
Hey Chicagoland Singles!
(To see the entire list of events, PLEASE CLICK HERE)
Memorial Day is unofficially the first day of summer. Which means fireworks return at Navy Pier this week, with temps heating up to the high 70's.
At the same time, the singles events scene is heating up in Chicagoland as well. Which is why I’m sending you this email on a holiday, so you’re equipped and ready to handle the heat! 🔥
So relax and enjoy the day off! But before that, let’s jump into this week’s events!
….P.S. Wishing you a Memorial Day that is both commemorative and restful!
Singles Events Happening This Week
Some events may not share certain criteria like age ranges. If you would like to be certain, please reach out to the organizers of the events you are interested in attending. Also, certain event titles below may state ‘SOLD OUT’. In some cases that is not true. Please ensure to visit the event listing site to confirm.
Orange - Suburb events
Pink - LGBTQ+ & inclusive events
Green - Ages 50+ singles events
Blue - Religious/Ethnic Community-based events
Monday, May 25
Ivy Dating | Ivy Dating app: Bringing Dating Back to Real Life — May 25 • An app that shows where singles are going out across Chicago each night. See which bars and clubs are active, where people are checked in, and choose your night based on where the energy is.
Tuesday, May 26
Meet IRL | Meet IRL | 30+ Queer Speed Dating at Way Out (Ages 30+) — May 26 @6:30 PM • Way Out - Tuesday, May 26, 2026 at Way Out, Chicago
Meet IRL | Meet IRL | Curated Speed Dating | Ages 25-35 ~Men's tickets sold out~ (Ages 25-35) — May 26 @6:30 PM • Midwest Coast Brewing Company, Chicago
Wednesday, May 27
MyCheekyDate | ✨ Chicago Speed Dating | Ages 25-39| Fancy a Go? (Ages 25–39) — May 27 @6:00 PM • Recess, Chicago
Shuffle Dating | Speed Dating (Men & Women) (Ages 35-50) — May 27 @7:00 PM • The Parlour at Park & Oak, Glen Ellyn, IL
Intelligent Singles Network | Intelligent Singles Mixer at Hyatt Hotel in Chicago! — May 27 @7:00 PM - 10:00 PM • Aire Rooftop Bar Chicago, Chicago, IL
CitySwoon | Speed Dating Chicago | CitySwoon® | 38-52 years | at La Bella Trattoria (Ages 38-52) — May 27 @7:30 PM • La Bella Trattoria, Chicago
Hot Potato Hearts | Bowling For Potato Soup — May 27 @7:30 PM • Avondale Bowl, Chicago
River Shannon | Singles Night — May 27 @8:00 PM • River Shannon, Chicago
Thursday, May 28
Meet IRL | Meet IRL | Singles Trivia Night! ~Women's tickets sold out!~ — May 28 @6:30 PM • Fatpour Wicker Park: Ultimate Chicago Sports Bar, Chicago
Rooftop Cinema Club | Singles Night (There’s Something About Mary Screening) (Ages 25–35) — May 28 @6:30 PM • Rooftop Cinema Club Fulton Market, Chicago
Thursday Dating | Thursday | Love is in the Air – an immersive singles event | Flyover Chicago, Navy Pier — May 28 @7:00 PM • Flyover, Chicago
THURSDAY Dating | Schaumburg Singles Night | Global Brew Taphouse — May 28 @7:30 PM • Global Brew Taphouse, Schaumburg, IL
Friday, May 29
Chicago First Dates | Singles Ages 30s & 40s - Online Speed Dating (Ages Women 30-45, Men 30-45) — May 29 @8:00 PM • Online, Online
Chaotic Singles Party | Chaotic Singles Salsa Night! — May 29 @8:00 PM - 11:00 PM • The Cubby Bear Chicago, Chicago, IL
Saturday, May 30
ThrowbackDating | Singles in Service: Beach Clean-Up (Ages 50+) — May 30 @9:00 AM • Gillson Beach, Michigan Avenue Wilmette
Hindu Vivah | Zoom Event | US/Canada Raised (Ages 26-45) — May 30 @11:00 AM - 1:00 PM • Online, Online
Thursday Dating | Saturday | Puppy Love @ PB&J | West Loop — May 30 @1:00 PM • PB&J: Pizza Beer and Jukebox, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Libertyville, IL Bar Crawl Starting at Morgan's — May 30 @6:30 PM • Morgan's - Saturday, May 30, 2026 at Morgan's Bar & Grill, Libertyville
Secret Supper Club Chicago | Red Flags Party | Singles Social Mixer — May 30 @7:00 PM - 9:00 PM • 3430 N Lincoln Ave, Chicago, IL
MyCheekyDate | MEN SOLD OUT✨ Chicago Speed Dating | Saturday Night Ages 25-39 (Ages 25–39) — May 30 @7:30 PM • Tabu, Chicago
Chicago First Dates | Singles Ages 40s & 50s - Online Speed Dating (Ages Women 44-57, Men 44-58) — May 30 @8:00 PM • Online, Online
Sunday, May 31
Shuffle Dating | Speed Dating (Men & Women) (Ages 25-40) — May 31 @4:00 PM • The Dandy Crown, Chicago, IL
Hot Potato Hearts | Sunday FunGAY — May 31 @5:00 PM • The Hi-Lo, Chicago
MyCheekyDate | ✨ Chicago Speed Dating | Ages 32-44 | Fancy a Go? (Ages 32–44) — May 31 @5:00 PM • Tabu, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Arlington Heights, IL Cooper's Hawk — May 31 @6:00 PM • Cooper's Hawk Winery & Restaurant, Arlington Heights
Know a single friend who’d love Where’s Your Boo? Forward this email to them, or send them this link to sign up!
And a Sneak Peek into a Few Events Coming Up in the following weeks:
Mary Jo McGuires | Singles Night (Every First Thursday of the month) — June 4 @7:00 PM • Mary Jo McGuires, Chicago
Jigsaw Dating | Singles Trivia Night 25-40, June 6th - Chicago (Ages 25-40) — June 6 @7:00 PM • Chicago
Shawn Travis Coaching | Win The Dating Game (Educational) — June 7 @2:30 PM - 4:00 PM • 834 Lake St, Oak Park, IL
Lauren Fondriest | Summer Dating Strategy (Educational - Women Only) (Ages Women Only) — June 10 @6:00 PM - 8:00 PM • Fabrik Chicago, Chicago, IL
West Town Social Club | Singles & Social Folks Rooftop Mixer @ Midwest Coast! — June 10 @6:30 PM - 9:00 PM • Midwest Coast Brewing Company, Chicago, IL
ADDVentures | Single Awareness Dinner Monthly: Downers Grove | Foodies + New Friends — June 13 @7:00 PM • Restaurant of the Month, Downers Grove, IL
The Rooted Space | Salsa Speed Dating (Ages 30-45) — June 20 @7:30 PM • The Rooted Space, Chicago, IL
Throwback Dating | Singles Group Trip to Summerfest (Ages 50+) — June 27 @10:00 AM - 12:00 AM • Milwaukee, WI
The City Social | Chicago Social Hour: Speed Dating For Ages 25-35 (Ages 25-35) — June 29 @6:30 PM - 9:30 PM • Barcocina Lakeview, Chicago, IL
(To see the entire list of events, PLEASE CLICK HERE)
That’s it for this week.
And as always, thank you for reading another edition of Where’s Your Boo?. Your boo is waiting for you. So get out there, and let us know how it goes!
And for more, subscribe to Where’s Your Boo?
