1. Hop on
Take a festive ride aboard the CTA Holiday Train. Adorned with thousands of twinkling lights, seasonal images, garland and holiday trees, the holly-jolly train delivers food baskets to charitable agencies in addition to delivering you to your destination. To spread as much cheer as possible, the CTA deploys a second festive train – the Elves’ Workshop Train – on weekends to follow the holiday train.
More festive fun: check out the CTA Holiday Bus schedule here.
Details: The train runs 3-5:45 p.m. Wednesday and Friday; 3:50-6:40 p.m. Thursday; 12:50-8 p.m. Saturday along the Orange and Brown lines. Free with regular CTA rider fare. The Holiday Train continues on select dates/times through Dec. 23.
Scrambling to find gifts during the shorter-than-usual usual holiday shopping season? (Yes, it really is shorter this year, though it might not feel like it yet.) With more than 600 merchants showcasing their wares at the One of a Kind Holiday Show, you’re bound to find something for everyone on your nice list. Gift options range from sweet treats to self-care products to artwork and pet products.
Details: 11 a.m.-8 p.m. Thursday and Friday; 10 a.m.-7 p.m. Saturday; 10 a.m.-5 p.m. Sunday at the Mart, 222 W. Merchandise Mart Plaza. $12 (tickets good for all four days); free for kids age 12 and under / MAP
Children of all ages and abilities are the stars of the Dance-Along Nutcracker, where they twist, turn and plié to the familiar music of Tchaikovsky’s holiday classic performed by the Lakeside Pride Music Ensemble. Kiddos can learn ballet basics at 9 a.m. and noon from members of Ballet Chicago.
Details: Performances at 10 a.m. and 1 p.m. Sunday at the Chicago Cultural Center, Preston Bradley Hall, 78 E. Washington St. Free / MAP
A Candlelight Walk at the Oak Park Conservatory immerses you in the beauty of the season. Dress the little ones up for photos with Santa surrounded by poinsettias. Bring home a poinsettia of your own or other winter fauna from the Winter Greens Market. Holiday carolers, desserts and cocktails are also on tap.
Details: 6-8 p.m. Friday and Saturday at the Oak Park Conservatory, 615 Garfield St., Oak Park. $15; $10 for kids / MAP
Chicago teens share their hopes, fears and dreams as young city residents in “All I Want for Chicago Is…” Written by youth, the play explores issues of equity, colorism, sexual orientation, discrimination and gun violence. Following the show, audience members are invited to reflect on the themes explored by the artists and share their own experiences.
Details: 7 p.m. Saturday; 7 p.m. Dec. 13 and Dec. 14, 3 p.m. Dec. 15 at Flat Iron Art Building, Collaboraction Studios, 1579 N. Milwaukee Ave. / MAP
Hand-printed greeting cards, artist books and prints by more than 75 artists are among the handcrafted goods for sale at the International Small Print Show and Holiday Sale. Enjoy hot-spiced cider, snacks and cake while browsing.
Details: 11 a.m.-7 p.m. Saturday and Sunday at the Chicago Printmakers Collaborative, 4912 N. Western Ave. Free / MAP
Celebrate the season with your furry friend at Jingle Paws. Pups can get photos with Santa, hunt for treats and participate in a costume contest. (Prizes will be awarded for best dog-owner look-alike costume, best costume and best overall holiday costume.) All dogs must have up-to-date vaccinations, and vaccination records must be submitted during online registration or brought to the event.
Details: Noon-2 p.m. Saturday at the Meineke Recreation Center, 220 E. Weathersfield Way, Schaumburg. $2-$3; $5-$7 for dogs / MAP
Politicians caught misbehaving have made local and national headlines this year, and they serve as fodder for the musical comedy revue “For Lying Out Loud!” More than 50 Chicago Bar Association lawyers will sing and dance in musical skits lampooning politicians and public figures. Expect to see imitations of President Donald Trump, Gov. J.B. Pritzker, Mayor Lori Lightfoot and indicted aldermen.
Details: Shows at 7:30 p.m. Thursday-Saturday at DePaul University’s Merle Reskin Theatre, 60 E. Balbo Drive. $35-$45 / MAP
9. Be jolly
Ice-carving demonstrations, caroling and meet-and-greets with reindeer are a few of the festivities at Hyde Park Holly-Day. Photos with Santa and Mrs. Claus, a free screening of “Frozen 2,” holiday crafts and dance performances are also on tap.
Details: 10 a.m.-4 p.m. Saturday at various locations in Hyde Park, including Harper Court, 5235 S. Harper Court. Free / MAP
Dreamcatchers, clothing, beadwork and pottery by indigenous artists are among the works you’ll find at the Native American Fine Arts Holiday Market. Stop in the Mitchell Museum of the American Indian to talk with artists as they work (free with museum admission).
Details: 10 a.m.-5 p.m. Saturday; noon-4 p.m. Sunday at 3009 Central St., Evanston. Free / MAP
Events listed are subject to change. We recommend double-checking times and locations before you head out the door. Want to share your upcoming events with us for consideration in a future roundup? Send us an email.