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ComedySportz Chicago
May23
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Friday, May 23rd
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Chicago’s Best Comedy Showcase
May23
Music & Comedy

Chicago’s Best Comedy Showcase

IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street, just east of the…

Friday, May 23rd
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Trapped in a Musical – an improvised musical
May23
Music & Comedy, Theatre & Performing Arts

Trapped in a Musical – an improvised musical

Trapped in a Musical is a completely improvised Broadway-style show created before your very eyes. It’s the opening and closing night of a brand new…

Friday, May 23rd
9:00 p.m.10:00 p.m.
ComedySportz Chicago
929 W. Belmont Ave.
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,
First Date Comedy Show
May23
Music & Comedy

First Date Comedy Show

The First Date is a comical hunt for love. Chicago’s funniest stand-up comedians hit the stage as one audience member is selected from the crowd…

Friday, May 23rd
7:00 p.m.8:30 p.m.
Laugh Factory, 3175 N. Broadway St, Chicago, IL 60657
3175 N. Broadway St
Grossman Ensemble – World Premieres III
May23
Music & Comedy, Theatre & Performing Arts

Grossman Ensemble – World Premieres III

Esteemed conductor Tim Weiss returns to lead the Grossman Ensemble for an eagerly anticipated third collaboration. Composers Christopher Stark, whose music The New York Times has called, “fetching…

Friday, May 23rd
7:30 p.m.9:00 p.m.
Logan Center for the Arts – Performance Hall
915 E. 60th St.
An Evening with Vince Gill
May23
Music & Comedy

An Evening with Vince Gill

Vince Gill will perform at The Chicago Theatre on Friday, May 23.

Friday, May 23rd
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
Bingo Loco: The Ultimate Bingo Party
May23
Festivals, Fairs & Special Events

Bingo Loco: The Ultimate Bingo Party

Bingo Loco is not your grandma’s bingo… it’s a bingo rave complete with comedian MCs, throwback anthems, lip sync battles, dance-offs, dancers, confetti showers, CO2 cannons,…

Friday, May 23rd
8:00 p.m.9:15 p.m.
Morgan MFG
401 North Morgan Street
Paul Simon – A Quiet Celebration Tour
May23
Music & Comedy

Paul Simon – A Quiet Celebration Tour

During “A Quiet Celebration Tour,” Paul Simon will present the live-debut performance of his critically acclaimed, Grammy-nominated album Seven Psalms, as well as perform a…

Friday, May 23rd
8:00 p.m.11:00 p.m.
Chicago Symphony Center
220 S Michigan Ave
Devil’s Daughter
May23
Music & Comedy

Devil’s Daughter

The hottest show in town Devil’s Daughter features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Friday, May 23rd
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Chicago’s Best Comedy Showcase
May23
Music & Comedy

Chicago’s Best Comedy Showcase

IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street, just east of the…

Friday, May 23rd
9:00 p.m.10:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Comedy Dance Chicago presents: 8-BITS
May23
Music & Comedy, Theatre & Performing Arts

Comedy Dance Chicago presents: 8-BITS

We’re back with all new bits! This joyful mixture of sketch comedy and dance is filled with a variety of characters that are sure to…

Friday, May 23rd
9:30 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
May23
Music & Comedy, Theatre & Performing Arts

Missed Call Sketch Comedy Show

Missed Call is a premier Chicago comedy group that writes and performs an entirely new sketch show every Friday — inspired by the audience’s suggestion!

Friday, May 23rd
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Chicago’s Best Standup
May23
Music & Comedy

Chicago’s Best Standup

Chicago’s Best Standup Comedy is back better than ever. We’ve compiled the absolute best standup comedy lineup that you will see in the city. Today’s…

Friday, May 23rd
9:15 p.m.10:45 p.m.
Laugh Factory, 3175 N. Broadway St, Chicago, IL 60657
3175 N. Broadway St
The Manns: Live Breathe Fight Tour
May23
Music & Comedy

The Manns: Live Breathe Fight Tour

Featuring Tamela and David Mann, Erica Campbell, Tye Tribbett and more. Award-winning power couple Tamela and David Mann are bringing faith, family, and phenomenal music…

Friday, May 23rd
8:00 p.m.11:00 p.m.
Hitch*Cocktails
May23
Music & Comedy, Theatre & Performing Arts

Hitch*Cocktails

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together…

Friday, May 23rd
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Chicago’s Best Stand Up
May23
May24
Music & Comedy

Chicago’s Best Stand Up

Chicago’s Best Standup Comedy is back better than ever. We’ve compiled the absolute best standup comedy lineup that you will see in the city. Today’s…

Friday, May 23rd
11:30 p.m.Saturday, May 24th
1:00 a.m.
Laugh Factory, 3175 N. Broadway St, Chicago, IL 60657
3175 N. Broadway St
The Official AC/DC High Voltage Pop-Up Storms Into Chicago and Cleveland
May24
Festivals, Fairs & Special Events

The Official AC/DC High Voltage Pop-Up Storms Into Chicago and Cleveland

The Official AC/DC High Voltage Pop-Up Storms Into Chicago and Cleveland Only a Few Stops Remain on the North American Leg of the PWR/UP Tour…

Saturday, May 24th
11:00 a.m.5:00 p.m.
329 N Dearborn St., Chicago, IL 60654
329 N Dearborn St.
Fleurs de Villes Downton Abbey
May24
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…

Saturday, May 24th
11:00 a.m.6:00 p.m.
900 North Michigan Shops
900 North Michigan Avenue
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
Memorial Day Wreath Laying Ceremony & Parade
May24
Festivals, Fairs & Special Events

Memorial Day Wreath Laying Ceremony & Parade

Chicago’s Memorial Day Parade honors all men and woman who made the ultimate sacrifice in defense of our country. The Wreath Laying Ceremony will begin…

Saturday, May 24th
11:00 a.m.1:00 p.m.
Daley Civic Center
50 W. Washington St.
Division Street Farmers Market
May24
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, May 24th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
40th Annual Belmont-Sheffield Music Fest – May 23-25
May24
Festivals, Fairs & Special Events

40th Annual Belmont-Sheffield Music Fest – May 23-25

CHICAGO (May 2025)—Celebrate the beginning of summer in the city at the 40th annual Belmont-Sheffield Music Fest, on Sheffield between Roscoe and Belmont, May 23-25.…

Saturday, May 24th
11:00 a.m.10:00 p.m.
3200 N. Sheffield Avenue, Chicago 60657
3200 N. Sheffield Avenue
Teatro Zinzanni
May24
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…

Saturday, May 24th
12:00 p.m.3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
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