January 2026 Chicago Events Guide

January in Chicago proves that winter doesn’t slow the city down — it simply brings a new lineup of experiences. From Broadway shows and Chicago Theatre Week ticket sales to stand-up comedy at Second City, live music, art exhibitions, and Chicago Restaurant Week, January 2026 is packed with events across Lincoln Park, Lakeview, and neighborhoods throughout the city.

This January 2026 Chicago events guide highlights the best things to do all month long, including theater, comedy, concerts, cultural exhibitions, culinary experiences, and family-friendly winter events. Organized by category and date, it’s designed to help you easily plan date nights, weekend outings, and everyday adventures in Chicago — even in the heart of winter.

🎤 Stories, Laughter & Live Performances

Now – FEB 1
The Phantom of the Opera
📍 Cadillac Palace Theatre — Broadway classic returns to Chicago.
🕚 Multiple showtimes daily

Tuesday, Jan 6, 2026
Chicago Theatre Week Tickets Go On Sale
🎟️ $15–$30 tickets for hundreds of Chicago shows
(The performances run in February, but planning starts now.)

Tuesday Jan 6, 13, 20
Ten Dollar Comedy Nights
📍 Second City
Low-cost stand-up showcases — great weeknight option.

Monday, Jan 12, 2026
Moth Hour: New Leaf | First-Timers
📍 The Den Theater | Wicker Park
🕚 7:00 PM (doors 6:00 PM)

Thursday, Jan 15, 2026
Taskmaster Live on Stage
📍 Riviera Theatre – Live version of the cult-favorite British comedy show.
🕕 7:30 PM
🎟️ Tickets: $848!!

Saturday, Jan 17, 2026
Brian Regan
📍 The Chicago Theatre
🕗 8:00 PM (doors 7:00 PM)

Monday, Jan 19, 2026
Crafting Character: The Costumes of Paul Tazewell
📍Kenneth C. Griffin Museum of Science and Industry
Academy Award winning designs.

Jan 21 – Feb 1
Chicago International Puppet Theater Festival
📍Multiple locations

Saturday, Jan 24 2026
❄️ Polar Adventure Day
📍 Northerly Island
Family-friendly winter fun: sled dogs, crafts, nature activities, cocoa
🕚 11:00 AM – 3:00 PM
🎟️ FREE

Jan 29 – Feb 1
The Roald Dahl Story Company & Chicago International Puppet Theater Festival present: Roald Dahl’s The Enormous Crocodile
📍The Studebaker Theater: Fine Arts Building
🕚 Multiple shows

🎨 Music, Art & Cultural Events

Now–Feb 22
Yoko Ono: Music of the Mind
📍 Museum of Contemporary Art (MCA) Chicago — Interactive and visionary retrospective.

Now – Jan 30, 2026
Buddy Guy takes up Residence for the month!
Buddy Guy’s Legends
🕚 Multiple days Thurs-Sun
🎟️$85-135, limit 4

Friday and Saturday Jan 9-10, 2026
Bill Murray & His Blood Brothers
📍Thalia Hall
🕚 8:00 PM (doors 7:00 PM)

Sunday, Jan 18, 2026
The Beatles – A Brunch Tribute with Phil Angotti and Nash String
📍City Winery | West Loop
🕚 Noon

🍷 Culinary & Lifestyle Classes

Friday, Jan 23 – FEB 8
🌟 Chicago Restaurant Week
Prix-fixe brunch, lunch & dinner menus at 500+ restaurants citywide
📍 Lincoln Park, Lakeview, West Loop, River North & beyond
🍽️ $30 brunch/lunch | $45–$60 dinner

Tuesday, Jan 27, 2026
L St Supper Club: French Decadence Edition
📍 Leavitt Street Inn & Tavern | Bucktown
🕚 Multiple times, starting at 5:45
🎟️ $125

🏃‍♀️ Fitness & Community Events

Monday, Jan 19, 2026 MLK Day
Commemorative Day | Martin Luther King Jr. Day
📍Chicago History Museum | Lincoln Park
🕚 10:00 AM – 4:00 PM

Sat, Jan 30, 2026
17th Annual F^3 Lake Half Marathon & 5k · Soldier Field
10:01 AM Half Marathon
10:28 AM 5 K

Chicago winter events are what make the season feel alive — and January 2026 offers no shortage of ways to experience the city. Whether you’re catching a Broadway show, laughing your way through a Second City performance, enjoying prix-fixe menus during Chicago Restaurant Week, or heading outdoors for Polar Adventure Day, there’s something for everyone this month.

If you love staying connected to what’s happening in Chicago — or you’re exploring new neighborhoods and imagining what life here could look like — I’d love to help. Subscribe to my newsletter for monthly Chicago event guides, neighborhood highlights, and local insights, or reach out anytime if you’re thinking about making a move within the city. Living in Chicago is about more than an address — it’s about enjoying everything the city has to offer.