May Events and Things to do in Chicago, IL

Down & Dirty: A Filthy Standup Showcase
Sat, May 9, 10:00 PM
Chicago · The Lincoln Lodge
Down & Dirty: A Filthy Standup Showcase
Sat, May 9, 10:00 PM
Chicago · The Lincoln Lodge
Comedians That Are Gay
Sun, May 10, 8:00 PM
Chicago · The Lincoln Lodge
Comedians That Are Gay
Sun, May 10, 8:00 PM
Chicago · The Lincoln Lodge
Gems of Chicago Comedy: Live Stand-Up Showcase
Sat, May 9, 9:30 PM
Chicago · The Lincoln Lodge
Gems of Chicago Comedy: Live Stand-Up Showcase
Sat, May 9, 9:30 PM
Chicago · The Lincoln Lodge
Booked! A Stand Up Comedy Show.
Sat, May 9, 7:45 PM
Chicago · Passages Wine and Books
Booked! A Stand Up Comedy Show.
Sat, May 9, 7:45 PM
Chicago · Passages Wine and Books
Red Lace Burlesque Show Chicago & Variety Show Chicago
Fri, May 1, 6:00 PM + 9 more
Chicago · Red Lace Burlesque Austin
Red Lace Burlesque Show Chicago & Variety Show Chicago
Fri, May 1, 6:00 PM + 9 more
Chicago · Red Lace Burlesque Austin
FRIDAY MAY 1: KELLY KELLZ
Fri, May 1, 9:00 PM
Chicago · The Comedy Bar - Chicago Main Stage
FRIDAY MAY 1: KELLY KELLZ
Fri, May 1, 9:00 PM
Chicago · The Comedy Bar - Chicago Main Stage
THURSDAY MAY 7: OHJAY LAMONT & FRIENDS
Thu, May 7, 7:00 PM
Chicago · The Comedy Bar - Chicago Main Stage
THURSDAY MAY 7: OHJAY LAMONT & FRIENDS
Thu, May 7, 7:00 PM
Chicago · The Comedy Bar - Chicago Main Stage
MONDAY MAY 4: LATE NITE MIC WITH VIK PANDYA
Mon, May 4, 7:00 PM
Chicago · The Comedy Bar - Chicago Main Stage
MONDAY MAY 4: LATE NITE MIC WITH VIK PANDYA
Mon, May 4, 7:00 PM
Chicago · The Comedy Bar - Chicago Main Stage
TUESDAY MAY 5: TOMATO THROW SHOW
Tue, May 5, 7:00 PM
Chicago · The Comedy Bar - Chicago Main Stage
TUESDAY MAY 5: TOMATO THROW SHOW
Tue, May 5, 7:00 PM
Chicago · The Comedy Bar - Chicago Main Stage
Spring Awards Luncheon 2026: AATF Chicago & Northern Illinois
Sat, May 2, 12:15 PM
Oak Park · Hemmingway's Bistro
Spring Awards Luncheon 2026: AATF Chicago & Northern Illinois
Sat, May 2, 12:15 PM
Oak Park · Hemmingway's Bistro
Wines of Georgia On Tour: Chicago
Thu, May 14, 5:00 PM
Chicago · Verve Wine Chicago
Wines of Georgia On Tour: Chicago
Thu, May 14, 5:00 PM
Chicago · Verve Wine Chicago
Day Play Social
Sat, May 9, 3:00 PM + 1 more
Chicago · Hue Chicago
Day Play Social
Sat, May 9, 3:00 PM + 1 more
Chicago · Hue Chicago
The Drag Queen Party Bus Columbus - The Ultimate Drag Experience
Fri, May 1, 8:00 PM + 24 more
Columbus · Drag Queen Party Bus Columbus
The Drag Queen Party Bus Columbus - The Ultimate Drag Experience
Fri, May 1, 8:00 PM + 24 more
Columbus · Drag Queen Party Bus Columbus
Chicago Online Speed Dating (33-42 age group)
Fri, May 1, 8:00 PM + 4 more
Chicago · Chicago Online Event
Chicago Online Speed Dating (33-42 age group)
Fri, May 1, 8:00 PM + 4 more
Chicago · Chicago Online Event
Painting Pottery
Fri, May 1, 12:30 PM + 83 more
Chicago · 5127 N Clark St
Painting Pottery
Fri, May 1, 12:30 PM + 83 more
Chicago · 5127 N Clark St
Startups Fund Raising Program
Fri, May 1, 7:00 PM + 4 more
Chicago · Chicago
Startups Fund Raising Program
Fri, May 1, 7:00 PM + 4 more
Chicago · Chicago
Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™
Mon, May 11, 6:00 PM
Chicago · Studio W.I.P.
Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™
Mon, May 11, 6:00 PM
Chicago · Studio W.I.P.
Ladylike
Wed, May 6, 8:00 PM
Chicago · The Lincoln Lodge
Ladylike
Wed, May 6, 8:00 PM
Chicago · The Lincoln Lodge
Art City BYOB Paint & Sip
Fri, May 1, 1:00 PM + 6 more
Chicago · Art City
Art City BYOB Paint & Sip
Fri, May 1, 1:00 PM + 6 more
Chicago · Art City
Drag Queen Party Bus Chicago - The Ultimate Drag Experience
Fri, May 1, 7:30 PM + 14 more
Chicago · 209 W Lake St
Drag Queen Party Bus Chicago - The Ultimate Drag Experience
Fri, May 1, 7:30 PM + 14 more
Chicago · 209 W Lake St

