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.
Saturday, October 25, 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 | |
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| Chicago Makers Summer Market | 11:00 am to 5:00 pm | $10.00 | Artifact Events |
| Slightly Spooky Saturday | 12:00 pm to 8:00 pm | FREE | Navy Pier |
| Island Party Hut Fall Fest | 12:00 pm to 8:00 pm | $5.00 | Island Party Hut |
| Pumpkin Party | 1:00 pm to 5:00 pm | FREE | Gallagher Way |
| 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 |
| Mexican Museum of Art Dia de los Muertos | 3:00 pm to 8:00 pm | FREE | National Museum of Mexican Art |
| 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 |
| Halloween Cruises with 312 Cruises | 8:00 pm to 11:00 pm | $20.00-35.00 | DuSable Harbor |
Sunday, October 26, 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 | ||
| Glenwood Sunday Market | 9:00 am to 2:00 pm | FREE | |
| Meet Me on Milwaukee | 10:00 am to 5:00 pm | FREE | |
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| Chicago Makers Summer Market | 11:00 am to 5:00 pm | $10.00 | 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, October 27, 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 | ||
| 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, October 28, 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 | ||
| Free admission for Illinois residents | 10:00 am to 9:00 pm | FREE | Museum of Contemporary Art |
| 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 |
Wednesday, October 29, 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 | |
| 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 |
| 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 |
| Ravenswood Costume Crawl | 5:30 pm to 8:30 pm | FREE | Teddy’s Ice Cream |
| World Music Wednesdays | 7:30 pm to 9:30 pm | FREE | Old Town School of Folk Music |
