Upcoming Chicago Events

Name: Archspire – Long Roads Big Loads Tour
Start: 2026-05-22T18:00:00-05:00
End: 2026-05-22T23:00:00-05:00
Location: House of Blues

Check out what's happening all around Chicago.

Featured Events

Festivals, Fairs & Special Events, Music & Comedy

Windy City Smokeout

United Center Parking Lot

Jul8

May 18, 2026: May18
Music & Comedy, Theatre & Performing Arts
Magic Mondays
Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…
Lincoln Park
Event details
Monday, May 18th
7:00 p.m. – 8:30 p.m.
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iO Theater
1501 N. Kingsbury St.
May18
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, May 18th
7:00 p.m. – 9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
May 19, 2026: May19
Music & Comedy
Chaos and Carnage: Thy Art Is Murder, Carnifex & Bodysnatcher
The Chaos and Carnage 2026 tour will be at the Ramova Theatre in Chicago on Tuesday, May 19, 2026. This year’s installment features a massive…
Event details
Tuesday, May 19th
4:45 p.m. – 10:00 p.m.
Ramova Theatre
3520 S. Halsted St.
May19
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, May 19th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
May19
Music & Comedy
Joe Jackson – Hope and Fury Tour
Joe Jackson and his band are scheduled for a two-night residency at Park West in Chicago on Tuesday, May 19, and Wednesday, May 20, 2026.…
Event details
Tuesday, May 19th
7:30 p.m. – 10:30 p.m.
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Park West
322 W Armitage Ave
May19
Music & Comedy
Best Night Ever
Your best bet for Tuesday night laughs with one of Chicago’s most critically acclaimed comedy showcases! Every Tuesday, we will bring you the best lineup…
Event details
Tuesday, May 19th
8:00 p.m. – 9:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
May19
Music & Comedy
Clever Comedy Show
A comedy showcase featuring acts ranging from the freshest comedy club killers to alt-comedy geniuses, musical acts & surprise drop-ins. Looking for a hilarious unique…
Event details
Tuesday, May 19th
9:00 p.m. – 10:15 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
May 20, 2026: May20
Music & Comedy
Crowd Work Wednesday at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Crowd Work Wednesday is a weekly…
River North
Event details
Wednesday, May 20th
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
May20
Music & Comedy
Chicago’s Late Night Talk Show: The Not That Late Show
A monthly late night style talk show featuring comedy, music and interviews with notable Chicagoans. Get the late night talk show experience without heading to…
Event details
Wednesday, May 20th
7:30 p.m. – 9:00 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
May20
Music & Comedy
Leftist political commentator Lily Eagla joins Chicago’s Late Night Talk Show
Get the late night talk show experience without heading to NYC or LA. The Not That Late Show is a POC- and queer-led late-night talk…
Event details
Wednesday, May 20th
7:30 p.m. – 9:00 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
May20
Music & Comedy
Khalid – It’s Always Summer Somewhere 2026 Tour
Multi-platinum artist Khalid /w special guest Lauv will perform live at Chicago’s Huntington Bank Pavilion at Northerly Island on May 20, 2026.
South Loop
Event details
Wednesday, May 20th
7:30 p.m. – 10:30 p.m.
Huntington Bank Pavilion at Northerly Island
1300 S. Linn White Dr.
May20
Music & Comedy
Chet Faker – A Love For Strangers World Tour
Chet Faker is scheduled to perform in Chicago on Wednesday, May 20, 2026, as part of his A Love For Strangers World Tour. This tour…
Event details
Wednesday, May 20th
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
May20
Music & Comedy
Joe Jackson – Hope and Fury Tour
Joe Jackson and his band are scheduled for a two-night residency at Park West in Chicago on Tuesday, May 19, and Wednesday, May 20, 2026.…
Event details
Wednesday, May 20th
7:30 p.m. – 10:30 p.m.
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Park West
322 W Armitage Ave
May20
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, May 20th
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
May20
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, May 20th
10:00 p.m. – 11:00 p.m.
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iO Theater
1501 N. Kingsbury St.
May 21, 2026: May21
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, May 21st
7:00 p.m. – 8:30 p.m.
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Morgan’s On Fulton
950 W Fulton Market
May21
Music & Comedy
OhJay Lamont & Friends at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry OhJay Lamont, born and raised on…
River North
Event details
Thursday, May 21st
7:00 p.m. – 9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
May21
Music & Comedy, Theatre & Performing Arts
Dark Side of the Pillow Sketch Comedy Show
The thoughts you have at 2 a.m.? We put them on stage. Looking for a night out that feels unmistakably Chicago? Dark Side of the…
Event details
Thursday, May 21st
7:30 p.m. – 8:30 p.m.
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The De Matt Theater at The Second City
230 W North Ave
May21
Music & Comedy, Theatre & Performing Arts
Dumb and Drummer
Chicago’s best comedians doing their best material over live jazz! Every third Thursday at The Lincoln Lodge Theatre, Hosted by Jamaal Sanders, Hunter Hirsch, and…
Event details
Thursday, May 21st
7:30 p.m. – 9:00 p.m.
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The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
May21
Music & Comedy
Concrete Boys – It’s Us Vol. 2 Tour
Concrete Boys is scheduled to perform in Chicago on Thursday, May 21, 2026, as part of their “It’s Us Vol. 2 Tour”.
Event details
Thursday, May 21st
7:30 p.m. – 10:30 p.m.
Park West
322 W Armitage Ave
May21
Music & Comedy
Cosmic Comedy Hour
Cosmic Comedy Hour is a one-hour live comedy show that combines magic, improv, and theatrical comedy into one fast-paced experience. Unlike traditional comedy shows, this…
Event details
Thursday, May 21st
8:00 p.m. – 9:00 p.m.
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cosmic underground theater
3433 W Fullerton Ave
May21
Music & Comedy
Late Night at The Lodge
Chicago’s premiere late night comedy talk show Late Night At The Lodge is the perfect mix of stand up comedy, and funny talk show banter.…
Event details
Thursday, May 21st
9:00 p.m. – 10:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
May 22, 2026: May22
Music & Comedy
Slide Away
The Slide Away 2026 festival will take place in Chicago over two nights, Friday, May 22, and Saturday, May 23, 2026. The festival features a…
Uptown
Event details
Friday, May 22nd
6:00 p.m. – 11:00 p.m.
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Aragon Ballroom
May22
Music & Comedy
Archspire – Long Roads Big Loads Tour
Archspire is bringing their “Long Roads Big Loads Tour” to the House of Blues Chicago on Friday, May 22, 2026. This high-velocity technical death metal…
River North
Event details
Friday, May 22nd
6:00 p.m. – 11:00 p.m.
House of Blues