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Upcoming Chicago Events

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Las Locas Comedy Presents: Sabado Night Laughs
May17
Music & Comedy

Las Locas Comedy Presents: Sabado Night Laughs

Sabado Night Laughs is back with a night of comedy from Chicago’s funniest locas, locos, and honorary locas/os! Every month, Las Locas Comedy & Pa…

Saturday, May 17th
8:00 p.m.9:30 p.m.
The Pocket at Surge Billiards Logan Square
3716 W. Fullerton Ave.
Anthony Hamilton & Vivian Green
May17
Music & Comedy

Anthony Hamilton & Vivian Green

Anthony Hamilton and Vivian Green will perform at The Chicago Theatre on May 17 with special guest Jadon Giuseppe!

Saturday, May 17th
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
Here 4 A Bit *Naughty Improv
May17
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 17th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Em Brown at The Comedy Bar
May17
Music & Comedy

Em Brown at The Comedy Bar

Em Brown began his comedy career while attending college in a small town in Southern Illinois. After graduating, he returned to Chicago, where he quickly…

Saturday, May 17th
9:00 p.m.10:30 p.m.
The Comedy Bar
500 N. LaSalle St.
I’m M$. B’havin with my $exagenarian$
May17
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

I’m M$. B’havin with my $exagenarian$

The music and entertainment of I’m M$. B’Havin and her Sexagenarians’ band is a unique blend of Blues, Jazz, R&B and a good time for…

Saturday, May 17th
9:00 p.m.11:30 p.m.
The Tonk
1800 S Racine Ave
Best Of Annoyance Sketch
May17
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 17th
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
May17
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 17th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Orbit
May17
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 17th
11:00 p.m.11:30 p.m.
iO Theater
1501 N. Kingsbury St.
Teatro Zinzanni
May18
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 18th
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Wolff’s Flea Market Opening Day
May18
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 18th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Division Street Farmers Market
May18
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.

Sunday, May 18th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Maxwell Street Market
May18
Festivals, Fairs & Special Events

Maxwell Street Market

Visitors to the Maxwell Street Market will experience an eclectic mix of foods and finds—including handmade crafts, resale housewares, clothing, and much more.

Sunday, May 18th
10:00 a.m.3:00 p.m.
Maxwell Street Market
800 S. Desplaines St.
Fourth Annual Pullman Railroad Days
May18
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Fourth Annual Pullman Railroad Days

Step into history at the Fourth Annual Pullman Railroad Days! The Fourth Annual Pullman Railroad Days is arriving May 17~18, 2025 with a station full…

Sunday, May 18th
10:00 a.m.5:00 p.m.
Pullman National Historic Park
614 E. 113th Street
Dan Nadel and Chris Ware on Robert Crumb
May18
Festivals, Fairs & Special Events

Dan Nadel and Chris Ware on Robert Crumb

Robert Crumb’s comics inspired generations of readers and cartoonists. Join us as curator and cultural writer Dan Nadel — who just published the first biography…

Sunday, May 18th
10:30 a.m.11:30 a.m.
Chicago History Museum
1601 N. Clark St.
The Swingin Sisters: Swingin thru the 60’s
May18
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

The Swingin Sisters: Swingin thru the 60’s

The Swingin’ Sisters use their amazing harmonies to interpret the swinging songs of the 1960s. This show will renew your love and appreciation for these…

Sunday, May 18th
12:00 p.m.1:30 p.m.
Le Piano
6970 N. Glenwood Ave.
Windy City Margarita Fest
May18
Festivals, Fairs & Special Events, Music & Comedy

Windy City Margarita Fest

Windy City Margarita Fest is back, so mark your calendars! We’re serving up 15+ kinds of margaritas—from OG classics to new flavors that’ll hit just…

Sunday, May 18th
12:00 p.m.8:00 p.m.
Pilsen
1400 W. Cermak Road
4th Annual Lincoln Park Mayfest
May18
Festivals, Fairs & Special Events

4th Annual Lincoln Park Mayfest

As Chicago’s premiere summer kickoff event, Lincoln Park Mayfest is a lively celebration of the neighborhood’s spirit and talent. Enjoy performances from top local bands…

Sunday, May 18th
12:00 p.m.9:00 p.m.
1000 W Armitage Ave
Spring Fun Fest at Parkway Bank Park
May18
Festivals, Fairs & Special Events

Spring Fun Fest at Parkway Bank Park

Families are invited to Parkway Bank Park on Sunday, May 18, from 1 p.m. to 5 p.m. for an afternoon of springtime fun with the…

Sunday, May 18th
1:00 p.m.5:00 p.m.
Parkway Bank Park Entertainment District
5501 Park Place
Buena Park PorchFest
May18
Festivals, Fairs & Special Events, Music & Comedy

Buena Park PorchFest

Enjoy a Sunday afternoon strolling through Buena Park and enjoying live music on front porches, courtyards, and gardens while connecting with the community! Join us…

Sunday, May 18th
1:00 p.m.5:30 p.m.
Buena Park
Gaijin Matsuri
May18
Festivals, Fairs & Special Events

Gaijin Matsuri

Join Gaijin for our third annual celebration of springtime, community, cuisine and culture, in partnership with Suntory Global Spirits, the Japan America Society of Chicago,…

Sunday, May 18th
1:00 p.m.7:00 p.m.
Gaijin
950 W Lake St
Cedille Records’ Emerging Artist Competition Final Round
May18
Music & Comedy

Cedille Records’ Emerging Artist Competition Final Round

Cedille Records, the pioneering, nonprofit Chicago-based classical music label led by President and Founder James Ginsburg, hosts its second Emerging Artist Competition, sponsored by the Zell Family Foundation.…

Sunday, May 18th
2:00 p.m.3:00 p.m.
Venue SIX10
610 S. Michigan Ave.
Andy Bossov & Friends Celebrate Allan Sherman at 100!
May18
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Andy Bossov & Friends Celebrate Allan Sherman at 100!

Who doesn’t remember “Hello Muddah, Hello Fadduh”? But parodist Allan Sherman wrote so many more songs than that and inspired all punny people after him.…

Sunday, May 18th
2:00 p.m.3:30 p.m.
Congregation Bene Shalom
4435 Oakton Street
Acts Of Kindness Cabaret — Final Bow
May18
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Acts Of Kindness Cabaret — Final Bow

Celebrate 20 years of music, kindness, and community with Acts Of Kindness Cabaret (AOKC) as we take our final bow. For two decades, AOKC has…

Sunday, May 18th
3:00 p.m.5:30 p.m.
Chicago Theater Works
1113 W. Belmont Ave.
Love, Chaos, and Dinner at Teatro Zinzanni
May18
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Love, Chaos, and Dinner at Teatro Zinzanni

The most unique and magical experience in Chicago! “You have to see to believe.” – Forbes Teatro ZinZanni’s signature show offers an unforgettable sensory experience.…

Sunday, May 18th
4:00 p.m.6:30 p.m.
Teatro ZinZanni
32 W Randolph St. 14th Floor
bean-night

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