What's Happening in Chicago This Week: January 20-26, 2026

Chicago has plenty of exciting events happening this week, January 20-26, 2026. Whether you're a local looking for entertainment or a traveler with a few hours to spend, here are the highlights you won't want to miss.

Theater & Performance Arts The Phantom of the Opera continues its run at the Cadillac Palace Theatre with performances throughout the week, including matinees on Wednesday and weekend shows. This timeless classic offers an unforgettable theatrical experience for both newcomers and longtime fans. Drama enthusiasts will appreciate the spectacular staging and world-class performances that have made this production a Chicago favorite.

Live Music & Concerts Music fans have excellent options this week. Glaive takes the stage at Metro on Wednesday, January 21 at 7 PM, bringing fresh indie rock energy to the venue. For a more intimate experience, Empty Bottle hosts Tarta Relena and Meara O'Reilly's Hockets for Two on Tuesday evening, showcasing local and emerging artists.

Comedy & Entertainment The Chicago Magic Lounge presents "The Showcase" on Monday, January 20 at 7 PM, featuring extraordinary illusions and mind-bending magic acts. Bookclub offers open mic night on Monday with Open Mic 018, providing a platform for comedians and performers to showcase their talent.

Travel Tips for Attendees For travelers flying into Chicago O'Hare to enjoy these events, consider the CTA Blue Line for convenient access from downtown venues. O'Hare is just 45 minutes from the Loop, making it easy to catch evening shows. Most venues are located in downtown Chicago, accessible via public transportation or rideshare services.

Plan your visit to Chicago and experience the city's vibrant cultural scene. Check venue websites for ticket availability and seating options before purchasing.