Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Name: October Brian Sketch Comedy presents…Goody!
Start: 2025-05-21T21:30:00-05:00
End: 2025-05-21T22:30:00-05:00
Location: Annoyance Theatre & Bar

Check out what's happening all around Chicago.

May 18, 2025: May18
Festivals, Fairs & Special Events
CASCADIA Board Game Tournament – Snakes & Lattes Chicago
Put your strategy to the test at Snakes & Lattes Chicago on May 18th for the CASCADIA Board Game Tournament! CASCADIA is a tile-drafting and token-laying board game where players create diverse habitats…
Event details
Sunday, May 18th
4:00 p.m. – 6:30 p.m.
Snakes & Lattes Chicago
1965 N. Milwaukee Avenue
May18
Music & Comedy
Drew Dunn at The Comedy Bar
Drew Dunn started his stand-up career in 2014, quickly gaining recognition in New England for his quick wit, voices, and unique style. After winning the…
River North
Event details
Sunday, May 18th
7:00 p.m. – 8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
May18
Music & Comedy
Authentic Flamenco Presents Patricia Donn in Chicago
After its international success, with over 225,000 attendees, Authentic Flamenco is back in Chicago with an all-new production and cast! The brand new show features…
Event details
Sunday, May 18th
7:00 p.m. – 8:30 p.m.
Athenaeum Center for Thought & Culture
2936 N. Southport Ave. , Chicago, IL, 60657
May18
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Sam Fazio Sings the Classics
Close out our Cabaret Week with Chicago-based vocalist Sam Fazio. Fazio has established a name for himself in the music scene over the years with…
Andersonville
Event details
Sunday, May 18th
7:00 p.m. – 9:00 p.m.
Vincent Restaurant
1475 W Balmoral Ave
May18
Music & Comedy
Beyoncé: Cowboy Carter Tour
Beyoncé returns to the stage for the COWBOY CARTER TOUR with three performances at Soldier Field May 15, 17 and 18!
South Loop
Event details
Sunday, May 18th
7:00 p.m. – 10:00 p.m.
See all events in series
Soldier Field
1410 Special Olympics Drive
May18
Music & Comedy
As Seen In Rolling Stone: Ellis Bullard Live
Chicago Alert: Ellis Bullard LIVE at Carol’s Pub! ⚡️ Mark your calendars, Windy City! The one and only ELLIS BULLARD is bringing his authentic Texas…
Event details
Sunday, May 18th
7:00 p.m. – 10:00 p.m.
Carol’s Pub
4659 North Clark Street
May 19, 2025: May19
Festivals, Fairs & Special Events
Division Street Farmers Market
Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.
Event details
Monday, May 19th
7:00 a.m. – 12:00 p.m.
See all events in series
30 W. Division St.
30 W. Division St.
May19
Festivals, Fairs & Special Events
Chefs Supporting Chefs Dinner with Petterino’s and Chloe Gould
It’s a night celebrating culinary creativity and collaboration. Join us for a one-of-a-kind experience featuring the bold, innovative flavors of Chef Chloe Gould of DixiePura…
Loop
Event details
Monday, May 19th
6:30 p.m. – 8:30 p.m.

