The 50 best things to do in Chicago right now

What is it? A free 45-minute walking tour in the heart of downtown that happens on the first and third Saturdays of each month.

Why go? Experience the wealth of public art decorating the city through the eyes of an expert. Each tour is led by a docent and covers a half-mile, beginning outside the Chicago Cultural Center and ending in Millennium Park. Throughout the tour, the docent offers context about each piece and its artist.

Don't miss: Before you embark on the tour, browse the wares at Buddy, the Chicago Cultural Center's hyper-local gift shop. 

What is it? Home of the Chicago White Sox, formerly (and, to some, currently) known as Comiskey Park.  

Why go? Okay, so the South Side team doesn't command the rabid following of its neighbors to the north (although the whole city went nuts when it clinched the World Series in 2005). But the stadium is much more spacious than Wrigley, and it's almost always possible to walk up and purchase tickets.

Don’t miss: You can get a corned beef sandwich and an Impossible dog, or satisfy your sweet tooth with a campfire milkshake.

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. 

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

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 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? 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 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? 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? 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: Don't miss Windfall, the world premiere of a new work by ensemble member Tarell Alvin McCraney that's receiving rave reviews.

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, one of the establishment’s most famous patrons.

What is it? The sweetest spot for indulging your sweet tooth.

Why go? This iconic far South Side shop, immediately recognizable by its bright pink exterior, has been making ice cream-ordering decisions easy since 1926 thanks to their namesake Rainbow Cone. The classic sugar cone is topped with colorful layers of chocolate, strawberry, Palmer House (New York vanilla with cherries and walnuts), pistachio and orange sherbet ice cream.

Don’t miss: If you’re still in need of another sugar rush, know that Rainbow also makes cakes, sundaes and shakes. 

What is it? A beloved annual music series that brings both emerging and well-established performers to Pritzker Pavilion twice a week from July through early-August. 

Why go? Who doesn't like a free concert? Grab a blanket and settle in for a balmy summer evening of music, whether you want to discover new artists or catch a performance from a genuine juggernaut (more on that below). 

Don’t miss: Grab post-show drinks at the nearby cocktail bar Cindy's, one of our favorite rooftop bars in the city.

What is it? The annual slate of summer festivals that take over Chicago streets and parks every year. 

Why go? Shop artisan goods made by local vendors, enjoy delicious bites and watch live performances at beloved neighborhood bashes like Wicker Park Fest and Taste of Randolph from May through September.

Don't miss: Bored of the cover bands and DJs that normally perform at Chicago’s street fests? Head to Ravenswood on August 22–23 for Thirsty Ears Festival, the city's only classical music festival.

What is it? Chicago's premiere arthouse theater. 

Why go? Aside from being one of the 50 most beautiful cinemas in the world, the Music Box's screens one of the best assortments of arthouse films, documentaries and foreign language pictures in the city. And if you prefer to turn your living room into a theater, Music Box Direct allows you to stream movies at home.

Don't miss: Performances on the theatre organ, which is played during weekend intermissions, monthly silent film screenings and other special presentations. 

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? The Balloon Museum's sprawling, interactive exhibition of 19 massive balloon-based artworks.

Why go? With soundstage-sized pieces like horned sculptures emitting soap bubbles, inflated spheres bedecked in abstract squiggles and surreal faceless figures hovering in space, “EmotionAir” reimagines the humble balloon as any other artistic medium—a conduit for creativity and emotion.

Don't miss: The "ball pit" zone featured in season three of Emily in Paris. 

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? The most romantic things to do Chicago.

Why go? February is the month of love, and we’ve got plenty of ways for you to show your affection. Treat you and your significant other to a luxurious spa treatment, book a table at one of the most romantic restaurants in Chicago or plan the perfect date night.

Don't miss: Looking for love? We’ve got you covered with the best places to meet singles.

What is it? Free outdoor fitness classes at Millennium Park's Great Lawn and Wrigley Square.

Why go? Work up a sweat without spending a dime! Every summer Saturday, the city hosts a series of 45-minute workouts including pilates, yoga and Zumba. Arrive early to enjoy tunes from sound healer Mecca Perry, folk guitarist Bill MacKay, and more.

Don't miss: Swing by Double Clutch Plaza (located just below Cloud Gate) with a workout mat for a complimentary mimosa with the purchase of an entrée.

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? 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? 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: ZooLights, an annual holiday display that strings up millions of LED blubs throughout the zoo.

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? 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? A historic house that Wright himself called "the cornerstone of modern architecture." 

