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, June 14, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| Old Town Art Fair | 10:00 am to 6:00 pm | FREE | Old Town Triangle Center |
| Andersonville Midsommerfest | 12:00 pm to 10:00 pm | FREE | |
| Puerto Rican Fest | 12:00 pm to 10:00 pm | Humboldt Park | |
| 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 |
| Grant Park Music Festival | 6:30 pm to 8:00 pm | FREE | Jay Pritzker Pavilion |
| ART on THE MART | 7:00 pm to 8:00 pm | FREE | Chicago Riverwalk The Marina |
Monday, June 15, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| 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 | |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| Millennium Park Summer Music Series | 6:30 pm to 9:00 pm | FREE | Jay Pritzker Pavilion |
| Grant Park Music Festival | 6:30 pm to 8:00 pm | FREE | Jay Pritzker Pavilion |
Tuesday, June 16, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| 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 | |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
| Grant Park Music Festival | 6:30 pm to 8:00 pm | FREE | Jay Pritzker Pavilion |
Wednesday, June 17, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| 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 | |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| 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 |
| Grant Park Music Festival | 6:30 pm to 8:00 pm | FREE | Jay Pritzker Pavilion |
| World Music Wednesdays | 7:30 pm to 9:30 pm | FREE | Old Town School of Folk Music |
| Summer Fireworks | 9:00 pm to 9:10 pm | FREE | Navy Pier |
Thursday, June 18, 2026
| Event | Time | Price | Location |
|---|---|---|---|
| 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 | |
| WInterland at Gallagher Way | 3:00 pm to 9:00 pm | FREE | Gallagher Way |
| Forte Happy Hour | 4:00 pm to 7:00 pm | $5.00-10.00 | Forte |
| Grant Park Music Festival | 6:30 pm to 8:00 pm | FREE | Jay Pritzker Pavilion |
| Millennium Park Summer Music Series | 6:30 pm to 9:00 pm | FREE | Jay Pritzker Pavilion |
| 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 |
