Discover the best things to do in Chicago, from iconic venues and views to cultural musts and late-night shenanigans.
No matter where your interests lie, you can always find something to get excited about in this no-nonsense Midwestern metropolis. The best things to do in Chicago run the gamut—from seriously fun to awesomely educational. Looking for culture? Spend a day exploring Chicago museums. Hungry? You've come to the right place, because Chicago is famous for its delicious cuisine. There are tons of amazing restaurants in Chicago that highlight the city's rich and diverse culinary landscape. (And plenty of uniquely Chicago bars that do the trick, too.) We've searched all across the city to assemble this list of the best things to do in Chicago. Follow it and never get bored here again.
Last updated January 22, 2025: Chicago has shifted into full winter wonderland mode, offering a wealth of things to see and do this winter. Whether you're interested in exploring iconic sights, diving into culture or embracing the season's cozy energy, the city has you covered. Read on to discover the best activities for kicking off the year.
You can also find out more about how Time Out selects the very best things to do all over the world, or take a look at our list of the best things to do in the world right now.
RECOMMENDED: Check out Time Out's interactive map of the best things to do in Chicago
What is it? The annual celebration of Chicago's restaurant scene.
Why go? More than 470 Chicagoland eateries will offer specially curated prix fixe menus for brunch ($30), lunch ($30) or dinner ($45/$60), saving you some serious coin.
Don't miss: Before devising your Restaurant Week plan, peep this viral spreadsheet compiled by Chicagoan Paige Serena breaking down every deal in the city.
What is it? All-season patios equipped with retractable roofs, heated igloos and outdoor fire pits.
Why go? Rooftop season doesn’t have to be confined to summer. These restaurants and bars atop downtown hotels and skyscrapers offer outdoor spaces that are suited for cold weather. So grab a hot cocktail and enjoy the gorgeous views even when the conditions are less than ideal.
Don't miss: The annual Rudolph’s Rooftop experience on the 22nd floor of LondonHouse Chicago, which features whimsical decor and plenty of great spots for a festive photo.
What is it? The crown jewel of Chicago's front yard.
Why go? Home to iconic public art installations such as Cloud Gate (a.k.a. "The Bean"), this 25-acre park is one of the most popular gathering spots in the city. Visitors can walk through the vegetation in the Lurie Garden—renowned for its beauty throughout all of Chicago's seasons—or grab a requisite selfie in front of the Bean's reflective surface.
Don’t miss: Crown Fountain, an interactive installation featuring two 50-foot-tall LED video structures.
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 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? Chicago restaurants and bars with fireplaces.
Why go? Dispel the chill with a warm drink or hearty meal next to the fire. Many of Chicago's best spots offer this comforting amenity—both inside and outdoors—so you don't have to stay cooped up at home all season long.
Don't miss: The moody digs at Logan Square cocktail destination Scofflaw, which houses two fireplaces and offers free cookies at midnight.
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: Peter Shaffer's 1979 masterwork Amadeus, which retells the rivalry between composers Antonio Salieri and Wolfgang Amadeus Mozart.
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? 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? 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? A winding, ice-covered path in the Loop that’s twice the length of a lap around a traditional rink.
Why go? It’s always tough to get excited about the start of winter, which is why we recommend easing into the season with some of the city’s best cold-weather offerings. The Maggie Daley Ice Ribbon, with its novel layout and superior skyline views, won’t completely erase your winter blues, but it’s one of the nicer ways to cope with biting temps and 4:45pm sunsets. The rink closes for the season on March 9.
Don’t miss: Grabbing a reservation online before you visit, as walk-in spots tend to fill up quickly.
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? 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? 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? 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? 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 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? 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? Sledding hills in the city and suburbs.
Why go? Love it or hate it, snow is part of the winter experience in Chicago. So when the snowflakes start falling and accumulating on the ground, grab a sled and head to the area's top slopes—from bunny hills to steep mounts—for some thrills.
Don't miss: No car at your disposal? Fear not: One can have an epic day trip off of nearly every Metra stop.
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? 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? “Music of the Mind,” a retrospective that celebrates key moments of Ono’s career.
Why go? Tracing Ono’s career back to the 1950s, the exhibition presents over 200 works across a variety of media including performance footage, music and sound recordings, scores, film, photography, installation and archival materials.
Don't miss: The instruction-based artworks scattered throughout the exhibition, which encourage visitors to interact with Ono's artworks.
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? 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? Set atop the building formerly known as the John Hancock Center, this observatory offers views of the city (and surrounding states) from 1,030 feet above the streets.
Why go? The sights from the 94th floor can't be beat, whether you're a longtime Chicagoan or a visitor. Stick around to enjoy a cocktail at 360 CHICAGO's bar or explore some of the interactive exhibits detailing the city's history.
Don't miss: 360 CHICAGO's most terrifying attraction: TILT. Guests board a glass-enclosed platform that slowly tilts over the side of the building at a 30-degree angle. Thrill seekers will want to fork over the additional fee for a ticket.
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? Cake and cookie decorating workshops taught by celebrated pastry chefs.
Why go? We're probably not alone in wanting to make an intricately decorated, Instagram-worthy cake, and Bon Vivant will give you the skills to elicit ooohs and ahhhs from your friends. After feasting on snacks and cocktails, a team of experienced bakers offers tips, tricks, and techniques for creating your own creative confections. Plus, you get to take your edible artworks home.
Don't miss: Bon Vivant's Happy Hour offerings, with themes like “Taylor Swift” and “Tini Time.”
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? A massive natural history museum that was founded to house the biological and anthropological collections for the World’s Columbian Exposition of 1893.
Why go? With 350,000 square feet of permanent exhibitions to explore, deciding what to see at the Field Museum can be a daunting task. We recommend starting in the institution's new Reptiles Alive! exhibit, where you'll explore the lives of reptiles with immersive activities and, of course, 20 live reptiles on view.
Don’t miss: The Grainger Hall of Gems, a breathtaking collection of more than 600 gemstones and 150 pieces of antique and contemporary jewelry.
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? The Chicago Cultural Center's hyper-local boutique representing over 400 artists and makers.
Why go? Buddy is a one-stop shop for any locavore on the hunt for the perfect gift—whether for a friend or just yourself. With an ever-growing fleet of Chicagoland vendors, options are abundant, from ceramics and clothing to zines and music.
Don't miss: AppleBuddy TV: an all-day, every-day animation festival playing on an old-school television set.
What is it? The best spas for a day of rest and relaxation.
Why go? Summertime's non-stop activities and sunshine can wreak havoc on our skin, which is a prime reason to escape the heat and rejuvenate with a visit to a spa. The city's top spots offer everything from luxurious treatments to tried-and-true massage therapy, and there's something for every budget. After all, a little self-care can go a long way.
Don't miss: Follow up a treatment at Bucktown's Spa Soak with an indulgent meal at the original Small Cheval, located just across the 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? 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? 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.
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