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.
Friday, February 13, 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 | ||
| 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 |
| 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 |
| Lincoln Park Blues and Gangster Tour | 2:00 pm to 4:00 pm | FREE | DePaul University |
| 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 |
| Bubbles & Beats Happy Hour | 5:00 pm to 7:00 pm | FREE | Hotel Zachary |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Saturday, February 14, 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 | ||
| 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 |
| Chicago RIverwalk and History Tour | 2:00 pm to 4:00 pm | FREE | Renaissance Chicago Downtown Hotel |
| Lincoln Park Blues and Gangster Tour | 2:00 pm to 4:00 pm | FREE | DePaul University |
| Revolution Brewing Tours | 2:00 pm to 4:45 pm | $10.00 | Revolution Brewing |
| The Paper Machete | 3:00 pm to 5:00 pm | FREE | The Green Mill |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| Hopewell Brewing Tour | 5:00 pm | $10.00 | Hopewell Brewing Co. |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Sunday, February 15, 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 | ||
| 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 16, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Free things to do during Chicago Winter | All Day | FREE | |
| I-Hop Free Bottomless Pancakes | All Day | IHOP | |
| Chicago Architecture Biennial | FREE | ||
| Ice Skating at Gallagher Way | Gallagher Way | ||
| Chicago Auto Show | 10:00 am to 8:00 pm | Discounted | McCormick Place |
| 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 17, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Free things to do during Chicago Winter | All Day | FREE | |
| I-Hop Free Bottomless Pancakes | All Day | IHOP | |
| Chicago Architecture Biennial | FREE | ||
| 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 |
