Looking for free events and discounts on events in Chicago? You're in the right place. Search our free & cheap Chicago events calendar for things to do and ways to have fun in the windy city. Look at upcoming events in list view, choose a specific date, or click on the month-view to see everything happening this month at a glance.
Don't forget to also check out our guide to what's free and cheap in Chicago this week, as well as some of our popular sections like Free Museum Days in Chicago, Half-Price Tickets to Chicago Entertainment, Things to Do with Kids in Chicago, and Chicago Restaurant Deals.
Today: Friday, January 23, 2026
Tomorrow: Saturday, January 24, 2026
Sunday, January 25, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Free things to do during Chicago Winter | All Day | FREE | |
| I-Hop Free Bottomless Pancakes | All Day | IHOP | |
| Chicago Restaurant Week | Discounted | ||
| Ice Skating at Gallagher Way | Gallagher Way | ||
| Chicago Architecture Biennial | FREE | ||
| Sky Rink | 10:00 am to 8:00 pm | FREE | Peninsula Chicago |
| Rudolph's Rooftop | 11:00 am to 12:00 am | FREE | LondonHouse Chicago |
| Chicago International Puppet Theater Festival | 11:00 am to 9:30 pm | FREE | Fine Arts Building |
| Maggie Daley Park Ice Skating Ribbon | 11:00 am to 10:00 pm | FREE | Maggie Daley Park |
| Lincoln Park Blues and Gangster Tour | 2:00 pm to 4:00 pm | FREE | DePaul University |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Monday, January 26, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Free things to do during Chicago Winter | All Day | FREE | |
| I-Hop Free Bottomless Pancakes | All Day | IHOP | |
| Chicago Restaurant Week | Discounted | ||
| Ice Skating at Gallagher Way | Gallagher Way | ||
| Chicago Architecture Biennial | FREE | ||
| Rudolph's Rooftop | 11:00 am to 12:00 am | FREE | LondonHouse Chicago |
| Chicago International Puppet Theater Festival | 11:00 am to 9:30 pm | FREE | Fine Arts Building |
| Maggie Daley Park Ice Skating Ribbon | 11:00 am to 10:00 pm | FREE | Maggie Daley Park |
| Happy Hour | 3:00 pm to 6:00 pm | Canal Street Eatery | |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
Tuesday, January 27, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Free things to do during Chicago Winter | All Day | FREE | |
| I-Hop Free Bottomless Pancakes | All Day | IHOP | |
| Chicago Restaurant Week | Discounted | ||
| Ice Skating at Gallagher Way | Gallagher Way | ||
| Chicago Architecture Biennial | FREE | ||
| Free admission for Illinois residents | 10:00 am to 9:00 pm | FREE | Museum of Contemporary Art |
| Chicago International Puppet Theater Festival | 11:00 am to 9:30 pm | FREE | Fine Arts Building |
| Maggie Daley Park Ice Skating Ribbon | 11:00 am to 10:00 pm | FREE | Maggie Daley Park |
| Happy Hour | 3:00 pm to 6:00 pm | Canal Street Eatery | |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
