December 1: CTA Holiday Train—Adorned in thousands of festive lights, the CTA Holiday Train returns for another year of merriment. This uniquely Chicago tradition started in 1992 when somebody placed a “Season’s Greetings” sign on a decommissioned Blue Line train and used it to deliver food to charities. Throughout the years, the spectacle has grown to include Santa, wreaths and reindeer, all while the CTA continues their mission of providing to the needy. This year, they plan to donate 500 food baskets to the less fortunate while supplying the city with Christmas joy. Try to find the holiday train on your route! Runs through December 21.
December 2: Death Cab For Cutie—The Washington-based indie rockers are performing tonight at the Aragon Ballroom in support of their new album, Thank You for Today. Lovelytheband and Elle King, whose hit single “Ex’s & Oh’s” steadily rose up the charts, get the night started.
December 3: Punch Drunk Soul Club—The always dapper Punch Drunk Soul Club takes over Punch House, located in the basement of Thalia Hall and Dusek’s in Pilsen, for a night of soul and funky sophistication. $5 punch specials help make this a night to remember.
December 4: Frosty’s: A Christmas Pop-Up—Located in the thick of River North, escape the ordinary and have a drink at this rowdy holiday-themed bar. The seasonal popup is full of ugly sweaters, sexy Santa hats and a jukebox of Christmas cheer that’ll keep the party going until 4 in the morning. Runs through January 5.
December 5: Peter Bjorn and John—The Swedish trio stops by Lincoln Hall to promote Darker Days, their eighth full-length album released in October. The latest release finds the band reflecting on a nearly two decade career, examining what it means to have longevity as a band. Despite the introspective tone, expect more of those fuzzy guitar pop riffs that helped skyrocket the band to success.
December 6: BrewLights—Lincoln Park Zoo has partnered with Goose Island, Founders, Sweetwater and several other prominent craft breweries to bring you BrewLights, an adults-only event where folks can cut loose and kick off the holiday season while surrounded by exotic animals and festive lights.
December 7: Krampus: A Haunted Christmas—The real nightmare before Christmas is a quick trip away in suburban Melrose Park. The notable 13th Floor Haunted House has transformed itself into an eerie winter wonderland reigned over by Krampus, the demonic beast of Christmas and his empire of evil elves. Also December 8.
December 8: One of A Kind Holiday Show —Full of vintage fashion and flair, the One of A Kind Holiday Show is your ultimate gift shopping destination for the holidays. The massive event takes over downtown Chicago’s Merchandise Mart with hip artwork and chic decor from more than 600 trendsetters from around the world. Also December 6-7 and 9.
December 9: Hanukkah Concert—Located a short Metra ride away in the northern suburb of Glencoe, Chicago Botanic Garden hosts a Hanukkah concert with festive music performed by the Maxwell Street Klezmer Band. Afterwards, explore the garden and lose yourself in greenhouses full of rare and wonderful plants.
December 10: Navy Pier Winter Wonderfest—Baby, it’s cold outside. Why don’t you go downtown to Navy Pier where 170,000 square feet of heated indoor fun awaits you instead? Make memories with loved ones while gazing at a 42-foot tall Christmas tree that has been expertly designed with sparkling lights. Take 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. Runs through January 6.
December 11: Pentatonix—The acclaimed a cappella group comes to the Rosemont Theatre for an evening of cool Christmas cheer. Expect creative renditions of classic holiday standards such as “Rockin’ Around the Christmas Tree” and “Here Comes Santa Claus” in addition to excellent covers of pop songs from artists such as Bruno Mars, Aaliyah and Demi Lovato. Also December 12.
December 12: Organic Beeswax Candle and Essential Oil Spray Class—This Christmas, make something special for your loved ones. Cafe at The Robey hosts an evening class that will teach you how to build beeswax candles and create essential oil based fragrance sprays to delight your friends and family this holiday season.
December 13: “A Christmas Carol”—An unforgettable tale that teaches the true meaning of the holiday season, Charles Dickens’ classic, “A Christmas Carol,” has become a tradition for audiences to enjoy for over 40 years. The classic story comes to life at the Goodman Theatre with heartwarming performances, joyful songs and impeccable stage production. Runs through December 30.
December 14: Caroling at Cloud Gate—Grab yourself a fresh brewed cup of hot cocoa and head downtown to Millennium Park to meet up with hundreds of fellow Chicagoans at Cloud Gate (commonly known as The Bean) for an evening of holiday caroling led by the Chicago Gay Men’s Chorus. Also December 7 and 12.
December 15: Greta Van Fleet—Raised on a musical diet of classic rock, Greta Van Fleet has a retro rock ‘n’ roll sound that is winning over some major fans. Robert Plant himself has given his Zeppelin seal of approval, saying that lead vocalist Josh Kiszka is “a beautiful little singer.” After winning over crowds at festivals like Lollapalooza, the Michigan-based band returns to Chicago to perform at the Aragon Ballroom. Come see what all the fuss is about. Also December 12 and 14.
December 16: Christmas Double Feature and Sing-A-Long—Now in its 35th year at the Music Box, the annual Chicago tradition pairs seasonal movie classics with joyful song. Santa Claus greets crowds at this popular event (snag tickets early) that runs weekends through December up until a last Christmas Eve showing. A live organist plays holiday carols while lyrics are projected on the theater’s screen, so no worries if you can’t remember all twelve days of Christmas.
