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, September 19, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Reeling Film Fest | Landmark Theatres | ||
| Chicago Architecture Biennial | FREE | ||
| 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 |
| 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 | |
| Jack's Pumpkin Pop Up | 4:00 pm to 11:00 pm | $22.00 | Goose Island |
| 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 |
| Bronzeville Art Trolley Tour | 6:00 pm to 9:00 pm | FREE | Southside Community Art Center |
| Englewood Jazz Fest | 6:00 pm to 8:00 pm | FREE | Hamilton Park Cultural Center |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Saturday, September 20, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Reeling Film Fest | Landmark Theatres | ||
| Chicago Architecture Biennial | FREE | ||
| Green City Market | 7:00 am to 1:00 pm | FREE | |
| Green City Market | 8:00 am to 1:00 pm | FREE | |
| Englewood Jazz Fest | 12:00 pm to 6:00 pm | FREE | Hamilton Park Cultural Center |
| Island Party Hut Fall Fest | 12:00 pm to 8:00 pm | $5.00 | Island Party Hut |
| West Loop Music & Art Fest | 12:00 pm to 10:00 pm | FREE | Fulton Market |
| Chicago Live! | 12:00 pm to 10:00 pm | FREE | Navy Pier |
| 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 |
| Jack's Pumpkin Pop Up | 4:00 pm to 11:00 pm | $22.00 | Goose Island |
| 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, September 21, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Reeling Film Fest | Landmark Theatres | ||
| Chicago Architecture Biennial | FREE | ||
| Glenwood Sunday Market | 9:00 am to 2:00 pm | FREE | |
| Andersonville Vintage Market | 10:00 am to 4:00 pm | FREE | Andersonville Vintage Market |
| Hyde Park Handmade | 11:00 am to 3:00 pm | FREE | The Promontory |
| Chicago Live! | 12:00 pm to 6:00 pm | FREE | Navy Pier |
| West Loop Art Fair | 12:00 pm to 10:00 pm | FREE | Fulton Market |
| Lincoln Park Blues and Gangster Tour | 2:00 pm to 4:00 pm | FREE | DePaul University |
| Jack's Pumpkin Pop Up | 4:00 pm to 11:00 pm | $22.00 | Goose Island |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Monday, September 22, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Reeling Film Fest | Landmark Theatres | ||
| Chicago Architecture Biennial | FREE | ||
| 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 | |
| Jack's Pumpkin Pop Up | 4:00 pm to 11:00 pm | $22.00 | Goose Island |
Tuesday, September 23, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Reeling Film Fest | Landmark Theatres | ||
| Chicago Architecture Biennial | FREE | ||
| 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 | |
| Jack's Pumpkin Pop Up | 4:00 pm to 11:00 pm | $22.00 | Goose Island |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
