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.
Friday, September 25, 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 | ||
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| 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 | |
| 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 | St. Alphonsus Church | |
| Bubbles & Beats Happy Hour | 5:00 pm to 7:00 pm | FREE | Hotel Zachary |
| Movies at Gallagher Way | 6:00 pm to 10:00 pm | FREE | Gallagher Way |
| 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 26, 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 | |
| Randolph Street Market | 10:00 am to 5:00 pm | $14.00 | Randolph Street Market |
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| St. Alphonsus Oktoberfest | 12:00 pm to 10:00 pm | St. Alphonsus Church | |
| Island Party Hut Fall Fest | 12:00 pm to 8:00 pm | $5.00 | Island Party Hut |
| Hyde Park Jazz Fest | 12:30 pm to 11:00 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 |
| 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. |
| Movies at Gallagher Way | 6:00 pm to 10:00 pm | FREE | Gallagher Way |
| 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 |
Sunday, September 27, 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 | |
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| Randolph Street Market | 10:00 am to 5:00 pm | $14.00 | Randolph Street Market |
| St. Alphonsus Oktoberfest | 12:00 pm to 7:00 pm | FREE | St. Alphonsus Church |
| Hyde Park Jazz Fest | 1:00 pm to 7:00 pm | FREE | |
| Lincoln Park Blues and Gangster Tour | 2:00 pm to 4:00 pm | FREE | DePaul University |
| Jazz N on the Steps | 4:00 pm to 6:00 pm | FREE | St. Moses The Black Parish |
| 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 |
| 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 |
Monday, September 28, 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 |
| Full Moon Jam | 6:00 pm to 10:00 pm | FREE | Chicago Full Moon Jam |
| Movies at Gallagher Way | 6:00 pm to 10:00 pm | FREE | Gallagher Way |
| World Music Festival Chicago | 7:00 pm to 9:00 pm | FREE | Chicago Cultural Center |
Tuesday, September 29, 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 |
| World Music Festival Chicago | 7:00 pm to 9:00 pm | FREE | Chicago Cultural Center |
