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.
Chicago Polar Bear Plunge
Photograph: Courtesy Chicago Polar Bear Club

It's another great weekend to get dinner, see a show and try to ignore the bitter temperatures outside. Celebrate the beginning of Chicago Restaurant Week by making a reservation at one of the city's best dining destinations (we have some suggestions). Once you're full, head to Navy Pier to take in "The Beach Chicago," a sprawling indoor installation that features a gigantic ball pit that’s filled with more than 1 million plastic balls. You can also stay warm at a taping of Chris Thile's Live From Here radio show at Symphony Center, catch retro rock duo the Lemon Twigs' gig at Metro, or take in the Cadillac Palace Theatre's touring production of Kinky Boots. Don't let yourself get snowed in—take a look at some of the best things to do in Chicago this weekend.

Things to do this weekend in Chicago

Photograph: Jaclyn Rivas

Chicago Restaurant Week

icon-location-pin Various venues, Loop

Open wide! Chicago Restaurant Week is back with 395 eateries offering dining deals from January 25 through February 7. For 14 belt-busting days, Chicagoans can cash in on special prix-fixe menus for brunch and lunch ($24) and dinner ($36–$48). Use the culinary event as an excuse to revisit an old favorite—like Blackbird, The Publican and mfk.—or explore a splashy new opening like Marisol, Le Sud or HaiSous. With 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.

Photograph: Courtesy Stan's Donuts
Things to do, Festivals

Donut Fest

icon-location-pin The Chop Shop, Wicker Park

The fancy doughnut trend is a bit played out at this point, but Chicago still boasts some of the finest purveyors of fried dough. Donut Fest brings together some of the city's best options (including Stan's, Longman & Eagle and Firecakes) for an afternoon of sampling, accompanied by coffee from Big Shoulders and Dark Matter. Attendees can choose from one of two sessions, dependent on how early you're willing to indulge in a sugar rush. 

People throwing balls in the Beach ball pit
Photograph: Daniel Boud
Art, Installation

“The Beach Chicago”

icon-location-pin Navy Pier, Grand Ballroom, Streeterville

Taking a dip at a Chicago beach in the dead of winter isn't a great idea unless you want to end up with hypothermia, but you can emulate one of your favorite warm-weather pastimes at Navy Pier's latest art installation. Design group Snarkitecture will set up an interactive piece called “The Beach Chicago” for two weeks in January, allowing visitors to jump into a sea of more than 1 million antimicrobial plastic balls. The tropical ball pit is surrounded by deck chairs, umbrellas and a lifeguard station—you'll just have to imagine the sweltering heat of a Chicago summer.

Polar Adventure Days
Photograph: Courtesy Chicago Park District
Kids, Quirky events

Polar Adventure Days

icon-location-pin Northerly Island, Downtown

Enjoy a free journey through Chicago's natural winter wonderland during one of three Polar Adventure Days on Northerly Island. Visitors will be able to check out birds of prey from Flint Creek Wildlife Rehabilitation, make nature-inspired winter crafts and see Siberian huskies and wolves. If there's snow on the ground, you can also strap on a pair of snowshoes and trudge around the island.

Chris Thile
Photograph: Devin Pedde
Things to do, TV, radio and podcast recordings

Live From Here with Chris Thile

icon-location-pin Symphony Center, Loop

Punch Brothers mandolinist Chris Thile brings his Nation Public Radio variety show Live From Here to Symphony Center, overseeing an evening of comedy, storytelling and musical performances. The live broadcast will feature performances from Thile and his special guest, singer-songwriter Jason Isbell.

Photo via Lincoln Square Ravenswood Chamber of Commerce
, Drinking

Winter Brew

icon-location-pin DANK Haus German American Cultural Center, Lincoln Square

The Lincoln Square Ravenswood Chamber of Commerce throws its annual Winter Brew fest, welcoming a lineup of local brewers to the Dank Haus for an evening of tastings. Past participants include local hops purveyors like Finch's Beer, 5 Rabbit and Half Acre.

