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Upcoming Chicago Events

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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.
Chicago Skyline Sail – Escape the City Hustle
May20
Tours & Attractions

Chicago Skyline Sail – Escape the City Hustle

Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…

Tuesday, May 20th
1:00 p.m.2:15 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
Chicago Skyline Sail – Escape the City Hustle
May20
Tours & Attractions

Chicago Skyline Sail – Escape the City Hustle

Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…

Tuesday, May 20th
3:00 p.m.4:15 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
90 Minute Architecture River Tour in Chicago
May20
Tours & Attractions

90 Minute Architecture River Tour in Chicago

Experience Chicago’s Best 90-Min Architecture Boat Tour starting May 3, 2025! Led by expert tour guides, this is perfect for all ages. Explore the city’s…

Tuesday, May 20th
5:00 p.m.7:00 p.m.
Summer Of George, 900 South Wells Street, Chicago, United States
Summer Of George, 900 South Wells Street, Chicago, United States
Flamenco and Fondue
May20
Festivals, Fairs & Special Events, Music & Comedy

Flamenco and Fondue

Celebrating 60 Years of Flamenco Guitarists and Fondue Dining! Get ready for an incredible evening of Flamenco and Fondue. Gather your friends and family at Geja’s Cafe on Tuesday,…

Tuesday, May 20th
6:00 p.m.9:00 p.m.
Geja’s Cafe
340 W Armitage Ave
Chicago White Sox vs. Seattle Mariners
May20
Tuesday, May 20th
6:40 p.m.9:00 p.m.
Guaranteed Rate Field
333 W 35th St
Titanique
May20
Theatre & Performing Arts

Titanique

Broadway In Chicago presents the Porchlight Music Theatre production of TITANIQUE All aboard NYC’s must-sea musical comedy! When the music of Céline Dion makes sweet Canadian…

Tuesday, May 20th
7:00 p.m.8:40 p.m.
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Shrek Trivia Night – Snakes & Lattes
May20
Festivals, Fairs & Special Events

Shrek Trivia Night – Snakes & Lattes

SomeBODY once told me there’s Shrek Trivia Night coming to Snakes & Lattes Chicago on May 20th! Get ready to dive into the swamp of Shrek knowledge. Get your tickets…

Tuesday, May 20th
7:00 p.m.9:00 p.m.
Snakes & Lattes Chicago
1965 N. Milwaukee Avenue
Big Bus Tours’ Sunset Live Tour
May20
Tours & Attractions

Big Bus Tours’ Sunset Live Tour

Big Bus Tours, the global leader in open-top bus sightseeing, invites visitors to experience the enhanced Sunset Live Tour in Chicago. Available May 8 through…

Tuesday, May 20th
7:30 p.m.9:00 p.m.
618 N Clark St.
618 N. Clark St
Tomato Throw Show at The Comedy Bar
May20
Music & Comedy

Tomato Throw Show at The Comedy Bar

Join us for the most fun interactive comedy show in Chicago, where the audience determines who’s the funniest (and the most unfunny) by throwing [fake]…

Tuesday, May 20th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Marriott Theatre Presents: Titanic The Musical
May21
Theatre & Performing Arts

Marriott Theatre Presents: Titanic The Musical

Chicagoland’s longest running musical theatre, Marriott Theatre, continues its 50th Anniversary Season celebration with the epic production of Titanic The Musical, directed and choreographed by…

Wednesday, May 21st
Marriott Theatre
10 Marriott Dr.
Division Street Farmers Market
May21
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, May 21st
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Seeing Connections: The Art of Richard Penn
May21
Museums, Galleries & Exhibitions

Seeing Connections: The Art of Richard Penn

Inspiration for art can come from many sources. Retired University of Chicago Medicine neurosurgeon and artist Richard Penn finds inspiration in nature, philosophy, science, and…

Wednesday, May 21st
9:00 a.m.4:45 p.m.
Special Collections Research Center Exhibition Gallery
1100 East 57th Street
Dressed in History: A Costume Collection Retrospective
May21
Museums, Galleries & Exhibitions, Tours & Attractions

