chicago polar plunge
Photograph: David T. Kindler
Photograph: David T. Kindler

The best things to do in Chicago this week

Find the very best things to do in Chicago this week, including cultural events, festivals and shows.

Shannon Shreibak
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Last updated January 16, 2026: Whether you’re diving into the Chicago Polar Plunge or tasting your way through Chicago Restaurant Week, there’s plenty to look forward to this week. Even on a budget, you can take advantage of free admission days at several Chicago institutions or go ice skating under the skyline at Millennium Park.

Read on for our curated guide to the best events happening around town this week.

RECOMMENDED: Discover the best things to do in Chicago in January 2026

Time Out Market Chicago

Best events in Chicago this week

  • Things to do
  • Exhibitions
  • Hyde Park

How are some of the most iconic costumes of the past century made? Costume designer Paul Tazewell pulls back the curtain in this behind-the-scenes exhibition. Highlights include costumes from Wicked, Janelle Monáe’s MET Gala looks and Steven Spielberg’s West Side Story. Sketches, videos and narration reveal how imagination becomes wearable art.

Open wide! Chicago Restaurant Week is back for its 19th year. More than 470 Chicagoland eateries will offer specially curated prix fixe menus for brunch ($30), lunch ($30) or dinner ($45/$60) between January 24 and February are 9. With more than two weeks to chow down, there's plenty of time to make a few reservations and check out some of the best restaurants in Chicago while saving some coin.

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  • Kids
  • Grant Park

Celebrate Dr. Martin Luther King Jr. with us at The Art Institute of Chicago's Ryan Learning Center. The museum is hosting an afternoon of family-friendly activities and performances inspired by Dr. King’s moving “What Is Your Life’s Blueprint?” speech. Admission to the Ryan Learning Center is always free for everyone, every day. While you’ll need a museum ticket for in-gallery activities, kids under 14 are always free. Plus, a special bonus for locals: Illinois residents enjoy free museum admission on King Day as part of the museum's Free Winter Weekdays program.

  • Music
  • Music festivals
  • Recommended

While all of the other music festivals are in hibernation, Tomorrow Never Knows has been bringing up-and-coming artists to venues all over the city for the past 20(!) years. Organized by the folks at Schubas and Lincoln Hall, the lineup usually sports an abundance of rising acts who perform at the organizing venues as well as Bridgeport's Ramova Theatre. This year, you'll be able to catch a variety of bands, including dream-folk luminary Cassandra Jenkins, Chicago instrumental two-piece Mute Duo, avant-pop sensation Perfume Genius and more. 

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  • Things to do
  • Lincoln Park
  • Recommended

Brave the cold and head to North Avenue Beach this March for the Chicago Polar Plunge, which sends thousands of shivering participants into the icy waters of Lake Michigan to raise money for Special Olympics Illinois. Can't make it to North Aveunue this year? You can still donate to the cause. All participating plungers will receive free parking at Lincoln Park Zoo, a souvenir T-shirt and towel when exiting the water.

  • Things to do
  • Hyde Park

In honor of Martin Luther King Jr. Day, the Griffin Museum of Science and Industry invites families to a day of activities celebrating the power of creativity and innovation. This event is a featured part of the Black Creativity Program, a long-running initiative that honors the history of Black innovation while championing STE(A)M opportunities for today’s youth. During the celebration, guests can participate in a collaborative community art experience, engage in a variety of family-friendly activities and explore the prestigious Black Creativity Juried Art Exhibition.

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  • Kids
  • Suburbs

Prepare for a magical adventure: Disney on Ice is coming to United Center and Allstate Arena for its latest show, Jump In! The ice-skating spectacle promises awe-inspiring visuals, thrilling stunts and mesmerizing choreography featuring over 50 of your favorite Disney characters. Along with aerial acrobatics and interactive elements, Disney on Ice will also welcome a few new characters to the crew: Anxiety, Joy, Sadness, Disgust, Anger and Fear from Inside Out 2 and multiple new characters from Moana 2 will be lacing up their skates.

  • Music
  • Folk, country and blues
  • Loop
  • Recommended

Most people call January “the first month of the year” or “four weeks of taking my resolutions seriously,” but Chicago blues fans know that it's actually “Buddy Guy month.” Throughout the month, the legendary bluesman picks up his polka-dot guitar and takes the stage during a residency at the South Loop blues clubs that bears his name. Guy performs every Thursday, Friday, Saturday and Sunday night, with a different supporting act joining him each evening. This year, you'll see Guy paired with folks like Bobby Rush, Katie Kadan and Michael Damani. Tickets to Guy's January residency aren't exactly cheap, but witnessing a bonafide blues icon perform in his hometown is the kind of experience that's worth the dough.

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  • 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.

