Upcoming Chicago Events

Name: Peso Pluma – Dinastia Tour 2026
Start: 2026-05-07T20:00:00-05:00
End: 2026-05-07T23:00:00-05:00
Location: United Center

Check out what's happening all around Chicago.

May 2, 2026: May2
May19
Music & Comedy, Theatre & Performing Arts
moonwatchers
It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…
Lincoln Park
Event details
Saturday, May 2nd
8:00 p.m. – Tuesday, May 19th
2:30 p.m.
See all events in series
Greenhouse Theater Center
2257 North Lincoln Avenue
May2
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, May 2nd
9:00 p.m. – 10:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
May2
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, May 2nd
9:30 p.m. – 10:30 p.m.
See all events in series
The Annoyance Theatre
851 W. Belmont Ave.
May2
Music & Comedy
Top Shelf Comedy
Top Shelf Comedy is all in the name! Join us every first Saturday of the month for an incredible night of laughs! Our production team’s…
Event details
Saturday, May 2nd
10:00 p.m. – 11:30 p.m.
See all events in series
The Lincoln Lodge
2040 North Milwaukee Avenue
May2
Music & Comedy
Top Shelf Comedy
Top Shelf Comedy is all in the name! Join us every first Saturday of the month for an incredible night of laughs! Our production team’s…
Event details
Saturday, May 2nd
10:00 p.m. – 11:30 p.m.
See all events in series
The Lincoln Lodge
2040 North Milwaukee Avenue
May 3, 2026: May3
Music & Comedy
Chicago Jazz Orchestra Presents: A Tribute to Roy Eldridge Featuring Jon Faddis with Alyssa Allgood
Join the Chicago Jazz Orchestra as they celebrate the legacy of jazz icon Roy Eldridge, one of the first black musicians to become part of…
Event details
Sunday, May 3rd
3:00 p.m. – 5:00 p.m.
Fine Arts Building – Studebaker Theater
410 S. Michigan Avenue
May3
Music & Comedy, Theatre & Performing Arts
HighQ
Is it a cannabis-themed game show or an uproarious, electively interactive live theatrical experience? Why can’t it be both? HighQ is an uplifting blend of…
Event details
Sunday, May 3rd
6:00 p.m. – 7:30 p.m.
See all events in series
The Lincoln Lodge
2040 North Milwaukee Avenue
May3
Music & Comedy
SatchVai Band: Joe Satriani & Steve Vai & Animals As Leaders
The SatchVai Band, featuring iconic rock guitarists Joe Satriani and Steve Vai, is scheduled to perform in Chicago, IL, on Sunday, May 3, 2026, as…
Loop
Event details
Sunday, May 3rd
7:00 p.m. – 10:00 p.m.
The Chicago Theatre
175 N. State
May3
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, May 3rd
7:30 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
May3
Music & Comedy
Caifanes: 2026 Tour
Legendary Mexican rock band Caifanes is scheduled to perform in Chicago on Sunday, May 3, 2026.
Uptown
Event details
Sunday, May 3rd
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
May3
Music & Comedy
They Might Be Giants – The Bigger Show Tour
They Might Be Giants are scheduled to perform a three-night residency in Chicago from Friday, May 1, through Sunday, May 3, 2026. These are their…
Event details
Sunday, May 3rd
8:00 p.m. – 11:00 p.m.
See all events in series
The Vic Theatre
3145 N. Sheffield
May3
May20
Music & Comedy, Theatre & Performing Arts
moonwatchers
It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…
Lincoln Park
Event details
Sunday, May 3rd
8:00 p.m. – Wednesday, May 20th
2:30 p.m.
See all events in series
Greenhouse Theater Center
2257 North Lincoln Avenue
May 5, 2026: May5
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 5th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
May5
Music & Comedy
Iron & Wine Live In Chicago
Indie folk songwriter Iron & Wine will perform two shows in Chicago, IL, at Thalia Hall in May 2026.
Pilsen
Event details
Tuesday, May 5th
8:00 p.m. – 11:00 p.m.
See all events in series
Thalia Hall
1807 South Allport Street
May 6, 2026: May6
Music & Comedy
NewDad
Welcome to the iconic Metro Chicago, where on May 6, 2026, the indie-rock sensation NewDad will be taking the stage at 7:30 PM. Hailing from…
Event details
Wednesday, May 6th
7:30 p.m. – 9:30 p.m.
Metro Chicago
May6
Music & Comedy
Iron & Wine Live In Chicago
Indie folk songwriter Iron & Wine will perform two shows in Chicago, IL, at Thalia Hall in May 2026.
Pilsen
Event details
Wednesday, May 6th
8:00 p.m. – 11:00 p.m.
See all events in series
Thalia Hall
1807 South Allport Street
May6
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 6th
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
May6
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 6th
10:00 p.m. – 11:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
May 7, 2026: May7
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 7th
7:00 p.m. – 8:30 p.m.
See all events in series
Morgan’s On Fulton
950 W Fulton Market
May7
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 7th
7:30 p.m. – 8:30 p.m.
See all events in series
The De Matt Theater at The Second City
230 W North Ave
May7
Music & Comedy
Mika – Spinning Out Tour North America
Internationally acclaimed pop artist Mika is scheduled to perform in Chicago on Thursday, May 7, 2026, as part of the “Spinning Out Tour North America”.
Uptown
Event details
Thursday, May 7th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
May7
Music & Comedy
Sooshi Mango – The Home Made World Tour 2026
The Australian comedy trio Sooshi Mango is scheduled to perform in Chicago, IL, on Thursday, May 7, 2026, as part of their “The Home Made…
Event details
Thursday, May 7th
8:00 p.m. – 10:00 p.m.
Historic Main Stage at Athenaeum Center
2936 N. Southport Ave
May7
Music & Comedy
Carlos Vives Live In Chicago – Tour al Sol
Carlos Vives will bring his electrifying Tour al Sol 2026 to Rosemont on May 7 at the Rosemont Theatre, delivering a night of high-energy music…
Event details
Thursday, May 7th
8:00 p.m. – 11:00 p.m.
Rosemont Theatre
May7
Music & Comedy
Peso Pluma – Dinastia Tour 2026
Mexican music star Peso Pluma is scheduled to perform in Chicago on Thursday, May 7, 2026, as the grand finale of his North American “DINASTÍA…
West Loop
Event details
Thursday, May 7th
8:00 p.m. – 11:00 p.m.
United Center
1901 W Madison St,