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 30, 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 |
| 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 |
| World Music Festival Chicago | 7:00 pm to 9:00 pm | FREE | Chicago Cultural Center |
Thursday, October 1, 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 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 |
| World Music Festival Chicago | 7:00 pm to 9:00 pm | FREE | Chicago Cultural Center |
| 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 2, 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 | |||
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| 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 |
| Lincoln Square Apple Fest | 3:00 pm to 7:00 pm | FREE | |
| St. Benedict Oktoberfest | 3:00 pm to 10:00 pm | St. Benedict Parish | |
| 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 |
| Bubbles & Beats Happy Hour | 5:00 pm to 7:00 pm | FREE | Hotel Zachary |
| 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 |
| B.A.D Waves Remix | 7:00 pm to 9:30 pm | $5.00-14.00 | Redline VR |
Saturday, October 3, 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 | |||
| City News Cafe Free Concert Series | FREE | City News Cafe | |
| Lincoln Square Ravenswood Apple Fest | 9:00 am to 6:00 pm | FREE | |
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| Island Party Hut Fall Fest | 12:00 pm to 8:00 pm | $5.00 | Island Party Hut |
| St. Benedict Oktoberfest | 1:00 pm to 10:00 pm | St. Benedict Parish | |
| 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. |
| 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, October 4, 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 | |||
| City News Cafe Free Concert Series | FREE | City News Cafe | |
| Lincoln Square Ravenswood Apple Fest | 9:00 am to 6:00 pm | FREE | |
| Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
| St. Benedict Oktoberfest | 1:00 pm to 7:00 pm | St. Benedict Parish | |
| 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 |
| 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 |
