Skip to consent to cookiesSkip navigation
events-cat-special-events

Upcoming Chicago Events

Check out what's happening all around Chicago.

Wolff’s Flea Market – Rosemont Opening Day
May12
Festivals, Fairs & Special Events

Wolff’s Flea Market – Rosemont Opening Day

Sunday Funday is back! Wolff’s Flea Market announces opening day April 28, 2024. Join us for our 33rd season outdoors at the Allstate Arena, Rosemont.…

Sunday, May 12th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market – Rosemont
6920 N Mannheim Rd
Shop Woman-Owned Brands for Mother’s Day At Luxury Boutique Hotel Pendry Chicago
May12
Festivals, Fairs & Special Events

Shop Woman-Owned Brands for Mother’s Day At Luxury Boutique Hotel Pendry Chicago

Support women-owned businesses while you pick the perfect gift for Mom at Pendry Chicago’s Mother’s Day Pop-up Market! Head to the hotel’s Michigan-Ave facing Billiards…

Sunday, May 12th
10:00 a.m.2:00 p.m.
Pendry Chicago
230 N Michigan Ave
Mother’s Day Brunch Buffet
May12
Festivals, Fairs & Special Events

Mother’s Day Brunch Buffet

Join us for a Mother’s Day Brunch Buffet with stunning riverside and city views with a special gift for mom from the River Roast Team!…

Sunday, May 12th
10:00 a.m.3:00 p.m.
River Roast
315 North La Salle Street
Play Unstoppable Festival
May12
Festivals, Fairs & Special Events

Play Unstoppable Festival

It’s time for a day of Unstoppable LEGO® Play! Join us as our LEGOLAND® Discovery Center gets taken over by the Play Unstoppable Festival. Be part of…

Sunday, May 12th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
Mother’s Day at CMB Catering
May12
May13
Festivals, Fairs & Special Events

Mother’s Day at CMB Catering

Celebrate Mom in style with CMB Catering’s decadent three-course brunch, including optional bottomless Bloody Marys and Mimosas! First Course (Choose two appetizers for your party…

Sunday, May 12th
10:00 a.m.Monday, May 13th
2:00 a.m.
CMB Catering
2853 North Kedzie Avenue
Mother’s Day Brunch at Pippin’s Tavern
May12
Festivals, Fairs & Special Events

Mother’s Day Brunch at Pippin’s Tavern

Mark your calendars for Mother’s Day Brunch on Sunday, May 12 from 11am to 3pm! Bring mom and enjoy bottomless MOMosas and Bloody Marys for…

Sunday, May 12th
11:00 a.m.3:00 p.m.
Pippin’s Tavern
39 E Chicago Ave
Mother’s Day at Punch Bowl Social
May12
Festivals, Fairs & Special Events

Mother’s Day at Punch Bowl Social

When it comes to celebrating moms this Mother’s Day, Punch Bowl Social is pulling out all the stops! On Sunday, May 12, in partnership with…

Sunday, May 12th
11:00 a.m.3:00 p.m.
Punch Bowl Social
310 N Green St
Swingin’ on a Star
May12
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Swingin’ on a Star

Join us for a lovely Mother’s Day Brunch. The fabulous harmonies of the Swingin’ Sisters will charm and uplift your spirits as we swing into…

Sunday, May 12th
12:00 p.m.1:30 p.m.
Le Piano
6970 N. Glenwood Ave.
Poetry Making Playground
May12
Festivals, Fairs & Special Events

Poetry Making Playground

Kuumba Lynx is proud to bring a Poetry Making Playground at 601 s California, on April 1st – 30th 2024, with an option to extend…

Sunday, May 12th
12:00 p.m.8:00 p.m.
601 s California
601 S California Ave
Miz Cracker – Big Gay Cabaret
May12
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Miz Cracker – Big Gay Cabaret

Miz Cracker is a New York City drag queen—and a writer, foodie, and comedienne. She launched her drag career in 2011 while participating in marches…

Sunday, May 12th
5:00 p.m.6:00 p.m.
Venus Cabaret Theater
3741 North Southport Avenue
Craig Pomranz: Berlin to Dylan to Simon & Garfunkel
May12
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Craig Pomranz: Berlin to Dylan to Simon & Garfunkel

Craig Pomranz returns to Chicago with his show Berlin to Dylan to Simon & Garfunkel: Songbook throughout the years. Critics rave “Best Male Vocalist!”,  “Tenor…

Sunday, May 12th
7:00 p.m.8:30 p.m.
Davenport’s Piano Bar and Cabaret
1383 North Milwaukee Avenue
Celebrate Mom all Week Long at Teatro ZinZanni
May12
Festivals, Fairs & Special Events, Theatre & Performing Arts

Celebrate Mom all Week Long at Teatro ZinZanni

This Mother’s Day, give your mom the gift of quality time with her family, plus fun photo opportunities, delicious food and drink, and an unforgettable…

