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, August 31, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Sicily Nights | All Day | Eataly | |
| Glenwood Sunday Market | 9:00 am to 2:00 pm | FREE | |
| Lincoln Park Blues and Gangster Tour | 2:00 pm to 4:00 pm | FREE | DePaul University |
| Live on the Lake | 3:00 pm to 9:30 pm | FREE | Navy Pier |
| Chicago Jazz Fest | 3:45 pm to 9:00 pm | FREE | Chicago Cultural Center |
Monday, September 1, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Under The Picasso Noontimes | 12:00 pm to 1:00 pm | FREE | Daley Plaza |
| Happy Hour | 3:00 pm to 6:00 pm | Canal Street Eatery |
Tuesday, September 2, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Free admission for Illinois residents | 10:00 am to 9:00 pm | FREE | Museum of Contemporary Art |
| Under The Picasso Noontimes | 12:00 pm to 1:00 pm | FREE | Daley Plaza |
| Happy Hour | 3:00 pm to 6:00 pm | Canal Street Eatery | |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
Wednesday, September 3, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Summerdance | FREE | Spirit of Music Garden | |
| Green City Market | 7:00 am to 1:00 pm | FREE | |
| Under The Picasso Noontimes | 12:00 pm to 1:00 pm | FREE | Daley Plaza |
| Andersonville Farmers Market | 3:00 pm to 7:00 pm | FREE | |
| Happy Hour | 3:00 pm to 6:00 pm | Canal Street Eatery | |
| 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 |
| World Music Wednesdays | 7:30 pm to 9:30 pm | FREE | Old Town School of Folk Music |
Thursday, September 4, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Summerdance | FREE | Spirit of Music Garden | |
| Under The Picasso Noontimes | 12:00 pm to 1:00 pm | FREE | Daley Plaza |
| 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 | |
| Wrigleyville Night Market | 4:00 pm to 8:00 pm | FREE | Gallagher Way |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
| Harper Court Summer Music Series | 6:00 pm to 9:00 pm | FREE | Harper Court |
| Vinyl Thursdays | 7:00 pm to 12:00 am | FREE | Hotel Zachary |
