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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

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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.

MillenniumSkating.venue.jpg
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.

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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

Trivia@Tony's

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.

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chi_fd_parsonschicken&fish_0715
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.

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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
Restaurants

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.

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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.

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

Chicago Polar Bear Plunge

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 cold the lake gets in January, so make sure that you bring something warm to wear (even if you're just there to watch).

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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.

Photograph: Nick Murway
Things to do, Festivals

Winter Brew

DANK Haus German American Cultural Center, Lincoln Square

Warm up during some of the coldest weeks of winter at the DANK Haus, where local breweries, cideries and distilleries will be serving their wares. Guests can attend one of two sessions and purchase tickets that can be redeemed for beer, cocktails and food provided by Fountainhead. Stick around for specialty tappings throughout the afternoon, including Half Acre's Benthic, Empirical's BRO.VALANCE and Temperance's Heaven Hill Barrel Aged Blueberry Maple Might Meets Right Imperial Stout.

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Time Out Chicago's Donut Party, June 12, 2016
Photograph: Jordan Avery
Things to do, Festivals

Donut Fest

The Chop Shop, Wicker Park

While fancy doughnuts are a bit played out at this point, Chicago still boasts some amazing purveyors of fried dough. The annual Donut Fest brings together some of the city's best shops (Roeser's Bakery, Stan's, Firecakes and Doughnut Vault) for an afternoon of sampling, accompanied by coffee from Dark Matter and La Colombe. With two sessions to choose from, you'll have to decide if you want an early-morning sugar rush or doughnuts for lunch.

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.

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Hallie Duesenberg
Things to do

Randolph Street Market Festival Pop-Up

Time Out Market Chicago, West Loop

Beloved vintage bazaar Randolph Street Market will host a pop-up installation at Time Out Market on January 25, offering guests a curated designer showcase packed with amazing finds—just in time for Valentine’s Day. Get some shopping done with a mimosa in hand before heading downstairs for lunch. Randolph Street Market returns to its usual outpost with 125 vendors at 1341 W Randolph Street on February 8 and 9.

Concerts in Chicago in January 2020

Photograph: Ryan Bourque
Music, Folk, country and blues

Buddy Guy

Buddy Guy's Legends, Loop

Most people call January "the first month of the year" or "three weeks of taking my resolutions seriously," but hardcore Chicago blues fans know that it's actually "Buddy Guy month." Throughout the entire 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 20-year-old Mississippi guitarist Kingfish, local singer Demetria Taylor and veteran singer-songwriter Jimmy Burns. 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 splurging for.

Chicago Sinfonietta MLK Tribute
Photograph: Jasmin Shah
Music, Classical and opera

Chicago Sinfonietta: MLK Tribute Concert

Symphony Center, Loop

Guest conductor Jonathan Rush leads a concert celebrating the life and work of Dr. Martin Luther King Jr., featuring The Voice semi-finalist Kymberli Joye and singers from three Chicagoland choruses. The stirring program includes an arrangement of Patty Griffin’s "Up to the Mountain," a rendition of John Legend and Common’s Academy Award-winning piece "Glory" from the film Selma and a performance of Mahler’s Symphony No.2 (Resurrection Symphony).

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Diane Coffee
Photograph: Alexa Viscius
Music, Rock and indie

Diane Coffee

Hideout, River West/West Town

A former child voice actor who played characters in animated series like Kim Possible and Lilo & Stitch: The Series, Shaun Fleming has tried on plenty of new identities through the albums he's released under the name Diane Coffee. After portraying King Herod in the Lyric Opera's production of Jesus Christ Superstar in 2018, Fleming entered the studio to write an album that deals with the anxieties of life in a digital age. On Internet Arms, Fleming approaches contemporary electro-pop music with the theatricality of his glam rock alter-ego, creating soaring synth-dappled anthems that recall the radio-friendly fare of Robyn and Lykke Li. Here, he headlines a two-night stand at the Hideout, where you might hear the debut of some new tunes.

