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Festivals, Fairs & Special Events, Music & Comedy

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October 25, 2026: Oct25
Music & Comedy
Matt Rife Live In Chicago – Stay Golden 2025-26 World Tour
Comedian Matt Rife will perform live at Chicago’s United Center on Oct. 25, 2026.
West Loop
Event details
Sunday, October 25th
8:00 p.m. – 10:00 p.m.
United Center
1901 W Madison St,
October 26, 2026: Oct26
Music & Comedy
Tedeschi Trucks Band – Future Soul 2026 Tour
Award-winning blues-rock powerhouse The Tedeschi Trucks Band will conclude their “Future Soul 2026 Tour” with a four-night stand in Chicago in October 2026.
Loop
Event details
Monday, October 26th
7:30 p.m. – 10:30 p.m.
See all events in series
The Chicago Theatre
175 N. State
Oct26
Music & Comedy
She Wants Revenge – 2026 Tour
She Wants Revenge is performing at the House of Blues Chicago on Monday, October 26, 2026. Special Guest: Rosegarden Funeral Party.
River North
Event details
Monday, October 26th
8:00 p.m. – 11:00 p.m.
House of Blues
October 27, 2026: Oct27
Music & Comedy
SiM – Hooman After All World Tour
Japanese reggae-punk and metal band SiM is scheduled to perform live in Chicago, Illinois on Tuesday, October 27, 2026, as part of their newly announced…
River North
Event details
Tuesday, October 27th
6:30 p.m. – 9:30 p.m.
House of Blues
Oct27
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, October 27th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Oct27
Music & Comedy
Joanne Mcnally – Pinotphile Tour
Joanne McNally is performing live in Chicago on Tuesday, October 27, 2026, as part of her hotly anticipated new North American stand-up comedy tour, “Pinotphile”.
Event details
Tuesday, October 27th
7:30 p.m. – 9:30 p.m.
The Vic Theatre
3145 N. Sheffield
Oct27
Music & Comedy
Tedeschi Trucks Band – Future Soul 2026 Tour
Award-winning blues-rock powerhouse The Tedeschi Trucks Band will conclude their “Future Soul 2026 Tour” with a four-night stand in Chicago in October 2026.
Loop
Event details
Tuesday, October 27th
7:30 p.m. – 10:30 p.m.
See all events in series
The Chicago Theatre
175 N. State
Oct27
Music & Comedy
Sienna Spiro – My House Tour
Sienna Spiro is performing live in Chicago on Tuesday, October 27, 2026, at The Riviera Theatre as part of her massive My House Tour world…
Uptown
Event details
Tuesday, October 27th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Oct27
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,…
Event details
Tuesday, October 27th
9:00 p.m. – 10:30 p.m.
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The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
October 28, 2026: Oct28
Music & Comedy
Shakey Graves – Fondness, Etc. Tour
Shakey Graves will bring his Fondness, Etc. Tour to Chicago on Wednesday, October 28, 2026. Special Guest: New York indie-rock band Wild Pink will open…
Event details
Wednesday, October 28th
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Oct28
Music & Comedy
Eros Ramazzotti – Una Storia Importante World Tour
Eros Ramazzotti is bringing his Una Storia Importante World Tour to the Rosemont Theatre on Wednesday, October 28, 2026. This tour celebrates his 40-year career…
Event details
Wednesday, October 28th
8:00 p.m. – 11:00 p.m.
Rosemont Theatre
Oct28
Music & Comedy, Theatre & Performing Arts
The Orbit
The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…
Lincoln Park
Event details
Wednesday, October 28th
9:00 p.m. – 10:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct28
Music & Comedy, Theatre & Performing Arts
Hooch & Holler Comedy Show
Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…
Event details
Wednesday, October 28th
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Oct28
Music & Comedy, Theatre & Performing Arts
The Fizz Show
Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…
Lincoln Park
Event details
Wednesday, October 28th
10:00 p.m. – 11:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
October 29, 2026: Oct29
Music & Comedy
DuSummer Live Music Series
DuSummer Music Series 2026 Get ready for an unforgettable summer of music at the DuSable Museum Outdoor Courtyard! Join us every other Thursday for some…
Event details
Thursday, October 29th
6:00 p.m. – 9:00 p.m.
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Dusable Black History Museum and Cultural Centwe
740 East 57th Place
Oct29
Music & Comedy
Morgan’s Laugh Lounge
Laugh your way into your new favorite Thursday tradition at Morgan’s Laugh Lounge, Chicago’s newest comedy hotspot. Every Thursday night from 6:00–9:30 PM, the lounge…
Event details
Thursday, October 29th
7:00 p.m. – 8:30 p.m.
See all events in series
Morgan’s On Fulton
950 W Fulton Market
Oct29
Music & Comedy
The Airborne Toxic Event
Orchestral indie rock band The Airborne Toxic Event is scheduled to perform live in Chicago, Illinois on Thursday, October 29, 2026.
Event details
Thursday, October 29th
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Oct29
Music & Comedy
Dweezil Zappa – DZ20: Like Father, Like Son Tour
Dweezil Zappa is performing live in Chicago on Thursday, October 29, 2026, as a premier stop on his newly announced North American run, “DZ20: Like…
Uptown
Event details
Thursday, October 29th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Oct29
Music & Comedy
Dresden Dolls – 25th-Anniversary Tour
Dark cabaret duo The Dresden Dolls will bring their 25th-anniversary tour to Chicago on Thursday, October 29, 2026.
Event details
Thursday, October 29th
8:00 p.m. – 11:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
October 30, 2026: Oct30
Music & Comedy
Periphery – A Pale White Dot North America Tour
Periphery is performing live in Chicago on Friday, October 30, 2026, as part of their newly announced “A Pale White Dot North America Tour”. Supporting…
Event details
Friday, October 30th
6:00 p.m. – 11:00 p.m.
Ramova Theatre
3520 S. Halsted St.
Oct30
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
Friday, October 30th
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
Oct30
Music & Comedy, Theatre & Performing Arts
The Last Word
The Last Word is the first 4 course craft cocktail progression paired with a screenplay. 6 actors come on stage and read through a high…
Lincoln Park
Event details
Friday, October 30th
7:00 p.m. – 9:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Oct30
Music & Comedy
Winyah – 2026 Tour
Winyah is scheduled to perform at the House of Blues Chicago on Friday, October 30, 2026.
River North
Event details
Friday, October 30th
7:00 p.m. – 10:00 p.m.
House of Blues
Oct30
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.…
Lincoln Park
Event details
Friday, October 30th
7:30 p.m. – 9:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.

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