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.
Thursday, September 25, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| 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 | |
| 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 |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
| Vinyl Thursdays | 7:00 pm to 12:00 am | FREE | Hotel Zachary |
Friday, September 26, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| 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 |
| St. Alphonsus Oktoberfest Chicago | 5:00 pm to 10:00 pm | FREE | St. Alphonsus Church |
| Bubbles & Beats Happy Hour | 5:00 pm to 7:00 pm | FREE | Hotel Zachary |
| World Music Festival Chicago | 7:00 pm to 9:00 pm | FREE | Chicago Cultural Center |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Saturday, September 27, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Green City Market | 7:00 am to 1:00 pm | FREE | |
| Green City Market | 8:00 am to 1:00 pm | FREE | |
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| St. Alphonsus Oktoberfest | 12:00 pm to 10:00 pm | FREE | St. Alphonsus Church |
| Hyde Park Jazz Fest | 1:30 pm to 10:30 pm | 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 |
| 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 |
| World Music Festival Chicago | 7:00 pm to 9:00 pm | FREE | Chicago Cultural Center |
Sunday, September 28, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Glenwood Sunday Market | 9:00 am to 2:00 pm | FREE | |
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| St. Alphonsus Oktoberfest | 12:00 pm to 7:00 pm | FREE | St. Alphonsus Church |
| Hyde Park Jazz Fest | 2:00 pm to 6:00 pm | FREE | |
| 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 |
| World Music Festival Chicago | 7:00 pm to 9:00 pm | FREE | Chicago Cultural Center |
Monday, September 29, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| 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 |
| World Music Festival Chicago | 7:00 pm to 9:00 pm | FREE | Chicago Cultural Center |