CHAI
Photograph: Julien Kelly-Gross
Music, Rock and indie

CHAI + Bunny

Empty Bottle, Ukrainian Village

The four women who make up CHAI hail from Japan, often wear matching pink jumpsuits and have been known to hang out with gigantic Japanese pop stars like Kyary Pamyu Pamyu. But this quartet isn't belting out processed four-part harmonies atop layers of synthesizers—CHAI is a rock band on a mission. On its latest album, PUNK, the group speaks out against the homogenized, hyper-cute "kawaii" beauty culture of Japan, championing individuality and inclusivity atop disco beats and fuzzed-out basslines. Even if you don't understand enough Japanese to decipher every lyric, the spirit of empowerment in CHAI's rebellious anthems is palpable. Local rockers Bunny open the show.

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Wu-Tang Clan performs at The Congress Theater, 1/8/11
Photograph: Max Herman
Music, Rap, hip-hop and R&B

GZA

Concord Music Hall, Logan Square

Wu-Tang Clan member GZA—also known as "the Genius"—was the first member of the group to sign an individual record deal (his debut was aptly titled Words from the Genius), but he saved his most memorable tracks for his 1995 release, Liquid Swords. The album was part of the first wave of Wu-Tang solo records, layering GZA's agile lyricism atop the kung-fu movie excerpts and dusty soul samples of producer the RZA. Though he's toured behind the album extensively in recent years, his latest stop in Chicago will bring the 25-year-old songs to life with the help of a live band.

The Art Institute of Chicago.
Photograph: Courtesy Art Institute of Chicago
Music, Rock and indie

John Cale

Art Institute of Chicago | Chicago, IL, Grant Park

A founding member of the Velvet Underground who went on to dabble in straight-ahead rock, avant-garde composition and classical music, John Cale has a reputation as a daring musician and an adventurous producer. After working on music with contemporary artists like Field Music and Marissa Nadler, Cale recently revisited and reinterpreted his 1982 art rock opus, Music For a New Society. Cale's performance at the Art Institute coincides with the closing of the “From A to B and Back Again” exhibition, which explores the work of artist—and, briefly, the Velvet Underground's manager and producer—Andy Warhol.

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Death Cab For Cutie
Photograph: Michael J. Chen
Music, Rock and indie

Benjamin Gibbard + Tara Jane O'Neil

Thalia Hall | Chicago, IL, Lower West Side

After more than two decades, Washington outfit Death Cab For Cutie is still synonymous with the kind of dramatic, lovelorn indie-rock balladry that always seems to find its way into TV soundtracks. Expect to hear plenty of classic Death Cab tunes when Benjamin Gibbard brings his solo tour to Thalia Hall for three nights, performing songs from throughout his memorable catalog. And just because we're completists, we're also hoping to hear a few cuts from Gibbard's full-album cover of Teenage Fanclub’s 1991 power pop classic, Bandwagonesque. Experimental singer-songwriter Tara Jane O'Neils opens the show each night.

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.

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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
Theater

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.

Mean Girls
Photograph: Courtesy Joan Marcus
Theater, Musicals

Mean Girls

James M. Nederlander Theatre, Loop

After debuting on Broadway in 2018, the musical version of Tina Fey's high school comedy Mean Girls is going to try to make "fetch" happen in Chicago. The James M. Nederlander Theatre will host the touring production of the stage adaptation for a five-week engagement from December 25, 2019 to January 26, 2020. Boasting a book by Fey, the Mean Girls musical follows home-schooled teenager Cady Heron as she begins attending a high school in the Chicago suburbs and contends with Regina George, the most popular (and meanest) girl in her class.

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Photograph: Austin Oie Photography
Theater

Working

Theo Ubique Cabaret Theatre, Evanston

Six actors embody an entire city of workers in this musical adaptation of Studs Terkel’s landmark 1974 book. In addition to music from the composer behind Wicked and Godspell, this updated version also includes original songs from Lin-Manuel Miranda. Terkel is essential reading for all Chicagoans, and Working should be required viewing for all wannabe Chicago theatre fans.

Photographs: Courtesy About Face Theatre
Theater

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.

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Photograph: Joe Mazza
Theater

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
Theater

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. 

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Photograph: Joe Martinez
Theater

Sheepdog

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
Theater

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.

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Steep Theatre Company
Photo: Grace Wiley
Theater

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
Theater

Roe

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. 

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Theater

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
Theater

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. 

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How To Defend Yourself
Photograph: Todd Rosenberg Photography
Theater

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.

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