Taste of Randolph
Jun21
Festivals, Fairs & Special Events, Music & Comedy

Taste of Randolph

The West Loop Community Organization presents the 29th annual Taste of Randolph™! Featuring some of the world’s best cuisine and leading entertainment right here in…

Sunday, June 21st
Taste Of Randolph
900 West Randolph Street
Make Music Chicago
Jun21
Festivals, Fairs & Special Events, Music & Comedy

Make Music Chicago

Unlike a typical music festival, Make Music Chicago is open to anyone who wants to take part. Every kind of musician—young and old, amateur and professional—takes…

Sunday, June 21st
City of Chicago
Motoblot
Jun21
Festivals, Fairs & Special Events, Music & Comedy

Motoblot

MOTOBLOT is a celebration of motorcycle and hot rod culture, where the bikes, the builders, the fashion and the music all come together.

Sunday, June 21st
12:00 p.m.10:00 p.m.
Ramova Theatre
3520 S. Halsted St.
“Outta This World!” An Original Play
Jun21
Music & Comedy, Theatre & Performing Arts

“Outta This World!” An Original Play

“Outta This World!” is an absurd comedic play about two aliens who land in mid-century Chicago after running out of fuel. In our story, the…

Sunday, June 21st
6:00 p.m.7:00 p.m.
iO Theater
1501 N. Kingsbury St.
UFO Case Files
Jun21
Music & Comedy

UFO Case Files

Men in Black meets Whose Line Is It Anyways? UFO Case Files is a live improv show in Logan Square where the cast creates a…

Sunday, June 21st
7:00 p.m.8:00 p.m.
cosmic underground theater
3433 W Fullerton Ave
Dominick Pupa’s This Is Not a Pride Show But It’s June and I’m Gay
Jun21
Music & Comedy, Theatre & Performing Arts

Dominick Pupa’s This Is Not a Pride Show But It’s June and I’m Gay

Dominick Pupa (FIXING FAMOUS PEOPLE, RAISING SPIRITS, LO on ROKU) returns to Chicago with his signature, no-nonsense approach to pop culture, gay singledom, important debates…

Sunday, June 21st
7:00 p.m.8:00 p.m.
The Newport Theater
956 West Newport Avenue
Ken Jones at The Comedy Bar
Jun21
Music & Comedy

Ken Jones at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Kendrick “Ken” Jones born August 7,…

Sunday, June 21st
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Katsura Sunshine’s Rakugo at The Comedy Bar
Jun21
Music & Comedy

Katsura Sunshine’s Rakugo at The Comedy Bar

Katsura Sunshine completed his grueling traditional apprenticeship in Rakugo comic storytelling under the great Rakugo Master Katsura Bunshi VI in 2011. His performances have delighted…

Sunday, June 21st
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Godzilla Comedy Show
Jun21
Music & Comedy

Godzilla Comedy Show

Godzilla Comedy is Chicago’s wildest fusion of stand‑up comedy and sketch, powered by two Japanese comedians (KT and Seiji) at the center of the chaos.…

Sunday, June 21st
7:00 p.m.9:00 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Wheel of Improv
Jun21
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday, June 21st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Now Extended Through June 21st: “Going Bacharach” Presenting the Greatest Hits of Bacharach at the Apollo Theater
Jun21
Music & Comedy, Theatre & Performing Arts

Now Extended Through June 21st: “Going Bacharach” Presenting the Greatest Hits of Bacharach at the Apollo Theater

Following the success of the Going Bacharach: The Songs Of An Icon Chicago debut, the musical revue has been extended to run through June 21 at the Apollo Theater. Rediscover the…

Sunday, June 21st
7:30 p.m.9:30 p.m.
Apollo Theater
2550 N. Lincoln Ave.
That 90s Throwback Comedy Show: Father’s Day Edition
Jun21
Music & Comedy, Theatre & Performing Arts

That 90s Throwback Comedy Show: Father’s Day Edition

Calling all 90s kids! This show is for you. Each month, Chicago’s hottest comedians share their favorite 90s obsessions while the audience battles over trivia…

