January 1: New Year’s Boozy Brunch—The festivities don’t have to end just because the ball dropped at midnight. Continue celebrating the march into 2019 at Frontier’s New Year’s Boozy Brunch, where they’ll be serving up hair of the dog alongside brunch fixings until 5 pm.
January 2: Comedians You Should Know—It’s no secret that comedy is big in Chicago. Before they were world famous, comedians like Tina Fey and Steve Carell got started right here in the Windy City. See the next big things at Timothy O’Toole’s tonight with sets by Amy Shanker, Marty DeRosa, and other promising talent.
January 3: Buddy Guy—The undisputed king of Chicago Blues has seen it all and shared the stage with seemingly everyone from Howlin’ Wolf to The Rolling Stones. Tonight, he kicks off a month-long residency at his South Loop club, Legends. Don’t miss this rare opportunity to see one of the best bluesmen of all time in an intimate setting. Also January 4-27.
January 4: Kami—A central part of SAVEMONEY, the local hip-hop crew which holds artists such as Chance the Rapper and Vic Mensa in its ranks, the performer Kami takes over Thalia Hall in support of his breakthrough EP, “Very Slight.”
January 5: White Mystery—The red-headed rockers of White Mystery take a break from playing shows around the world with the likes of Iggy Pop and Patti Smith to play at the beloved Wrigleyville institution, Cubby Bear. Come on over and shake your hips to some of Chicago’s best garage rock.
January 6: Winter WonderFest—Chicago is famous for having brutal winters. Today is your last chance to escape the cold by going to Navy Pier where 170,000 square feet of heated indoor fun awaits you! Make memories with loved ones while taking a photo on a giant rocking horse. Hop on thrilling carnival rides such as hot cocoa cups that spin around and so much more at this festive winter fair. Also January 1-5.
January 7: Neapolitan Crèche—Today is the last day to take a peek and marvel at the intricate detail of the 18th-century Neapolitan creche, one of the few examples of this style of art outside of Naples. The piece, on display at the Art Institute, debuted in 2013 and features more than 200 figures staged inside a gorgeous Baroque cabinet. Because it’s so fragile due to its delicate silk and embroidery it can only be on view to the public a few weeks every year. Also January 1-6.
January 8: 80 Minutes Around the World—Curated by local storyteller, Nestor Gomez, “80 Minutes Around the World” debuts tonight at the Steppenwolf Theatre and features extraordinary reports from immigrants across the globe. Also January 9.
January 9: ASAP Rocky—The prolific rapper from Harlem stops by the Credit 1 Union Arena, formerly known as the UIC Pavillion, for an evening of psychedelic beats paired with well-crafted tales of a morally ambiguous pursuit of the American Dream.
January 10: Bowie Ball—Head to Boystown’s LGBTQ+ friendly bar, Berlin, to pay homage to the Starman at this annual event on his birthday. The soundtrack will include much of Bowie’s extensive body of work, while artists pay homage to the fashion of Bowie throughout the night with beloved Chicago nightlife queen Lucy Stoole as your mistress of ceremonies for the evening.
January 11: Cendrillon—Cinderella comes to life tonight at the Lyric Opera for the first of only three performances in January. With a romantically whimsical musical score by French composer Jules Massenet, and anchored by an enchanting performance by Australian soprano Siobhan Stagg as Cinderella, this baroque reimagining of the classic fairytale is an fabulous way to start your new year. Also January 17-20.
January 12: PAW Patrol Live!—Get the family together and go downtown to the Chicago Theatre for a delightful afternoon of cute pups saving the day with this stage production based on Nickelodeon’s hit TV show. Also January 13.
January 13: Vinyasa and Vino—Start your new year with a new you. Stop by City Winery in the West Loop for a lovely pairing of yoga and wine tastings that’ll strengthen your mind, body, soul and wine palate.
January 14: Chicago Sketch Comedy Festival—Head on over to Stage 773 in Lakeview for America’s largest festival dedicated to the art of sketch comedy that aims to be a melting pot of everything from award-winning international ensembles to emerging local upstarts. Also January 10-13 & 15-20.
January 15: Tarot Tuesdays—Still seeking clarity for the new year? Stop by Broken Shaker during its Tuesday Happy Hour and receive a gratis reading from Ancestral Method Tarot. Even if you don’t find the guidance you’re looking for, you can still enjoy one of the tasty beverages offered up at this downtown kitschy bar.
January 16: Charly Bliss—As part of the Tomorrow Never Knows annual tastemaker concert series, these Brooklyn-based art punks take over Lincoln Hall for a night of elegant power pop in support of their breakthrough album, “Guppy.”
January 17: Jen Kirkman—Cure those winter blues with a night of laughs as comedian Jen Kirkman stops by Thalia Hall. Kirkman, a New York Times bestselling author, has appeared on shows like “Chelsea Lately” and “The Late Show with Stephen Colbert,” has two Netflix specials under her belt, and also is a writer for the critically acclaimed Amazon show “The Marvelous Mrs. Maisel.”