Chicago Polar Bear Plunge
Photograph: Courtesy Chicago Polar Bear Club
Things to do, Quirky events

Chicago Polar Bear Plunge

icon-location-pin Oak Street Beach, Gold Coast

Not to be confused with the Chicago Polar Plunge, which takes place in March, this frigid tradition is organized by the Chicago Polar Bear Club and challenges participants to take a dip in Lake Michigan to raise money for local families in need. No matter how much time you spend on the beach during the summer, you're probably not going to be prepared for just how freezing cold the Lake gets in January, so make sure you bring something warm to wear (even if you're just there to watch).

Photograph: Ryan Bourque
Music, Folk, country and blues

Buddy Guy

icon-location-pin Buddy Guy's Legends, Loop

January in Chicago is Buddy Guy season, when the legendary bluesman picks up his polka-dot guitar and takes the stage for a series of shows at the South Loop blues club that bears his name. The month-long residency takes place Thursday through Sunday during January, pairing Guy with a different supporting act each night, including young Mississippi guitarist Kingfish and CTA bus driver Toronzo Cannon. Tickets to Guy's January residency aren't cheap, but seeing a blues icon perform in his hometown is the kind of experience that's worth splurging for.

La Boheme
Photograph: Ivor Kerslake, Courtesy Royal Opera House
Music, Classical and opera

La bohème

icon-location-pin Civic Opera House | Chicago, IL, Loop

If you've ever seen Rent, you'll probably recognize the plot of the Italian opera it was based on. In La bohème, four young Bohemians living in Paris struggle to pay the rent as they make art, fall in love and quarrel with one another. Giacomo Puccini's is one of the most popular operas (and a great place for first-time opera-goers to start) thanks to the identifiable narrative about being young and broke. Produced in collaboration with London’s Royal Opera House-Covent Garden and Teatro Real Madrid, this classic production kicks off the Lyric's latest season before returning to the stage in January.  

Handmade Market Chicago at the Empty Bottle

Handmade Market Chicago

icon-location-pin Empty Bottle, Ukrainian Village

Here’s your game plan: Grab brunch at Bite Cafe then head next door to sip mimosas and shop funky jewelry, clothing, handbags and paper crafts at this monthly fair. You'll find more than 30 vendors selling their creations at this monthly indoor market, so feel free to stock up on gifts for yourself and others.

The Lemon Twigs
Photograph: Autumn de Wilde
Music, Rock and indie

The Lemon Twigs

icon-location-pin Metro Chicago, Wrigleyville

Young Long Island duo the Lemon Twigs don't just look like they've stepped out of another era, the pair's conceptual new album Go to School harkens back to a time when sprawling rock operas outfitted with orchestral arrangements and whimsical narratives were in vogue. Thankfully, Brian and Michael D'Addario have the chops to compellingly deliver a collection of songs about a monkey that goes to school, unabashedly mining the classic rock tropes attributed to the Beatles, Big Star and the Beach Boys.

Kinky Boots
Photo: Matthew Murphy
Theater, Musicals

Kinky Boots

icon-location-pin Cadillac Palace Theatre, Loop

Step right up and witness the 2013 Tony Award winner about a failing shoe factory and the drag queen who helps turn it around. The high-heeled Broadway hit struts through Chicago for six nights this month. 

Photograph: Michael Brosilow

La Ruta

icon-location-pin Steppenwolf Theatre Company, Lincoln Park

Chicago-based playwright Isaac Gomez makes his Steppenwolf debut with this tale of the women who live, work and too often disappear from the American-owned factories in Juarez, Mexico, along the U.S. border. Sandra Marquez directs an all-female, primarily Latinx cast featuring newly minted Steppenwolf ensemble member Karen Rodriguez.

