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Upcoming Chicago Events

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Tomato Throw Show at The Comedy Bar
May27
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 27th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Big Bus Tours’ Sunset Live Tour
May27
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 27th
7:30 p.m.9:00 p.m.
618 N Clark St.
618 N. Clark St
Summer & Fall Afterwork Sunset Cruises on Lake Michigan
May27
Tours & Attractions

Summer & Fall Afterwork Sunset Cruises on Lake Michigan

 Experience summer on Lake Michigan with our weekday evening cruises featuring fireworks*, sunsets, skyline views, and cocktails starting May 27th, 2024. Unwind after work with…

Tuesday, May 27th
7:30 p.m.10:00 p.m.
DuSable Harbor 200 N Breakwater Access
DuSable Harbor 200 N Breakwater Access
Comic Court: The Best Comedy Show in the World
May27
Music & Comedy, Theatre & Performing Arts

Comic Court: The Best Comedy Show in the World

Would you rather be able to fly or be able to turn invisible? Who are we more tired of: Ryan Reynolds or Dwayne Johnson? Would…

Tuesday, May 27th
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Franz West: Millennium Park
May28
Museums, Galleries & Exhibitions, Tours & Attractions

Franz West: Millennium Park

Franz West” Millennium Park features two monumental installations by West: Stonehenge (2011) and Dorit (2002), set against the iconic backdrop of Millennium Park. Stonehenge, with…

Wednesday, May 28th
Millennium Park
201 E Randolph St
Marriott Theatre Presents: Titanic The Musical
May28
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 28th
Marriott Theatre
10 Marriott Dr.
Dressed in History: A Costume Collection Retrospective
May28
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 28th
9:30 a.m.4:30 p.m.
Chicago History Museum
1601 N. Clark St.
Tom Torluemke: LIVE! ON PAPER, 1987 – 2024
May28
Museums, Galleries & Exhibitions

Tom Torluemke: LIVE! ON PAPER, 1987 – 2024

Tom Torluemke is a contemporary artist whose practice spans 40+ years and includes works in painting, drawing, sculpture, performance, and various mediums. Tom is known…

Wednesday, May 28th
10:00 a.m.4:45 p.m.
Chicago Cultural Center
78 E Washington St
Tropical Wednesdays
May28
Tours & Attractions

Tropical Wednesdays

Immerge yourself in a cultural experience as Latin dances come alive on Taylor street – Salsa, Bachata, Cumbia, and Cha Cha Cha with margarita!

Wednesday, May 28th
6:00 p.m.8:00 p.m.
Vintage Bar Chicago
1449 W. Taylor St.
Titanique
May28
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 28th
7:00 p.m.8:40 p.m.
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Joe Fenti at The Comedy Bar
May28
Music & Comedy

Joe Fenti at The Comedy Bar

Joe Fenti is a Boston-based comedian who sometimes makes silly videos for the internet (@FentiFriedChicken). He also has a full time job working in Corporate…

Wednesday, May 28th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Big Bus Tours’ Sunset Live Tour
May28
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…

Wednesday, May 28th
7:30 p.m.9:00 p.m.
618 N Clark St.
618 N. Clark St
Las Locas Comedy Presents: Delightfully Unbothered
May28
Music & Comedy

Las Locas Comedy Presents: Delightfully Unbothered

Las Locas Comedy Presents is back at Lincoln Lodge with a brand new comedy showcase – with a brand new name (formerly known as Women…

Wednesday, May 28th
8:00 p.m.9:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Chicago Fireworks Cruise Sail into the Night, with Sparkles in the Sky
May28
Tours & Attractions

Chicago Fireworks Cruise Sail into the Night, with Sparkles in the Sky

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in…

Wednesday, May 28th
9:00 p.m.10:30 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
Franz West: Millennium Park
May29
Museums, Galleries & Exhibitions, Tours & Attractions

Franz West: Millennium Park

Franz West” Millennium Park features two monumental installations by West: Stonehenge (2011) and Dorit (2002), set against the iconic backdrop of Millennium Park. Stonehenge, with…

Thursday, May 29th
Millennium Park
201 E Randolph St
Marriott Theatre Presents: Titanic The Musical
May29
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…

Thursday, May 29th
Marriott Theatre
10 Marriott Dr.
Dressed in History: A Costume Collection Retrospective
May29
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…

Thursday, May 29th
9:30 a.m.4:30 p.m.
Chicago History Museum
1601 N. Clark St.
Tom Torluemke: LIVE! ON PAPER, 1987 – 2024
May29
Museums, Galleries & Exhibitions

Tom Torluemke: LIVE! ON PAPER, 1987 – 2024

Tom Torluemke is a contemporary artist whose practice spans 40+ years and includes works in painting, drawing, sculpture, performance, and various mediums. Tom is known…

Thursday, May 29th
10:00 a.m.4:45 p.m.
Chicago Cultural Center
78 E Washington St
Maifest Chicago 2025
May29
Festivals, Fairs & Special Events

Maifest Chicago 2025

Maifest is Back! Admission is free & open to all agesJoin us May 29 – June 1, 2025at our same awesome temporary spot:4521 N. Lincoln…

Thursday, May 29th
5:00 p.m.10:00 p.m.
Maifest Chicago
4521 N. Lincoln Avenue
Teatro Zinzanni
May29
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Thursday, May 29th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Live Performance: Davis Plays Ellington
May29
Museums, Galleries & Exhibitions

Live Performance: Davis Plays Ellington

Join Chicago’s Emmy Award-winning trumpeter, composer, and educator Orbert Davis for an unforgettable tribute to jazz legend Duke Ellington. More than a pianist, Ellington used his orchestra…

Thursday, May 29th
6:30 p.m.9:00 p.m.
Illinois Holocaust Museum & Education Center
9603 Woods Drive
Titanique
May29
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…

Thursday, May 29th
7:00 p.m.8:40 p.m.
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
The End of Reality
May29
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 29th
7:00 p.m.9:00 p.m.
Theatre Y
3611 W Cermak Rd
Rockin’ in the Park 2025 Free Summer Concert Series
May29
Music & Comedy

Rockin’ in the Park 2025 Free Summer Concert Series

Rosemont’s Parkway Bank Park entertainment district (5501 Park Place, Rosemont) will turn up the volume this summer with the return of its popular “Rockin’ in…

Thursday, May 29th
7:00 p.m.10:00 p.m.
Parkway Bank Park Entertainment District
5501 Park Place
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