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May 2026 Events and Things to do in Westchester, IL

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Journey vs Foreigner: A Tribute performed by Hi Infidelity
Tomorrow at 8:00 PM
Elmhurst · Stage 119
Sales end soon
Journey vs Foreigner: A Tribute performed by Hi Infidelity
Tomorrow at 8:00 PM
Elmhurst · Stage 119
Sales end soon
Trash People of Humboldt Park: Community Clean-Up!
Sunday at 11:30 AM
Chicago · Suncatcher Brewing
Sales end soon
Trash People of Humboldt Park: Community Clean-Up!
Sunday at 11:30 AM
Chicago · Suncatcher Brewing
Sales end soon
Crawfish Boil & Live Auction
Saturday at 1:00 PM
Willow Springs · The Irish Legend
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Crawfish Boil & Live Auction
Saturday at 1:00 PM
Willow Springs · The Irish Legend
Almost full
Summer Saturday: Garden Party
Saturday at 10:00 AM
Lisle · Sensory Garden Playground
Almost full
Summer Saturday: Garden Party
Saturday at 10:00 AM
Lisle · Sensory Garden Playground
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A Taste of Black Excellence — Chicago’s Top Cultural Dining Experience
Saturday at 5:00 PM
Broadview · Schroeder Park
Sales end soon
A Taste of Black Excellence — Chicago’s Top Cultural Dining Experience
Saturday at 5:00 PM
Broadview · Schroeder Park
Dykes 4 Abortion: a Fundraiser for the Chicago Abortion Fund
Today at 7:00 PM
Chicago · Dorothy
Dykes 4 Abortion: a Fundraiser for the Chicago Abortion Fund
Today at 7:00 PM
Chicago · Dorothy
Almost full
House Music is Home at Navy Pier. Free w RSVP.
Sat, May 30, 4:30 PM
Chicago · Navy Pier
Almost full
House Music is Home at Navy Pier. Free w RSVP.
Sat, May 30, 4:30 PM
Chicago · Navy Pier
TECHSPO Chicago 2026 Technology Expo (AdTech ~ MarTech)
Tuesday at 9:00 AM
Chicago · Soldier Field Stadium
TECHSPO Chicago 2026 Technology Expo (AdTech ~ MarTech)
Tuesday at 9:00 AM
Chicago · Soldier Field Stadium
Almost full
Mahjong 101 Beginner Class - DGSRC Member Exclusive
Today at 7:00 PM
Downers Grove · Downers Grove Swim and Racquet Club (DGSRC)
Almost full
Mahjong 101 Beginner Class - DGSRC Member Exclusive
Today at 7:00 PM
Downers Grove · Downers Grove Swim and Racquet Club (DGSRC)
Going fast
BLISS CARIBBEAN PARTY SERIES!! Memorial Day Weekend Edition
Sat, May 23, 9:00 PM
Chicago · The Wild Hare & Singing Armadillo Frog Sanctuary
Going fast
BLISS CARIBBEAN PARTY SERIES!! Memorial Day Weekend Edition
Sat, May 23, 9:00 PM
Chicago · The Wild Hare & Singing Armadillo Frog Sanctuary
Ravenswood Spring Vintage & Artisan Fest presented by Windy City Market
Sat, May 23, 12:00 PM
Chicago · Artifact Events
Ravenswood Spring Vintage & Artisan Fest presented by Windy City Market
Sat, May 23, 12:00 PM
Chicago · Artifact Events
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FRIDAYZ @ MASADA: Afrobeats, Amapiano, Dancehall, RnB
Tomorrow at 9:30 PM
Chicago · Masada
Sales end soon
FRIDAYZ @ MASADA: Afrobeats, Amapiano, Dancehall, RnB
Tomorrow at 9:30 PM
Chicago · Masada
Fresa Fests - Halfway To Halloween Market ✨ Spooky + Trinket Market
Sun, May 24, 12:00 PM
Chicago · 1657 N Kostner Ave
Fresa Fests - Halfway To Halloween Market ✨ Spooky + Trinket Market
Sun, May 24, 12:00 PM
Chicago · 1657 N Kostner Ave
Almost full
Ladies Love RNB Day Party at Joy District FT: Sean Mac
Saturday at 3:00 PM
Chicago · Joy District
Almost full
Ladies Love RNB Day Party at Joy District FT: Sean Mac
Saturday at 3:00 PM
Chicago · Joy District
A Just Brew: An AAPI Happy Hour FUNdraiser
Thu, May 21, 6:00 PM
Chicago · Pilot Project Brewing - Logan Square
A Just Brew: An AAPI Happy Hour FUNdraiser
Thu, May 21, 6:00 PM
Chicago · Pilot Project Brewing - Logan Square
Going fast
John Doyle in Concert
Tuesday at 7:30 PM
Chicago · Chief O'Neill's Pub Restaurant Beer Garden
Going fast
John Doyle in Concert
Tuesday at 7:30 PM
Chicago · Chief O'Neill's Pub Restaurant Beer Garden
Going fast
Squats & Mimosas
Saturday at 11:30 AM
Franklin Park · 9100 Belden Ave
Going fast
Squats & Mimosas
Saturday at 11:30 AM
Franklin Park · 9100 Belden Ave
Almost full
Sunshine & Build - Women's Rooftop Networking
Sunday at 12:00 PM
Chicago · Paradise Park | Pizza & Patio
Almost full
Sunshine & Build - Women's Rooftop Networking
Sunday at 12:00 PM
Chicago · Paradise Park | Pizza & Patio
Going fast
Crew Love: R&B vs Trap
Tomorrow at 7:00 PM
Bellwood · Elements
Going fast
Crew Love: R&B vs Trap
Tomorrow at 7:00 PM
Bellwood · Elements
Almost full
Meet IRL | Curated Speed Dating | Ages 32-42 ~Women's tickets sold out~
Tuesday at 6:30 PM
Chicago · Wolf & Company
Almost full
Meet IRL | Curated Speed Dating | Ages 32-42 ~Women's tickets sold out~
Tuesday at 6:30 PM
Chicago · Wolf & Company

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