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January 2020 events calendar for Chicago

Begin the new year with events, festivals, concerts, theater and more great things to do in Chicago in January

Chicago snow
Photograph: Grace DuVal

Here's one New Year's resolution that's easy to keep: Make 2020 the year that you attend more events, see more shows and discover new things to do in Chicago. January is packed with way to begin accomplishing this goal, with concerts, art openings and outdoor activities galore (including slippery fun at Chicago ice skating rinks). Laugh yourself silly during the Chicago Sketch Comedy Festival at Stage 773, head to Chicago music venues to catch rising bands during the Tomorrow Never Knows festival or strip down to join the annual No Pants Subway Ride on the Red Line. You can even pretend that it's summertime while eating some of Chicago's best fried chicken during a Parson's Chicken and Fish patio pop-up at the Chicago Athletic Association. Make this month one to remember by finding some amazing things to do in Chicago on our January events calendar.

RECOMMENDED: Events calendar for Chicago in 2020

Featured events in January 2020

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

Winterland at Gallagher Way

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, family-friendly activities, including an 8,000-square-foot ice rink, curling and skating lessons, holiday movie screenings and visits from Santa Claus. Beloved holiday bazaar Christkindlmarket also hosts an outpost at Gallagher Way, bringing shopping and glühwein north of the Loop. Plus, look out for wreath-making workshops, breakfasts with Santa and a tree lot at Big Star.

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

Ice Skating in Millennium Park

Millennium Park | Chicago, IL, Millennium Park

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 Sundays at 9am. If it seems too warm to skate, call ahead—this rink is open through March 8, weather permitting.

Photograph: Courtesy Maggie Daley Park
Things to do, Ice skating

Ice Skating at Maggie Daley Park

Maggie Daley Park | Chicago, IL, 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. Admission to the Skating Ribbon is always free, and skate rentals are available for $13–$15. The Ribbon stays open through March (weather permitting) and even offers limited hours on Thanksgiving Day, Christmas Eve, Christmas Day, New Year's Eve and New Year's Day.

Photograph: JACK X LI
Things to do


Time Out Market Chicago, West Loop

Assemble your smartest friends and put your brain to work at Trivia@Tony's, hosted at Time Out Market's third-floor rootop bar. Participants will be treated to six rounds of themed questions, and everyone on the winning team will snag a complimentary ticket to the Laugh Factory in Lakeview, courtesy of Brain Sportz Trivia. Can’t make it? Don’t worry—we’ll host Trivia@Tony’s regularly on Thursday nights, so look out for our next event.

Photograph: Clayton Hauck
Restaurants, Soul and southern American

Parson’s Chicken and Fish Pop-up

Chicago Athletic Association, Loop

One of the biggest bummers about a cold Chicago winter is not being able to have a meal (and a couple of Negroni Slushies) on either of the Parson’s Chicken and Fish patios. To tide you over until the warmer months arrive, Chicago Athletic Association is hosting a three-week pop-up that replicates the experience of a summer afternoon spent eating fried chicken under a red- and white-striped umbrella. The hotel's Tank will be transformed into an indoor version of a Parson's patio, complete with Ping Pong tables, strings of twinkling lights and menu of chicken sandwiches, hush puppies and fried fish. And yes, you'll also be able to order the aforementioned Negroni Slushy, as well as highballs, picklebacks and a housemade pickle soda. It's no replacement for real patio weather, but we'll take what we can get.

Photograph: Martha Williams
Things to do

Soup & Bread

Hideout, River West/West Town

This pay-what-you-can, family-friendly weekly event raises money for local food pantries, enlisting local chefs (professionals and amateurs) to cook a variety of soups that are accompanied by bread donated by Publican Quality Bread. Each gathering is accompanied by music from a local DJ—just make sure you arrive early if you're hoping to sample some of the soups, because the crockpots aren't bottomless.

Maija Tammi, One of Them is Human
Photograph: Courtesy Maija Tammi
Art, Photography

“In Real Life”

Museum of Contemporary Photography, Loop

Take a peek at how artificial intelligence “sees” the world around it through this high-tech exhibition, which features images that were captured with the help of machines or generated through the use of complex algorithms. Photos by seven artists explore the repercussions of surveillance, the questionable ethics of data collection and the ways in which the biases of the humans who develop technology can seep into the underlying code.

