Chicago Events Calendar

Ryan Chrys & the Rough Cuts, the Jeff Givens Band, Medicinal Moonshine

12:00 AM · Reggie's Music Joint

Webinar: il Concorso AD5 per le Istituzioni Europee

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

The House of Boleyn

12:00 AM · Eventbrite API

Job Fair for Canadian Immigrants & Networking

12:00 AM · York Civic Centre

Wednesday Night Jazz w/ MATT KAVANAUGH!

12:30 AM · FITZGERALDS SIDEBAR

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

Chicago White Sox vs. Minnesota Twins

5:10 PM · Guaranteed Rate Field

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

Troy Doherty

11:00 PM · Bottom Lounge

LAWRENCE TOME / WOODROW HART & THE HAYMAKER / COYOTE VERDE AND THE WILD PACK / LYDIA CASH

11:00 PM · Cubby Bear

Monty Python's Spamalot (Chicago)

11:00 PM · CIBC Theatre

Here Come the Mummies

11:00 PM · House of Blues Chicago

Pachanka Music Presents: Olya Prohorova’s Soviet Jazz!

11:00 PM · FITZGERALDS PATIO

Brahms, Strauss and Ravel La valse with CSO

11:30 PM · Orchestra Hall - IL

Dan Tyminski Band

11:30 PM · Dance Spaces at Columbia College Chicago

Jim Ryan's Classic Albums Night Presented By Bulleit:

12:00 AM · Reggie's Music Joint

Emerson Woolf & The Wishbones with Jordan Smart

12:00 AM · Joe's on Weed Street

Peel Region/GTA North Career Fair and Training Expo Canada - May 28, 2026

12:00 AM · Pearson Convention Center

Hayden Coffman - Take The Lonely Tour with Zach Crean

12:00 AM · Carol's Pub

Art Vancouver 2026

12:00 AM · Vancouver Convention Centre East

2026 CPAC Job Fair

12:00 AM · North York Memorial Community Hall

Trasparenza Retributiva: cosa cambia davvero nelle aziende italiane

12:00 AM · Eventbrite API

Curare la Persona con il Neo-Funzionalismo/ Webinar Gratuito

12:00 AM · Eventbrite API

Previdenza integrativa: tra novità normative e opportunità da cogliere

12:00 AM · Eventbrite API

Anakana Schofield: Library of Brothel

12:00 AM · Bram & Bluma Appel Salon

Create a Custom Mug ( 6-12 yrs)

12:00 AM · Central Branch (Richmond Hill Public Library)

Strengthening K-12 Cybersecurity: Simple Steps for Safer Schools

12:00 AM · Eventbrite API

*SOLD OUT* The Black Angels: Passover 2026 Tour with L.A. Witch

12:00 AM · Thalia Hall

Stygian Bough, 40 Watt Sun

12:00 AM · Reggies Rock Club

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

12:00 AM · Second City-Chicago: Mainstage

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

12:30 AM · FITZGERALDS SIDEBAR

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

12:30 AM · FITZGERALDS NIGHTCLUB

Belle & Sebastian DJ Set

3:00 AM · Three Top Lounge

The Chicago Theatre Tour Experience

4:00 AM · The Chicago Theatre Tour Experience

Chicago Architecture Center River Cruise Aboard First Lady

4:00 AM · Chicago Architecture Center - First Lady

Classic Stadium Tour

2:00 PM · Soldier Field

Balloon Museum | EmotionAir - Art You Can Feel - Chicago

4:00 PM · The Fields Studios

Brahms, Strauss & Ravel La valse

5:30 PM · Orchestra Hall - IL

**The GRAND FINALE!** FITZGERALDS TEACHER HAPPY HOUR on the Patio w/ THE BLOCK PARTY BROS!

7:00 PM · FITZGERALDS PATIO

Studio 18 Recital

8:30 PM · George Van Dusen Theatre at North Shore Center

Chicago Sky vs. Minnesota Lynx

10:30 PM · Wintrust Arena

Chicago White Sox vs. Detroit Tigers

10:40 PM · Guaranteed Rate Field

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

Monty Python's Spamalot (Chicago)

11:00 PM · CIBC Theatre

Friday Night on the Patio w/ THE HEARTWRECKERS!

11:00 PM · FITZGERALDS PATIO

Summer Walker: Still Finally Over It Tour

11:30 PM · United Center

Going Bacharach: The Songs of An Icon

11:30 PM · Apollo Theater

WGCI Tone Kapone Day with special guest Jacquees

12:00 AM · House of Blues Chicago

Land of Linkin, Sugar, We're a Fall Out Boy Tribute, Savior

12:00 AM · Reggie's Music Joint

SOLD OUT-BELLE & SEBASTIAN: IF YOU'RE FEELING SINISTER + CLASSIC SONGS

12:00 AM · The Salt Shed Indoors (Shed)

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

12:00 AM · GRETA Bar YVR

Chicago Gay Mens Chorus: Cher The Love

12:00 AM · Harris Theater

Riftbound Regional Qualifier: Vancouver

12:00 AM · Vancouver Convention Centre East

Creative Edge Dance Company Season 4 Showcase

12:00 AM · Princess Sheila Nageira Theatre

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

Belle & Sebastian - 2 Day General Admission Pass (VALID 5/28-5/29)

12:00 AM · The Salt Shed Indoors (Shed)

Dumpstaphunk

12:00 AM · Garcia's Chicago

Elijah Cruise W/ Glamor Mirage + Oudi + Bre Morrissey

12:00 AM · Reggies Bananna's Shack

*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

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

12:30 AM · ChiTown Movies

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

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

1:00 AM · FITZGERALDS SIDEBAR

First and Third

1:30 AM · Carol's Pub

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

2:00 AM · Joe's on Weed Street

ChiTown Drive-In Presents - Friday the 13th

2:30 AM · ChiTown Movies

Adrian Younge (21+ Event)

3:00 AM · The Empty Bottle

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

**Off-Site!*** The "WHAT'S BLOOMIN' BAR" By FITZGERALDS & BABYGOLD at What's Blooming on Harrison!

3:00 PM · FITZGERALDS NIGHTCLUB

JAZZ BRUNCH on the PATIO ft. ALYSSA ALLGOOD!