December 17: South Side Salsa—Head down to Hyde Park and let the rhythm take control. Tonight, trendy Hyde Park nightclub The Promontory hosts a free dance lesson that’ll teach you how to do the salsa. Afterwards, put those caliente moves to work as their DJs play the very best in Latin dance all night long.
December 18: mySpa’s Luxury for Longer—Consider mySpa’s “Luxury for Longer” special after plodding along through Chicago winter. Through the end of the month, receive a complimentary upgrade to an 80-minute session with the booking of any full price 50-minute service. Double down by booking a seasonal treat like the indulgent cinnamon vanilla brown sugar body scrub. Check out mySpa’s website or contact them for booking information.
December 19: Amy Schumer—Amy Schumer brings her brand of unabashed comedy to a two-night run at the Chicago Theatre. Chicago has long been a city where Schumer has tested out new material at surprise shows during the holidays, so it wouldn’t be a shock if she pops up last-minute at a smaller club warming up before she takes the stage on State Street. Also December 20
December 20: Ice Skating at Gallagher Way—Ever since the Cubs won the World Series, Wrigleyville has transformed seemingly overnight. One of the newer attractions is ice skating at Gallagher Way, the park right outside of The Friendly Confines. Admission to the rink is only $5, but free for kids under 12. Runs through January 27.
December 21: Ski and Dine with Santa—You don’t need to go all the way to places like Colorado or Vermont to get in a good weekend of skiing! Adorned with 120 acres of picturesque snow with 23 trails, 7 lifts and a luxury resort, Wilmot Mountain is only a quick road trip away near the scenic Wisconsin border. This afternoon, Santa and Mrs. Claus will be at Wilmot bringing Christmastime joy to all the good boys and girls. After a long day of hitting the slopes, enjoy a glass of wine while enjoying dinner with Santa at Wilmot’s bistro.
December 22: Kurt Vile and The Violators—Garage rock king Kurt Vile stops by the Riviera Theatre during an international tour supporting the recent release of his album Bottle It In, which Vile recorded while on tour across the country and features contributions from the likes of Kim Gordon and Cass McCombs. Expect lots of fuzzy lo-fi guitar melodies to warm you up on a cold winter night.
December 23: The Chicago Symphony Orchestra's Merry, Merry Chicago!—Dive deeper into the holiday spirit with a Chicago institution as the CSO teams up with the Young Naperville Singers and vocalist Storm Large to perform a wide variety of classic Christmas favorites. Also December 22.
December 24: Christkindlmarket—A Chicago institution, Christkindlmarket is a month-long, open-air winter market located downtown in Daley Plaza (with locations in Milwaukee and Naperville as well) modeled after Germanic Christmas markets that date back to the mid-16th century. Today is your last chance to grab yourself a freshly cooked bratwurst, some goulash and a collectible mug of mulled wine while browsing through cuckoo clocks and everything you need to make your holiday season magical. Also December 1-23.
December 25: Halfway to Summer—It might be chilly outside but you can spend the day dreaming of warmer months at JCC Chicago’s annual event that starts the countdown to summer. The free party includes activities for the whole family, from indoor swimming to crafts and snacks. Halfway to Summer parties will be at both the Rogers Park and Northbrook Jewish Community Center locations.
December 26: Chicago Helicopter Tour—Now you can admire the city the same way Santa Claus does as you takeoff in a luxury helicopter that has been adorned in hundreds of festive holiday lights from a private heliport just south of the Loop. Marvel at downtown Chicago’s stunning architecture in a tour that’s guaranteed to bring joy to the holiday season. Runs through December 31.
December 27: Holiday Magic at Brookfield Zoo—Chicagoland’s largest and longest running lights festival celebrates its 37th year with over a million twinkling lights, caroling, skating, live ice carving and so much more holiday fun at the annual event. Enjoy massive light features and make sure to stop by and check out the 41-foot talking tree.
December 28: Trans-Siberian Orchestra—Arena rock energy meets holiday cheer when the Trans-Siberian Orchestra rolls into town. Since releasing Christmas Eve and Other Stories, their debut rock opera in 1996, the band has been putting their signature hard rock spin on Christmas classics. The band’s long-running theatrical light and stage show is a perfect way to kick out those last seasonal jams before December ends.
December 29: Noname—Blurring the lines between spoken word and hip-hop, Noname is an impressive lyricist who writes deeply personal poems that explore the uncertainty of young adulthood and are built on the foundations of cosmic jazz and neo-soul. Her newest album, Room 25, came out to critical acclaim this summer and she has spent much of the year travelling the world on tour. Tonight, Noname finally returns home for the first of three shows at Thalia Hall. Also December 30-31st.
December 30: The Nutcracker—It’s the last night to catch this reimagined holiday favorite performed by the Joffrey Ballet. In 2016, renowned choreographer Christopher Wheeldon took the beloved Nutcracker storyline and set it against the backdrop of the Chicago 1893 World’s Fair. Although the setting is different, the classic tale of a young girl setting off on a Christmas Eve adventure still rings true in this seasonal hit. Also December 1-29.
December 31: Mucca Pazza—Boogie into the new year with Mucca Pazza, a local marching band with punk rock flourishes that are sure to ring in 2019 in the most joyous way. Performing original music as well as pieces that cover a range of styles (from Bartok to Zappa, the band claims), the outfit is also backed up by a cheer squad. Live, the group is known for jumping into the crowd and joining the party on the dance floor, so get ready to cut a rug with a tuba or trombone at Lincoln Hall tonight.