Sunday, May 12th
7:00 p.m.9:00 p.m.
Teatro ZinZanni Chicago
32 West Randolph Street
Play Unstoppable Festival
May13
Festivals, Fairs & Special Events

Play Unstoppable Festival

It’s time for a day of Unstoppable LEGO® Play! Join us as our LEGOLAND® Discovery Center gets taken over by the Play Unstoppable Festival. Be part of…

Monday, May 13th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
Studs’ Place – One more time (Musical Mondays)
May13
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Studs’ Place – One more time (Musical Mondays)

A musical salute to Chicago’s own Studs Terkel by Chicago Cabaret Professionals. Studs Terkel, the great writer/interviewer, produced essays and conversations on almost every genre…

Monday, May 13th
7:30 p.m.9:30 p.m.
The Rhapsody Theater
1328 W Morse Ave
Play Unstoppable Festival
May14
Festivals, Fairs & Special Events

Play Unstoppable Festival

It’s time for a day of Unstoppable LEGO® Play! Join us as our LEGOLAND® Discovery Center gets taken over by the Play Unstoppable Festival. Be part of…

Tuesday, May 14th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
A Smashing Hot Evening with Lynne Jordan
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

A Smashing Hot Evening with Lynne Jordan

In a city brimming with classic blues and jazz divas, Lynne Jordan stands apart. Not only do her soaring vocals dip effortlessly into blues, jazz,…

Tuesday, May 14th
5:00 p.m.9:00 p.m.
The Cliff Dwellers
200 S. Michigan Ave, 22nd Fl
AAPI Heritage Month Event at Alma
May14
Festivals, Fairs & Special Events

AAPI Heritage Month Event at Alma

Celebrate Asian American and Pacific Islander (AAPI) Heritage Month at Alma with an evening of diverse flavors and culture! On Tuesday, May 14 from 5-10…

Tuesday, May 14th
5:00 p.m.10:00 p.m.
Alma at Hotel Zachary
3630 North Clark Street
Café Carly – When I Grow Up
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Café Carly – When I Grow Up

Café Carly cabaret show — featuring Chicago’s most talented young musical theater performers, wrangled into a uniquely themed show by hometown girl (and former NYC…

Tuesday, May 14th
7:30 p.m.
Hey Nonny
10 S. Vail Ave.
Chicago’s Best Standup
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Chicago’s Best Standup

Chicago’s Best Standup Comedy is back better than ever. We’ve compiled the absolute best standup comedy lineup that you will see in the city. Today’s…

Tuesday, May 14th
7:30 p.m.9:00 p.m.
Laugh Factory, 3175 N. Broadway St, Chicago, IL 60657
3175 N. Broadway St
Play Unstoppable Festival
May15
Festivals, Fairs & Special Events

Play Unstoppable Festival

It’s time for a day of Unstoppable LEGO® Play! Join us as our LEGOLAND® Discovery Center gets taken over by the Play Unstoppable Festival. Be part of…

Wednesday, May 15th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
The Six Pack: A Discussion with Brad Balukjian
May15
Festivals, Fairs & Special Events

The Six Pack: A Discussion with Brad Balukjian

Join The Book Stall (811 Elm Street in Winnetka) on Wednesday, May 15 at 6:30 pm for an evening of fun and nostalgia with author Brad Balukjian as…

Wednesday, May 15th
6:30 p.m.7:30 p.m.
The Book Stall
The Book Stall, 811 Elm Street
Bob Solone with Guest Singers and Open Mic
May15
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Bob Solone with Guest Singers and Open Mic

Monsignor Murphy’s is a friendly neighborhood bar in Lakeview Chicago, where every Wednesday 8 to 11pm is presented live music featuring Bob Solone at the…

Wednesday, May 15th
8:00 p.m.11:00 p.m.
Monsignor Murphy’s
3019 N Broadway
Why Can’t a Woman….?
May16
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Why Can’t a Woman….?

Why CAN’T a Woman…? is an “honest-to-goodness work of art” (BroadwayWorld) by acclaimed New York cabaret star Lianne Marie Dobbs. Enjoy this one-night-only Chicago premiere…

Thursday, May 16th
7:30 a.m.5:00 p.m.
Hey Nonny
10 S. Vail Ave.
Play Unstoppable Festival
May16
Festivals, Fairs & Special Events

Play Unstoppable Festival

It’s time for a day of Unstoppable LEGO® Play! Join us as our LEGOLAND® Discovery Center gets taken over by the Play Unstoppable Festival. Be part of…

Thursday, May 16th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
bean-night

Explore hotels, flights, deals, and more

Plan your trip

Expedia
Expedia
Expedia
Expedia

CTA Newsletter

Chicago Newsletter

Stay in the know

Sign up

visitors_guide_2024_cover

Visitors Guide

Start planning today

Get the guide