Want to know what’s happening this weekend in Chicago? Look no further. There’s a whole calendar of exciting events, exhibits, and activities taking place all over the city this month in Chicago.

A few of highlights this weekend include:

Check out just a few of the events and happening in Chicago this weekend, Oct. 2 – 4, 2026.

World Music Festival Chicago_Humboldt Park 2
Sept. 25 – Oct. 4
World Music Festival

The 26th annual World Music Festival is your passport to musical acts from across the globe.

This free, city-wide festival features artists from around the world at iconic venues around Chicago, including the Chicago Cultural Center and Humboldt Park.

Friday September 25, 2026 — Sunday October 4, 2026

Citywide

Lincoln Square Ravenswood Apple Fest 2026
Oct. 2 - 4
Lincoln Square Ravenswood Apple Fest 2026

The 39th Annual Apple Fest runs on N. Lincoln Avenue between W. Lawrence and W. Sunnyside Avenues in Lincoln Square. Hours are Friday, October 2,…

Oct. 2 - 4, 2026
Giddings Plaza in Lincoln Square
4733 N Lincoln Ave, Chicago, IL 60625
Commemorative Day | Latine Heritage Month
Oct. 3
Commemorative Day | Latine Heritage Month

Chicago History Museum marks Latine Heritage Month with a Commemorative Day on Saturday, October 3, from 11 a.m. to 3 p.m. The Museum invites visitors…

Saturday October 3, 2026
Chicago History Museum
1601 N. Clark St.
Maxwell Street
Oct. 4
Maxwell Street

Visitors to Maxwell Street will experience an eclectic mix of foods and finds—including handmade crafts, resale housewares, clothing, and much more.

Oct. 4, 2026
Maxwell Street
Halsted & Maxwell
Chicago Bears vs. New York Jets
Oct. 4
Sunday October 4, 2026
Soldier Field
1410 Special Olympics Drive
Creepy Cruise
Oct. 2 - 4
Creepy Cruise

From strange sightings to eerie haunts, mobsters and more, our latest nighttime tour takes you into Chicago's shadowy past. Cruise along the Chicago River as…

Oct. 2 - 4, 2026
Chicago’s First Lady Cruises
112 E Wacker Drive
16th Annual West Town Art Walk
Oct. 2 - 4
16th Annual West Town Art Walk

Celebrate Chicago’s creative community at the 16th Annual West Town Art Walk, a free, neighborhood-wide celebration featuring local artists, galleries, small businesses, music, food and…

Oct. 2 - 4, 2026
SAUCED Night Market
Oct. 2 - 3
SAUCED Night Market

The south side of Chicago is about to get a little saucier. On Friday and Saturday, October 2 and 3 from 5 to 10 p.m. at HOSTE (1857…

Oct. 2 - 3, 2026
HOSTE
1857 W 16th St
Operation Mincemeat: A New Musical
Oct. 2 - 4
Operation Mincemeat: A New Musical

How did a dead body, a fake love letter, and — of all people — Ian Fleming turn the tide of World War II? Olivier…

Sept. 30 - Oct. 11, 2026
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Fall Fest at Lincoln Park Zoo
Oct. 2 - 4
Fall Fest at Lincoln Park Zoo

Chicago’s favorite free and family-friendly festival is back at Lincoln Park Zoo for another season of harvest-time fun! From September through October, stop by the…

Sept. 25 – Nov. 1, 2026
The 5th Annual Latina Comedy Festival
Oct. 1 - 3
The 5th Annual Latina Comedy Festival

For five years running, the Latina Comedy Festival has done something the comedy industry doesn't do often often enough: handing the mic to Latina comedians…

Oct. 1 - 3, 2026
The Lincoln Lodge
2040 N Milwaukee Ave
Destinos: Chicago International Latino Theater Festival
Oct. 2 - 4
Destinos: Chicago International Latino Theater Festival

The 9th annual Destinos International Latino Theater Festival showcases Latino theatre companies from Chicago and across the country. Choose from a variety of works staged at some of the city’s top independent theatre venues.

Monday September 14, 2026 — Sunday October 11, 2026

Citywide

The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago Venues
Oct. 2 - 4
The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago Venues

Curious Theatre Branch, with co-producers Chicago Danztheater Ensemble, Chicago Dramatists and Labyrinth Club, are pleased to announce the 37th annual Rhinoceros Theater Festival, September 20…

Sept. 20 – Oct 26, 2026
Facility Theatre
1138 N California Ave, Chicago, IL, 60622
The Chicks – Taking The Long Way 20th Anniversary Tour
Oct. 3 - 4
The Chicks – Taking The Long Way 20th Anniversary Tour

The Chicks are performing live in Chicago for a special two-night stand on Saturday, October 3, 2026, and Sunday, October 4, 2026, as part of…

Oct. 3 - 4, 2026
Auditorium
50 East Ida B. Wells Drive
Chicago Horror Film Festival
Oct. 2 - 4
Chicago Horror Film Festival

The 28th Annual Chicago Horror Film Festival takes over Landmark’s Century Centre Cinema October 2–4, bringing 150+ independent horror films to two big movie theater…

Oct. 2 - 4, 2026
Landmark’s Century Centre Cinema
2828 N Clark St
Start Exploring Route 66
World Premiere of The Humanities
Oct. 2 - 4
World Premiere of The Humanities

The Humanities is a provocative play by Zayd Ayers Dohrn in which faculty and students at an elite American university grapple with issues of gender, race,…

Sunday September 13, 2026
Victory Gardens Theater
2433 N. Lincoln Ave.
Jekyll& Hyde
Oct. 2 - 4
Jekyll& Hyde

Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…

Sept. 8 – Nov. 8, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
BOO! at the Zoo
Oct. 3 - 4
BOO! at the Zoo

Get ready for a boo-tiful day of Halloween fun at BOO! at the Zoo, Brookfield Zoo Chicago's family-friendly fall tradition! Enjoy festive décor, not-so-scary surprises,…

Oct. 3 - 25, 2026
Brookfield Zoo Chicago
3300 Golf Rd

Explore our events calendar for more Chicago events and happenings.

Please note that all events are subject to change.