Sunday, June 21st
8:00 p.m.9:00 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
French Montana – Wave Gods: Narcos Tour
Jun21
Music & Comedy

French Montana – Wave Gods: Narcos Tour

French Montana is scheduled to perform in Chicago on Sunday, June 21, 2026, at the Riviera Theatre. This concert is part of the Wave Gods:…

Sunday, June 21st
8:00 p.m.11:00 p.m.
The Riveria Theater
4746 N Racine Ave
Chicago Comedy Hour
Jun21
Music & Comedy

Chicago Comedy Hour

The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in…

Sunday, June 21st
9:00 p.m.10:00 p.m.
de Maat Theatre at Second City
230 W North Ave
Millennium Park Summer Music Series
Jun22
Music & Comedy

Millennium Park Summer Music Series

Millennium Park Summer Music Series features a wide variety of music from established and emerging artists at the iconic Jay Pritzker Pavilion. Sheila E. Melody…

Monday, June 22nd
6:30 p.m.9:00 p.m.
Millennium Park
201 E. Randolph St.
Michael Charles and Band on The Tall Ship Windy Music Concert Series
Jun22
Music & Comedy

Michael Charles and Band on The Tall Ship Windy Music Concert Series

We’ll help you chase your “Monday blues”, aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of…

Monday, June 22nd
7:00 p.m.9:00 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
Cult Canyon w/ Strings, Moon Type (Solo), Jules Klee
Jun22
Music & Comedy

Cult Canyon w/ Strings, Moon Type (Solo), Jules Klee

Cult Canyon performs songs from their recently released LP Smoke Tricks with band leader Josh Chicoine on vocals and guitar, Marianne Vincent on cello, Andrea Nott…

Monday, June 22nd
7:00 p.m.10:30 p.m.
CAFE MUSTACHE
2313 N MILWAUKEE AVE
Joji – Solaris Tour
Jun23
Music & Comedy

Joji – Solaris Tour

Joji is scheduled to perform in Chicago on Tuesday, June 23, 2026, as part of his newly announced SOLARIS global arena tour. Special Guests: The…

Tuesday, June 23rd
6:30 p.m.10:30 p.m.
United Center
1901 W Madison St,
Tuesday Good Show
Jun23
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, June 23rd
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
A Musical Tribute to John Williams & Steven Spielberg
Jun23
Music & Comedy

A Musical Tribute to John Williams & Steven Spielberg

Celebrate the legendary collaboration between composer John Williams and filmmaker Steven Spielberg as the Chicago Symphony Orchestra brings to life some of cinema’s most iconic…

Tuesday, June 23rd
7:30 p.m.9:00 p.m.

220 S. Michigan Ave.
The Human League, Soft Cell & Alison Moyet – The Generations Tour
Jun23
Music & Comedy

The Human League, Soft Cell & Alison Moyet – The Generations Tour

The Human League, Soft Cell, and Alison Moyet are co-headlining The Generations Tour 2026, which stops in Chicago on Tuesday, June 23, 2026. This “once…

Tuesday, June 23rd
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
Comic Court: Chicago’s #1 Comedy Court Show
Jun23
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Comic Court: Chicago’s #1 Comedy Court Show

Order in the court!Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM. Comedians argue ridiculous cases like actual lawyers,…

Tuesday, June 23rd
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
Jazzin’ at the Shedd
Jun24
Museums, Galleries & Exhibitions, Music & Comedy

Jazzin’ at the Shedd

Live jazz revels at Shedd Aquarium! Join us for the popular midweek  Jazzin’ at the Shedd series with unforgettable evenings of music, mingling and marine life.…

Wednesday, June 24th
5:00 p.m.10:00 p.m.
Shedd Aquarium
1200 S. Lake Shore Dr.
Black Monument Ensemble
Jun24
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Black Monument Ensemble

Illinois Humanities is proud to present Damon Locks’ world-renowned Black Monument Ensemble live at Garfield Park Conservatory & Gardens on Wednesday, June 24, 2026. In partnership with the Garfield Park Conservatory…

Wednesday, June 24th
6:00 p.m.7:30 p.m.
Garfield Park Conservatory & Gardens
300 N. Central Park Avenue