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Upcoming Chicago Events

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Fourth Annual Pullman Railroad Days
May17
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Fourth Annual Pullman Railroad Days

Step into history at the Fourth Annual Pullman Railroad Days! The Fourth Annual Pullman Railroad Days is arriving May 17~18, 2025 with a station full…

Saturday, May 17th
10:00 a.m.5:00 p.m.
Pullman National Historic Park
614 E. 113th Street
Chicago Greeter InstaGreeter Walks of the Loop
May17

Chicago Greeter InstaGreeter Walks of the Loop

InstaGreeter Downtown walks Looking for a quick and easy way to see downtown Chicago’s top sights? Let InstaGreeter take you on a free hour-long guided…

Saturday, May 17th
11:30 a.m.1:00 p.m.
Meet at Chicago Cultural Center – Welcome Desk – Randolph St. Entrance
The End of Reality
May17
Theatre & Performing Arts

The End of Reality

“The End of Reality” is [Richard Maxwell’s] most eloquent statement to date on the blurring of despair and apathy in American lives. – Ben Brantley,…

Saturday, May 17th
3:00 p.m.5:00 p.m.
Theatre Y
3611 W Cermak Rd
The Jury Experience: An Immersive Courtroom Case
May17
Theatre & Performing Arts

The Jury Experience: An Immersive Courtroom Case

Step into the heart of a high-stakes trial with The Jury Experience in Chicago. In this live theater show, you are the jury—the power to deliver justice…

Saturday, May 17th
6:00 p.m.7:15 p.m.
Chopin Theatre
1543 West Division Street
Freedom From and Freedom To
May17
Music & Comedy, Theatre & Performing Arts

Freedom From and Freedom To

Freedom From and Freedom To is an exploration and celebration of artistic circumstance. Movement and sound improvisors from all around Chicago gather in front of…

Saturday, May 17th
7:00 p.m.8:30 p.m.
Links Hall
3111 North Western Avenue
The End of Reality
May17
Theatre & Performing Arts

The End of Reality

“The End of Reality” is [Richard Maxwell’s] most eloquent statement to date on the blurring of despair and apathy in American lives. – Ben Brantley,…

Saturday, May 17th
7:00 p.m.9:00 p.m.
Theatre Y
3611 W Cermak Rd
Wolff’s Flea Market Opening Day
May18
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, May 18th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Fourth Annual Pullman Railroad Days
May18
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Fourth Annual Pullman Railroad Days

Step into history at the Fourth Annual Pullman Railroad Days! The Fourth Annual Pullman Railroad Days is arriving May 17~18, 2025 with a station full…

Sunday, May 18th
10:00 a.m.5:00 p.m.
Pullman National Historic Park
614 E. 113th Street
Chicago Greeter InstaGreeter Walks of the Loop
May18

Chicago Greeter InstaGreeter Walks of the Loop

InstaGreeter Downtown walks Looking for a quick and easy way to see downtown Chicago’s top sights? Let InstaGreeter take you on a free hour-long guided…

Sunday, May 18th
11:30 a.m.1:00 p.m.
Meet at Chicago Cultural Center – Welcome Desk – Randolph St. Entrance
Spring Fun Fest at Parkway Bank Park
May18
Festivals, Fairs & Special Events

Spring Fun Fest at Parkway Bank Park

Families are invited to Parkway Bank Park on Sunday, May 18, from 1 p.m. to 5 p.m. for an afternoon of springtime fun with the…

Sunday, May 18th
1:00 p.m.5:00 p.m.
Parkway Bank Park Entertainment District
5501 Park Place
Stitching Stories: Quilting Trunk Treasures
May18
Museums, Galleries & Exhibitions

Stitching Stories: Quilting Trunk Treasures

A trunk show is a special presentation of quilts that honors the rich traditions, cultural significance, and artistic practices of quilting. In this intimate gathering,…

Sunday, May 18th
2:00 p.m.4:00 p.m.
Heritage Museum of Asian Art
3FL, 3500 S Morgan St, Chicago, IL, 60609
The End of Reality
May18
Theatre & Performing Arts

The End of Reality

“The End of Reality” is [Richard Maxwell’s] most eloquent statement to date on the blurring of despair and apathy in American lives. – Ben Brantley,…

Sunday, May 18th
3:00 p.m.5:00 p.m.
Theatre Y
3611 W Cermak Rd
The Farmer at The Green
May20
Festivals, Fairs & Special Events

