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NewSidequest

Your city is full of side quests — events, concerts, food, comedy, and hidden gems waiting to be discovered.

Cities

Atlanta
Austin
Baltimore
Boston
Calgary
Charlotte
Chicago
Cincinnati
Cleveland
Dallas

View all cities →

Explore

All Events
Calendar
Map
Submit an Event

Company

About
Contact
Terms
Privacy

Home Events Map Groups Sign In

Chicago Events Calendar

month week day

May 2026 Today

All 🎵Music 🎭Theatre 😂Comedy 🍽️Food & Drink 🌙Nightlife 🎨Art & Museums 🏆Sports 🌲Outdoors 🏪Markets 🎉Festivals 👶Family 🎓Classes & Workshops 🏛️Tours & Attractions 🎬Film 👥Community ❤️Free Events 💕Date Ideas 👥Group Activities

Sun

Mon

Tue

Wed

Thu

Fri

Sat

Friday, May 81 event

Balloon Museum | EmotionAir - Art You Can Feel - Chicago

4:00 AM · The Fields Studios

Wednesday, May 273 events

Chicago Architecture Center River Cruise Aboard First Lady

4:00 AM · Chicago Architecture Center - First Lady

Monty Python's Spamalot (Chicago)

5:00 PM · CIBC Theatre

Balloon Museum | EmotionAir - Art You Can Feel - Chicago

5:00 PM · The Fields Studios

Thursday, May 285 events

The House of Boleyn

Balloon Museum | EmotionAir - Art You Can Feel - Chicago

273

Chicago Architecture Center River Cruise Aboard First Lady Monty Python's Spamalot (Chicago)Balloon Museum | EmotionAir - Art You Can Feel - Chicago

285

The House of Boleyn The Second City Mainstage 114th Revue (Minors must be accompanied by an adult)Chicago Architecture Center River Cruise Aboard First Lady +2 more

297

Anakana Schofield: Library of Brothel The Second City Mainstage 114th Revue (Minors must be accompanied by an adult)Chicago Architecture Center River Cruise Aboard First Lady +4 more

3010

Hannah Dance-tana : Disney Stars Dance Party @ Greta Vancouver Babes & Brews Speed Dating Ages 28-38@ Royal City Brewing (Guelph)ChiTown Drive-In Presents - GOAT (With Stephen Curry)+7 more

3112

We Them One's Comedy Tour House of Burlesque Mixed Tape Social Club -- Moncton in May +9 more

An Evening with Eckhart Tolle in Ottawa Whistler One Day Writing Retreat COMPLET - Atelier de dessin d'après modèle vivant - Anne Émélie +4 more

Women in Leadership: Leadership, Legacy & Impact Balloon Museum | EmotionAir - Art You Can Feel - Chicago

The Second City Mainstage 114th Revue (Minors must be accompanied by an adult)Going Bacharach: The Songs of An Icon

The Second City Mainstage 114th Revue (Minors must be accompanied by an adult)Honey with DJ CashEra

The Second City Mainstage 114th Revue (Minors must be accompanied by an adult)Opening Future - Gestione dello stress e delle emozioni ChiTown Drive-In Presents - The Housemaid +1 more

ChiTown Drive-In Presents - Mean Girls (the orginal!)ChiTown Drive-In Presents - Nightmare on Elm Street Going Bacharach: The Songs of An Icon +1 more

12:00 AM · Eventbrite API

The Second City Mainstage 114th Revue (Minors must be accompanied by an adult)

12:00 AM · Second City-Chicago: Mainstage

Chicago Architecture Center River Cruise Aboard First Lady

4:00 AM · Chicago Architecture Center - First Lady

Balloon Museum | EmotionAir - Art You Can Feel - Chicago

5:00 PM · The Fields Studios

Monty Python's Spamalot (Chicago)

11:00 PM · CIBC Theatre

Friday, May 297 events

Anakana Schofield: Library of Brothel

12:00 AM · Bram & Bluma Appel Salon

The Second City Mainstage 114th Revue (Minors must be accompanied by an adult)

12:00 AM · Second City-Chicago: Mainstage

Chicago Architecture Center River Cruise Aboard First Lady

4:00 AM · Chicago Architecture Center - First Lady

The Chicago Theatre Tour Experience

4:00 AM · The Chicago Theatre Tour Experience

Balloon Museum | EmotionAir - Art You Can Feel - Chicago

4:00 PM · The Fields Studios

Monty Python's Spamalot (Chicago)

11:00 PM · CIBC Theatre

Going Bacharach: The Songs of An Icon

11:30 PM · Apollo Theater

Saturday, May 3010 events

Hannah Dance-tana : Disney Stars Dance Party @ Greta Vancouver

12:00 AM · GRETA Bar YVR

Babes & Brews Speed Dating Ages 28-38@ Royal City Brewing (Guelph)

12:00 AM · Royal City Brewing Company

ChiTown Drive-In Presents - GOAT (With Stephen Curry)

12:30 AM · ChiTown Movies

ChiTown Drive-In Presents - Friday the 13th

2:30 AM · ChiTown Movies

Chicago Architecture Center River Cruise Aboard First Lady

4:00 AM · Chicago Architecture Center - First Lady

The Chicago Theatre Tour Experience

4:00 AM · The Chicago Theatre Tour Experience

Balloon Museum | EmotionAir - Art You Can Feel - Chicago

2:00 PM · The Fields Studios

Cocktail Class - Summer Cocktails (Early)

4:00 PM · Dance Spaces at Columbia College Chicago

Going Bacharach: The Songs of An Icon

6:30 PM · Apollo Theater

The Second City Mainstage 114th Revue (Minors must be accompanied by an adult)

11:00 PM · Second City-Chicago: Mainstage

Sunday, May 3112 events

We Them One's Comedy Tour

12:00 AM · Wintrust Arena

House of Burlesque

12:00 AM · Foundation Room at House of Blues Chicago

Mixed Tape Social Club -- Moncton in May

12:00 AM · Crowne Plaza Moncton Downtown by IHG

ChiTown Drive-In Presents - Grease

12:45 AM · ChiTown Movies

Throwback 100.3 Presents: 2010s Dance Party

1:30 AM · Joe's Live Rosemont

ChiTown Drive-In Presents - Texas Chainsaw Massacre (the original!)

2:45 AM · ChiTown Movies

Chicago Architecture Center River Cruise Aboard First Lady

4:00 AM · Chicago Architecture Center - First Lady

The Chicago Theatre Tour Experience

4:00 AM · The Chicago Theatre Tour Experience

Balloon Museum | EmotionAir - Art You Can Feel - Chicago

2:00 PM · The Fields Studios

Monty Python's Spamalot (Chicago)

5:00 PM · CIBC Theatre

Going Bacharach: The Songs of An Icon

5:00 PM · Apollo Theater

The Second City Mainstage 114th Revue (Minors must be accompanied by an adult)

11:00 PM · Second City-Chicago: Mainstage