west loop wedding walk
Photograph: Emma Mullins Photography
Photograph: Emma Mullins Photography

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.

Jeffy Mai
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Welcome to another weekend! Winter is here, so embrace the cold weather and find fun things to do outdoors, like ice skating at Millennium Park and Maggie Daley Park. If you prefer to stay warm, there are plenty of indoor activities as well, plus museum exhibits and winter rooftops equipped with heated patios. Also happening this weekend is Stan's Donut Fest, the West Loop Wedding Walk and the Architecture & Design Film Festival. So ready to make the most of your time off? Check out the rest of the best things to do in Chicago this weekend.

RECOMMENDED: Discover the best things to do in Chicago right now

Time Out Market Chicago

We've rounded up the best chefs in the city to join us at Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market featuring more than 15 kitchens, three bars and one drop-dead gorgeous rooftop terrace—all spread across three floors.

Best events in Chicago this weekend

  • Things to do
  • Film events
  • Loop

This touring film festival returns to the Gene Siskel Film Center to showcase movies that span a variety of architecture and design topics. This year's fest includes picks like The House: 6 Points of Departure, which explores the creative process behind the Crawford House in Montecito, California, and This Is Not a House, the story of one of the most unique homes in the world. Tickets are $20 per screening, $15 for Chicago Architecture Center and Gene Siskel Film Center Members, and $8 for students.

  • Things to do
  • River North

Indulge your sweet tooth with a host of delectable, sugary treats from Stan's. The chain is hosting its second annual donut fest, where attendees can try 12 different tastings, including flavors like Cinnamon Toast Crunch, Mini Cinnamon Roll, Cannoli Bombolini, Brown Butter Glazed and more. Upgrade to a VIP ticket to enjoy early entry and two drinks with your donuts.

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  • Things to do
  • Conventions
Chicago Travel & Adventure Show
Chicago Travel & Adventure Show

In the mood for a vacation? Start planning your next big trip at the Chicago Travel & Adventure Show, which gathers travel experts and ambassadors from destinations across the globe. This year, travel writer and Brat Pack member Andrew McCarthy and CBS News travel editor Peter Greenberg are among the keynote speakers. Guests can attend seminars on how to book cheap flights—an ever-salient issue, given airfare prices these days—get packing tips and snag sweet deals on trips at the convention.

  • Things to do
  • Irving Park

The Irish American Heritage Center celebrates the legacy and music of The Man in Black, Johnny Cash, for the 20th year running. Three stages showcase bands playing Cash's greatest hits and rare songs. Performers include Chicken Wire Empire, Iron Horse, Hoodie Snitch, Union Avenue and more. Best of all, proceeds benefit Pat Mac's Pack, a charity that raises funds for pediatric brain tumor research and provides financial assistance to young cancer patients and their families. 

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  • Things to do
  • West Loop

Bring the little ones to the Market on February 1 for a donut decorating class. 2d Restaurant will teach young chefs how to create a Lunar New Year lantern and three different mochi donuts with a variety of toppings and sprinkles. All of the necessary ingredients will be provided, and kids will be able to take their delicious sweet treats home.

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  • Things to do
  • Festivals
  • Lincoln Square

This Chicago Beer Society–sponsored event pairs niche local beers with bites from corresponding brewpubs, asking attendees to vote for their favorites. Half Acre hosts the annual event, which will conclude with an awards ceremony at the end of the evening. Partipating breweries include Haymarket, Off Color, Old Irving, Other Half and more.

  • Things to do
  • Lake View

Discover one-of-a-kind treasures from over 100 local small businesses at this curated indoor marketplace. You’ll be able to check out the best in Chicago food, fashion, home goods and art, as well as chat with vendors to learn about how the products are made. Well-behaved dogs are welcome to join the fun, and tickets are discounted when purchased in advance.

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  • Things to do
  • Loop

The sixth annual West Loop Wedding Walk returns on February 2. Couples can spend the afternoon touring 12 of the neighborhood's premier event venues—which have been staged for the occasion—while enjoying food and drinks and meeting more than 200 vendors. Transportation between venues will be provided. Once you've had your fill, head over to Galleria Marchetti for an afterparty hosted by Bluewater Kings.

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  • Things to do
  • Streeterville

Celebrate the life and career of Chicago actor and comedian Harold Ramis at Harry Caray’s Tavern Navy Pier on February 2. Cast members from the celebrated comedy Groundhog Day—including Stephen Tobolowsky, Peggy Roeder and Richard Henzel—will be on hand for a Groundhog Day ceremony, during which Chicago Harry, a live groundhog, will emerge from his tree stump to reveal if he sees his shadow. Harry Caray’s Tavern will also offer food and beverages inspired by the film’s Tip Top Café.

