Hey Chicagoland Singles!
The holidays are closing in, and after that brutally cold Chicagoland weekend, I would not blame you for staying home. As travel and family plans ramp up, the number of singles events naturally starts to thin out. Still, this week brings a solid mix of mixers, speed dating, volunteer nights, and even sauna and cold-plunge socials for the brave.
This is also when New Year’s energy quietly starts to build. Holiday parties and ugly sweater events lead straight into a strong lineup of New Year’s Eve singles parties. Fewer events doesn’t mean fewer chances, it just means more focused rooms and better timing before the calendar flips.
Now, let’s get into this week’s events!
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, December 16
Meet IRL | Meet IRL | Singles Volunteer Evening | Ages 35+ (Ages 35+) — December 16 @6:00 PM • The Parlor, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Schaumburg, IL Fox and Hound — December 16 @6:30 PM • Fox & Hound, Schaumburg
Meet IRL | Meet IRL | Curated Speed Dating for Ages 28 - 42 *Women's tickets sold out! (Ages 28-42) — December 16 @6:30 PM • Midwest Coast Brewing Company, Chicago
Wednesday, December 17
Dorothy | IRL: Singles Mixer at Dorothy (LGBT community) — December 17 @6:00 PM • Dorothy, Chicago
Chicago First Dates | Singles Ages 30s & 40s - In-Person Speed Dating (Ages Women 33-45, Men 35-47) — December 17 @7:00 PM • Moretti's Ristorante & Pizzeria - Edison Park, Chicago
Thursday Dating | Wednesday | Sauna / Cold Plunge Singles Social | Oak St Beach — December 17 @7:30 PM • Oak St. Sauna, Chicago
MyCheekyGayDate | Gay Men Speed Dating @ TABU - December 17th 2025 (Ages 22–44) — December 17 @8:00 PM • TABU, Chicago
Thursday, December 18
Meet IRL | Meet IRL | A Cute Little (Singles) Holiday Party | Ages 30+ (Ages 30+) — December 18 @6:30 PM • Verve Wine Chicago, Chicago
Chicago First Dates | Singles Ages 20s & 30s - In-Person Speed Dating (Ages Women 24-38, Men 25-39) — December 18 @7:00 PM • Moretti's Ristorante & Pizzeria - Edison Park, Chicago
The Shaka Club | Gold Coast Singles: Late 20s/30s Ugly Holiday Sweater Happy Hour | The Shaka Club (Ages Late 20s/30s) — December 18 @7:00 PM • Hopsmith, Chicago
Intelligent Singles Network | Intelligent Singles Mixer — December 18 @ 7:00 PM • Bar Tabu, Chicago
Thursday Dating | Thursday | Singles Trivia Night | Fatpour Works, Wicker Park — December 18 @7:30 PM • Fatpour Wicker Park: Ultimate Chicago Sports Bar, Chicago
Friday, December 19
Break The Ice Social Events LLC | Singles Social Mixer Schaumburg Westwood Tavern — December 19 @6:30 PM • Westwood Tavern, Schaumburg
Thursday Dating | Friday | Meet Me Under the Mistletoe – Matchamaking Mixer | River North — December 19 @7:30 PM • Hubbard Inn, Chicago
Salsa For Singles | Singles Event In Chicago — December 19 @8:00 PM • Stereo Nightclub, Chicago
Saturday, December 20
Jigsaw Dating | Coffee Shop Speed Dating, December 20th- Chicago (Ages 25-45+) — December 20 @3:00 PM • Goddess and the Baker, Chicago
Prāzbar | Single Christians Ugly Sweater Holiday Party — December 20 @ 7:00 PM • Prazbar, Chicago
Jigsaw Dating | Singles Holiday Happy Hour, December 20th - Chicago (Ages 25-40) — December 20 @7:00 PM • Singles Holiday Happy Hour, December 20th - Chicago, Chicago
A Non-Alcoholic Wine Shop | Single & Sober Ugly Sweater Bash — December 20 @8:00 PM • A Non-Alcoholic Wine Shop, Chicago
Remaining events this month:
CitySwoon | Speed Dating Chicago | CitySwoon® | 32-44 years | at Carnivale (Ages 32-44) — December 23 @7:30 PM • Carnivale, Chicago
Abto | Christian Singles Speed Dating — December 26 @ 7:00 PM • Chicago
Right – Muslim Social App | Chicago Muslim Singles Event — December 27 @ 4:00 PM • Chicago
Break The Ice Social Events LLC | Singles Social Mixer Naperville Spartan Ale House — December 27 @6:30 PM • Spartan Ale House, Naperville
Chicago First Dates | Singles Ages, 40s & 50s - In-Person Speed Dating (Ages Women 44-56, Men 45-58) — December 28 @5:00 PM • Moretti's Ristorante & Pizzeria - Edison Park, Chicago
CitySwoon | Speed Dating Chicago | CitySwoon® | 38-52 years | at Carnivale (Ages 38-52) — December 30 @7:30 PM • Carnivale, Chicago
Thursday Dating | Wednesday | New Years Eve Singles Spark | Mosaic, River North — December 31 @9:00 PM • Mosaic Events, Chicago
Cassidy Davis | Chaotic Singles NYE Party! (Chicago) — December 31 @9:00 PM • Hubbard Inn, Chicago
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And a Sneak Peek into a Few Events Coming Up Next Year:
CitySwoon | Speed Dating Chicago | CitySwoon® | 35-49 years | at Bar Moxy (Ages 35-49) — January 3 @6:00 PM • Bar Moxy, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Palatine Emmett's Brewery — January 3 @6:30 PM • Emmett's Brewing Company, Palatine
Meet IRL | Meet IRL | Queer Speed Dating | Ages 30+ (Ages 30+) — January 6 @6:30 PM • Solemn Oath Brewery Still Life, Chicago
MyCheekyGayDate | Gay Men Speed Dating @ Tabu - January 7th 2026 (Ages 22–44) — January 7 @8:00 PM • Tabu, Chicago
West Town Social Club | Thirsty Thursday Singles Night! — January 8 @7:00 PM • The Low Horse, Chicago
Thursday Dating | Thursday | Singles Shuffleboard | Royal Palms, Wicker Park — January 8 @7:30 PM • Royal Palms Shuffleboard Club, Chicago
Jigsaw Dating | Singles Trivia Night, January 10th - Chicago (Ages 25-45+) — January 10 @7:00 PM • Elston Electric, Chicago
Meet IRL | Meet IRL | Singles Volunteer Evening | Ages 30+ (Ages 30+) — January 14 @6:00 PM • The Parlor, Chicago
The Shaka Club | Early/Mid-20s Electric Shuffle Happy Hour (River North) | The Shaka Club (Ages Early/Mid-20s) — January 15 @7:00 PM • Electric Shuffle Chicago, Chicago
Quirk Events | Board Game Speed Dating (AgeAges 20s & 30s) — January 29 @7:00 PM • Big Star Wrigleyville, Chicago
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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!
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