Photograph: Jay Wennington

Chicago Restaurant Week

Various venues, Loop

Open wide! Chicago Restaurant Week is back with nearly 400 eateries offering dining deals from January 24 through February 9. For 17 belt-busting days, Chicagoans can cash in on special prix-fixe menus for brunch and lunch ($24) and dinner ($36 and/or $48). Use the culinary event as an excuse to revisit an old favorite or explore a splashy new opening. 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.

Snow winter
Photograph: Unsplash
Kids, Quirky events

Polar Adventure Days

Northerly Island, Museum Campus

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 the 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.

Giuseppe Porta. Bearded Man with his Right Arm Raised, 1562/64.
Photograph: The Art Institute of Chicago, gift of Richard and Mary L. Gray
Art, Drawing

“Pure Drawing: Seven Centuries of Art from the Gray Collection”

Art Institute of Chicago | Chicago, IL, Grant Park

Assembled from the collection of art dealer Richard Gray and his wife, the art historian Mary L. Gray, this exhibition of drawings spans 700 years of Western art. Visitors will be able to see work by artists like Vincent van Gogh, François Boucher and Giuseppe Porta, ranging from rough sketches of landscapes to intricate renderings of the human form.

Maxwell Street Market
Photograph: CC/Wikimedia Commons/Edsel Little
Shopping, Markets and fairs

Maxwell Street Market

Maxwell Street Market, West Loop

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on nearby Desplaines Street (between Roosevelt and Howard) every Sunday, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and ocassional performances by local bands and dance troupes. Don't let the cold or wet weather scare you away—the Maxwell Street Market takes place outdoors year-round.

Concerts in Chicago in January 2020

Iron and Wine
Photograph: Piper Ferguson
Music, Folk, country and blues

Iron & Wine + Calexico

Thalia Hall | Chicago, IL, Lower West Side

When Florida folk singer Sam Beam and Latin rock band Calexico teamed up on the In The Reins EP in 2005, the two acts struck gold by marrying Beam's gentle lyrics with grandiose pedal-steel-dappled arrangements. It's no surprise that Beam and Calexico got back together nearly a decade-and-a-half later to records a follow, Years to Burn, which showcases the evolution of both groups of artists. The collection of dusty folk ballads and slow burning rock numbers is another successful collaboration, playing to the strengths of both parties even if it doesn't exactly blaze any new territory. Local singer-songwriter Gia Margaret opens on January 29 and Los Angeles guitar virtuoso Madison Cunningham supports on January 30.

Smart Bar
Photograph: Courtesy Smart Bar
Music, Dance and electronic

Derrick Carter

Smart Bar, Wrigleyville

House music luminary Derrick Carter has been producing and spinning tracks in Chicago since the late ’80s, working behind the counter at DJ destination Gramaphone Records and becoming a Smart Bar resident along the way. Taking a break from his busy touring schedule in Europe (where house music is still a bona fide cultural phenomenon), Carter gets behind the decks for the entire evening on the final evening of January.

Makaya McCraven
Photograph: David Marques
Music, Jazz

Makaya McCraven

Symphony Center, Loop

Drummer and composer Makaya McCraven is the J Dilla of Chicago's jazz scene, but instead of chopping up his record collection and molding the samples into new beats, he uses tapes of improvised performances to craft taut grooves in the studio. On the heels of his 2018 album, Universal Beings, which found McCraven collaborating with a global cast of players, the bandleader makes his Symphony Center debut with the premiere of a new composition. Entitled "In These Times," the multimedia creation draws inspiration from black activists and musicians, performed with the support of an ensemble that includes Marquis Hill on trumpet, Junius Paul on bass and Greg Ward on saxophone.

Theater in Chicago in January 2020

Photograph: Lowell Thomas

Dance Nation

Steppenwolf Theatre Company, Lincoln Park

Caroline Neff, Tim Hopper, Audrey Francis and Karen Rodriguez star in this tale of a pre-teen dance group fighting for a spot in nationals in scenic Tampa Bay. Writer Clare Barron (You Got Older) calls for a multi-generational group of women to play the young protagonists, and director/choreographer Lee Sunday Evans promises to put them all through their paces.