In the month Elon Musk joined the White House staff and US tech giants unveiled a new $500bn AI initiative, director Drew Hancock releases his debut film, Companion. Talk about timely. His feminist comedy-horror dives headfirst into a world involving a sentient sexbot going violently rogue. Which, right now, feels like next Tuesday.

Heretic's Sophie Thatcher is Iris, the robot at the story's centre. She meets Josh (The Boys’ Jack Quaid) in classic romcom fashion: he knocks over a display of tangerines near her at the supermarket. But the meet-cute is short-lived, as Josh whisks her away to a luxurious but isolated mansion where she discovers the truth: she’s not human. 

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Georgia Evans
Commercial Editor, Time Out
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  • Loop

Open wide! Chicago Restaurant Week is back for its 18th year. More than 470 Chicagoland eateries will offer specially curated prix fixe menus for brunch ($25), lunch ($25) 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.

  • Kids
  • United Center

Parents, bring the family to the United Center for a day of Disney magic. Kids will enjoy the timeless stories of Wish, Frozen 2, Moana, Lion King and Little Mermaid through memorable performances on ice by their favorite characters. You can also purchase a character meet-and-greet experience that includes a sing-along, crafting, interactive time and photos with Anna and Elsa.

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  • Music
  • Folk, country and blues
  • Loop

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 Wayne Baker Brooks, Bobby Rush and Laretha Weathersby. 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.

  • Things to do
  • Suburbs

On the last night of Frida Kahlo’s life, viewers of Frida…A Self Portrait are transported to La Casa Azul, the famous Mexican artist’s home. The one-woman production is written and performed by Vanessa Severo, and sees the artist reminisce about her life. Throughout the 75-minute play, Severo connects her own life’s experience to the famed artist’s, and explores Kahlo’s works, addiction, physical limitations and romances. The play is running at Writers Theatre, a non-profit theatre company, in suburban Glencoe.

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  • Things to do
  • Lincoln Park

At a motel in the Mojave Desert, two lovers, or fools as the play would suggest, meet up and clash. With just three main cast members, Fool for Love is a haunting drama that explores the deeply complex relationship between the trio. The play was written in 1983 by noted playwright Sam Shepard, whose works also include A Lie of the Mind and Buried Child, for which he won the Pulitzer Prize for Drama in 1979.

  • Things to do
  • Loop

The modern-day adaptation of Shakespeare’s Hamlet tells the story of Juicy, a young, queer Black man grappling with his identity at a backyard cookout. The Pulitzer Prize-winning and Tony-nominated play by James Ijames is playing at the Goodman Theatre through March.

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  • Things to do
  • Hyde Park

There’s a good chance that you’ve heard of A Raisin in the Sun. If you’re a fan of theatre, maybe you’ve even seen it or read it. The play, written by Lorraine Hansberry, depicts the experience of a black family on Chicago’s South Side as they try to improve their financial circumstances after the death of the family’s patriarch. The plot deals with still-relevant issues, like housing discrimination and racism. A Raisin in the Sun is being performed at Court Theatre in Hyde Park, the professional theatre of the University of Chicago.

  • Things to do
  • Rush & Division

During its original Broadway run in 2015, Fun Home won seven Tony Awards, including Best Musical, Best Original Score and Best Leading Actor in a Musical. Now, the award-winning musical has moved on from New York and is playing in Chicago during Chicago Theatre Week. Fun Home was based off of the graphic novel memoir of the same name written by Alison Bechdel. Both the novel and musical follow Bechdel as the writer comes of age: Bechdel’s experience of coming out as a lesbian and her relationship with her father, who was a closeted gay man.

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  • Things to do
  • Streeterville

The South Loop Farmers Market heads indoors for the season, bringing more than 75 vendors each Sunday to the fourth level of Water Tower Place. Shop for fresh produce, preserved veggies, cheeses, meats and more while enjoying live entertainment. Guests can also check out a kids' play zone, capture special moments with family and pet photography, and play some virtual reality games.

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  • Shopping
  • Markets and fairs
  • Wicker Park

Chicago farmers market season is well past its peak, but you can still get in on the fresh produce action during this winter edition of the Wicker Park market, which pops up inside The Robey on select Sundays from December through March. Browse goods from more than 15 local, rotating vendors like Donutistry, Hook Point Fisheries and The Love U Collective—and you can always grab a coffee from Cafe Robey to sip on while you stock up.

