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Upcoming Chicago Events

Check out what's happening all around Chicago.

Chicago Pizza Pass
Aug6
Dec31
Festivals, Fairs & Special Events

Chicago Pizza Pass

Say hello to the Choose Chicago Pizza Pass — your ticket to exploring the city’s iconic pizza scene one slice at a time. Choose Chicago…

Wednesday, August 6th
5:00 p.m.Wednesday, December 31st
7:00 p.m.
City wide
Chicago Gourmet
Sep25
Sep28
Festivals, Fairs & Special Events

Chicago Gourmet

Guests, start your appetites! One of the nation’s top food festivals, Chicago Gourmet, powered by Invesco QQQ, is hitting the field this fall for the…

Thursday, September 25th
6:00 p.m.Sunday, September 28th
3:00 p.m.
Millennium Park
201 E Randolph St
Czech Heritage Week 2025
Sep28
Festivals, Fairs & Special Events, Theatre & Performing Arts

Czech Heritage Week 2025

A vibrant celebration of Czech culture in Chicago! From September 20 to 28, 2025, a wide variety of Czech-themed events will take place across the…

Sunday, September 28th
Chicago
Wolff’s Flea Market Opening Day
Sep28
Festivals, Fairs & Special Events

Wolff’s Flea Market Opening Day

Wolff’s Flea Market announces opening day April 20, 2025. Join us for our 34th season outdoors at the Allstate Arena, Rosemont. Sundays 6am-2pm through October…

Sunday, September 28th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Division Street Farmers Market
Sep28
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Sunday, September 28th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Glenwood Sunday Market in Rogers Park
Sep28
Festivals, Fairs & Special Events

Glenwood Sunday Market in Rogers Park

The nonprofit Rogers Park Business Alliance (RPBA) announces 23 local vendors for the 16th anniversary season of the Glenwood Sunday Market, which will operate every…

Sunday, September 28th
9:00 a.m.2:00 p.m.
Glenwood Alfresco
Aladerri International Film Festival
Sep28
Festivals, Fairs & Special Events

Aladerri International Film Festival

Aladerri International Film Festival (AIFF) is dedicated to the celebration of ‘Short Films’ a multi-day event in Chicago supporting filmmakers and giving them an opportunity…

Sunday, September 28th
10:00 a.m.8:00 p.m.
Facets Cinema
1517 W. Fullerton
23rd Annual St. Alphonsus Oktoberfest Chicago
Sep28
Festivals, Fairs & Special Events

23rd Annual St. Alphonsus Oktoberfest Chicago

Put on your Dirndls and your Lederhosen and polka on down to St. Alphonsus Oktoberfest in Chicago. It will be held Friday, Sept. 26  through…

Sunday, September 28th
12:00 p.m.7:00 p.m.
1429 W. Wellington Ave in Chicago.
1429 W. Wellington Ave
Chicago a cappella Presents Cantaré
Sep28
Music & Comedy

Chicago a cappella Presents Cantaré

Pack your (musical) bags! We’re heading to Mexico with songs commissioned through our ¡Cantaré! program, showcasing the vibrant voices of this beautiful country. Through music, you’ll discover…

Sunday, September 28th
3:00 p.m.4:30 p.m.
Nichols Concert Hall, Music Institute of Chicago
1490 Chicago Avenue
Chicago Symphony Orchestra: Ravel Piano Concertos & Suite from Carmen
Sep28
Music & Comedy, Theatre & Performing Arts

Chicago Symphony Orchestra: Ravel Piano Concertos & Suite from Carmen

Overview Ravel’s jazz-fueled Piano Concerto in G Major fits Alice Sara Ott “like a custom suit,” raves The New York Times. Ott presents the glittering score…

Sunday, September 28th
3:00 p.m.5:00 p.m.
Chicago Symphony Center
220 S Michigan Ave
Oktoberfest Biergarten Party w/ The Polkaholics
Sep28
Festivals, Fairs & Special Events

