
Hey Chicagoland Singles!
(To see the entire list of events, PLEASE CLICK HERE)
The first full week of May has arrived and singles and speed dating events are in full swing.
Whether you are into pickleball, volunteering, boxing, spring flings, red flags, happy hours, or plain-old shenanigans….there are events for you.
Just don’t forget to say hi to your Boo while you are doing those activities.
For those of you who are new to this newsletter, allow me to re-introduce myself. My name is Ashvin and this is Where’s Your Boo?, your guide to weekly singles and speed dating events happening all over Chicagoland. We have been in publication for nearly 9 months and the goal is simple, making sure you know where to be so you are no longer Boo-less.
With that being said, let’s get into this week’s events!
Oh….and May the 4th be with you 😉
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.
Monday, May 4
Ivy Dating | Ivy Dating app: Bringing Dating Back to Real Life — May 4 • 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.
Hot Potato Hearts | Ace/Grey/Demi Speed Dating — May 4 @7:00 PM • Cafe Mustache, Chicago
Tuesday, May 5
Meet IRL | Meet IRL | Curated Speed Dating | Ages 30-39 ~Women's tickets sold out~ (Ages 30-39) — May 5 @6:30 PM • Solemn Oath Brewery Still Life, Chicago
Shuffle Dating | Shuffle Dating Chicago (Professional Theme) (Ages 28–38) — May 5 @7:00 PM • Navigator Taproom, Chicago
Wednesday, May 6
Meet Sweet | 20s–30s Singles Meet Up (Ages 20s–30s) — May 6 @6:00 PM – 9:00 PM • 88 Marketplace, Chicago
Meet Sweet | 20s–30s Singles Meet Up (Ages 20s–30s) — May 6 @6:00 PM – 9:00 PM • 88 Marketplace, Chicago
Chicago First Dates | Singles Ages, 40s & 50s - In-Person Speed Dating (Ages Women 44-56, Men 45-58) — May 6 @7:00 PM • Zia's Social, Chicago
CitySwoon | Speed Dating Chicago | CitySwoon® | 25-35 years | at Mexican Radio (Ages 25-35) — May 6 @7:30 PM • Mexican Radio, Chicago
Thursday, May 7
OnLoveXperiences | Singles Party: Lesbians, Bisexual Women, Nonbinary & Trans Singles — May 7 @5:30 PM – 8:00 PM • Lone Owl, Chicago
Meet IRL | Meet IRL x Trash People: Singles Community Clean Up — May 7 @6:00 PM • Consignment Lounge, Chicago
Stars and Garters Theater | Date Night: Live — May 7 @7:00 PM – 9:00 PM • Stars and Garters Theater, Chicago
Mary Jo McGuires | Singles Night (Every First Thursday of the month) — May 7 @7:00 PM • Mary Jo McGuires, Chicago
CitySwoon | Speed Dating Chicago | CitySwoon® | 35-49 years | at Dearly Beloved (Ages 35-49) — May 7 @7:30 PM • Dearly Beloved, Chicago
Thursday Dating | Thursday | SPRING FLING🌸 Singles Mixer | The Alston, Gold Coast — May 7 @7:30 PM • The Alston, Chicago
Shuffle Dating | Shuffle Dating Chicago (Ages 30–45) — May 7 @7:30 PM • The Parlour at Park & Oak, Glen Ellyn
Friday, May 8
Jigsaw Dating | Singles Pickleball 40-55, May 8th - Chicago (Ages 40-55) — May 8 @7:00 PM • Singles Pickleball 40-55, May 8th - Chicago, Chicago
Shuffle Dating | Shuffle Dating Chicago (Queer Women) (Ages 25–40) — May 8 @7:00 PM • The Albion Manor, Chicago
Secret Supper Club Chicago | Red Flags Party | Singles Social Mixer — May 8 @7:00 PM - 9:00 PM • 3430 N Lincoln Ave, Chicago, IL
Break The Ice Social Events LLC | Singles Social Mixer Antioch, IL Black Velvet Lounge — May 8 @7:30 PM • Black Velvet Lounge, Antioch
Matchify | Singles Mingle Dinner Party — May 8 @7:30 PM – 9:30 PM • Beatnik West Town, Chicago
Saturday, May 9
HinduVivah | Hindu Singles Speed Dating (Online) (Ages 40+) — May 9 @11:00 AM - 1:00 PM • Online, Online
Isaiah Parks | GOD Gone Work It Out II (Boxing Class) — May 9 @11:45 AM – 1:00 PM • Dark Horse Gym, Chicago
Miral Shah | Aura Matchmaking — May 9 @1:00 PM - 5:00 PM • Global Brew Tap House, Schaumburg, IL
Jigsaw Dating | Coffee Shop Speed Dating 40-55, May 9th - Chicago (Ages 40-55) — May 9 @3:00 PM • Necessary & Sufficient Coffee - Printers Row, Chicago
MyCheekyGayDate | Gay Men Speed Dating @ Tabu - May 9th 2026 (Ages 22–44) — May 9 @5:00 PM • Tabu, Chicago
CitySwoon | Speed Dating Chicago | CitySwoon® | 43-55 years | at Bar Moxy (Ages 43-55) — May 9 @6:00 PM • Bar Moxy, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Palatine, IL Emmett's Brewery — May 9 @6:30 PM • Emmett's Brewing Company, Palatine
Jigsaw Dating | Singles Happy Hour 40-55, May 9th - Chicago (Ages 40-55) — May 9 @7:00 PM • Elston Electric, Chicago
Ermantourage Sports | Dinner with New Friends: Chicago | Single Parents Edition — May 9 @7:00 PM • Restaurant of the Week, Chicago, IL
MyCheekyDate | ✨Chicago Speed Dating | Saturday Night Ages 27-42 | Fancy a Go? (Ages 27–42) — May 9 @7:30 PM • Tabu, Chicago
Sunday, May 10
MyCheekyDate | ✨ Chicago Speed Dating | Ages 36-48| Fancy a Go? (Ages 36–48) — May 10 @6:00 PM • Recess, Chicago
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:
ADDVentures | Single Awareness Dinner Monthly: Downers Grove | Foodies + New Friends — May 13 @7:00 PM • Restaurant of the Month, Downers Grove, IL
Quirk Events | Board Game Speed Dating (Queer Women) — May 13 @7:00 PM – 9:00 PM • Uptown Taproom, Chicago
The Tantra Institute | Tantra Speed Date Chicago — May 16 @5:30 PM – 8:30 PM • Moksha Yoga Center, Chicago
Single N Minglin LLC | Spring Fling Speed Dating — May 23 @8:00 PM – 1:00 AM • 6947 S South Chicago Ave, Chicago
River Shannon | Singles Night — May 27 @8:00 PM • River Shannon, 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
ThrowbackDating | Singles in Service: Beach Clean-Up (Ages 50+) — May 30 @9:00 AM • Gillson Beach, Michigan Avenue Wilmette
Thursday Dating | Saturday | Puppy Love @ PB&J | West Loop — May 30 @1:00 PM • PB&J: Pizza Beer and Jukebox, Chicago
(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?