Trends in Chicago

Explore more trends

Down & Dirty: A Filthy Standup Showcase

Down & Dirty: A Filthy Standup Showcase

Comedians That Are Gay

Comedians That Are Gay

Gems of Chicago Comedy: Live Stand-Up Showcase

Gems of Chicago Comedy: Live Stand-Up Showcase

Booked! A Stand Up Comedy Show.

Booked! A Stand Up Comedy Show.

Red Lace Burlesque Show Chicago & Variety Show Chicago

Red Lace Burlesque Show Chicago & Variety Show Chicago

FRIDAY MAY 1: KELLY KELLZ

FRIDAY MAY 1: KELLY KELLZ

THURSDAY MAY 7: OHJAY LAMONT & FRIENDS

THURSDAY MAY 7: OHJAY LAMONT & FRIENDS

MONDAY MAY 4: LATE NITE MIC WITH VIK PANDYA

MONDAY MAY 4: LATE NITE MIC WITH VIK PANDYA

TUESDAY MAY 5: TOMATO THROW SHOW

TUESDAY MAY 5: TOMATO THROW SHOW

Spring Awards Luncheon 2026: AATF Chicago & Northern Illinois

Spring Awards Luncheon 2026: AATF Chicago & Northern Illinois

Wines of Georgia On Tour: Chicago

Wines of Georgia On Tour: Chicago

Day Play Social

Day Play Social

The Drag Queen Party Bus Columbus - The Ultimate Drag Experience

The Drag Queen Party Bus Columbus - The Ultimate Drag Experience

Chicago Online Speed Dating (33-42 age group)

Chicago Online Speed Dating (33-42 age group)

Painting Pottery

Painting Pottery

Startups Fund Raising Program

Startups Fund Raising Program

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

Ladylike

Ladylike

Art City BYOB Paint & Sip

Art City BYOB Paint & Sip

Drag Queen Party Bus Chicago - The Ultimate Drag Experience

Drag Queen Party Bus Chicago - The Ultimate Drag Experience

Things to do around Chicago

Trends in Chicago

1. St pattys day river north bar crawl

2. Bar crawl

3. March

4. St patrick day

5. St patricks day

6. River north bar crawl

7. St patricks day bar crawl

8. St patrick's day bar crawl

9. April events

10. Job fair

11. St patrick

12. Bollywood