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.
Sunday, February 8, 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 |
| Chicago Theatre Week: Tickets $15 and $30 Tickets on sale | 10:00 am to 11:30 pm | Discounted | |
| 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, February 9, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Free things to do during Chicago Winter | All Day | FREE | |
| I-Hop Free Bottomless Pancakes | All Day | IHOP | |
| Ice Skating at Gallagher Way | Gallagher Way | ||
| Chicago Architecture Biennial | FREE | ||
| Chicago Theatre Week: Tickets $15 and $30 Tickets on sale | 10:00 am to 11:30 pm | Discounted | |
| 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, February 10, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Free things to do during Chicago Winter | All Day | FREE | |
| I-Hop Free Bottomless Pancakes | All Day | IHOP | |
| Ice Skating at Gallagher Way | Gallagher Way | ||
| Chicago Architecture Biennial | FREE | ||
| Chicago Theatre Week: Tickets $15 and $30 Tickets on sale | 10:00 am to 11:30 pm | Discounted | |
| Free admission for Illinois residents | 10:00 am to 9:00 pm | FREE | Museum of Contemporary Art |
| 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 |
Wednesday, February 11, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Free things to do during Chicago Winter | All Day | FREE | |
| I-Hop Free Bottomless Pancakes | All Day | IHOP | |
| Ice Skating at Gallagher Way | Gallagher Way | ||
| Chicago Architecture Biennial | FREE | ||
| Chicago Theatre Week: Tickets $15 and $30 Tickets on sale | 10:00 am to 11:30 pm | Discounted | |
| 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 |
| Adler at Night | 4:00 pm to 10:00 pm | FREE | Adler Planetarium |
| Free Live Jazz Shows | 5:00 pm to 8:30 pm | FREE | The Ritz Carlton Chicago |
Thursday, February 12, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Free things to do during Chicago Winter | All Day | FREE | |
| I-Hop Free Bottomless Pancakes | All Day | IHOP | |
| Ice Skating at Gallagher Way | Gallagher Way | ||
| Chicago Architecture Biennial | FREE | ||
| Chicago Theatre Week: Tickets $15 and $30 Tickets on sale | 10:00 am to 11:30 pm | Discounted | |
| Maggie Daley Park Ice Skating Ribbon | 11:00 am to 10:00 pm | FREE | Maggie Daley Park |
| Chicago Cultural Center Tours | 1:15 pm to 12:00 am | FREE | |
| Chicago RIverwalk and History Tour | 2:00 pm to 4:00 pm | FREE | Renaissance Chicago Downtown Hotel |
| 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 |
| Vinyl Thursdays | 7:00 pm to 12:00 am | FREE | Hotel Zachary |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
