Taste of Randolph
Jun20
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…

Saturday, June 20th
Taste Of Randolph
900 West Randolph Street
Motoblot
Jun20
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.

Saturday, June 20th
12:00 p.m.10:00 p.m.
Ramova Theatre
3520 S. Halsted St.
Chicago 2026 – Summer Concert Series
Jun20
Music & Comedy, Theatre & Performing Arts

Chicago 2026 – Summer Concert Series

Varrick Chorus Inc. is excited to bring its 2026 Summer Concert Series to the vibrant city of Chicago for an evening of music, inspiration, and…

Saturday, June 20th
5:00 p.m.7:00 p.m.
Hyde Park Union Church
5600 S. Woodlawn Ave.
Morgan Wallen Live In Chicago – Still The Problem Tour 2026
Jun20
Music & Comedy

Morgan Wallen Live In Chicago – Still The Problem Tour 2026

Country megastar Morgan Wallen brings the Still The Problem Tour to Chicago for two back-to-back nights at Soldier Field  on June 19 and 20, 2026,…

Saturday, June 20th
5:30 p.m.10:00 p.m.
Soldier Field
1410 Special Olympics Drive
The Infinite Wrench
Jun20
Music & Comedy, Theatre & Performing Arts

The Infinite Wrench

Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…

Saturday, June 20th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Katsura Sunshine’s Rakugo
Jun20
Music & Comedy

Katsura Sunshine’s Rakugo

A show of hilarity and culture in equal doses! Katsura Sunshine completed his grueling traditional apprenticeship in Rakugo comic storytelling under the great Rakugo Master…

Saturday, June 20th
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Ms. Renee Live: One Night Only Tour II at The Comedy Bar
Jun20
Music & Comedy

Ms. Renee Live: One Night Only Tour II at The Comedy Bar

HollywoodGenGen, widely recognized as “Miss Renee”, is an acclaimed actor, comedian, and social media influencer celebrated for their ability to connect with audiences through humor…

Saturday, June 20th
7:00 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Godsmack – The Rise of Rock World Tour
Jun20
Music & Comedy

Godsmack – The Rise of Rock World Tour

Godsmack /w special guests Stone Temple Pilots & Dorothy will perform live at Credit Union 1 Amphitheatre on June 20, 2026.

Saturday, June 20th
7:00 p.m.10:00 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
You’re Invited To The Juneteenth Comedy Festival: A Celebration of Black Comedians
Jun20
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts, Tours & Attractions

You’re Invited To The Juneteenth Comedy Festival: A Celebration of Black Comedians

You’re Invited To The Juneteenth Comedy Festival: A Celebration of Black Comedians is a vibrant comedy variety show that spotlights some of the most exciting…

Saturday, June 20th
7:00 p.m.10:00 p.m.
iO Theater
1501 N. Kingsbury St.
Baby Wants Candy! The Original Completely Improvised Musical
Jun20
Music & Comedy, Theatre & Performing Arts

Baby Wants Candy! The Original Completely Improvised Musical

“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…

Saturday, June 20th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Jun20
Music & Comedy, Theatre & Performing Arts

Clued In

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…

Saturday, June 20th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Copland Symphony No. 3
Jun20
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Copland Symphony No. 3

Giancarlo Guerrero conducts Aaron Copland’s Symphony No. 3, a masterful synthesis of the composer’s expansive American musical style. Piano virtuoso Stewart Goodyear returns to the…

Saturday, June 20th
7:30 p.m.9:00 p.m.
Millennium Park
201 E Randolph Street
Corn Productions’ Match Game
Jun20
Music & Comedy

Corn Productions’ Match Game

It’s time for another game! Do you ever miss the wacky antics of Game Shows from back in the day? Like way back in the…

Saturday, June 20th
7:30 p.m.9:00 p.m.
Cornservatory
4210 N Lincoln Ave
Now Extended Through June 21st: “Going Bacharach” Presenting the Greatest Hits of Bacharach at the Apollo Theater
Jun20
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…

Saturday, June 20th
7:30 p.m.9:30 p.m.
Apollo Theater
2550 N. Lincoln Ave.
Joshua Slone – Thinking Too Much Tour
Jun20
Music & Comedy

Joshua Slone – Thinking Too Much Tour

Joshua Slone is scheduled to perform in Chicago on Saturday, June 20, 2026, as part of his “Thinking Too Much Tour”. This concert celebrates his…

Saturday, June 20th
7:30 p.m.10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Rosalía – Lux 2026 Tour
Jun20
Music & Comedy

Rosalía – Lux 2026 Tour

Spanish singer-songwriter Rosalía will perform in Chicago on Saturday, June 20, 2026, at the United Center as part of her “LUX Tour 2026”.

Saturday, June 20th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St,
Tash Sultana: North American Tour 2026
Jun20
Music & Comedy

Tash Sultana: North American Tour 2026

Australian multi-instrumentalist Tash Sultana is bringing their North American Tour 2026 to Chicago on Saturday, June 20, 2026.

Saturday, June 20th
8:00 p.m.11:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
R&B Music Experience: Tyrese, Tank & Tamar Braxton
Jun20
Music & Comedy

R&B Music Experience: Tyrese, Tank & Tamar Braxton

The R&B Music Experience is returning to Chicago for an exclusive Juneteenth Celebration on Saturday, June 20, 2026. Lineup: The concert features Tyrese, Tank, Tamar…

Saturday, June 20th
8:00 p.m.11:00 p.m.
Secret Sketch Show
Jun20
Music & Comedy

Secret Sketch Show

Shhhhh! It’s a secret! Don’t tell anyone but your favorite iO performers are hosting a wild night of variety and sketch. Secret sketch show is…

Saturday, June 20th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Jun20
Music & Comedy, Theatre & Performing Arts

Best Of Annoyance Sketch

Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…

Saturday, June 20th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Slumber Party Comedy Show
Jun20
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Slumber Party Comedy Show

Slumber Party! A Comedy Show for Gossip Lovers A night of giggles, gossip, and games with your favorite Chicago comedians. Welcome to Slumber Party! Come…

Saturday, June 20th
9:30 p.m.11:00 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
Queerly Lit: Late Night Variety Hour
Jun20
Music & Comedy, Theatre & Performing Arts

Queerly Lit: Late Night Variety Hour

Join Corn Productions for your Pride celebrations with this late-night comedy variety show! Featuring new acts every night!

Saturday, June 20th
10:00 p.m.11:00 p.m.
Cornservatory
4210 N Lincoln Ave
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