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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
Denver
Detroit
Edmonton
Guadalajara
Halifax
Honolulu
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Indianapolis
Kansas City
Las Vegas
Los Angeles
Mexico City
Miami
Milwaukee
Minneapolis
Monterrey
Montreal
Nashville
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New York
Orlando
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Philadelphia
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Pittsburgh
Portland
Quebec City

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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

Wednesday, May 271 event

THE CLOSE OUT! ft..., Mee-ow, Inertia, Sycamore

11:30 PM · Do312

Thursday, May 284 events

Wednesday Night Jazz w/ MATT KAVANAUGH!

12:30 AM · FITZGERALDS SIDEBAR

Chicago Comedy Club

10:00 PM · Foundation Room at House of Blues Chicago

Mike Wheeler Blues Band/Nicholas Alexander Blues Band

10:00 PM · Kingston Mines - Chicago Blues Center

Here Come the Mummies

11:00 PM · House of Blues Chicago

Friday, May 296 events

THE CLOSE OUT! ft..., Mee-ow, Inertia, Sycamore

Wednesday Night Jazz w/ MATT KAVANAUGH!Chicago Comedy Club Mike Wheeler Blues Band/Nicholas Alexander Blues Band +1 more

Jim Ryan's Classic Albums Night Presented By Bulleit:The JACKIE VENSON Residency at FITZGERALDS Nightclub (Night 4 of 4)GERALD DOWD'S Song Of The Month Club w/ Special Guest Jon Goldfine!+3 more

Hannah Dance-tana : Disney Stars Dance Party @ Greta Vancouver Babes & Brews Speed Dating Ages 28-38@ Royal City Brewing (Guelph)Davie Studios Presents: Blues Vol.6 +14 more

Mixed Tape Social Club -- Moncton in May Gozu, Restless Spirit, Unto the Earth, Ghost Pipe CINEMA VIOLENCE / YOU DIED / RADAR WAVES / THE LOCALS +8 more

Jason Kane & the Jive, Natalie Lynch Oxygen Destroyer, Drawn & Quartered, Fister, Mudtomb The Best of The Second City

POST WDCB Bluesday Tuesday Blues in the SIDEBAR w/ The GERRY HUNDT TRIO!

Wednesday Night Jazz w/ The Andy Brown Trio!Honey with DJ CashEra Rico McFarland Blues Band/Joanna Connor Blues Band +1 more

Domani w. Special Guest KING Blues Fest Pre-Party: All-Star Harmonica Blast Ellis Bullard with The Rangers +5 more

Bub City and Busch Light Present: Road to Smokeout with Landon Wilks Boogie Down Broadway | The Hollywood Theatre | Vancouver Cabeza De Chivo 'In the Round' with Vatos Tristes and Eva Maria (DJ Set)+14 more

Jim Ryan's Classic Albums Night Presented By Bulleit:

12:00 AM · Reggie's Music Joint

The JACKIE VENSON Residency at FITZGERALDS Nightclub (Night 4 of 4)

12:30 AM · FITZGERALDS NIGHTCLUB

GERALD DOWD'S Song Of The Month Club w/ Special Guest Jon Goldfine!

12:30 AM · FITZGERALDS SIDEBAR

Belle & Sebastian DJ Set

3:00 AM · Three Top Lounge

Vino Louden Blues Band/Nora Jean Bruso Blues Band

11:00 PM · Kingston Mines - Chicago Blues Center

THE NIGHT PAINTERS / WIDE ORBIT / LA CERCA

11:00 PM · Cubby Bear

Saturday, May 3017 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

Davie Studios Presents: Blues Vol.6

12:00 AM · Cassette

WGCI Tone Kapone Day with special guest Jacquees

12:00 AM · House of Blues Chicago

Elijah Cruise W/ Glamor Mirage + Oudi + Bre Morrissey

12:00 AM · Reggies Bananna's Shack

Hot Stove Jimmy, the Crombies, Run and Punch, Burn Rebuild, DJ Chuck W

12:30 AM · Reggies Rock Club

Emo Night Brooklyn

12:30 AM · Bottom Lounge

*FREE* Friday Night In The NIGHTCLUB w/ CANNOBALL!!!

12:30 AM · FITZGERALDS NIGHTCLUB

Hairbangers Ball - 25 Year Anniversary Bash

12:30 AM · Joe's Live Rosemont

Friday Night in the SIDEBAR w/ DOC WATTSON & FRIENDS!

1:00 AM · FITZGERALDS SIDEBAR

Sarah's Place: A Zach Bryan & Noah Kahan Tribute

2:00 AM · Joe's on Weed Street

Adrian Younge (21+ Event)

3:00 AM · The Empty Bottle

The Best of The Second City

7:00 PM · Second City-Chicago: Mainstage

Lee Burridge + Oliver Koletzki - Ages 21+

8:00 PM · Castaways

Of The Trees - Park Service

9:30 PM · The Salt Shed Outdoors (Fairgrounds)

Vino Louden Blues Band/Nora Jean Bruso Blues Band

11:00 PM · Kingston Mines - Chicago Blues Center

The Knocks x Dragonette x Aquaria REVELATION

11:30 PM · House of Blues Chicago

Sunday, May 3111 events

Mixed Tape Social Club -- Moncton in May

12:00 AM · Crowne Plaza Moncton Downtown by IHG

Gozu, Restless Spirit, Unto the Earth, Ghost Pipe

12:00 AM · Reggie's Music Joint

CINEMA VIOLENCE / YOU DIED / RADAR WAVES / THE LOCALS

12:00 AM · Cubby Bear

House of Burlesque

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

We Them One's Comedy Tour

12:00 AM · Wintrust Arena

RENNIE DAY 2026 (A Warehouse Function)

12:00 AM · 131 McCormack St

Sam Bush

12:00 AM · Dance Spaces at Columbia College Chicago

JON CLEARY at FITZGERALDS Nightclub

12:30 AM · FITZGERALDS NIGHTCLUB

Throwback 100.3 Presents: 2010s Dance Party

1:30 AM · Joe's Live Rosemont

The Best of The Second City

7:00 PM · Second City-Chicago: Mainstage

Mike Wheeler Blues Band/Gerry Hundt Blues Band

9:30 PM · Kingston Mines - Chicago Blues Center