Hey Chicagoland Singles!
2026 is right around the corner and we have some big New Years Eve events lined up this week. You won’t want to miss them!
And as the year comes to a close, I’d also love your feedback on how useful Where’s Your Boo has been for you. I’ve included a short survey link below and would really appreciate you taking a few minutes to share your thoughts. Your input will directly shape what comes next.
Please fill out this short survey!
Starting next week, Where’s Your Boo will launch a website along with a monthly singles events calendar. As more singles events are popping up, newsletter real estate is getting crowded and I’m not in the business of sending you lengthy emails every Monday morning when you get enough of that already!
More updates coming soon. Stay tuned.
And with that, let’s wrap up 2025 and get on with this week’s events.
Oh, and how could I forget. Happy New Year! 🎉
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 30
CitySwoon | Speed Dating Chicago | CitySwoon® | 38-52 years | at Carnivale (Ages 38-52) — December 30 @7:30 PM • Carnivale, Chicago
Wednesday, December 31
Cassidy Davis | Chaotic Singles NYE Party! — December 31 @9:00 PM • Hubbard Inn, Chicago
Thursday Dating | Wednesday | New Years Eve Singles Spark | Mosaic, River North — December 31 @9:00 PM • Mosaic Events, Chicago
Thursday, January 1
MyCheekyDate | Find Your Match IRL — MyCheekyDate Speed Dating Nationwide — January 1 @8:30AM • Chicago
Friday, January 2
ThrowbackDating | Dial-Up Dating (Ages 45+)— January 2 @7:00 PM • (Virtual), Chicago
Saturday, January 3
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
The Dinner App | Only Single: Just a Sunset Run — January 3 @7:00 PM - 10:00 PM • Millennium Monument, Chicago
MyCheekyDate | MEN SOLD OUT✨ Chicago Speed Dating | Saturday Night Ages 25–39 (Ages 25–39) — January 3 @7:30 PM • Tabu, Chicago
ChicagoCrawls.com | Chicago Singles Bar Crawl — January 3 @9:00 PM - 12:00 AM • Wrigleyville Bars (TBA), Chicago
Single N Minglin LLC | New Year, New Vibes: Singles Night at Privilege — January 3 @9:00 PM • Privilege, Chicago
Sunday, January 4
MyCheekyDate | ✨ Chicago Speed Dating | Ages 36-48 | Fancy a Go? (Ages 36–48) — January 4 @6:00 PM • Tabu, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Gurnee, IL Cooper's Hawk — January 4 @6:00 PM • Cooper’s Hawk Winery & Restaurant, Gurnee
Next week’s events:
Break The Ice Social Events LLC | Singles Social Mixer Naperville, IL Uncle Julio's — January 6 @6:30 PM • Uncle Julio's Naperville, Naperville
Meet IRL | Meet IRL | Curated Speed Dating at Hopsmith | Ages 24-32 (Ages 24-32) — January 6 @6:30 PM • Hopsmith Chicago, Chicago
Meet IRL | Meet IRL | Queer Speed Dating | Ages 30+ sold out - add to waitlist! (Ages 30+) — January 6 @6:30 PM • Solemn Oath Brewery Still Life, Chicago
Hot Potato Hearts | Queer Flirting League Singles Mixer— January 6 @7:00 PM • Babe's Sports Bar, Chicago
MyCheekyGayDate | Gay Men Speed Dating @ Tabu - January 7th 2026 (Ages 22–44) — January 7 @8:00 PM • Tabu, Chicago
Chicago First Dates | Singles 20s & 30s Speed Dating (Ages Women 24-38, Men 25-39) — January 8 @7:00 PM - 9:00 PM • Ivy Hotel – Streeterville, Chicago
West Town Social Club | Thirsty Thursday Singles Night! — January 8 @7:00 PM • The Low Horse, Chicago
CitySwoon | Speed Dating Chicago | CitySwoon® | 30-45 years | at Carnivale (Ages 30-45) — January 8 @7:30 PM • Carnivale, Chicago