Dressed in History: A Costume Collection Retrospective

What do a red sequin burlesque costume, a pair of original Air Jordan 1s, a baby’s wool bathing suit, and an enormous white tulle Christian…

Wednesday, May 21st
9:30 a.m.4:30 p.m.
Chicago History Museum
1601 N. Clark St.
Flight of Butterflies
May21
Museums, Galleries & Exhibitions

Flight of Butterflies

ntroducing the Flight of Butterflies! This city-wide exhibit merges nature, art, and story telling, creating a memorable experience for all in Chicago. Local artists adorn…

Wednesday, May 21st
10:00 a.m.4:00 p.m.
Homeschool Days at PEPPA PIG World of Play Chicago
May21
Tours & Attractions

Homeschool Days at PEPPA PIG World of Play Chicago

Join us for Homeschool Days at Peppa Pig World of Play Chicago, where preschool families can enjoy an OINKTASTIC discount! Experience the magic of Peppa…

Wednesday, May 21st
10:00 a.m.5:00 p.m.
Peppa Pig World of Play Chicago
5 Woodfield Mall
Peter Pan at Chicago Kids Company
May21
Music & Comedy

Peter Pan at Chicago Kids Company

Follow Peter Pan and Tinkerbell to Neverland! The adventures are endless in a world of pirates and mayhem. Let your imagination fly to a place…

Wednesday, May 21st
10:30 a.m.11:30 a.m.
Morgan Park Academy
2153 W 111th Street
Fleurs de Villes Downton Abbey
May21
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Tours & Attractions

Fleurs de Villes Downton Abbey

Fusing floral design and bespoke fashion, global sensation Fleurs de Villes returns to 900 North Michigan Shops May 21-25 with new show Fleurs de Villes Downton Abbey – a fresh…

Wednesday, May 21st
11:00 a.m.6:00 p.m.
900 North Michigan Shops
900 North Michigan Avenue
Chicago Skyline Sail – Escape the City Hustle
May21
Tours & Attractions

Chicago Skyline Sail – Escape the City Hustle

Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…

Wednesday, May 21st
1:00 p.m.2:15 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
Titanique
May21
Theatre & Performing Arts

Titanique

Broadway In Chicago presents the Porchlight Music Theatre production of TITANIQUE All aboard NYC’s must-sea musical comedy! When the music of Céline Dion makes sweet Canadian…

Wednesday, May 21st
1:00 p.m.2:40 p.m.
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Chicago White Sox vs. Seattle Mariners
May21
Wednesday, May 21st
1:10 p.m.3:30 p.m.
Guaranteed Rate Field
333 W 35th St
Chicago Skyline Sail – Escape the City Hustle
May21
Tours & Attractions

Chicago Skyline Sail – Escape the City Hustle

Experience Chicago’s Stunning Skyline from the Water! AVAILABLE NOW SAIL DAILY May 16, THROUGH Sept 28! Leave the hustle and bustle behind! Explore Chicago’s shores with…

Wednesday, May 21st
3:00 p.m.4:15 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
90 Minute Architecture River Tour in Chicago
May21
Tours & Attractions

90 Minute Architecture River Tour in Chicago

Experience Chicago’s Best 90-Min Architecture Boat Tour starting May 3, 2025! Led by expert tour guides, this is perfect for all ages. Explore the city’s…

Wednesday, May 21st
5:00 p.m.7:00 p.m.
Summer Of George, 900 South Wells Street, Chicago, United States
Summer Of George, 900 South Wells Street, Chicago, United States
Titanique
May21
Theatre & Performing Arts

Titanique

Broadway In Chicago presents the Porchlight Music Theatre production of TITANIQUE All aboard NYC’s must-sea musical comedy! When the music of Céline Dion makes sweet Canadian…

Wednesday, May 21st
7:00 p.m.8:40 p.m.
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
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