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, October 30, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Destinos Latino Theater Fest | National Museum of Mexican Art | ||
| Chicago Architecture Biennial | FREE | ||
| First Lady Cruise | Chicago Riverwalk The Marina | ||
| 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 |
| The Other Art Fair | 6:00 pm to 10:00 pm | Artifact Events | |
| 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, October 31, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Destinos Latino Theater Fest | National Museum of Mexican Art | ||
| Chicago Architecture Biennial | FREE | ||
| First Lady Cruise | Chicago Riverwalk The Marina | ||
| 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 |
| The Other Art Fair | 5:00 pm to 10:00 pm | Discounted | Artifact Events |
| Bubbles & Beats Happy Hour | 5:00 pm to 7:00 pm | FREE | Hotel Zachary |
| Haunted Halsted Halloween Parade | 6:30 pm to 10:00 pm | FREE | |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Saturday, November 1, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Destinos Latino Theater Fest | National Museum of Mexican Art | ||
| Chicago Architecture Biennial | FREE | ||
| First Lady Cruise | Chicago Riverwalk The Marina | ||
| Green City Market | 7:00 am to 1:00 pm | FREE | |
| Green City Market | 8:00 am to 1:00 pm | FREE | |
| The Other Art Fair | 11:00 am to 7:00 pm | Discounted | Artifact Events |
| 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, November 2, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Destinos Latino Theater Fest | National Museum of Mexican Art | ||
| Chicago Architecture Biennial | FREE | ||
| First Lady Cruise | Chicago Riverwalk The Marina | ||
| The Other Art Fair | 11:00 am to 6:00 pm | Artifact Events | |
| 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, November 3, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Chicago Architecture Biennial | FREE | ||
| First Lady Cruise | Chicago Riverwalk The Marina | ||
| Happy Hour | 3:00 pm to 6:00 pm | Canal Street Eatery |
