Upcoming Chicago Events

Name: Best of the Second City
Start: 2026-12-25T20:00:00-06:00
End: 2026-12-25T21:30:00-06:00
Location: The Second City

Check out what's happening all around Chicago.

December 20, 2026: Dec20
Music & Comedy, Theatre & Performing Arts
Pigeon Gets a Big Time Holiday Extravaganza
The Squirrels have decked the halls, and Elephant and Piggie are ready to celebrate the season. But will Pigeon join the festivities—or fly off to…
Lincoln Park
Event details
Sunday, December 20th
11:00 a.m. – 12:00 p.m.
See all events in series
Greenhouse Theater Center
2257 North Lincoln Avenue
Dec20
Music & Comedy, Theatre & Performing Arts
Pigeon Gets a Big Time Holiday Extravaganza
The Squirrels have decked the halls, and Elephant and Piggie are ready to celebrate the season. But will Pigeon join the festivities—or fly off to…
Lincoln Park
Event details
Sunday, December 20th
1:00 p.m. – 2:00 p.m.
See all events in series
Greenhouse Theater Center
2257 North Lincoln Avenue
Dec20
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Drunk Christmas Carol
Drunk Christmas Carol, presented by the Drunk Shakespeare Society, brings a boozy twist on Charles Dickens’ holiday classic to Chicago for a limited run at…
Event details
Sunday, December 20th
5:00 p.m. – 7:00 p.m.
See all events in series
182 N. Wabash Ave., Chicago
182 N. Wabash Ave.
Dec20
Music & Comedy
Baby Smoove – Chicago, IL – Purple Heart Tour
Baby Smoove will be performing live in Chicago on Sunday, December 20, 2026, as part of his Purple Heart Tour.
River North
Event details
Sunday, December 20th
5:00 p.m. – 9:00 p.m.
House of Blues
Dec20
Music & Comedy
Marquee: Musical Improv
Musical theatre and improv collide as Marquee presents you with an hour of fully improvised musical comedy, spontaneously creating entire scenes, songs, and stories based…
Lincoln Park
Event details
Sunday, December 20th
6:00 p.m. – 7:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Dec20
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, December 20th
7:00 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Dec20
Music & Comedy
Lightly Toasted Standup Showcase
Lightly Toasted is a standup showcase at The Home Comedy Theater in the Lakeview neighborhood of Chicago every third Sunday of the month featuring up…
Event details
Sunday, December 20th
7:00 p.m. – 9:00 p.m.
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The Home Comedy Theater
2843 North Halsted Street
Dec20
Music & Comedy
Mariachi Herencia de México – Chicago, IL – A Mariachi Christmas
Mariachi Herencia de México will perform their holiday concert, “A Mariachi Christmas,“ live in Chicago on Sunday, December 20, 2026. The Latin GRAMMY-nominated group will…
Pilsen
Event details
Sunday, December 20th
7:00 p.m. – 10:00 p.m.
Thalia Hall
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614
Dec20
Music & Comedy, Theatre & Performing Arts
Vape! The Grease Parody
Vape! lovingly pokes fun at all of the wonderful moments, sexual innuendos, outrageous characters, rivalries and secret romances from the original musical. The hair products may…
Event details
Sunday, December 20th
7:30 p.m. – 8:55 p.m.
See all events in series
Apollo Theater
2550 N. Lincoln Ave.
Dec20
Music & Comedy
ONEUS – Chicago, IL – 2026 ONEUS World Tour: Full Moon
K-pop boy band ONEUS will bring their dynamic live show to Chicago, Illinois on Sunday, December 20, 2026. This highly anticipated performance is part of…
Jefferson Park
Event details
Sunday, December 20th
7:30 p.m. – 10:30 p.m.
Copernicus Center
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614
December 21, 2026: Dec21
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Drunk Christmas Carol
Drunk Christmas Carol, presented by the Drunk Shakespeare Society, brings a boozy twist on Charles Dickens’ holiday classic to Chicago for a limited run at…
Event details
Monday, December 21st
5:00 p.m. – 7:00 p.m.
See all events in series
182 N. Wabash Ave., Chicago
