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.
Today: Friday, September 18, 2026
Tomorrow: Saturday, September 19, 2026
Sunday, September 20, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| First Lady Cruise | All Day | Chicago Riverwalk The Marina | |
| Destinos Latino Theater Fest | National Museum of Mexican Art | ||
| Greektown Public Art Exhibit | |||
| Chicago Summer Free Museum Days | FREE | ||
| City News Cafe Free Concert Series | FREE | City News Cafe | |
| Maxwell Street Market | 10:00 am to 3:00 pm | FREE | Maxwell Street Market |
| World Dumpling Fest | 11:00 am to 8:00 pm | $10.00 | Wrightwood Park |
| Chicago Live! | 12:00 pm to 6:00 pm | FREE | Navy Pier |
| Retro on Roscoe | 12:00 pm to 8:00 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 |
| Movies at Gallagher Way | 6:00 pm to 10:00 pm | FREE | Gallagher Way |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Monday, September 21, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| First Lady Cruise | All Day | Chicago Riverwalk The Marina | |
| Destinos Latino Theater Fest | National Museum of Mexican Art | ||
| Greektown Public Art Exhibit | |||
| Chicago Summer Free Museum Days | FREE | ||
| Under The Picasso Noontimes | 10:30 am to 1:30 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 |
| Movies at Gallagher Way | 6:00 pm to 10:00 pm | FREE | Gallagher Way |
Tuesday, September 22, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| First Lady Cruise | All Day | Chicago Riverwalk The Marina | |
| Destinos Latino Theater Fest | National Museum of Mexican Art | ||
| Greektown Public Art Exhibit | |||
| Chicago Summer Free Museum Days | FREE | ||
| Free admission for Illinois residents | 10:00 am to 9:00 pm | FREE | Museum of Contemporary Art |
| Under The Picasso Noontimes | 10:30 am to 1:30 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 |
| Movies at Gallagher Way | 6:00 pm to 10:00 pm | FREE | Gallagher Way |