  • Museum Campus

Kick off Chicago Restaurant Week with a blowout bash at the Field Museum. More than 60 of the city's top chefs will be on hand to offer delicious food tastings, plus beer, wine and cocktail pairings. Hosted by chef Jonathon Sawyer, the event features participating restaurants like Piccolo Sogno, Hawksmoor Chicago, UMMO and many more.

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  • Things to do
  • Exhibitions
  • Grant Park

Known for his groundbreaking homes spanning across the United States and rejection of minimalist conventions, Bruce Goff—whose lifelong mentor was Frank Lloyd Wright—is one of the modern world's most celebrated architects. To celebrate his legacy, The Art Institute of Chicago will be hosting the first major exhibition of Goff’s work in 30 years. The show will feature more than 200 works celebrating every phase of Goff's creative practice, from elaborate architectural drawings and models to a selection of Goff's lesser-known artistic output in abstract painting.

  • Things to do
  • Exhibitions
  • Loop

The Museum of Contemporary Photography celebrates its 50th anniversary with a sweeping look at its collection. Each of the museum's five galleries will represent a decade of collecting, beginning with its most recent acquisitions (2016-2026) in the first gallery, then rewinding through time. The retrospective features rarely exhibited and newly acquired works by influential photographers including Dorothea Lange, Harry Callahan and Robert Frank.

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  • 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. Note that you'll need to make a free online reservation for both regular skating and lessons, and if it seems too warm to skate, call ahead.

  • Things to do
  • Talks and lectures

As we gear up for Super Bowl LX, we’re offering a unique opportunity to dive deep into Puerto Rican history through the lens of this year’s halftime headliner, Bad Bunny. The global superstar has collaborated with Professor Jorell Meléndez-Badillo, acclaimed author of Puerto Rico: A National History, to curate an exclusive visual presentation. This immersive experience explores the historical context and cultural inspirations behind the tracks on Bad Bunny’s latest multi-platinum album, Debí Tirar Más Photos.

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  • Museums
  • Museum Campus

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, 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. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

  • LGBTQ+
  • Bucktown

Produced by World of Wonder—the company behind Drag Race and the global DragCon conventions—the attraction casts visitors as the main character inside some of the show’s most iconic spaces. You can strut the Main Stage, snap a selfie in the Werk Room, film a confessional and flip through racks of costumes pulled straight from the runway. Roll up with your squirrel friends and you’ll have a day that’s pure eleganza.

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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. 

  • Shopping
  • Markets and fairs
  • Edgewater

For five Saturdays, the Edgewater Indoor Market brightens the Chicago winter with a massive makers market at the Broadway Armory. Each event hosts more than 50 food vendors, artists and artisans. Come hungry—you’ll find an abundance of fresh baked goods, seasonal produce and locally made treats.

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  • 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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  • 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.

  • 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. Every corner is crafted to ignite curiosity and inspire a sense of awe we, whether you’re a kid seeing it all for the first time or an adult who forgot what it feels like to play.

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  • 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.

  • Drama
  • Lincoln Park
  • 5 out of 5 stars
  • Recommended

In Peter Shaffer’s Amadeus, genius is not just a blessing: It’s a declaration of war. Composer Antonio Salieri sees himself as one of its principal casualties. Once the darling of the 18th-century Viennese court, he watches in mounting horror as “the creature”—his term for the rising musical prodigy Wolfgang Amadeus Mozart—launches an artistic takeover that endangers not just Salieri’s career but his very conception of himself.

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  • Things to do
  • Exhibitions
  • River West/West Town

The newly renovated Intuit Art Museum is the perfect place to visit the exhibition, “Catalyst: Im/migration and Self-Taught Art in Chicago.” This exhibition is part of a citywide initiative highlighting Chicago's artistic heritage and creative communities. “Catalyst” focuses on the impact of immigration and migrant experiences within the self-taught artist community. The featured works investigate the inciting incidents for artists' displacement and subsequent settling in Chicago, offering a unique perspective on artistic practice as a personal narrative.

  • 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.

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  • Sports and fitness
  • Yoga & Pilates
  • Streeterville
  • Recommended

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levelsyou just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

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  • 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. Stay up-to-date by visiting the Chicago Architecture Biennial website.

  • 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.

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  • Museums
  • Movies and TV
  • River North

Visiting “The Land of Oz: Beyond the Page” at the Gold Coast’s Driehaus Museum feels a bit like opening a very elegant jewelry box: beautifully crafted, lovingly arranged and also...surprisingly compact. Tucked away into two rooms on the museum’s top floor, the film-inspired exhibit offers a curated peek behind the yellow brick road—costumes, concept art, early editions of L. Frank Baum’s original book and just enough memorabilia to spark a pleasant jolt of nostalgia.

  • Comedy
  • Uptown
  • Recommended

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

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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. 

  • Experimental
  • Uptown

For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

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