temps start to dip, there are few better places in Chicago to escape the cold than Garfield Park Conservatory, where you can wander through eight indoor display gardens full of greenery. Marvel at towering tropical plants in the 65-foot Palm House, admire cacti in the Desert House and imagine the primordial settings of Illinois millions of years ago among the lush Fern Room.   

Don't miss: Swing by Horticulture Hall from Friday through Sunday for a lavender oat milk cold brew made by Monday Coffee Co., the conservatory's resident coffee pop-up.

What is it? Where Bill Murray, Tina Fey, Gilda Radner, Chris Farley and Steve Carell cut their comedic teeth. 

Why go? Before they joined the cast of Saturday Night Live or became big-screen stars, those folks above practiced their craft on the mainstage at the Second City. The venue's premiere revue features some of the institution's most talented performers in a series of loosely-connected, topical comedy sketches.

Don't miss: Itching to take the stage yourself? Sign up for a class at the Second City Training Center.

What is it? One of the last free zoos in the country, this 35-acre attraction connects visitors with animals from all over the world.

Why go? More than 1,000 critters are waiting for you to visit them—free of charge—in Lincoln Park. From mammals (beavers, lions, otters and bears) to birds (penguins, eagles and parrots) to reptiles (snakes, crocodiles and turtles), there's something for every animal lover. 

Don’t miss: The expansive Regenstein Macaque Forest, where snow monkeys swing from branch to branch. 

What is it? The observation deck on the 103rd floor of the third tallest building in the U.S. 

Why go? If you're looking to see more of Chicago than you'd be able to take in on a walking tour, the Skydeck is your best bet. On a clear day, you can see up to four states and 50 miles out. The Skydeck's main attraction, The Ledge, features glass boxes hanging out over the building, offering a thrilling experience and even better views from 1,353 feet off the ground. 

Don't miss: Pie in the Sky, the Skydeck's dining experience that includes a three-course meal catered by Giordano's.

What is it? Hiking trails around Chicagoland.

Why go? Now that it's warm out, it's the perfect time to go hiking. Visit a state park or nature preserve for an adventurous escape from the city. These sprawling, winding paths will take you through historic sites, sand dunes, woodlands and much more.

Don't miss: Try your luck at spotting roaming buffalo at Buffalo Rock State Park—just a two-hour drive from Chicago.

What is it? An ace place to lose it to house music, right in the city that invented the genre. 

Why go? In the ’80s, Chicago served as the epicenter of the creation of a new sound that still influences the work of modern hip-hop and electronic artists. If you want to experience house music, there's no more authentic environment than Smart Bar. Within the subterranean Wrigleyville club, skilled DJs, drag performers and sweaty revelers come together to the steady pulse of a house beat.

Don’t miss: The crowded Queen! dance party, which takes place nearly every Sunday night.

What is it? Designed by activist and artist Yoko Ono, Skylanding is composed of 12 large steel lotus petals jutting from the ground of the Garden of the Phoenix in Jackson Park.

Why go? Calling all public-art fanatics. This gleaming installation from the famed artist has become a major draw in the 600-acre park. The photogenic sculpture was erected as a symbol of peace, taking up residence on the site of a pavilion built by the Japanese government for the 1893 World’s Columbian Exposition.  

Don’t miss: The park is also home to a beautiful, traditional Japanese respite dubbed the Garden of the Phoenix. 

What is it? An Uptown institution that books smart bebop and free jazz with a discriminating ear. 

Why go? In the ’20s, Chicago gangsters like Al Capone were known to frequent the Green Mill, but ever since Prohibition, the club has garnered a reputation for hosting live jazz every night. 

Don’t miss: Taking a picture under the glittering marquee, which wasn't actually destroyed in Michael Mann's 1981 neo-noir film Thief. 

What is it? A ’40-era drive-in that still sends uniformed servers to your car, delivering hot dogs, burgers, milkshakes and more fast food delights—recently dubbed the best hot dog stand in Chicago by Time Out.

Why go? As its name suggests, Superdawg specializes in Chicago-style hot dogs, which add piccalilli and a pickled green tomato to the usual array of toppings. Every super dish comes in a cute box (usually on a bed of crisp French fries) and can be ordered from your car or at a walk-up window.

Don't miss: Try the Superonionchips instead of the Superfries—they're like onion rings, but better.

What is it? A string of art galleries located on Chicago Avenue between Ashland Avenue and Wood Street. 

Why go? A combination of favorable real estate, happenstance and collaborative spirit has drawn some of Chicago's finest galleries—including Matthew Rachman Gallery, DOCUMENT, Rhona Hoffman, Chicago Truborn and many others—to this multi-block stretch in West Town, creating a concentrated (and not to mention, free) tour of curated work. Plan an afternoon around the exhibitions that pique your interest, and don't forget to make a reservation at each gallery ahead of time. 

