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Upcoming Chicago Events

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We’re Better Together Public Safety Community Fair
Sep27
Festivals, Fairs & Special Events

We’re Better Together Public Safety Community Fair

This exciting community fair brings together public safety professionals, city agencies, and neighbors to connect, learn about safety resources, experience hands-on demonstrations, engage in kid-friendly…

Saturday, September 27th
11:00 a.m.4:00 p.m.
City of Chicago Public Safety Headquarters
3510 S. Michigan Avenue
Musika SamaSama Filipino Festival 2025
Sep27
Festivals, Fairs & Special Events

Musika SamaSama Filipino Festival 2025

Chicago’s only Filipino Cultural Festival presented by Chicago Park District Date and time   Saturday, September 27 · 12 – 4pm CDT Location   Field…

Saturday, September 27th
12:00 p.m.4:00 p.m.
Field (Eugene) Park
5100 N. Ridgeway Ave.
Hubbard Haus Oktoberfest
Sep27
Festivals, Fairs & Special Events, Music & Comedy

Hubbard Haus Oktoberfest

Hubbard Street turns Bavarian for one unforgettable day. Hubbard Haus Oktoberfest takes over River North with steins, street eats, and Chicago nightlife at full throttle.…

Saturday, September 27th
12:00 p.m.9:00 p.m.
Hubbard Street between LaSalle & Clark
110 W Hubbard St
St. Helen Carnival
Sep27
Festivals, Fairs & Special Events

St. Helen Carnival

From September 25th-28th, Augusta Boulevard will be filled with rides, live music, and delicious food and drinks for this four-day event.

Saturday, September 27th
12:00 p.m.10:00 p.m.
2347 W Augusta Blvd, Chicago, IL 60622
2347 W Augusta Blvd
FashionBar The Shows: October 2025 – Designer Reveal
Sep27
Festivals, Fairs & Special Events, Theatre & Performing Arts

FashionBar The Shows: October 2025 – Designer Reveal

The opening event of FashionBar The Shows: October 2025, the Designer Reveal introduces all participating designers for the season. Each designer will present 1–2 looks,…

Saturday, September 27th
3:00 p.m.6:00 p.m.
Water Tower Place
835 N Michigan Ave
Goose Island 312 Block Party
Sep27
Festivals, Fairs & Special Events

Goose Island 312 Block Party

We’re BACK. Chicago’s favorite end-of-summer festival – the 312 Block Party – returns on Saturday, September 27th at the Goose Island Taproom, with performances by…

Saturday, September 27th
3:00 p.m.10:00 p.m.
Goose Island Taproom
1800 W. Fulton 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
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
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.
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.
Division Street Farmers Market
Oct1
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.

Wednesday, October 1st
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Division Street Farmers Market
Oct2
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.

Thursday, October 2nd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
FashionBar The Shows: October 2025 – Trans Media Fashion
Oct2
Festivals, Fairs & Special Events, Theatre & Performing Arts

FashionBar The Shows: October 2025 – Trans Media Fashion

Trans Media Fashion celebrates diversity, inclusion, and self-expression, with collections created to amplify LGBTQ voices through fashion. This runway experience blends identity and artistry with…

Thursday, October 2nd
6:00 p.m.9:00 p.m.
Water Tower Place
835 N Michigan Ave
Ear Taxi Festival
Oct3
Festivals, Fairs & Special Events

Ear Taxi Festival

The Ear Taxi Festival 2025, themed “The Composer’s Voice,” is a landmark event showcasing contemporary concert music across Chicagoland from October 3 through November 2,…

Friday, October 3rd
Division Street Farmers Market
Oct3
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.

Friday, October 3rd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Wicker Park Bucktown’s “First Fridays” Art Walk
Oct3
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Wicker Park Bucktown’s “First Fridays” Art Walk

The “First Fridays Art Walk,” organized by the Wicker Park Bucktown Chamber of Commerce, welcomes art enthusiasts to explore the neighborhoods’ vibrant arts scene. All…

Friday, October 3rd
6:00 p.m.8:00 p.m.
Jackson Junge Gallery
1389 N Milwaukee Ave
Ear Taxi Festival and Bella Voce present “Lost Objects”
Oct3
Festivals, Fairs & Special Events, Music & Comedy

Ear Taxi Festival and Bella Voce present “Lost Objects”

Bella Voce opens the 2025 Ear Taxi Festival with Lost Objects, a genre-defying oratorio by Bang on a Can founders Gordon, Wolfe, and Lang. Combining…

Friday, October 3rd
7:30 p.m.9:30 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Ear Taxi Festival
Oct4
Festivals, Fairs & Special Events

Ear Taxi Festival

The Ear Taxi Festival 2025, themed “The Composer’s Voice,” is a landmark event showcasing contemporary concert music across Chicagoland from October 3 through November 2,…

Saturday, October 4th
Division Street Farmers Market
Oct4
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.

Saturday, October 4th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Boo! at the Zoo
Oct4
Festivals, Fairs & Special Events

Boo! at the Zoo

Get ready for a fang-tastic time at BOO! at the Zoo, Brookfield Zoo Chicago’s family-friendly Halloween celebration. This event is packed with not-so-scary thrills, festive decorations,…

Saturday, October 4th
10:00 a.m.5:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
bean-night

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