THIS WEEKEND IN CHICAGO – Keeping the Magic of the Holiday Season Going!
Even though Christmas 2025 is officially in the books, we still have time to enjoy the many, various holiday events in Chicago. Here are a few unique holiday events that wrap up this weekend and a few that last an additional week. Join us in keeping the magic of the holiday season going!
Enjoy a newly revised production of Charles Dickens Begrudgingly Performs ‘A Christmas Carol’ Again this final Saturday (3 p.m. or 8 p.m.) or final Sunday (3 p.m.) at Theater Wit (1229 W. Belmont Ave.) in the Lakeview neighborhood. This show paints an intimate and slightly absurd portrait of the famous author Charles Dickens as he is once again booked to perform his popular Christmas tale just as he has every December since 1853. However, he might have other ideas. This production is recommended for ages 15+ and runs 95 minutes with no intermission. Perhaps you can create a charming new holiday tradition to share with family and friends!
Another of Theater Wit’s holiday hits has returned for its 5th year with Who’s Holiday! which is also wrapping up this weekend as well. The tot from The Grinch has grown — Cindy Lou Who, now 40, retells the story of the sordid events after meeting the Grinch from her trailer home in this adults-only romp. It’s been said that she’s cursing and drinking, super messy, and has had nothing but trouble after five years at the Wit. In fact, they fear she might make it a double. Why not come see for yourself if Cindy Lou does indeed make it a double!
Explore Chicago’s vibrant downtown, historic landmarks, cultural institutions and hidden gems all decked out for the holidays on a Big Bus Tours’ Hop-On, Hop-Off Tour through December 31 (10 a.m.-5 p.m.). Buses arrive every 20-30 minutes at Chicago Riverwalk (98 E. Wacker Dr.) in The Loop and last approximately two hours. In addition, their local guides have inside knowledge of what you should see and things you should do while on your hop-on, hop-off tour. It’s a great way to have fun and learn all about Chicago at the same time!
Take in an original play for young audiences at the Cornservatory (4210 N. Lincoln Ave.) in the North Center neighborhood as they present their newest show The Cozy Cabin Tales now through January 4, 2026. This series of wintry fables and folktales is told by a group of friends waiting out a snowstorm in their cabin with only a small fire to keep them warm as they pass the time by bringing their fantastical tales to life and learning some real-life lessons as well. These vignettes are a heartwarming way to spend even more time with your family this holiday season!
There’s no better way to celebrate the season than 103 stories above the city at Holidays at Skydeck now through January 4, 2026, at the Skydeck Chicago (233 S. Wacker Dr.) in The Loop. In addition to the spectacular views from the Skydeck, Willis Tower also sparkles with a dazzling holiday tree, appearances by a strolling Grinch, special surprise live performances from local entertainers, and a holiday market. Enjoy a festive celebration that’s warm, bright, and indoors!
Since our Bears will be in San Francisco taking on the 49ers this Sunday, here in Chicago the Chicago Bulls will take on the Milwaukee Bucks this Saturday (7 p.m.) and the Chicago Blackhawks will take on the Pittsburgh Penguins this Sunday (6 p.m.) at the United Center (1901 W. Madison St.) in the West Loop!
Sue Moss and Dean’s Team Chicago