The Farmer at The Green

The Farmer at The Green, presented by BMO, is a downtown Chicago farmers market. Shop for fresh, seasonal produce and locally made products from Chicago-based…

Tuesday, May 20th
11:00 a.m.3:00 p.m.
The Green at 320
320 S. Canal St.
Tuesday Good Show
May20
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, May 20th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Blue Hour
May21
Theatre & Performing Arts

Blue Hour

CONTACT: Marty McConnell, Blue Hour curator, marty@poetrycenter.org The Chicago Poetry Center invites you to this year’s final three editions of Blue Hour, voted “Chicago’s best…

Wednesday, May 21st
7:30 p.m.9:00 p.m.
Haymarket House
800 W. Buena Ave.
The End of Reality
May22
Theatre & Performing Arts

The End of Reality

“The End of Reality” is [Richard Maxwell’s] most eloquent statement to date on the blurring of despair and apathy in American lives. – Ben Brantley,…

Thursday, May 22nd
7:00 p.m.9:00 p.m.
Theatre Y
3611 W Cermak Rd
Chicago Greeter InstaGreeter Walks of the Riverwalk
May23

Chicago Greeter InstaGreeter Walks of the Riverwalk

Explore the Chicago Riverwalk with our knowledgeable volunteers! InstaGreeter walks take you on a free hour-long guided walk of the Riverwalk, without the need to…

Friday, May 23rd
11:30 a.m.1:00 p.m.
Vietnam Veteran’s Memorial
Chicago Greeter InstaGreeter Walks of the Loop
May23

Chicago Greeter InstaGreeter Walks of the Loop

InstaGreeter Downtown walks Looking for a quick and easy way to see downtown Chicago’s top sights? Let InstaGreeter take you on a free hour-long guided…

Friday, May 23rd
11:30 a.m.1:00 p.m.
Meet at Chicago Cultural Center – Welcome Desk – Randolph St. Entrance
Wicker Park Bucktown’s “First Fridays” Art Walk
May23
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, May 23rd
6:00 p.m.8:00 p.m.
Jackson Junge Gallery
1389 N Milwaukee Ave
Every Brilliant Thing
May23
Music & Comedy, Theatre & Performing Arts

Every Brilliant Thing

CIRCA Pintig, Chicago’s Filipino American theatre company in its 34th year, presents EVERY BRILLIANT THING, the groundbreaking one-performer play written by Duncan Macmillan with Jonny Donahue.…

Friday, May 23rd
7:00 p.m.8:30 p.m.
1332 W Irving Park Rd, Chicago, IL 60613
1332 W Irving Park Rd
Voila: The Improvised Musical
May23
Music & Comedy, Theatre & Performing Arts

Voila: The Improvised Musical

iO Chicago presents: a fully made-up, off-off-off Broadway style musical every Friday at 10pm in the Fremont Theater. Spend your Friday night with us. See…

Friday, May 23rd
10:00 p.m.11:30 p.m.
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
Chicago Greeter InstaGreeter Walks of the Riverwalk
May24

Chicago Greeter InstaGreeter Walks of the Riverwalk

Explore the Chicago Riverwalk with our knowledgeable volunteers! InstaGreeter walks take you on a free hour-long guided walk of the Riverwalk, without the need to…

Saturday, May 24th
11:30 a.m.1:00 p.m.
Vietnam Veteran’s Memorial
Chicago Greeter InstaGreeter Walks of the Loop
May24

Chicago Greeter InstaGreeter Walks of the Loop

InstaGreeter Downtown walks Looking for a quick and easy way to see downtown Chicago’s top sights? Let InstaGreeter take you on a free hour-long guided…

Saturday, May 24th
11:30 a.m.1:00 p.m.
Meet at Chicago Cultural Center – Welcome Desk – Randolph St. Entrance
Chicago Puzzle Club – 1-Year Anniversary Puzzle Party & Swap
May24
Festivals, Fairs & Special Events

Chicago Puzzle Club – 1-Year Anniversary Puzzle Party & Swap

Chicago Puzzle Club is a Chicago-based group with the mission to build and grow the puzzle community in and around Chicago. We host puzzle competitions…

Saturday, May 24th
11:30 a.m.4:00 p.m.
Chicago Hope Academy
2189 West Bowler Street
bean-night

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