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Upcoming Chicago Events

Check out what's happening all around Chicago.

July 26, 2026: Jul26
Music & Comedy
iO Fest 2026
iO Fest 2026 — Chicago’s largest improv festival returns on July 23-26! Featuring over 135 acts and 11 headliners, including: Baby Wants Candy, Improvised Shakespeare…
Lincoln Park
Event details
Sunday, July 26th
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iO Theater
1501 N. Kingsbury St.
Jul26
Music & Comedy, Theatre & Performing Arts
Best of The Second City
Find out for yourself why The Second City has been the first name in laughter for over sixty years! From the stages that launched the…
Old Town
Event details
Sunday, July 26th
3:30 p.m. – 5:00 p.m.
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The Second City
1616 N. Wells St.
Jul26
Music & Comedy
Boleros de Noche Chicago September 25 at the Harris Theater
Boleros De Noche returns to the Windy City following a successful Chicago debut in 2025. Already a beloved tradition in Los Angeles, where the concert…
Event details
Sunday, July 26th
5:00 p.m. – 7:00 p.m.
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Harris Theater
205 E. Randolph Street
Jul26
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, July 26th
6:00 p.m. – 7:30 p.m.
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Malarkey Comedy
1501 N. Kingsbury St.
Jul26
Music & Comedy
Slightly Stoopid – Road Trippin’ Summer Tour
Slightly Stoopid is bringing their “Road Trippin’ Summer Tour 2026” to Chicago on Sunday, July 26, 2026. Special Guests: The lineup includes supporting acts The…
Event details
Sunday, July 26th
6:30 p.m. – 10:00 p.m.
The Salt Shed
1357 N Elston
Jul26
Music & Comedy, Theatre & Performing Arts
Pandemonium, Please Hold
The Second City’s 114th Mainstage Revue Pandemonium, Please Hold is a loud, fast, and gloriously unhinged night of comedic mayhem. The Second City’s six-person cast…
Old Town
Event details
Sunday, July 26th
7:00 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Jul26
Music & Comedy, Theatre & Performing Arts
Reality Detox: The Improv Experience
Reality Detox: The Improv Experience is a high-energy night of improvisation from The Second City, with a few sketch surprises mixed in along the way. Built…
Old Town
Event details
Sunday, July 26th
7:00 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Jul26
Music & Comedy
Hilary Duff – The Lucky Me Tour
Hilary Duff will bring her “The Lucky Me Tour” to the Chicago area for a performance at the Credit Union 1 Amphitheatre in Tinley Park…
Event details
Sunday, July 26th
7:00 p.m. – 10:00 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
Jul26
Music & Comedy
Emmylou Harris & Graham Nash Live In Concert
Emmylou Harris and Graham Nash are scheduled to perform in Highland Park on Sunday, July 26, 2026, as part of the Ravinia Festival. This co-headlining…
Event details
Sunday, July 26th
7:00 p.m. – 10:00 p.m.
Hunter Pavilion At Ravinia
200-201 Ravinia Park Road
Jul26
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, July 26th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Jul26
Music & Comedy
Daniel Caesar – Son of Spergy Tour
Daniel Caesar is scheduled to perform at the United Center in Chicago on Sunday, July 26, 2026, as part of his Son of Spergy Tour.…
West Loop
Event details
Sunday, July 26th
7:30 p.m. – 10:30 p.m.
United Center
1901 W Madison St,
Jul26
Music & Comedy
T.I. – The King Succession Tour
T.I. is performing at the Riviera Theatre in Chicago on Sunday, July 26, 2026.
Uptown
Event details
Sunday, July 26th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Jul26
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, July 26th
8:00 p.m. – 9:00 p.m.
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Malarkey Comedy Company
1501 N Kingsbury St
Jul26
Music & Comedy
The Improvised Movie: Summer Blockbusters
Are you ready for a cinematic showdown where your favorite song lyrics inspire completely improvised, never-seen-before, and never-seen-again summer movies? Join us Saturdays in July…
Event details
Sunday, July 26th
9:30 p.m. – 10:30 p.m.
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de Maat Theatre at Second City
230 W North Ave
July 27, 2026: Jul27
Music & Comedy
Boleros de Noche Chicago September 25 at the Harris Theater
Boleros De Noche returns to the Windy City following a successful Chicago debut in 2025. Already a beloved tradition in Los Angeles, where the concert…
Event details
Monday, July 27th
5:00 p.m. – 7:00 p.m.
See all events in series
Harris Theater
205 E. Randolph Street
Jul27
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. Featuring: Aterciopelados La…
Event details
Monday, July 27th
6:30 p.m. – 9:00 p.m.
Millennium Park – Jay Pritzker Pavilion
201 E Randolph St
Jul27
Music & Comedy, Theatre & Performing Arts
Best of The Second City
Find out for yourself why The Second City has been the first name in laughter for over sixty years! From the stages that launched the…
Old Town
Event details
Monday, July 27th
7:00 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Jul27
Music & Comedy
Late Nite Mic with Vik Pandya at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Vik Pandya is a nationally touring…
River North
Event details
Monday, July 27th
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Jul27
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…
Event details
Monday, July 27th
7:00 p.m. – 9:00 p.m.
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Tall Ship Windy
600 East Grand Avenue Navy Pier
Jul27
Music & Comedy
Zayn – The Konnakol Tour 2026
English singer, songwriter and multi-platinum recording artist ZAYN will perform at the United Center in Chicago on Monday, July 27, 2026. This stop is part…
West Loop
Event details
Monday, July 27th
8:00 p.m. – 11:00 p.m.
United Center
1901 W Madison St,
July 28, 2026: Jul28
Music & Comedy
Boleros de Noche Chicago September 25 at the Harris Theater
Boleros De Noche returns to the Windy City following a successful Chicago debut in 2025. Already a beloved tradition in Los Angeles, where the concert…
Event details
Tuesday, July 28th
5:00 p.m. – 7:00 p.m.
See all events in series
Harris Theater
205 E. Randolph Street
Jul28
Music & Comedy
Grant Park Music Festival String Fellows at Lake Shore Park
The Grant Park Music Festival String Fellow Quartet will present a free concert on Tuesday, July 28 at 7 PM outdoors at Lake Shore Park.…
Event details
Tuesday, July 28th
7:00 p.m. – 8:00 p.m.
Lake Shore Park
808 N Lake Shore Drive
Jul28
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.…
Event details
Tuesday, July 28th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Jul28
Music & Comedy
Tomato Throw Show at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Join us for the most fun…
River North
Event details
Tuesday, July 28th
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611

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