  • Things to do
  • Ice skating
  • Millennium Park

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—this rink is open through February 2, weather permitting.

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  • Things to do
  • Ice skating
  • Millennium Park

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.

Admission to the Skating Ribbon is free Monday through Thursday and for 11am sessions Friday through Sunday (and $5 for other time slots Friday through Sunday, as well as holidays) if you bring your own skates. No skates? Entry is $17–$23 if you need to rent a pair. The Ribbon stays open through March (weather permitting) and even offers hours on Thanksgiving Day, Christmas Eve, Christmas Day, New Year's Eve and New Year's Day.

  • 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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  • Nightlife
  • Pop-ups and food events
  • Loop

Immerse yourself in a picture-perfect whimsical décor, sparkling lights and breathtaking Chicago skyline views from the 22nd floor and indulge in a delightful selection of holiday-themed cocktails, including steaming spiced mulled wine and chilled festive drinks. LondonHouse Chicago's rooftop also offers cozy heated igloos, which can be booked by contacting rsvp@londonhouse.com; reservations require a $600 food and drink minimum.

  • Things to do
  • Near North Side

There’s plenty of cold weather fun to be had on the Art Deco-inspired terrace at the Gwen Hotel, which offers curling lanes plus fire pits and hot cocktails so you can warm up between rounds. Heat lamps are set up around the perimeter to keep things toasty and you can also hang out with a group around one of the fire tables.

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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.

  • Things to do
  • Loop

Look out over Lake Michigan and Millennium Park from the glass atrium on top of the Chicago Athletic Association hotel. The outdoor terrace is accessible year round and features fire pits to keep you toasty while you sip drinks. Cindy’s is running an après ski-inspired pop-up, with classic cold weather cocktails and themed decorations that transport guests to a snowy mountain getaway, daily through February 28.

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  • Nightlife
  • Pop-ups and food events
  • Loop

Fairmont Chicago has brought back its seasonal experience, Fairmont Lodge, for another year of wintry fun. The hotel’s lobby is transformed into a wonderland featuring themed décor, festive programming and seasonal menus. Guests can reserve a Lodge experience and indulge in hand-crafted cocktails and sweet and savory fondue, capped off with some tabletop s'mores. There’s also live entertainment Thursday through Saturday.

  • Loop

The six-time Tony Award-winning production kicks off its national tour with a five-month run in Chicago. Nineteen years after Harry, Ron, and Hermione saved the wizarding world, they’re back on a most extraordinary new adventure—joined by a brave new generation, including Harry’s son Albus—that threatens to change the past and future forever. The play has sold over 10 million tickets worldwide since its world premiere in London in July 2016, and holds a record 60 major honors.

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  • Things to do
  • Streeterville

Iconic chocolate brand Hershey has brought its first-ever immersive attraction to Water Tower Place, transporting guests to a whimsical, real-life candyland. Upon entering the indoor play experience, guests will explore various themed zones to discover what makes Hershey treats so special. From navigating a Twizzlers maze to celebrating the perfect combination in Reese’s Peanut Butter Cups, it’s family-friendly fun that tugs at the heartstrings. Plus, when you’re finished, stop by the retail store to snag limited-edition merch.

  • Things to do
  • Suburbs

This new exhibition from Chicago Gamespace and the Cleve Carney Museum explores the history of legendary Chicago video game company Midway and its rise to prominence in the ‘90s. Take a look at behind-the-scenes videos, interviews with former game designers, and art, or try your hand at any of the 15 playable arcade games. Midway’s celebrated legacy includes hits like NARC, Smash TV, Terminator 2, Mortal Kombat, NBA Jam and Cruis’N USA.

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  • Things to do
  • Hyde Park

The Griffin Museum of Science and Industry has debuted an exhibit dedicated to the science and technology behind the world’s longest-running film franchise, James Bond. Fans can check out 13 vehicles and over 90 additional artifacts, including the prototype jetpack used in Thunderball, an MI6 Retina Scanner from GoldenEye and the Parahawk snowmobile hybrid from The World Is Not Enough. You’ll also be able to step into a lab space inspired by “Q” and test your skills developing the perfect vehicle for spy activities, designing stunts and more.

  • Sports and fitness
  • Yoga & Pilates
  • Streeterville

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 N 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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  • 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.

  • Comedy
  • Uptown

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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