Upcoming Chicago Events
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Music & Comedy
Jahari Stampley Trio
About the Performance While people Jahari Stampley’s age may be quipping about staving off quarter-life crises, the 25-year-old Chicago-native pianist is understandably more focused on…
Music & Comedy
Martha Wash One-Night-Only Stop on Her Love & Conflict Tour
Legendary vocalist and two-time Grammy nominee Martha Wash will take center stage at City Winery Chicago on Friday, May 2, 2025, for a one-night-only performance…
Music & Comedy
Lucy Dacus – Forever Is A Feeling Tour
Indie singer-songwriter Lucy Dacus brings the Forever is a Feeling Tour to The Chicago Theatre on May 2.
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 decade.…
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…
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…
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,…
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…
Music & Comedy, Theatre & Performing Arts
Trapped in a Musical – an improvised musical
Trapped in a Musical is a completely improvised Broadway-style show created before your very eyes. It’s the opening and closing night of a brand new…
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…
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…
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…
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…
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,…
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…
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!…
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…
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…
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…
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…
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…
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 * …
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.…
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…
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