Thursday Dating | Thursday | Singles Shuffleboard | Royal Palms, Wicker Park — January 8 @7:30 PM • Royal Palms Shuffleboard Club, Chicago
OnLoveXperiences | Singles Party (Lesbian, Bi, NB & Trans) (Ages 25-40) — January 9 @5:30 PM - 9:00 PM • Park & Field – Logan Square, Chicago
Jigsaw Dating | Coffee Shop Speed Dating, January 10th - Chicago (Ages 25-45+) — January 10 @3:00 PM • Coffee Shop Speed Dating, January 10th - Sip & Savor, Chicago
Jigsaw Dating | Singles Trivia Night, January 10th - Chicago (Ages 25-45+) — January 10 @7:00 PM • Elston Electric, Chicago
MyCheekyDate | ✨ Chicago Speed Dating | Saturday Night Ages 25–39 | Fancy a Go? (Ages 25–39) — January 10 @7:30 PM • Tabu, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Burr Ridge Cooper's Hawk — January 11 @1:00 PM • Cooper’s Hawk Winery & Restaurant, Burr Ridge
MyCheekyDate | ✨ Chicago Speed Dating | Ages 32-44| Fancy a Go? (Ages 32–44) — January 11 @6:00 PM • Recess, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Arlington Heights Cooper's Hawk — January 11 @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:
Meet IRL | Meet IRL | Singles Volunteer Evening | Ages 30+ women's tickets sold out (Ages 30+) — January 14 @6:00 PM • The Parlor, Chicago
Green Flag Matchmaking | Speed Dating + Matchmaking — January 14 @6:00 PM • Adamus Lounge, Chicago
What if Social | Winter Mix and Mingle West Loop — January 15 @6:00 PM • Bandit
Holy Nation Matchmaking | Virtual Christian Speed Dating — January 15 @6:15 PM • online
MyCheekyDate | ✨ Chicago Speed Dating | Ages 24-36 | Fancy a Go? (Ages 24–36) — January 15 @7:00 PM • Untitled Supper Club, 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
Shuffle Dating | Speed Dating (Ages 30-40) — January 15 @7:00 PM • Navigator Taproom, Chicago
Chicago First Dates | Singles 20s & 30s Speed Dating (Ages Women 24-38, Men 25-39) — January 15 @7:00 PM • Moretti's Ristorante & Pizzeria – Edison Park, Chicago
CitySwoon | Speed Dating Chicago | CitySwoon® | 38-52 years | at 101 Bar (Ages 38-52) — January 15 @7:30 PM • 101 Bar, Chicago
Break The Ice Social Events LLC | Singles Social Mixer McHenry, IL DC Cobbs — January 16 @6:30 PM • D.C. Cobb's McHenry, McHenry
Social Lab | Bingo Dating at Hamburger Mary's — January 17 @4:00 PM • Hamburger Mary's – Chicago, Chicago
The Tantra Institute | Tantra Speed Date® - Chicago! (Meet Singles Speed Dating) — January 17 @5:30 PM • Moksha Yoga Center, Chicago
Jigsaw Dating | Singles Happy Hour 40+, January 17th - Chicago (Ages 40+) — January 17 @7:00 PM • Elston Electric, Chicago
MyCheekyGayDate | Gay Men Speed Dating @ Tabu - January 20TH 2026 (Ages 22–44) — January 20 @8:00 PM • Tabu, Chicago
Birds of a Feather | Non-Monogamous Speed Dating & Mingling (Ages 45 and under) — January 21 @6:00 PM • Bar Moxy, Chicago
Thursday Dating x Level Up Social Club | Thursday | New Year, New Connections | House of Blues, Foundation Room — January 22 @6:00 PM • House of Blues Chicago, Chicago
Meet Sweet | Latin Singles Meet Up — January 25 @6:00 PM • Punch House, Chicago
Quirk Events | Board Game Speed Dating (Ages 20s & 30s) — January 29 @7:00 PM • Big Star Wrigleyville, Chicago
Intelligent Singles Network | Intelligent Singles Mixer at Marriott Autograph Collection Chicago! — January 29 @7:00 PM • Marriott Autograph Collection Chicago!, Chicago
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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