Oktoberfest Biergarten Party w/ The Polkaholics

Oktoberfest Biergarten Party at The Dawson Sunday, September 28 | 3–6PM Celebrate Oktoberfest in The Dawson’s Biergarten with an afternoon of beer, bites, and live…

Sunday, September 28th
3:00 p.m.6:00 p.m.
The Dawson
730 W Grand Ave
Barbara Smith & Friends pres. “Off to Paris”, Feat. Various Performers Paris Cabaret Concert Preview
Sep28
Music & Comedy

Barbara Smith & Friends pres. “Off to Paris”, Feat. Various Performers Paris Cabaret Concert Preview

Get ready to be transported to Paris with a delightful preview of Chicago cabaret performers Barbara Smith and Friends’ upcoming concert performance! This event promises…

Sunday, September 28th
4:00 p.m.6:00 p.m.
Copernicus Center
5216 West Lawrence Avenue
Shakin’ it Show 9 Year Anniversary Burlesque Cabaret
Sep28
Music & Comedy, Theatre & Performing Arts

Shakin’ it Show 9 Year Anniversary Burlesque Cabaret

Join Aunt Nance, Chicago’s Musical Comedy Cougar, as she celebrates NINE years of her silly + sensual burlesque cabaret, The Shakin’ it Show at Lakeview’s…

Sunday, September 28th
6:00 p.m.8:00 p.m.
The Newport Theater
956 West Newport Avenue
Embarrassed by Night – Vietnamese-American comedy show
Sep28
Museums, Galleries & Exhibitions, Music & Comedy, Theatre & Performing Arts

Embarrassed by Night – Vietnamese-American comedy show

The Foundation fos Asian American Media and HAIBAYO proudly present an night of humor and healing, with an exclusive screening of the documentary The Empathizer…

Sunday, September 28th
6:00 p.m.9:00 p.m.
Haibayo
1132 W Argyle St
Country Cruisin’ with Colt Ford
Sep28
Music & Comedy, Tours & Attractions

Country Cruisin’ with Colt Ford

Colt Ford, the Southern star blending country sounds with rap grit, is bringing a hard-hitting performance to Lake Michigan with City Cruises Live. Forget the…

Sunday, September 28th
6:00 p.m.10:00 p.m.
City Cruises Chicago – Navy Pier
600 E Grand Ave
Wheel of Improv
Sep28
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday, September 28th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Division Street Farmers Market
Sep29
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Monday, September 29th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Garbage – Happy Endings Tour
Sep29
Music & Comedy

Garbage – Happy Endings Tour

Multi-Platinum rockers Garbage will perform live at The Salt Shed Indoors on Sep. 29, 2025 /w special guests Starcrawler.

Monday, September 29th
7:00 p.m.10:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
The Late Nite Mic at The Comedy Bar
Sep29
Music & Comedy

The Late Nite Mic at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Vik Pandya is a nationally touring…

Monday, September 29th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
REDACTED: A League of Their Own
Sep29
Music & Comedy, Theatre & Performing Arts

REDACTED: A League of Their Own

Monday, September 29 312unes Presents REDACTED: A League of Their Own written by Allison Shoemaker Suggested Donation at Door / 21 & Over / Doors:…

Monday, September 29th
7:30 p.m.9:30 p.m.
GMan Tavern
3740 N Clark St
Ludovico Einaudi – The Summer Portraits Tour
Sep29
Music & Comedy

Ludovico Einaudi – The Summer Portraits Tour

Pianist and composer Ludovico Einaudi has announced a 2025 North American fall tour, including stops in New York, Los Angeles, Toronto, and Chicago.

Monday, September 29th
7:30 p.m.10:30 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Division Street Farmers Market
Sep30
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Tuesday, September 30th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Tuesday Good Show
Sep30
Music & Comedy

Tuesday Good Show

Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…

Tuesday, September 30th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Tomato Throw Show
Sep30
Music & Comedy

Tomato Throw Show

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Join us for the most fun…

Tuesday, September 30th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
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