Why go? Nearby Oak Park may be a mecca for Frank Lloyd Wright enthusiasts, but you can see some of the architect's finest work without leaving the city. The Robie House in Hyde Park exemplifies Wright's signature Prairie School style, both in its external appearance and interior design. You can take a peek inside the historic home (and get some decorating ideas) by taking a tour led by the Frank Lloyd Wright Trust, offered five days a week.

Don’t miss: The bevy of beautiful art-glass windows and the furniture (also designed by Wright). 

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? Motorized vessels equipped with hot tubs.

Why go? Boating season doesn't have to end just because it's cold out. The Chicago Boat Company is bringing back hot tub boats this year, offering passengers the opportunity to float down the Chicago River while staying warm in heated water. Cruises are 90 minutes long and can accommodate up to six people, and BYO drinks are allowed on board. Don't wait too long to book—reservations fill up quickly!

Don't miss: End your cruise at Chicago Boat Company's Avondale dock to enjoy a nightcap at Judson & Moore, a distillery just steps away from the water. 

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? 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 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? 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? 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? 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? 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? The city’s dreamy green spaces, from Chicago parks to sprawling botanical gardens.

Why go? Reconnect with nature before snow swallows the city 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 worker-owned bookstore, offering new and used books for in-store browsing and curbside pickup.

Why go? You can support a local business while chipping away at your reading list by ordering something from this Pilsen shop. Submit an order online or call and talk to a human during business hours if you need a recommendation.

Don't miss: Add a donation to the Liberation Library to your order to support the purchase of books for incarcerated youth.

What is it? A West Town cafe-meets-gift shop that looks like it was designed by Wes Anderson.

Why go? Step inside and you're greeted by a velvet-upholstered counter, sticker-covered clipboards and sleek, futuristic-font signs declaring that the space is "not a cult." Cake-shaped candles, fluorescent tea boxes and handmade ceramics are artfully arranged on shelves and tables, every detail carefully curated. With a menu stacked with delectable drinks—like the Sugoi Strawberry Matcha—you'll never want to leave.

Don't miss: The Rawson pop-up shop—overflowing with vintage workwear, elevated basics, bespoke charms and more—in COE's back room. 

What is it? The best damn rock club in the States.

Why go? For more than a quarter of a century, a gig at the Empty Bottle has served as a rite of passage for local and touring musicians. The nondescript club on the edge of Ukrainian Village is far from the biggest venue in town (capacity is around 300), but the folks who book it have a knack for landing rockers, electronic acts and experimental musicians on the rise. Grab an Old Style, find a spot on the stairs by the stage and take in a sure-to-be memorable show. 

Don’t miss: A slice of pizza before (or after) the show at next door's Pizza Friendly Pizza. 

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 regular bingo night hosted by a leorpard print-wearing, Metamucil-drinking Midwestern cougar. 

Why go? Twice a month, Carol's Pub transforms into a rowdy bingo hall helmed by Aunt Nance, a delightfully eccentric character masterminded by local comedian Brittny Congleton. Throughout the night, Nance calls out bingo numbers with the flair of a tipsy Midwest aunt, mixing in musical interludes, sharp one-liners and the occasional George Michael reference.

Don't miss: The mid-bingo round “seventh-inning stretch,” which often paves the way for unpredictable madness, like a conga line running through Aunt Nance's dressing room.

What is it? A theater where performance art is populist and fun AF. 

Why go? You never know what you'll see when you attend the Neo-Futurists' signature show, Infinite Wrench, but it's nearly always entertaining. The ensemble races against the clock to cram 30 miniature, two-minute plays into a 60-minute show that bristles with madcap energy. Over the course of the evening, you might witness a dramatic monologue, a funny song or simply stare at someone eating a sandwich. 

Don’t miss: Grab a seat toward the front of the stage if you're game for interacting directly with the show's performers (their plays occasionally call for audience participation). 

What is it? A store that's not for the faint of heart and is one hell of a conversation starter.

Why go? You never know what you'll find at this popular Andersonville antique store, which prides itself on stocking items that are "resurrected from the past." Taxidermy, diving helmets, military supplies and other interesting knick-knacks typically line the shelves.

Don’t miss: The anatomy items, medical stuff, skull bones (of all kinds) and skeletons.

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? Chicago's only aquarium, home to thousands of colorful fish and other aquatic creatures.

Why go? Permanent exhibitions like "Wild Reef" and "Amazon" allow you to gaze at fish, stingrays, an anaconda and sharks. But the interactive experiences may be the biggest draw, allowing visitors to get up close and personal with some of the animals that live at the Shedd Aquarium and learn more about them.

Don't miss: The internet-famous rockhopper penguins, known for exploring the Shedd (and other Chicago institutions) during lockdown in 2020. You can say hi to them in the Polar Play Zone exhibit.

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? 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? 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.