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Upcoming Chicago Events

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R&B Invitation Tour
May2
Music & Comedy

R&B Invitation Tour

The R&B Invitation Tour, featuring R&B legends Joe, Musiq Soulchild and Eric Benét, will take over the Arie Crown Theater in Chicago on May 2, 2025, for an evening of smooth vocals and timeless…

Friday, May 2nd
8:00 p.m.10:00 p.m.
Arie Crown Theater
2301 S. Jean Baptiste Point DuSable, S Lake Shore Dr
STAND-UP MOMEDY: Mother’s Day kickoff with Kristen Toomey
May2
Music & Comedy

STAND-UP MOMEDY: Mother’s Day kickoff with Kristen Toomey

Moms. You know one. You have one. You may even BE one. They’re everywhere. And BOY, could they use a laugh. Luckily, we’ve got just what…

Friday, May 2nd
8:00 p.m.10:00 p.m.
The Laughing Academy
3230 Glenview Road
R&B Invitation Tour: Joe, Musiq Soulchild & Eric Benet
May2
Music & Comedy

R&B Invitation Tour: Joe, Musiq Soulchild & Eric Benet

The R&B Invitation Tour, featuring R&B legends Joe, Musiq Soulchild and Eric Benét, will take over the Arie Crown Theater in Chicago on May 2,…

Friday, May 2nd
8:00 p.m.11:00 p.m.
Arie Crown Theater
2301 S. Jean Baptiste Point DuSable, S Lake Shore Dr
Lowkey Funny Comedy Show
May2
Music & Comedy, Theatre & Performing Arts

Lowkey Funny Comedy Show

This monthly show will shine light on some of Chicago’s emerging talent in stand-up, improv/ sketch comedy, and up and coming music artists. Break away…

Friday, May 2nd
8:30 p.m.11:00 p.m.
Laugh Factory, 3175 N. Broadway St, Chicago, IL 60657
3175 N. Broadway St
Comedy Dance Chicago presents: 8-BITS
May2
Music & Comedy, Theatre & Performing Arts

Comedy Dance Chicago presents: 8-BITS

We’re back with all new bits! This joyful mixture of sketch comedy and dance is filled with a variety of characters that are sure to…

Friday, May 2nd
9:30 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Voila: The Improvised Musical
May2
Music & Comedy, Theatre & Performing Arts

Voila: The Improvised Musical

iO Chicago presents: a fully made-up, off-off-off Broadway style musical every Friday at 10pm in the Fremont Theater. Spend your Friday night with us. See…

Friday, May 2nd
10:00 p.m.11:30 p.m.
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
Hitch*Cocktails
May2
Music & Comedy, Theatre & Performing Arts

Hitch*Cocktails

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together…

Friday, May 2nd
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Comic Book Day Comic Shop Crawl
May3
Festivals, Fairs & Special Events

Comic Book Day Comic Shop Crawl

Every year, on the first Saturday in May, the industry comes together to give away free comics and encourage both curious, first-time comic book readers…

Saturday, May 3rd
Goblin Market Manga & Curiosities
2868 N Lincoln Ave
Marché Privé
May3
Festivals, Fairs & Special Events

Marché Privé

 Marché Privé, a curated luxury pop-up market, is proud to announce its returning event celebrating Chicago’s BIPOC creative entrepreneurs. Scheduled to coincide with Derby Day,…

Saturday, May 3rd
10:00 a.m.3:00 p.m.
The Promontory
5311 S. Lake Park Ave. W
May Mercadito Artisan Fair
May3
Festivals, Fairs & Special Events

May Mercadito Artisan Fair

The Mercadito (Spanish for “minimarket”) is a craft fair that showcases artist vendors offering a diverse range of handmade crafts. Visitors will find unique artisanal…

Saturday, May 3rd
10:00 a.m.3:00 p.m.
GROW/PROGRESANDO
7056 N Clark St
Chicago Spring Market
May3
Festivals, Fairs & Special Events

Chicago Spring Market

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

Saturday, May 3rd
11:00 a.m.5:00 p.m.
Artifact Events
4325 North Ravenswood Avenue
Polish Constitution Day Parade
May3
Festivals, Fairs & Special Events

Polish Constitution Day Parade

Polish May 3rd Constitution Day Parade celebrates the first in Europe and the Second n the World, after the US democratic Constitution of 1791. This…