Don’t miss: Looking to splurge on, say, a mid-century Danish sofa or a luxury cowhide rug? Make an appointment at Matthew Rachman Gallery to view the furniture collection available for sale, where you'll find items from iconic designers like Vladimir Kagan, Jens Risom and Eero Saarinen.  

What is it? A Wicker Park destination for discerning record nerds.

Why go? The "dusty grooves" of course refer to the wonderous global rhythms found in the smartly curated bins, sorted into Tropicalia, Afrobeat, reggae, vintage soul, French pop, blues, jazz and other genres. 

Don’t miss: Obscure titles that you'll have a hard time finding elsewhere in the city.

What is it? Leaf peeping season in full swing.

Why go? There are plenty of leafy parks and preserves where you can spot fall foliage in Chicago when the weather becomes crisp. But when you’re eager for a weekend escape, you’ll find expansive national forests, steep trails and scenic drives that immerse you in the season’s changing colors.

Don't miss: Use this handy interactive map to help you plan your leaf peeping expedition around the season's peak colors. 

What is it? A neighborhood that serves as one of the primary hubs of Chicago's Chinese community, filled with restaurants, shops and incredible nods to East Asian architecture.

Why go? Chinatown is a great place to mosey from shop to shop and spend some time outdoors, whether you're walking through Chinatown Square or admiring the sweeping skyline views from Ping Tom Memorial Park. 

Don't miss: Dumplings from QYX, bubble tea from the walk-up window at Joy Yee, Peking duck from BBQ King House, cocktails at Nine Bar... the list goes on. Start at Chinatown Square and work your way south down Wentworth, passing under the street's famous gate and into its central commercial strip.

What is it? One of the best places to sit on a rock and look at tall buildings from afar.

Why go? Just north of the Museum of Science and Industry, this man-made peninsula is a short jaunt from the Lakefront Trail. When the sun is out, it's a beloved spot for picnics, lounging and canoodling on the rock steps that line the perimeter of the point.

Don’t miss: The Promontory Point Field House, an extremely popular wedding venue that looks like a miniature castle.

What is it? This smoke shack was born when the steel industry was thriving and the area was populated by hungry day laborers.

Why go? Located near a bridge featured in The Blues Brothers just west of the Indiana border, Calumet Fisheries slings smoked shrimp, trout, sable and more. There's no seating inside, so you'll need to take your paper bag full of seafood outside, where you can find a spot along the bridge to chow down or just eat it inside your car. 

Don’t miss: Don't forget to get some crackers and coleslaw to pair with your expertly smoked fish.

What is it? A collection of murals and street art on an old railroad embankment in Pilsen that stretches from the Chicago River to Western Avenue.

Why go? Take a stroll across 16th Street and you'll spot murals by local artists like JC Rivera and Hebru Brantley as well as international talents like The Yok and Sheryo.

Don't miss: An infamous painting of a severed possum by Belgian street artist ROA, located just west of 16th and Laflin Street.

What is it? A nearly 200-foot-high Ferris wheel.

Why go? You won't find many sights that can rival the ones from Centennial Wheel. Riders are treated to 360-degree views of the skyline and Lake Michigan while sitting in enclosed, climate-controlled gondolas.

Don't miss: After your ride, head to the Original Rainbow Cone at Navy Pier for a tasty sweet treat.

What is it? A love letter to all things magic hidden behind what appears to be a laundromat.

Why go? After three years of performances at Uptown Underground, the Chicago Magic Lounge’s brick-and-mortar manifestation opened in early 2018. The spot sports three performance spaces. There’s the front bar, where you can enjoy a drink and some sleight-of-hand. Then there’s the 120-seat Blackstone Cabaret mainstage, where ticketed shows take place, as well as a smaller back room, dubbed the 654 Club, offers up-close magic.

Don’t miss: While enjoying your cocktail in the bar, check out the magician’s table built into the center of the bar itself. 

What is it? Exactly what it sounds like—a terrible portrait drawn by local artist Jacob Ryan Reno.

Why go? Reno has gone viral for his $5 terrible portraits, drawn in “five terrible minutes.” Every Sunday, Reno camps out at the Logan Square Farmers Market along the 606 trail—equipped with a meager folding table, a sketchbook and a box of markers. The caricatures he creates aren't just a much-needed dose of levity—they're also a beacon of authenticity in an optimization-obsessed world.

Don't miss: Of course, don't pass up strolling through the Logan Square Farmer's Market, where you can buy anything from locally grown veggies to thrifted clothing.