garfield park conservatory
Photograph: Jaclyn Rivas for Time Out
Photograph: Jaclyn Rivas for Time Out

The best things to do in Chicago this weekend

Find the best things to do in Chicago this weekend with our guide to concerts, exhibitions, festivals and more.

Shannon Shreibak
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We’re probably not alone in saying that the weekend is always on our minds here at Time Out Chicago HQ. Like you (probably), we spend the workweek daydreaming about the next restaurant to obsess over and obsessively updating our concert calendars. Whether you’re museum-hopping, plotting a day trip to escape the city, or ready to ghost your original plans for something spontaneous, you’ll find plenty of ways to make the most of your weekend in Chicago.

Last updated December 29, 2025: Looking for the best things to do in Chicago this weekend? Whether you’re the designated group chat planner or just looking for last-minute inspiration, we’ve got you covered. This weekend’s highlights include New Year’s Eve celebrations at Time Out Market and The Salt Shed, an interactive Yoko Ono retrospective and the final days of the Garfield Park Conservatory Winter Flower Show. On a budget? We’ve rounded up some of the best free events in Chicago, too. Scroll down to discover the best events across the city!

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Time Out Market Chicago

The best things to do in Chicago this weekend

  • Attractions
  • Parks and gardens
  • East Garfield Park

Feeling stressed by winter's cold weather and lack of leaves on the trees? Take a calming walk through hyacinth, zinnias, salvias, cosmos and other flowering blooms at Garfield Park Conservatory's annual winter flower show (which is titled "Merry & Bright" this year for ultimate festiveness). Like the rest of the Conservatory, access to the show is free—just be sure to make an online reservation ahead of your visit. 

  • Things to do
  • Exhibitions
  • Hyde Park

Every year, the Griffin Museum of Science and Industry puts up its four-story Grand Tree and surrounds the towering pine with more than 50 trees that represent Chicago's various communities and their respective holiday celebrations. Visitors will be able to take in even more seasonal cheer at the accompanying Holidays of Light exhibit, which recognizes the traditions of Chinese New Year, Diwali, Kwanzaa, Ramadan, Hanukkah, Visakha Puja Day and St. Lucia Day. 

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  • Things to do
  • Late openings
  • Lincoln Park

To see one of the largest displays of holiday lights within city limits, you need to head to Lincoln Park Zoo, where the annual ZooLights display strings up millions of LED blubs. While most of the animals will be keeping warm inside, visitors are welcome to wander through the park, snapping photos of the various displays and taking part in a variety of activities throughout the holiday season. 

  • Things to do
  • Exhibitions
  • Suburbs

The Chicago Botanic Garden hosts this annual (and quick to sell out) display of festive lights, giving guests a host of shimmering reasons to visit the forest preserve during the holiday season. Set along an illuminated path, the after-dark experience features a series of installations to explore, including a 110-foot tunnel made up of 100,000 lights and a group of trees festooned in bulbs that “sing” holiday songs. 

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  • Things to do
  • Streeterville

Pinkmas at the Museum of Ice Cream is more than your run-of-the-mill holiday outing—it's a dazzling, immersive holiday experience. Visitors can share their wildest dreams with a Wishing Tree, walk through a life-size snowglobe, and feast on festive treats and ice cream creations, all while taking advantage of countless photo opportunities.

  • Nightlife
  • Pop-ups and food events
  • Loop

Happy’s is back for its farewell season, and they're closing out a holly, jolly run in full holiday spirit. Situated on the ground floor of the Chicago Athletic Association, Happy's transforms the hotel's Tank space into a holly, jolly wood-paneled dive bar serving cocktails and bar bites. Admission is free, and the pop-up is just a short walk from the Millennium Park ice skating rink.

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  • Nightlife
  • Pop-ups and food events
  • River North

Soak in multiple floors of themed decor at the Christmas Inn, the expansive holiday pop-up that takes over the Hubbard Inn for the season. Grab a cocktail, like Reindeer Fuel, and explore an elegant white Christmas setting. The pop-up will also offer different programming each day, from boozy craft nights to music bingo.

  • Things to do
  • Ice skating
  • Millennium Park
  • Recommended

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Plus, take advantage of free skating lessons on most Saturdays and Sundays, where you can learn both beginner- and intermediate-level skills. 

