Skip to consent to cookiesSkip navigation
Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Check out what's happening all around Chicago.

ComedySportz Chicago
May3
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Saturday, May 3rd
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Heather McMahan – Bamboozled Tour
May3
Music & Comedy

Heather McMahan – Bamboozled Tour

Heather McMahan will bring The Bamboozled Tour to The Chicago Theatre on Saturday, May 3.

Saturday, May 3rd
8:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Here 4 A Bit *Naughty Improv
May3
Music & Comedy, Theatre & Performing Arts

Here 4 A Bit *Naughty Improv

Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…

Saturday, May 3rd
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Gl
May3
Festivals, Fairs & Special Events, Music & Comedy

Gl

>Presented by  United By Comedy Join us for a night of comedy with stand-up comedian Glenn Raymond, who is a throwback to legends Lenny Bruce…

Saturday, May 3rd
9:00 p.m.10:00 p.m.
The Den Theatre
1331 N Milwaukee Ave
Best Of Annoyance Sketch
May3
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…

Saturday, May 3rd
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
May3
Music & Comedy, Theatre & Performing Arts

LET’S PLAY A GAME: Chicago’s scariest short-form show

Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…

Saturday, May 3rd
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Orbit
May3
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…

Saturday, May 3rd
11:00 p.m.11:30 p.m.
iO Theater
1501 N. Kingsbury St.
Teatro Zinzanni
May4
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Sunday, May 4th
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Wolff’s Flea Market Opening Day
May4
Festivals, Fairs & Special Events

Wolff’s Flea Market Opening Day

Wolff’s Flea Market announces opening day April 20, 2025. Join us for our 34th season outdoors at the Allstate Arena, Rosemont. Sundays 6am-2pm through October…

Sunday, May 4th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Chicago Spring Market
May4
Festivals, Fairs & Special Events

Chicago Spring Market

Markets for Makers is coming back to the Artifact Events Center in Chicago on Saturday May 3 & Sunday May 4 from 11am – 5pm…

Sunday, May 4th
11:00 a.m.5:00 p.m.
Artifact Events
4325 North Ravenswood Avenue
The Indoor Farmers Market at Water Tower Place
May4
Festivals, Fairs & Special Events

The Indoor Farmers Market at Water Tower Place

Date/Time: Sundays, 12pm – 4pm, from January 12th through Sunday, March 30th Location: Water Tower Place (835 N. Michigan Ave), Level 4 Description: Chicago’s Water Tower Place has…

Sunday, May 4th
12:00 p.m.4:00 p.m.
Water Tower Place
821 N. Michigan Ave.
Savor Asia: AAPI Heritage Celebration
May4
Festivals, Fairs & Special Events

Savor Asia: AAPI Heritage Celebration

Join us for Savor Asia, a vibrant celebration of food, culture, and community in honor of AAPI Heritage Month! This exciting event brings together flavors…

Sunday, May 4th
1:00 p.m.4:00 p.m.
Time Out Market Chicago
916 West Fulton Market
South Asian Music Ensemble
May4
Music & Comedy

South Asian Music Ensemble

The South Asian Music Ensemble’s spring concert showcases the entire ensemble, featuring instrumentalists, singers, and dancers. The program highlights South Asian raga-based music with themes…

Sunday, May 4th
3:00 p.m.
Logan Center for the Arts – Penthouse, 901
915 E 60th St
Black Oak Ensemble
May4
Music & Comedy

Black Oak Ensemble

About the Performance A kaleidoscopic string trio that “fully inhabits the spirit of the works they are playing in the moment, with as ardent a…

Sunday, May 4th
3:00 p.m.5:00 p.m.
Ravinia Festival
418 Sheridan Road
Star Wars VILLAINOUS Board Gaming Event – Snakes & Lattes Chicago
May4
Festivals, Fairs & Special Events

Star Wars VILLAINOUS Board Gaming Event – Snakes & Lattes Chicago

MAY THE FOURTH BE WITH YOU! Come celebrate Star Wars Day at Snakes & Lattes Chicago on May the 4th. Become an iconic Star Wars Villain! Use your…

Sunday, May 4th
3:00 p.m.6:00 p.m.
Snakes & Lattes Chicago
1965 N. Milwaukee Avenue
You Win Some, You Dim Sum
May4
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

You Win Some, You Dim Sum

We don’t celebrate our wins enough!! Carve out some time in your week to come to You Win Some, You Dim Sum, a show where…

Sunday, May 4th
5:00 p.m.7:00 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
For the Record | NoMI Lounge
May4
Festivals, Fairs & Special Events

For the Record | NoMI Lounge

FOR THE RECORD AT NoMI LOUNGE Every Sunday from April 6 – May 11 | 5:00 PM – 9:00 PM Reserve Now Ease into Sunday…

Sunday, May 4th
5:00 p.m.9:00 p.m.
NoMI Lounge
800 N. Michigan Ave
Expo League
May4
Music & Comedy, Theatre & Performing Arts

Expo League

Welcome to Expo League, where competition and exhibition meet to make an entertaining and interactive experience you’ll never forget! Like the Savannah Bananas and Harlem…

Sunday, May 4th
6:00 p.m.7:30 p.m.
ComedySportz Chicago
929 W. Belmont Ave.
Keon Polee at The Comedy Bar
May4
Music & Comedy

Keon Polee at The Comedy Bar

Keon Polee is the missing link to comedy, acting, and writing. Keon Polee is from the Bay area. In 2023, Keon broke out with a…

Sunday, May 4th
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
October London & Tamar Braxton – The October Nights Tour: Calling All Lovers
May4
Music & Comedy

October London & Tamar Braxton – The October Nights Tour: Calling All Lovers

October London & Tamar Braxton will perform live at The Chicago Theatre on May 4, 2025.

Sunday, May 4th
7:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
“PAWS on the Plaza” at The Langham, Chicago
May5
Festivals, Fairs & Special Events

“PAWS on the Plaza” at The Langham, Chicago

To celebrate National Pet Week, The Langham, Chicago is partnering with PAWS Chicago for a heartwarming “PAWS on the Plaza” event on Monday, May 5.…

Monday, May 5th
4:30 p.m.6:30 p.m.
Outdoor Plaza at The Langham, Chicago
330 N Wabash Ave
Tuesday Good Show
May6
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.…

Tuesday, May 6th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
The White Lotus Trivia Night – Snakes & Lattes Chicago
May6
Festivals, Fairs & Special Events

The White Lotus Trivia Night – Snakes & Lattes Chicago

*This trivia will cover seasons 1, 2 and 3. Escape to paradise – or chaos – at Snakes & Lattes Chicago on May 6th for…

Tuesday, May 6th
7:00 p.m.9:00 p.m.
Snakes & Lattes Chicago
1965 N. Milwaukee Avenue
Peter Pan at Chicago Kids Company
May7
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…

Wednesday, May 7th
10:30 a.m.11:30 a.m.
Morgan Park Academy
2153 W 111th Street
bean-night

Explore Chicago hotels, flights, deals, and more

Plan your trip

Expedia
Expedia
Expedia
Expedia

CTA Newsletter

Chicago Newsletter

Stay in the know

Sign up

OVG25_enews_cover_for website footer

Chicago Visitors Guide

Start planning today

Get the guide