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, December 21, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Macy's Holiday Celebrations | FREE | Macy’s | |
| Music Box Christmas Sing a Long | Music Box Theatre | ||
| Chicago Architecture Biennial | FREE | ||
| Chistmas Around the World | 9:30 am to 5:30 pm | Museum of Science and Industry | |
| Lincoln Park Conservatory Winter Flower Show | 10:00 am to 3:00 pm | FREE | Lincoln Park Conservatory |
| Garlfiel Park Conservatory Holiday Flower Show | 10:00 am to 5:00 pm | FREE | Garfield Park Conservatory |
| Sky Rink | 10:00 am to 8:00 pm | FREE | Peninsula Chicago |
| Winter Wonderfest | 10:00 am to 10:00 pm | Navy Pier | |
| Hyde Park Handmade | 11:00 am to 3:00 pm | FREE | The Promontory |
| WInterland at Gallagher Way | 11:00 am to 7:00 pm | FREE | |
| Christkindlmarket Chicago | 11:00 am to 9:00 pm | FREE | Daley Plaza |
| Maggie Daley Park Ice Skating Ribbon | 11:00 am to 10:00 pm | FREE | Maggie Daley Park |
| CTA Holiday Train | 2:00 pm to 7:00 pm | $2.00 | |
| Lincoln Park Blues and Gangster Tour | 2:00 pm to 4:00 pm | FREE | DePaul University |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| Jack Frost Fulton Market | 4:00 pm to 10:00 pm | $21.00-66.00 | Fulton Market |
| Zoo Lights | 4:30 pm to 10:00 pm | $7.00 | Lincoln Park Zoo |
| Art on the Mart | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Monday, December 22, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Macy's Holiday Celebrations | FREE | Macy’s | |
| Chicago Architecture Biennial | FREE | ||
| Chistmas Around the World | 9:30 am to 5:30 pm | Museum of Science and Industry | |
| Winter Wonderfest | 10:00 am to 10:00 pm | Navy Pier | |
| WInterland at Gallagher Way | 11:00 am to 7:00 pm | FREE | |
| Christkindlmarket Chicago | 11:00 am to 9:00 pm | FREE | Daley Plaza |
| Maggie Daley Park Ice Skating Ribbon | 11:00 am to 10:00 pm | FREE | Maggie Daley Park |
| CTA Holiday Train | 2:00 pm to 7:00 pm | $2.00 | |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| Happy Hour | 3:00 pm to 6:00 pm | Canal Street Eatery | |
| Jack Frost Fulton Market | 4:00 pm to 10:00 pm | $21.00-66.00 | Fulton Market |
| Zoo Lights | 4:30 pm to 10:00 pm | $7.00 | Lincoln Park Zoo |
| Art on the Mart | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Tuesday, December 23, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Macy's Holiday Celebrations | FREE | Macy’s | |
| Chicago Architecture Biennial | FREE | ||
| Chistmas Around the World | 9:30 am to 5:30 pm | Museum of Science and Industry | |
| Winter Wonderfest | 10:00 am to 10:00 pm | Navy Pier | |
| Free admission for Illinois residents | 10:00 am to 9:00 pm | FREE | Museum of Contemporary Art |
| WInterland at Gallagher Way | 11:00 am to 7:00 pm | FREE | |
| Christkindlmarket Chicago | 11:00 am to 9:00 pm | FREE | Daley Plaza |
| Maggie Daley Park Ice Skating Ribbon | 11:00 am to 10:00 pm | FREE | Maggie Daley Park |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| Happy Hour | 3:00 pm to 6:00 pm | Canal Street Eatery | |
| Jack Frost Fulton Market | 4:00 pm to 10:00 pm | $21.00-66.00 | Fulton Market |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
| Zoo Lights | 4:30 pm to 10:00 pm | $7.00 | Lincoln Park Zoo |
| Art on the Mart | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Wednesday, December 24, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Macy's Holiday Celebrations | FREE | Macy’s | |
| Chicago Architecture Biennial | FREE | ||
| Chistmas Around the World | 9:30 am to 5:30 pm | Museum of Science and Industry | |
| Lincoln Park Conservatory Winter Flower Show | 10:00 am to 3:00 pm | FREE | Lincoln Park Conservatory |
| Garlfiel Park Conservatory Holiday Flower Show | 10:00 am to 5:00 pm | FREE | Garfield Park Conservatory |
| Winter Wonderfest | 10:00 am to 10:00 pm | Navy Pier | |
| WInterland at Gallagher Way | 11:00 am to 7:00 pm | FREE | |
| Christkindlmarket Chicago | 11:00 am to 9:00 pm | FREE | Daley Plaza |
| Maggie Daley Park Ice Skating Ribbon | 11:00 am to 10:00 pm | FREE | Maggie Daley Park |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| Happy Hour | 3:00 pm to 6:00 pm | Canal Street Eatery | |
| Jack Frost Fulton Market | 4:00 pm to 10:00 pm | $21.00-66.00 | Fulton Market |
| Adler at Night | 4:00 pm to 10:00 pm | FREE | Adler Planetarium |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
| Zoo Lights | 4:30 pm to 10:00 pm | $7.00 | Lincoln Park Zoo |
| Free Live Jazz Shows | 5:00 pm to 8:30 pm | FREE | The Ritz Carlton Chicago |
| Art on the Mart | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Thursday, December 25, 2025
| Event | Time | Price | Location |
|---|---|---|---|
| Chicago Architecture Biennial | FREE | ||
| Chistmas Around the World | 9:30 am to 5:30 pm | Museum of Science and Industry | |
| Lincoln Park Conservatory Winter Flower Show | 10:00 am to 3:00 pm | FREE | Lincoln Park Conservatory |
| Garlfiel Park Conservatory Holiday Flower Show | 10:00 am to 5:00 pm | FREE | Garfield Park Conservatory |
| Winter Wonderfest | 10:00 am to 10:00 pm | Navy Pier | |
| WInterland at Gallagher Way | 11:00 am to 7:00 pm | FREE | |
| Maggie Daley Park Ice Skating Ribbon | 11:00 am to 10:00 pm | FREE | Maggie Daley Park |
| 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 |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| Happy Hour | 3:00 pm to 6:00 pm | Canal Street Eatery | |
| Jack Frost Fulton Market | 4:00 pm to 10:00 pm | $21.00-66.00 | Fulton Market |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
| Zoo Lights | 4:30 pm to 10:00 pm | $7.00 | Lincoln Park Zoo |
| Art on the Mart | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
| 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 |