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  • Things to do
  • Suburbs

Just when you thought the state's largest mall couldn't surprise you anymore, Woodfield Mall announces WONDRA, a sprawling new immersive experience. Inside, you’ll wander through enchanted meadows that respond to the sound of your voice, stumble across bioluminescent landscapes and drift into crystal caves and celestial gardens that blur the line between digital spectacle and raw wonder. 

  • Things to do
  • Armour Square

See Christmas lights while staying warm at this pandemic-era innovation that allows visitors to drive through a gleaming tunnel of more than one million LED lights synchronized with holiday music. Plus, the show takes place in Bridgeport at Rate Field, home of the Chicago White Sox.

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  • Things to do
  • Millennium Park
  • Recommended

Every year, Millennium Park is adorned with an epic Christmas tree that remains on display until the beginning of the new year. The larger-than-life attraction is festooned with twinkling lights and crowned with an illuminated star. Spectators can check out the festive tree near Washington Street and Michigan Avenue through early January.

  • Things to do
  • Streeterville

Located on the terrace of The Peninsula Chicago, the 2,100-square-foot Sky Rink offers ice skating in the shadows of the city's tallest buildings, all while overlooking Michigan Avenue. Show off your skills in a winter wonderland featuring snowflake lighting and festive music, and when you need to warm up, grab a hot drink and snack at the Chalet.

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  • Things to do
  • Exhibitions
  • Avondale

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. 

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  • Kids
  • Streeterville

Relive cherished holiday memories—and make plenty of new ones—at Navy Pier's Winter WonderFest. Admire twinkling light displays bedecking Navy Pier's Festive Hall and prepare to be awed by a 42-foot holiday tree. Plus, there's no shortage of activities—for both kids and adults—at Winter WonderFest: Enjoy live music and special performances at the Winter Wonder Stage, lace up for a round of ice skating, enjoy tasty treats and sips and much more.

  • Things to do
  • River West/West Town

If you're jonesing for an outdoor Christmas adventure this year, the folks behind Jack's Pumpkin Pop-Up are bringing back its winter sibling in Fulton Market. The sprawling two-acre attraction boasts a Christmas market, photo opportunities and a variety of activties like ice skating, bumper cars, axe throwing, curling and more. You'll also have the opportunity to sip on boozy hot cocoa and other holiday cocktails while wandering through a light-filled Christmas tree walk.

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  • Things to do
  • Festivals
  • Suburbs

Ready to get into the holiday spirit? The Morton Arboretum's annual holiday light show returns for its 13th anniversary as a mile-long, walk-through spectacle of LED lights and music, featuring a blend of new and returning light displays set amid 50 acres of trees. Back again this year is "Electric Illumination," a series of late-night parties with DJ-curated playlists that will synchronize progressive house and '80s dance beats with the light shows, as well as "IllumiBrew," a special evening where guests can sample beers and ciders from local breweries. 

  • Things to do
  • Exhibitions
  • Streeterville

“Music of the Mind” is a retrospective that celebrates key moments of Ono’s career, showcasing art driven by ideas and expressed in poetic, humorous and profound ways. Tracing Ono’s career back to the 1950s, “Music of the Mind” presents over 200 works across a variety of media including performance footage, music and sound recordings, scores, film, photography, installation and archival materials. 

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  • Musicals
  • Loop

Andrew Lloyd Webber's bombastic megamusical haunts the Cadillac Palace for a spectacular eight-week run. The age-old tale of love, loss and revenge unfolds against the Baroque interior of the Cadillac Palace Theatre—transporting you straight to late 19th-century Paris. 

  • Things to do
  • Ice skating
  • Millennium Park
  • Recommended

Situated in the heart of downtown Chicago with the city's sweeping skyline as a backdrop, the Skating Ribbon at Maggie Daley Park is a winter attraction unlike any other. Skaters can lace up and wind around a winding ice-covered path that's twice the length of a lap around a traditional rink. Reservations for the popular ice rink should be made in advance, as they tend to fill up quickly.

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  • Things to do
  • Exhibitions
  • Washington Park

The DuSable Black History Museum and Education Center's newest exhibition, “Paris in Black” charts the journeys of Black artists, performers and intellectuals who found a safe haven and creative incubator in 20th century Paris. Experience the City of Lights through the eyes of visionaries like Langston Hughes, James Baldwin and Henry Ossawa Tanner, who lived and created in defiance of American racism. The exhibition houses over 100 objects, including magnificent paintings, historic photographs and multimedia elements—all telling the story of Black resilience and artistry.

