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Festivals, Fairs & Special Events, Music & Comedy

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June 27, 2026: Jun27
Music & Comedy
Ed Sheeran Live in Chicago – LOOP 2026 Tour
Ed Sheeran announces the North American leg of his LOOP Tour. On the Chicago stop at Soldier Field on June 27, 2026, he will be…
South Loop
Event details
Saturday, June 27th
5:30 p.m. – 10:00 p.m.
Soldier Field
1410 Special Olympics Drive
Jun27
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…
Lincoln Park
Event details
Saturday, June 27th
6:00 p.m. – 7:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Jun27
Music & Comedy
Hecklers’ Happy Hour
Hecklers’ Happy Hour is Chicago’s interactive stand-up comedy showcase where the audience isn’t just watching — they’re part of the act. And we’ve got an…
Event details
Saturday, June 27th
6:00 p.m. – 7:30 p.m.
Lincoln Lodge, 2040 N Milwaukee Ave, Chicago, IL 60647
2040 N Milwaukee Ave, Chicago, IL 60647, United States
Jun27
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…
Andersonville
Event details
Saturday, June 27th
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
Jun27
Music & Comedy
AMERICA – The Happy Trails Tour 2026
Iconic classic-rock band AMERICA is scheduled to perform in Chicago area on June 27, 2026.
Loop
Event details
Saturday, June 27th
7:00 p.m. – 10:00 p.m.
The Chicago Theatre
175 N. State
Jun27
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…
Old Town
Event details
Saturday, June 27th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Jun27
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…
Old Town
Event details
Saturday, June 27th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St., Theater on the Second Floor
Jun27
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…
Event details
Saturday, June 27th
7:30 p.m. – 9:00 p.m.
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Cornservatory
4210 N Lincoln Ave
Jun27
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Tchaikovsky Piano Concerto No. 1
Conductor Edwin Outwater takes the podium for Tchaikovsky’s dazzling Piano Concerto No. 1, featuring award-winning pianist Sara Davis Buechner. Jimmy López’s Loud, Lou Harrison’s Elegiac Symphony No. 2,…
Event details
Saturday, June 27th
7:30 p.m. – 9:30 p.m.
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Harris Theater
205 E. Randolph Street
Jun27
Music & Comedy
Chuyin Live in Concert
Regional Mexican rising star Chuyin makes his first-ever solo Chicago stop at The Vic Theatre on June 27, where he’ll perform his debut album, Los…
Event details
Saturday, June 27th
7:30 p.m. – 10:00 p.m.
The Vic Theatre
3145 N. Sheffield
Jun27
Music & Comedy
Weird Al’ Yankovic – The Bigger and Weirder 2026 Tour
Weird Al brings his legendary full-production multimedia comedy rock show back to the concert stage with the BIGGER & WEIRDER 2026 Tour, playing his iconic…
West Loop
Event details
Saturday, June 27th
8:00 p.m. – 11:00 p.m.
United Center
1901 W Madison St,
Jun27
Music & Comedy
Josh Groban Live In Chicago – Gems Tour 2026
Multi-platinum vocalist Josh Groban/w special guest Jennifer Hudson will perform live at Rosemont‘s Allstate Arena on June 27, 2026.
Event details
Saturday, June 27th
8:00 p.m. – 11:00 p.m.
Allstate Arena
6920 Mannheim Road
Jun27
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…
Lincoln Park
Event details
Saturday, June 27th
9:00 p.m. – 10:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Jun27
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…
Lakeview
Event details
Saturday, June 27th
9:30 p.m. – 10:30 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
Jun27
Music & Comedy
El Gran Combo de Puerto Rico
El Gran Combo de Puerto Rico is scheduled to perform in Chicago on Saturday, June 27, 2026, for their “Un Verano en Chicago” concert.
Uptown
Event details
Saturday, June 27th
9:30 p.m. – 11:30 p.m.
The Riveria Theater
4746 N Racine Ave
Jun27
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!
Event details
Saturday, June 27th
10:00 p.m. – 11:00 p.m.
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Cornservatory
4210 N Lincoln Ave
June 28, 2026: Jun28
Music & Comedy
ORGULLO
ORGULLO is a free Latin Pride celebration bringing together LGBTQ+ talent, allies, and the Chicago community for an afternoon of music, connection, and self-expression. Join…
Event details
Sunday, June 28th
12:00 p.m. – 7:00 p.m.
3505 N Clark St, Chicago, IL 60657
3505 N Clark St
Jun28
Music & Comedy, Theatre & Performing Arts
Malarkey Comedy Expo League
Welcome to Expo League, where competition and exhibition meet to make an entertaining and interactive experience you’ll never forget! Like the Savannah Bananas and Harlem…
Event details
Sunday, June 28th
6:00 p.m. – 7:30 p.m.
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Malarkey Comedy
1501 N. Kingsbury St.
Jun28
Music & Comedy
Joe Fenti at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Joe Fenti is a Boston-based stand-up…
River North
Event details
Sunday, June 28th
6:30 p.m. – 8:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Jun28
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…
Event details
Sunday, June 28th
7:00 p.m. – 8:00 p.m.
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cosmic underground theater
3433 W Fullerton Ave
Jun28
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!)…
Old Town
Event details
Sunday, June 28th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Jun28
Music & Comedy
Mike Sherm – Sherm Summer Tour
Mike Sherm is performing at the House of Blues Chicago on Sunday, June 28, 2026, for his “Sherm Summer” tour.
River North
Event details
Sunday, June 28th
7:30 p.m. – 10:30 p.m.
House of Blues
Jun28
Music & Comedy, Theatre & Performing Arts
Improvised DCOM
Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage with…
Event details
Sunday, June 28th
8:00 p.m. – 9:00 p.m.
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Malarkey Comedy Company
1501 N Kingsbury St
Jun28
Music & Comedy
K-Pop Comedy Night Presents: BTS Bootcamp
Do you know K-Pop? These comedians don’t. Join us for a show where local Chicago comedians give introductions to the iconic K-Pop groups we love.…
Event details
Sunday, June 28th
8:00 p.m. – 10:00 p.m.
Lincoln Lodge, 2040 N Milwaukee Ave, Chicago, IL 60647
2040 N Milwaukee Ave, Chicago, IL 60647, United States

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