Saturday, May 3rd
11:30 a.m.1:30 p.m.
Columbus Dr./Balbo Dr.
700 S. Columbus Dr.
Teatro Zinzanni
May3
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…

Saturday, May 3rd
12:00 p.m.3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench is Off to the Races
May3
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts, Tours & Attractions

The Infinite Wrench is Off to the Races

Giddy on up and gallop on down to The Neo-Futurarium on Saturday, May 3rd at 3:00PM… because THE INFINITE WRENCH IS OFF TO THE RACES. In honor of the…

Saturday, May 3rd
3:00 p.m.4:30 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
WindSync
May3
Music & Comedy

WindSync

About the Performance WindSync embraces classics from across centuries of music writing, using their vibrant “fourth wall”-breaking approach to performance to make standard repertoire a…

Saturday, May 3rd
3:00 p.m.5:00 p.m.
Ravinia Festival
418 Sheridan Road
Down & Derby at Utopian Tailgate
May3
Festivals, Fairs & Special Events, Music & Comedy, Tours & Attractions

Down & Derby at Utopian Tailgate

Enjoy a lively Kentucky Derby watch party in perfect form at Utopian Tailgate; Old Town’s premier rooftop and high-energy party landscape. Saturday, May 3rd  * …

Saturday, May 3rd
3:00 p.m.6:00 p.m.
Utopian Tailgate
1608 North Wells Street
Kentucky Derby Watch Party at Joy District Rooftop
May3
Festivals, Fairs & Special Events, Music & Comedy, Sports & Recreation, Tours & Attractions

Kentucky Derby Watch Party at Joy District Rooftop

Enjoy the Kentucky Derby with a “Grand Stand” experience at the Rooftop of JOY District.  This picture-perfect setting is sure to deliver a high-roller’s party scene like no other.…

Saturday, May 3rd
3:00 p.m.6:00 p.m.
Joy District
112 W Hubbard St
Kentucky Derby Watch Party at J. Parker
May3
Festivals, Fairs & Special Events, Music & Comedy, Sports & Recreation, Tours & Attractions

Kentucky Derby Watch Party at J. Parker

Enjoy the Kentucky Derby with no stakes and high limits at The J. Parker Rooftop.  This Lincoln park attraction is sure to impress with its indoor/outdoor viewing…

Saturday, May 3rd
3:00 p.m.6:00 p.m.
The J. Parker
1816 North Clark Street
Kentucky Derby Watch Party at Happy Camper Wrigleyville
May3
Festivals, Fairs & Special Events, Sports & Recreation, Tours & Attractions

Kentucky Derby Watch Party at Happy Camper Wrigleyville

Enjoy a Kentucky Derby watch party with fashionable “infield vibes” at Happy Camper (Wrigleyville).  Where high energy awaits with exceptional viewing screens, retractable roof, group tables and big…

Saturday, May 3rd
3:00 p.m.6:00 p.m.
Happy Camper Wrigleyville
3458 N Clark St
Kentucky Derby Watch Party
May3
Festivals, Fairs & Special Events

Kentucky Derby Watch Party

Run for the Roses at Hubbard Inn – A Kentucky Derby Watch Party Saturday, May 3rd | 4:30PM – 7:30PM 2nd Floor Cocktail Lounge |…

Saturday, May 3rd
4:30 p.m.7:30 p.m.
Hubbard Inn
110 West Hubbard Street
Glenn Raymond “Not A Safe Space” The Den Theatre
May3
Festivals, Fairs & Special Events, Music & Comedy

Glenn Raymond “Not A Safe Space” The Den Theatre

Presented by  United By Comedy Join Stand up comedian Glenn Raymond as he brings his “Not A Safe Space Tour” to The Den Theatre. Be…

Saturday, May 3rd
5:00 p.m.7:00 p.m.
The Den Theatre
1331 N Milwaukee Ave
Teatro Zinzanni
May3
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…

Saturday, May 3rd
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
May3
Music & Comedy, Theatre & Performing Arts

The Infinite Wrench

Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…

Saturday, May 3rd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Glenn Raymond “Not Safe Space”
May3
Music & Comedy

Glenn Raymond “Not Safe Space”

GLENN RAYMOND “NOT A SAFE SPACE” Presented by  United By Comedy Join us for a night of comedy with stand-up comedian Glenn Raymond, who is…

Saturday, May 3rd
7:00 p.m.8:00 p.m.
The Den Theatre
1331 N Milwaukee Ave
bean-night

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