Photographs: Courtesy About Face Theatre

The Gulf

Theater Wit, Lake View

Kendra and Betty are spending most of their fishing trip on the Alabama Delta arguing about their relationship and their regrets. And that’s before their boat breaks down, stranding them on open water. Megan Carney directs Kelli Simpkins and Deanna Meyer in this drama from writer Audrey Cefaly.

Photograph: Joe Mazza

The Mousetrap

Court Theatre, Hyde Park

If Knives Out got you hungry for a good old-fashioned murder mystery—one with plenty of twists and turns—then Court Theatre has you covered with this production of Agatha Christie’s renowned The Mousetrap. And in the hands of a theatrical mischief-maker like director Sean Graney, this production promises to be extra twisty. 

Photograph: Dan Gold via Unsplash

The Tasters

Rivendell Theatre, Edgewater

In Meghan Brown’s satirical thriller—directed here in its world premiere by Devon de Mayo—a rash of high-profile poisonings leads all top-tier government officials to employ “tasters.” When resistance leader Elyse is captured and forced to work as a taster, her captors have no idea what she’s got in store for them. 

Photograph: Joe Martinez


Theater Wit, Lake View

Two Cleveland police officers are falling deeply in love until the search for truth following an officer-involved shooting threatens to tear them apart. Leslie Ann Sheppard and Drew Schad star in this two-hander from playwright Kevin Artigue directed by Wardell Julius Clark for Shattered Globe Theatre.

Photograph: DJ Paine via Unsplash

Top Girls

Theater Wit, Lake View

Caryl Churchill’s Thatcher-era classic tackles issues surrounding feminism, ambition and capitalism in ways that have only grown more prescient in a post-Lean In world. Keira Fromm directs this theatrically daring, stone-cold brilliant script for Remy Bumppo Theatre Company with Linda Gillum in the starring role.

Steep Theatre Company
Photo: Grace Wiley

The Leopard Play, or sad songs for boys

Steep Theatre, Edgewater

In this thrilling, moving new play from beloved local playwright Isaac Gomez, a young man reckons with a violent history when he returns to his home along the border between the U.S. and Mexico to solve the mystery of his uncle’s disappearance. Laura Alcalá Baker directs this world premiere production for Steep Theatre. 

Photograph: Courtesy Goodman Theatre


Goodman Theatre | Chicago, IL, Loop

In Lisa Loomer’s Roe, the 1973 Supreme Court ruling that legalized abortion in the U.S. isn’t the end of the story—it’s the beginning. In following the twin stories of attorney Sarah Weddington and plaintiff Norma McCorvey, Roe traces how abortion access has become one of the most polarizing issues in a country that’s full of issues. 


Once On This Island

Cadillac Palace Theatre, Loop

A wager between the gods leads to an epic love story set amidst the tangled legacy of French colonialism in the Caribbean. Featuring a beautiful score from Ragtime composer Stephen Flaherty, this tour of the 2018 Tony winner for Best Revival of a Musical features American Idol alum Tamyra Gray as the villainous demon Papa Ge.

Photograph: Jordan Matter

The Adult in the Room

Victory Gardens Biograph Theater, Sheffield & DePaul

Haven’t had your fill of politics for the decade? This one-woman show chronicles the life and times of House Speaker Nancy Pelosi as she builds her career and shifts from achieving consensus to fighting the good partisan fight. Broadway actress Orlagh Cassidy stars as Pelosi in a script from Bill McMahon in a world premiere production at the Victory Gardens Richard Christiansen Theatre. 

How To Defend Yourself
Photograph: Todd Rosenberg Photography

How to Defend Yourself

Victory Gardens Biograph Theater, Sheffield & DePaul

In Liliana Padilla’s How to Defend Yourself, A self-defense class for seven college students turns into a crucible for female rage and a razor-edged inquiry into rape culture. This world premiere, helmed by Cambodian Rock Band director Marti Lyons, was developed as a part of  Victory Gardens Theater's 2018 Ignition Festival.