January 18: The Heat: A Kitchen (R)evolution—The “bad boy” chef persona and crude, abrasive kitchen culture that has long been a part of the restaurant industry is seeing a shift as more women take charge of top dining destinations around the globe. From acclaimed American chef Anita Lo to Anne-Sophie Pic, the only three-Michelin starred female chef in France, this documentary shares the obstacles these women must overcome, fighting harassment and inequality as they change an industry from the inside. It makes its Chicago debut tonight at Facets Cinematheque. Also January 19-24.
January 19: Erykah Badu—Operating at the intersection of smooth jazz and R&B, Erykah Badu emerged in the late ‘90s as a leader of the neo-soul genre with deeply personal songs that explore both the beauty and struggle of being a woman of color. Tonight, she performs at the Aragon Ballroom for what will be an evening to remember.
January 20: Hyde Park Handmade—Stop by The Promontory in the stylish Hyde Park neighborhood for an afternoon of shopping for locally handcrafted candles, jewelry, artwork and everything your home needs to become the envy of your friends. Afterwards, head on downstairs and treat yourself to brunch with a menu that Bon Appetit has called a “gem.”
January 21: Minding the Gap—A top contender for the Oscar for Best Documentary, the winner of a prestigious award at Sundance and one of Barack Obama’s favorite films of 2018, “Minding the Gap” examines the uncertainty of young adulthood through the lens of teenage skateboarders in Rockford. An exclusive to Hulu, it stops by the Music Box Theatre for one night only. Come see what all the fuss is about.
January 22: Kinky Boots—Based on a 2005 British film, Kinky Boots tells the story of a struggling men’s shoe factory that finds a new and surprising (and much more glamorous) clientele after meeting Lola, a performer looking for sturdy stilettos offered in larger sizes. The stage adaptation includes music from pop diva Cyndi Lauper and garnered six Tony Awards, including best musical and best score. It plays at the Cadillac Palace Theatre. Also January 23-27.
January 23: La Ruta—Finding inspiration in the beauty and strength of women of color who work along the US/Mexico border, “La Ruta” uses live performances of song and dance to evoke protest marches and social change. It made its world debut last month at the Steppenwolf Theatre and it ends its critically acclaimed run this weekend. Also January 1-22, 25-27.
January 24: Mineral—Pioneers of emo and indie rock, Mineral broke up in in the early ‘90s. In recent years, they’ve become mythologized as modern artists such as Jimmy Eat World and The National have championed their work. Mineral are celebrating their 25th anniversary with new music and a rare tour that stops by Lincoln Hall tonight.
January 25: Mean Girls—To celebrate the 15th anniversary of the cult classic film, the Music Box is offering up a midnight screening. Lindsay Lohan stars as a transfer teen who leaves behind her life growing up in Africa with her zoologist parents to enter the jungle of an American high school. How fetch! Also January 26.
January 26: Winter Wine and Cheese Fest—To celebrate Eataly’s 12th global birthday, the culinary epicenter of all things Italian is hosting a tasting event of favorite wines and cheeses from their extensive collection. Admission gets you access to 15 wine and cheese pairings, a commemorative wine glass and holder, and a 10% off discount in Eataly’s marketplace so you can take home your favorites. Also January 25.
January 27: Donut Fest—If you’re looking for a serious sugar rush, head to Donut Fest at Chop Shop. Now in its sixth year, the festival brings together some of the best fried dough from across the city to battle it out for top spot. Local coffee is also included in the price of admission, a perfect pairing and an excellent choice for your Sunday breakfast plans.
January 28: Chicago Restaurant Week—The annual two-week event showcases exclusive menus and prix fixe steals at some of the best restaurants across the city. Diners can enjoy offerings (after making reservations) from acclaimed hot spots like Rick Bayless’ Lena Brava and Stephanie Izard’s Duck Duck Goat, or check out newcomers to this year’s events such as the much buzzed about BiXi Beer brewpub in Logan Square or cajun delights from Ina Mae in Wicker Park. Runs through February 7.
January 29: Rachael Yamagata—The self-proclaimed troubadour of heartbreak, and a former resident of the Second City, stops by City Winery to smooth over the crowd with her sultry, emotive voice. Yamagata kicks off her winter tour with two nights in Chicago before hitting the road in support of her recently released EP, “Porch Songs.” Also January 30.
January 30: Disney On Ice—Get the kids together and join Mickey Mouse, The Little Mermaid, Aladdin and so much more at United Center for a spellbinding afternoon of adventure filled with world-class ice skating and thrilling stunts that will delight the entire family. Runs through February 6.
January 31: Kacey Musgraves—The country crooner and Grammy Award-winning singer-songwriter stops by The Chicago Theatre during her Oh, What A World Tour. Expect a lot of heart and a little heartbreak from the “Space Cowboy” singer as she touches down in Chicago. Her fourth studio album, “Golden Hour,” was a critical darling that made many a best of 2018 lists and shot the songstress up the charts to claim her third number one debut.