4:00 PM · FITZGERALDS PATIO

Cocktail Class - Summer Cocktails (Early)

4:00 PM · Dance Spaces at Columbia College Chicago

Chicago White Sox vs. Detroit Tigers

5:10 PM · Guaranteed Rate Field

Monty Python's Spamalot (Chicago)

6:00 PM · CIBC Theatre

Going Bacharach: The Songs of An Icon

6:30 PM · Apollo Theater

The Best of The Second City

7:00 PM · Second City-Chicago: Mainstage

Lee Burridge + Oliver Koletzki - Ages 21+

8:00 PM · Castaways

Saturday afternoon on the PATIO w/ Michelle Billingsley

8:00 PM · FITZGERALDS PATIO

Of The Trees - Park Service

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

Dance Center Evanston

10:30 PM · George Van Dusen Theatre at North Shore Center

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

11:00 PM · Second City-Chicago: Mainstage

Saturday Night on the PATIO w/ Greg Jacks & Brother Help!

11:00 PM · FITZGERALDS NIGHTCLUB

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

Brahms, Strauss and Ravel La valse with CSO

11:30 PM · Orchestra Hall - IL

*SOLD OUT* hemlocke springs - the apple tree under the sea tour

11:30 PM · Thalia Hall

Hemlocke Springs

11:30 PM · Thalia Hall

CINEMA VIOLENCE / YOU DIED / RADAR WAVES / THE LOCALS

12:00 AM · Cubby Bear

RENNIE DAY 2026 (A Warehouse Function)

12:00 AM · 131 McCormack St

Mixed Tape Social Club -- Moncton in May

12:00 AM · Crowne Plaza Moncton Downtown by IHG

SSOD Presents "Toy Story" Show #3 (Green)

12:00 AM · Isabel Bader Theatre

Laura Pausini - Yo Canto World Tour

12:00 AM · Rosemont Theatre

City of Calgary Emergency Services Career Fair

12:00 AM · City of Calgary Multi-Agency Training (MAT) Centre

Gozu, Restless Spirit, Unto the Earth, Ghost Pipe

12:00 AM · Reggie's Music Joint

SSOD Presents "Toy Story" Show #4 (Yellow)

12:00 AM · Isabel Bader Theatre

Gala InfluenceCréation 2026 — 4e Édition

12:00 AM · Place Bell

Ardbeg Day 2026

12:00 AM · NSLC

FAMILY DAY Edmonton Grand Opening | Free Kids Activities & Food!

12:00 AM · 18439 104 Ave NW

Gardeners' Gathering at the Natural Dye Garden

12:00 AM · Colour Me Local Dye Garden

Sam Bush

12:00 AM · Dance Spaces at Columbia College Chicago

The Black Queen

12:00 AM · Bottom Lounge

House of Burlesque

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

We Them One's Comedy Tour

12:00 AM · Wintrust Arena

JON CLEARY at FITZGERALDS Nightclub

12:30 AM · FITZGERALDS NIGHTCLUB

ChiTown Drive-In Presents - Grease

12:45 AM · ChiTown Movies

Throwback 100.3 Presents: 2010s Dance Party

1:30 AM · Joe's Live Rosemont

Bootleggers

1:30 AM · Carol's Pub

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

2:45 AM · ChiTown Movies

The Chicago Theatre Tour Experience

4:00 AM · The Chicago Theatre Tour Experience

Chicago Architecture Center River Cruise Aboard First Lady

4:00 AM · Chicago Architecture Center - First Lady

Balloon Museum | EmotionAir - Art You Can Feel - Chicago

2:00 PM · The Fields Studios

SummerSalt Market

3:00 PM · The Salt Shed Outdoors (Fairgrounds)

Dance Center Evanston

3:00 PM · George Van Dusen Theatre at North Shore Center

Bluegrass Brunch with Wild Scallions

4:00 PM · Garcia's Chicago

Country Brunch on the Patio w/ DIAMONDBACK!

4:00 PM · FITZGERALDS PATIO

Chicago Stars FC vs. San Diego Wave FC

4:00 PM · Martin Stadium

Going Bacharach: The Songs of An Icon

5:00 PM · Apollo Theater

Monty Python's Spamalot (Chicago)

5:00 PM · CIBC Theatre

Chicago White Sox vs. Detroit Tigers

5:10 PM · Guaranteed Rate Field

Z-O-M-B-I-E-S Dance Party

6:00 PM · Joe's Live Rosemont

Brahms, Strauss & Ravel La valse

7:00 PM · Orchestra Hall - IL

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

Big Band & BBQ w/ The DANA LEGG STAGE BAND wsg The Addison Trail High School Band!

10:30 PM · FITZGERALDS NIGHTCLUB

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

11:00 PM · Second City-Chicago: Mainstage