150 N. Dearborn St.
May19
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 19th
7:00 p.m. – 8:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
May19
Music & Comedy
Late Nite Mic with Vik Pandya at The Comedy Bar
IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street, just east of the…
River North
Event details
Monday, May 19th
7:30 p.m. – 9:30 p.m.
See all events in series
The Comedy Bar
500 N. LaSalle St.
May19
Music & Comedy, Theatre & Performing Arts
[REDACTED] Presents: The 5th Element
Funny people reenact a movie they love, or hate, or love to hate. They’ll make you laugh. They’ll make you cry. They’ll insert a movie…
Event details
Monday, May 19th
8:00 p.m. – 9:30 p.m.
Music Box Lounge
3733 N Southport Ave
May 20, 2025: May20
Festivals, Fairs & Special Events
Division Street Farmers Market
Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.
Event details
Tuesday, May 20th
7:00 a.m. – 12:00 p.m.
See all events in series
30 W. Division St.
30 W. Division St.
May20
Festivals, Fairs & Special Events
The Farmer at The Green
The Farmer at The Green, presented by BMO, is a downtown Chicago farmers market. Shop for fresh, seasonal produce and locally made products from Chicago-based…
Event details
Tuesday, May 20th
11:00 a.m. – 3:00 p.m.
See all events in series
The Green at 320
320 S. Canal St.
May20
Festivals, Fairs & Special Events, Music & Comedy
Flamenco and Fondue
Celebrating 60 Years of Flamenco Guitarists and Fondue Dining! Get ready for an incredible evening of Flamenco and Fondue. Gather your friends and family at Geja’s Cafe on Tuesday,…
Event details
Tuesday, May 20th
6:00 p.m. – 9:00 p.m.
Geja’s Cafe
340 W Armitage Ave
May20
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 20th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
May20
Festivals, Fairs & Special Events
Shrek Trivia Night – Snakes & Lattes
SomeBODY once told me there’s Shrek Trivia Night coming to Snakes & Lattes Chicago on May 20th! Get ready to dive into the swamp of Shrek knowledge. Get your tickets…
Event details
Tuesday, May 20th
7:00 p.m. – 9:00 p.m.
Snakes & Lattes Chicago
1965 N. Milwaukee Avenue
May20
Music & Comedy
Tomato Throw Show at The Comedy Bar
Join us for the most fun interactive comedy show in Chicago, where the audience determines who’s the funniest (and the most unfunny) by throwing [fake]…
River North
Event details
Tuesday, May 20th
7:30 p.m. – 9:00 p.m.
See all events in series
The Comedy Bar
500 N. LaSalle St.
May20
Music & Comedy
Billy Idol & Joan Jett and The Blackhearts – It’s A Nice Day To…Tour Again!
Billy Idol & Joan Jett and The Blackhearts will perform live at Credit Union 1 Amphitheatre on May 20, 2025.
Event details
Tuesday, May 20th
7:30 p.m. – 10:30 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
May 21, 2025: May21
Festivals, Fairs & Special Events
Division Street Farmers Market
Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.
Event details
Wednesday, May 21st
7:00 a.m. – 12:00 p.m.
See all events in series
30 W. Division St.
30 W. Division St.
May21
Music & Comedy
Peter Pan at Chicago Kids Company
Follow Peter Pan and Tinkerbell to Neverland! The adventures are endless in a world of pirates and mayhem. Let your imagination fly to a place…
Event details
Wednesday, May 21st
10:30 a.m. – 11:30 a.m.
See all events in series
Morgan Park Academy
2153 W 111th Street
May21
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Tours & Attractions
Fleurs de Villes Downton Abbey
Fusing floral design and bespoke fashion, global sensation Fleurs de Villes returns to 900 North Michigan Shops May 21-25 with new show Fleurs de Villes Downton Abbey – a fresh…
Event details
Wednesday, May 21st
11:00 a.m. – 6:00 p.m.
See all events in series
900 North Michigan Shops
900 North Michigan Avenue
May21
Music & Comedy
Ruben Ramirez at The Comedy Bar
IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street, just east of the…
River North
Event details
Wednesday, May 21st
7:30 p.m. – 9:00 p.m.
See all events in series
The Comedy Bar
500 N. LaSalle St.
May21
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 21st
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
May21
Music & Comedy, Theatre & Performing Arts
October Brian Sketch Comedy presents…Goody!
A 55-minute folk horror-sketch comedy show about a cursed Puritan village spiraling into chaos — told one town meeting at a time. Hear ye, hear…
Lakeview
Event details
Wednesday, May 21st
9:30 p.m. – 10:30 p.m.
See all events in series
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.