Photograph: Neil Burger

Curling Cabin

icon-location-pin The Gwen, River North

The weather outside may be frightful, but The Gwen's holiday pop-up is downright delightful. Located on the hotel's fifth-floor terrace, Curling Cabin is a bar within a bar that includes seating for up to 15. Once inside the cabin, which is outfitted with ski-lodge decor, you and your friends can order hot bites and sips. Reserve the cabin or enjoy the bar's outdoor curling rink while sipping a warm cocktail ($25 per person for 30 minutes). Both experiences can be booked through OpenTable.

Yayoi Kusama Infinity Mirror Room “Let’s Survive Forever”
Photograph: Courtesy wndr museum
Art, Installation

wndr museum

icon-location-pin 1130 W Monroe St, West Loop

Step inside one of Japanese artist Yayoi Kusama's famous Infinity Mirror Rooms at this new pop-up exhibition, which features installations that blend art and science. Other attractions include a “zero-gravity ball pit” that uses helium balloons and fans to simulate a weightless version of the childhood attraction, a floor that reacts to your footsteps and a gigantic screen that replicates your image with black and white discs. According to a press release, the exhibit will remain on display for a “limited, but undetermined, amount of time,” so you might want to book tickets sooner rather than later. Oh, and if you happen to use the restroom during your visit, definitely go ahead and press the red button.

Gallagher Way
Photograph: Heidi Zeiger Photography
Things to do, Ice skating

Winterland at Gallagher Way

icon-location-pin Gallagher Way, Wrigleyville

The Cubs may be hibernating for the winter, but Gallagher Way provides some excellent reasons to hang out in Wrigleyville during baseball's off-season. The public square's Winterland event series offers an array of seasonal activities, including an ice skating rink and curling. Guests under the age of 12 can skate on Gallagher Way's rink for free, while older skaters will have to pay $5 to slide around the ice (skate rentals are available for $10). This weekend, attendees will be able to paint the ice rink before it goes away for the season between 2 and 4pm.

Theo Ubique

The Full Monty

icon-location-pin Theo Ubique Cabaret Theatre, Evanston

Looking back, it’s not surprising that composer David Yazbeck was able to make Tootsie into a great stage musical. After all, he’d already done it before with The Full Monty. This intimate production from the storefront musical maestros at Theo Ubique is the first in their new cabaret-style space on the Evanston side of Howard Avenue.

Photograph: Patrick L. Pyszka
Things to do, Ice skating

Ice Skating in Millennium Park

icon-location-pin McCormick Tribune Plaza & Ice Rink, Downtown

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Admission to the rink is free, and you can rent skates for $13–$15. The most popular time to hit the rink is in the evening, so show up earlier if you don't feel like waiting in line for your chance to slide around. Take advantage of free skating lessons on Fridays at 11am and Saturdays and Sunday at 9am. If it seems too warm to skate, call ahead—this rink is open through March 10, weather permitting.

Photograph: Courtesy Chicago Cultural Center
Art, Design

“African American Designers in Chicago: Art, Commerce and the Politics of Race”

icon-location-pin Chicago Cultural Center | Chicago, IL, Loop

Black designers such as Charles Dawson, Emmett McBain and Eugene Winslow take the spotlight in the Chicago Cultural Center's latest exhibition, which explores how African American professionals used their work to portray their race. “African American Designers in Chicago: Art, Commerce and the Politics of Race” includes examples of cartooning, architectural signage, illustration, product design and more that was developed in Chicago between 1900 and 1980.

Maggie Daley Skating Ribbon
Courtesy Maggie Daley Park
Things to do, Ice skating

Ice Skating at Maggie Daley Park

icon-location-pin Maggie Daley Park | Chicago, IL, Millennium Park

The Maggie Daley Park ice ribbon looks like a Mario Kart track, but you won't have to worry about dodging banana peels while you glide around the quarter-mile circuit. As you skate around the park's climbing wall and admire skyline views, you'll be able to stop for a cup of hot chocolate. The ribbon stays open through March (weather permitting) and will host a Skate with Santa on Saturday, December 15 from 10am to noon. 

GYG Chicago TTD