182 N. Wabash Ave.
Dec21
Music & Comedy
The Armando Diaz
It’s the best comedy show in the city. Created in 1995 by iO alum Armando Diaz, Armando is a historic improvisational form where actors improvise a series…
Lincoln Park
Event details
Monday, December 21st
7:00 p.m. – 8:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Dec21
Music & Comedy
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, December 21st
7:00 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
December 22, 2026: Dec22
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Drunk Christmas Carol
Drunk Christmas Carol, presented by the Drunk Shakespeare Society, brings a boozy twist on Charles Dickens’ holiday classic to Chicago for a limited run at…
Event details
Tuesday, December 22nd
5:00 p.m. – 7:00 p.m.
See all events in series
182 N. Wabash Ave., Chicago
182 N. Wabash Ave.
December 23, 2026: Dec23
Music & Comedy
Trans-Siberian Orchestra – Rosemont, IL – The Ghosts of Christmas Eve Tour
Trans-Siberian Orchestra is bringing their 30th-anniversary The Ghosts of Christmas Eve Tour to the Allstate Arena in Rosemont on Wednesday, December 23, 2026. This special…
Event details
Wednesday, December 23rd
2:45 p.m. – 10:00 p.m.
Allstate Arena
6920 Mannheim Road
Dec23
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Drunk Christmas Carol
Drunk Christmas Carol, presented by the Drunk Shakespeare Society, brings a boozy twist on Charles Dickens’ holiday classic to Chicago for a limited run at…
Event details
Wednesday, December 23rd
5:00 p.m. – 7:00 p.m.
See all events in series
182 N. Wabash Ave., Chicago
182 N. Wabash Ave.
Dec23
Music & Comedy
Play Time
A showcase of 3 short plays by select writing teams and featuring a cast of iO Theater performers. It’s experimental, it’s follow-the-fun, it’s Play Time. Plays…
Lincoln Park
Event details
Wednesday, December 23rd
7:30 p.m. – 9:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
December 24, 2026: Dec24
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Drunk Christmas Carol
Drunk Christmas Carol, presented by the Drunk Shakespeare Society, brings a boozy twist on Charles Dickens’ holiday classic to Chicago for a limited run at…
Event details
Thursday, December 24th
5:00 p.m. – 7:00 p.m.
See all events in series
182 N. Wabash Ave., Chicago
182 N. Wabash Ave.
Dec24
Music & Comedy, Theatre & Performing Arts
Vape! The Grease Parody
Vape! lovingly pokes fun at all of the wonderful moments, sexual innuendos, outrageous characters, rivalries and secret romances from the original musical. The hair products may…
Event details
Thursday, December 24th
7:30 p.m. – 8:55 p.m.
See all events in series
Apollo Theater
2550 N. Lincoln Ave.
December 25, 2026: Dec25
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Drunk Christmas Carol
Drunk Christmas Carol, presented by the Drunk Shakespeare Society, brings a boozy twist on Charles Dickens’ holiday classic to Chicago for a limited run at…
Event details
Friday, December 25th
5:00 p.m. – 7:00 p.m.
See all events in series
182 N. Wabash Ave., Chicago
182 N. Wabash Ave.
Dec25
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
Friday, December 25th
6:30 p.m. – 8:00 p.m.
See all events in series
The Second City
1616 N. Wells St.
Dec25
Music & Comedy, Theatre & Performing Arts
Vape! The Grease Parody
Vape! lovingly pokes fun at all of the wonderful moments, sexual innuendos, outrageous characters, rivalries and secret romances from the original musical. The hair products may…
Event details
Friday, December 25th
7:30 p.m. – 8:55 p.m.
See all events in series
Apollo Theater
2550 N. Lincoln Ave.
Dec25
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…
Lincoln Park
Event details
Friday, December 25th
7:30 p.m. – 9:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Dec25
Music & Comedy
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
Friday, December 25th
8:00 p.m. – 9:30 p.m.
See all events in series
The Second City
1616 N. Wells St.