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.
Sunday, October 19, 2025
Event | Time | Price | Location |
---|---|---|---|
Destinos Latino Theater Fest | National Museum of Mexican Art | ||
Chicago Architecture Biennial | FREE | ||
Chicago Fashion Week | |||
Glenwood Sunday Market | 9:00 am to 2:00 pm | FREE | |
Andersonville Vintage Market | 10:00 am to 4:00 pm | FREE | Andersonville Vintage Market |
Fall Fest | 10:00 am to 5:00 pm | FREE | Lincoln Park Zoo |
Open House Chicago | 10:00 am to 5:00 pm | FREE | |
Festival del Arte popular | 10:00 am to 5:00 pm | FREE | National Museum of Mexican Art |
Hyde Park Handmade | 11:00 am to 3:00 pm | FREE | The Promontory |
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 20, 2025
Event | Time | Price | Location |
---|---|---|---|
Destinos Latino Theater Fest | National Museum of Mexican Art | ||
Chicago Architecture Biennial | 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 |
Tuesday, October 21, 2025
Event | Time | Price | Location |
---|---|---|---|
Destinos Latino Theater Fest | National Museum of Mexican Art | ||
Chicago Architecture Biennial | FREE | ||
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 22, 2025
Event | Time | Price | Location |
---|---|---|---|
Destinos Latino Theater Fest | National Museum of Mexican Art | ||
Chicago Architecture Biennial | FREE | ||
Green City Market | 7:00 am to 1:00 pm | FREE | |
Andersonville Farmers Market | 3:00 pm to 7:00 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 |
World Music Wednesdays | 7:30 pm to 9:30 pm | FREE | Old Town School of Folk Music |
Thursday, October 23, 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 | ||
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 |
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 |