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.
Wednesday, January 21, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Chicago Architecture Biennial | FREE | ||
| 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, January 22, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Chicago Architecture Biennial | FREE | ||
| 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 |
Friday, January 23, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Chicago Architecture Biennial | FREE | ||
| 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, January 24, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Chicago Architecture Biennial | FREE | ||
| 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, January 25, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Chicago Architecture Biennial | FREE | ||
| 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 |
