October is here, and fall energy is in the air. Whether you’re into theatre, neighborhood runs, family fun, or wellness experiences, this month is full of reasons to get out and explore. We rounded up can’t-miss picks to help you make the most of the season. You’ll also find a few citywide gems to inspire adventures beyond the South Side.
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Big White Fog
Date: Wednesday, October 1st – Sunday, October 12th
Location: Court Theatre, 5535 S. Ellis, Chicago, IL, 60637
Cost: $10 Discount for Chicago Southsider readers, CODE: FogSouthsider
Learn more about the Big White Fog here.
Charting Imaginary Worlds Exhibit
Date: Thursday, October 2nd – December 12th
Location: Special Collections Research Center Exhibition Gallery, 1100 East 57th Street. Chicago, IL 60637
Cost: FREE
Learn more about the Charting Imaginary Worlds Exhibit here.
Gyotaku Impressions of the Sea
Date: Thursday, October 2nd
Location: 3500 S Morgan St, Chicago, IL, 60609
Cost: Varies
Learn more about the Gyotaku Impressions of the Sea Exhibit here.
The World Within: Chicago’s Original & Best Architecture Interiors Tour
Date: Friday, October 3rd
Location: Chicago Loop & River North, Chicago IL, 60654
Cost: Varies
Learn more about the Chicago’s Original & Best Architecture Interiors Tour here.
The Lion King
Date: Friday, October 3rd – Sunday, October 19th
Location: 151 W. Randolph St. , Chicago, IL, 60601
Cost: Varies
Learn more about the Lion King here.
Ear Taxi Festival
Date: Friday, October 3rd – Sunday, November 12th
Location: The Harris Theater for Music and Dance, 205 East Randolph Street, Chicago,60601
Cost: FREE
Learn more about the Ear Taxi Festival here.
Building Wealth Today For Tomorrow
Date: Saturday, October 4th
Location: UIC Forum – 1213 S. Halsted St. Chicago, IL 60607
Cost: FREE
Learn more about the Building Wealth Today For Tomorrow here.
2025 Bronzeville 5K Run/Walk
Date: Sunday, October 5th
Location: Lillian Armstrong Park, 4433 South St. Lawrence Ave. Chicago, IL 60653
Cost: FREE
Learn more about the Bronzeville 5K Run/Walk here.
Sullivan Fortner & His Galactic Friends
Date: Friday, October 10th
Location: Logan Center for the Arts – Performance Hall, 915 E 60th St, Chicago,60637
Cost: Varies
Learn more about the Sullivan Fortner & His Galactic Friends concert here.
SCP Jazz: Christian McBride & Brad Mehldau
Date: Friday, October 10th
Location: Chicago Symphony Center, 220 S Michigan Ave, Chicago, IL,60604
Cost: Varies
Learn more about the Christian McBride & Brad Mehldau concert here.
Escape the Museum at Griffin MSI
Date: Sunday, October 12th – Friday October 17th & October 24th
Location: Griffin Museum of Science and Industry, 5700 S DuSable Lake Shore Drive, Chicago,60637
Cost: Varies
Learn more about the Escape the Museum nights here.
61st St. Farmers Market
Date: Saturday, October 18th
Location: 1400 E. 61st Street
Learn more about the 61st St. Farmers Market here.
A Night In Bronze Fashion Showcase
Date: Saturday, October 18th
Location: CityPoint Loft, 4338 South Prairie Ave, Chicago, IL 60653
Cost: Varies
Learn more about the A Night In Bronze Fashion Showcase here.
Chicago Bears vs. New Orleans Saints
Date: Sunday, October 19th
Location: Soldier Field, 1410 Special Olympics Dr, Chicago, IL 60605
Cost: Varies
Learn more about the Chicago Bears vs. New Orleans Saints game here.
Under The Dome Concert
Date: Thursday, October 23rd
Location: Chicago Cultural Center, 78 E. Washington Street, Chicago, IL 60602
Cost: FREE
Learn more about the Under The Dome Concert here.
Upside Down Halloween Parade
Date: Saturday, October 25th
Location: Washington Park on Russell Drive
Cost: Free candy provided by MARS and FERRARA.
Learn more about the Upside Down Halloween Parade here.
61st St. Farmers Market
Date: Saturday, October 25th
Location: 1400 E. 61st Street, Chicago, IL 60637
Cost: FREE
Learn more about the 61st St. Farmers Market here.
The Boy is Mine Tour
Date: Saturday, October 25th
Location: Wintrust Arena at DePaul University, Chicago, IL
Cost: Varies
Learn more about the The Boy is Mine Concert featuring Brandy with Monica, Coco Jones, and Muni Long.
Chicago Blackhawks vs. Los Angeles Kings
Date: Sunday, October 26th
Location: United Center, 1901 W Madison St, Chicago, IL 60612
Cost: Varies
Learn more about the Chicago Blackhawks vs. Los Angeles Kings match here.
Chicago Blackhawks vs. Los Angeles Kings
Date: Sunday, October 26th
Location: United Center, 1901 W Madison St, Chicago, IL 60612
Cost: Varies
Learn more about the Chicago Blackhawks vs. Los Angeles Kings match here.
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