Hey Chicagoland Singles!
100+ singles events every month is basically the new normal. To see the entire list of events, PLEASE CLICK HERE.
Quick re-introduction: I’m Ashvin, and this is Where’s Your Boo, your weekly guide to singles and dating events across Chicagoland. We’ve been publishing for 5 months, and the community is growing every week.
My mission is simple: make it obvious that IRL dating events are everywhere and you actually have options beyond the apps.
And the options keep expanding for two reasons:
more varieties of singles events are popping up, and
more neighborhoods and suburbs are hosting them.
That feeling that dating apps are the only option is so 2025.
So start freeing up your calendar, because finding your Boo is closer (and easier) than you think.
Let’s get into this week’s events.
(And if you have a moment, would love it if you can fill out this feedback survey if you haven’t done so already last week. Your feedback is greatly appreciated.)
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.
Tuesday, January 20
Break The Ice Social Events LLC | Singles Social Mixer Schaumburg, IL Fox & Hound — January 20 @6:30 PM • Fox & Hound, Schaumburg
MyCheekyGayDate | Gay Men Speed Dating @ Tabu - January 20th 2026 (Ages 22–44) — January 20 @8:00 PM • Tabu, Chicago
Wednesday, January 21
Birds of a Feather | Non-monogamous Speed Dating + Mingling for Individuals 45 and Under (Ages Under 45) — January 21 @6:00 PM - 9:00 PM • Bar Moxy, Chicago
Hot Potato Hearts | Speed Dating (Casual & Inclusive) — January 21 @7:00 PM - 9:30 PM • Easy Does It, Chicago
Shuffle Dating | Speed Dating (Ages 27-35) — January 21 @7:30 PM • District Brew Yards, Chicago
Thursday, January 22
Thursday Dating | Thursday | New Year, New Connections | House of Blues, Foundation Room — January 22 @6:00 PM • House of Blues Chicago, Chicago
Meet IRL | Meet IRL | Singles Only Speed Friending & Social — January 22 @6:30 PM • Wolf & Company, Chicago
Meet IRL | Winter Warmer Singles Mixer ❄️ — January 22 @6:30 PM • Barcocina Lakeview, Chicago
Jigsaw Dating | Singles Arcade Night (Ages 25-45+) — January 22 @7:00 PM • Dave and Busters, Rosemont
The Shaka Club | Fulton Market Singles: Late 20s/30s Winter Olympics Happy Hour | (Ages Late 20s/30s) — January 22 @7:00 PM • Punch Bowl Social, Chicago
Chicago First Dates | Singles Ages 30s & 40s - In-Person Speed Dating (Ages Women 33-45, Men 35-48) — January 22 @7:00 PM • Moretti's Ristorante & Pizzeria - Edison Park, Chicago
CitySwoon | Speed Dating Chicago | (Ages 27-39) — January 22 @7:30 PM • Bandol Brasserie & Raw Bar, Chicago
Friday, January 23
Thursday Dating | Friday | FLIRT BINGO — January 23 @6:00 PM • Hopsmith Chicago, Chicago
Break The Ice Social Events LLC | Singles Social Mixer — January 23 @6:30 PM • Miller's Ale House, Lombard
CitySwoon | Speed Dating Chicago | (Ages 40-55) — January 23 @7:30 PM • Roanoke, Chicago
Chicago First Dates | Singles Ages 20s & 30s - Online Speed Dating (Ages Women 21-35, Men 23-37) — January 23 @8:00 PM • Online
Cassidy Davis | Chaotic Singles Party! — January 23 @8:00 PM - 11:00 PM • Moxy Chicago Downtown, Chicago
Saturday, January 24
Jigsaw Dating | Coffee Shop Speed Dating (Ages 25-45+) — January 24 @3:00 PM • Coffee Shop Speed Dating, January 24th- Chicago
Break The Ice Social Events LLC | Singles Social Mixer — January 24 @6:30 PM • Spartan Ale House, Naperville
Jigsaw Dating | Singles Happy Hour (Ages 25-45+) — January 24 @7:00 PM • Singles Happy Hour, January 24th - Chicago
The Dinner App | ONLY SINGLE, JUST A SUNSET RUN/CHICAGO — January 24 @7:00 PM • Millennium Monument, Chicago
MyCheekyDate | ✨ Chicago Speed Dating | Fancy a Go? (Ages 25–39) — January 24 @7:30 PM • Tabu, Chicago
ChicagoCrawls | Chicago Singles Bar Crawl — January 24 @9:00 PM - 12:00 AM • Wrigleyville Bars (TBA), Chicago
Sunday, January 25
Break The Ice Social Events LLC | Singles Social Mixer — January 25 @1:00 PM • Cooper’s Hawk Winery & Restaurant, Oak Lawn
Chicago First Dates | Singles Ages 20s & 30s - In-Person Speed Dating (Ages Women 24-38, Men 25-39) — January 25 @5:00 PM • Moretti's Ristorante & Pizzeria - Edison Park, Chicago
Break The Ice Social Events LLC | Singles Social Mixer — January 25 @6:00 PM • Cooper’s Hawk Winery & Restaurant, Oak Park
Shuffle Dating | Shuffle Dating Singles Night (Ages 28-38) — January 25 @6:00 PM • The Dandy Crown, Chicago
Meet Sweet | Latin Singles Meet Up — January 25 @6:00 PM - 9:00 PM • Punch House (1227 W 18th St), 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:
Meet IRL | Meet IRL | Curated Speed Dating @ Palmhouse Evanston| (Ages 25-39) — January 29 @6:30 PM • PALMHOUSE, Evanston
Quirk Events | Board Game Speed Dating (Ages 20s & 30s) — January 29 @7:00 PM • Big Star Wrigleyville, Chicago
Jigsaw Dating | Singles Pickleball (Ages 25-45+) — February 6 @7:00 PM • Singles Pickleball, February 6th - Chicago
Timber Lanes | Singles Bowling Mixer — February 14 @8:00 PM - 11:00 PM • Timber Lanes Bowling Alley, Chicago
ThrowbackDating | Slow Dance Dating (Ages 45+) — February 15 @1:00 PM • Fireside Bowl, West Fullerton Avenue Chicago
To see the entire list of events, PLEASE CLICK HERE.
And if you have a moment, would love it if you can fill out this feedback survey if you haven’t done so already last week. Your feedback is greatly appreciated.
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?