  • Things to do
  • Festivals
  • Recommended

Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This edition’s theme is “SHIFT: Architecture in Times of Radical Change,” bringing together over 100 projects by architects, artists and designers from 30 countries—each piece engaging with the cultural, social and environmental fluxes transforming our world. Not sure where to start? Check out our first-timer's guide to the exhibition.

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  • Things to do
  • River North

The Godfrey’s rooftop becomes a winter wonderland when the temperatures plunge, featuring clear heated igloos decorated with festive lights that can be booked for groups of up to 10 people indulging in bottle service. Even if you’re not going all out, you can hang out at a booth under the retractable roof or gather around an outdoor fire pit for s’mores and a hot cocktail.

  • Art
  • Contemporary art
  • Hyde Park

Until February 2026, the University of Chicago's Smart Museum of Art hosts “Unto Thee,” Theaster Gates's first solo museum exhibition in his hometown of Chicago. Known for his installations merging sculpture, performance and social practice, Gates has become a driving force in the contemporary art world and beyond. “Unto Thee” embodies the relationships Gates has fostered throughout Chicago, underpinning his belief that art has the capacity to connect and transform communities.

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  • Drama
  • Lincoln Park

Peter Shaffer's 1979 masterwork brings to life the rivalry between composers Antonio Salieri (Ian Barford) and Wolfgang Amadeus Mozart (David Darrow). Salieri is the Court Composer and the established standard of the day—his compositions are palatable, albeit restrained. Enter Mozart, a wild child prodigy with climbing notoriety and the ability to make music like no one has ever heard. Mozart's music moves Salieri to tears, but also awakens a destructive jealousy that compells him to supress Mozart at every turn. 

  • Nightlife
  • Pop-ups and food events
  • Lake View

Chicago's only Hanukkah-themed pop-up takes over The Graystone Tavern in Wrigleyville for another year, filling the bar and weatherproof patio with more than 30,000 blue-and-white lights, dreidel ornaments, lighted menorah and a Hanukkah sweater wall (among other festive bits of decor). Dine on Hanukkah classics like latkes and matzo ball soup alongside not-so-classic options like boozy jelly donuts. 

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  • Nightlife
  • Pop-ups and food events
  • Wrigleyville

This immersive, multi-level Christmas pop-up bar boasting wall-to-wall holiday decor returns to Wrigleyville, taking over Stolen Saddle during the most festive time of the year. You'll find photo ops galore as well as drinks decked out with decorative garnishes and garlands, including large-format cocktails. Feeling hungry? Feast upon festive options like Santa's Smash Burger, Festive Fry Flight and Grinch Shake. 

  • Kids
  • Exhibitions
  • Streeterville

“Take Care with Peanuts: The Exhibit” is an immersive fan experience inspired by a global initiative of the same name. Based on the captivating world depicted in Charles M. Schulz’s iconic comic strip, the exhibit brings the beloved Peanuts gang to life through interactive displays and hands-on activities promoting self-care, empathy and environmental stewardship. 

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  • Nightlife
  • Pop-ups and food events
  • Lake View

The 2003 holiday movie Elf takes center stage at this Wrigleyville pop-up located inside of Stretch Bar & Grill, which gets dressed up with more than 1,000 decorative elves, Christmas trees and plenty of festive Christmas lights. Take a seat at tables stocked with the four main food groups (candy, candy canes, candy corn and syrup) and treat yourself to a plate of Buddy's breakfast pasta (spaghetti loaded with maple syrup, chocolate fudge and syrup, mini marshmallows and strawberry frosted pop tarts) or a beer served in a 36-ounce elf boot. 

  • Things to do
  • Suburbs

Bring a thermos of hot chocolate and a cozy blanket to accompany your ride through Willow Hill Lights, a drive-through holiday light experience in suburban Northbrook. Located at Willow Hill Golf Course, the 2.5-mile display of glittering lights features holiday favorites like Rudolph and Frosty the Snowman—not to mention a 30-foot-tall Christmas tree. Proceeds from the show benefit Misericordia, a not-for-profit that supports more than 600 children and adults with intellectual and developmental disabilities.

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