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.
Wednesday, September 16, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| 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 | |
| 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 |
| Movies at Gallagher Way | 6:00 pm to 10:00 pm | FREE | Gallagher Way |
Thursday, September 17, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Greektown Public Art Exhibit | |||
| Chicago Summer Free Museum Days | FREE | ||
| Under The Picasso Noontimes | 10:30 am to 1:30 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 | |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
| Englewood Jazz Fest | 5:30 pm to 8:00 pm | FREE | Hamilton Park Cultural Center |
| Movies at Gallagher Way | 6:00 pm to 10:00 pm | FREE | Gallagher Way |
| 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, September 18, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Greektown Public Art Exhibit | |||
| Chicago Summer Free Museum Days | FREE | ||
| Under The Picasso Noontimes | 10:30 am to 1:30 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 | |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
| Retro on Roscoe | 5:00 pm to 10:00 pm | FREE | |
| Bubbles & Beats Happy Hour | 5:00 pm to 7:00 pm | FREE | Hotel Zachary |
| Englewood Jazz Fest | 5:30 pm to 8:30 pm | FREE | Hamilton Park Cultural Center |
| Bronzeville Art Trolley Tour | 6:00 pm to 9:00 pm | FREE | Gallery Guichard |
| 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 |
Saturday, September 19, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Greektown Public Art Exhibit | |||
| Chicago Summer Free Museum Days | FREE | ||
| City News Cafe Free Concert Series | FREE | City News Cafe | |
| World Dumpling Fest | 11:00 am to 10:00 pm | $10.00 | Wrightwood Park |
| Englewood Jazz Fest | 12:00 pm to 6:00 pm | FREE | Hamilton Park Cultural Center |
| Retro on Roscoe | 12:00 pm to 10:00 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 |
| Hopewell Brewing Tour | 5:00 pm | $10.00 | Hopewell Brewing Co. |
| Englewood Jazz Fest | 5:30 pm to 8:30 pm | FREE | Hamilton Park Cultural Center |
| 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 |
Sunday, September 20, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| 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 |
| 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 |
| 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 |
