Hey Chicagoland Singles!
Today is a bittersweet day! The bitter part: Halloween 2025 is officially over 😢 , and our costumes have been laid to rest, possibly forever (unless you’re that person who proudly reuses costumes every year).
Halloween might be over Chicagoland, but the sweet part: the fun just keeps getting better 🎉 !
This month alone, there are over 45 singles events across Chicagoland! And I’ve found even more organizations jumping into the mix, meaning more chances, more scenes, and maybe, just maybe, your boo.
And some of these events are not your typical events. We got board games! We got AI matchmaking! We got basketball games! We even got scavenger hunts! November’s got range my friend.
Now, I know what you’re thinking. It’s November, it’s cold, and the couch with cider sounds mighty tempting. Maybe even a getaway to Bali. I get it.
But while Chicagoland’s weather is cooling down, its IRL dating scene is heating up. And with this month’s variety, you might be one RSVP away from your boo.
So, let’s call it what it is: No-Skip November. Because this is the month your future boo won’t want you to skip.
Now, on to the events!
Singles Events Happening This Week
Tuesday, November 4
meet irl | Curated Speed Dating (Ages 30–39) — Nov 4 @6:30 PM • Solemn Oath Brewery Still Life, Chicago
Wednesday, November 5
CitySwoon | Speed Dating Chicago | CitySwoon® | 35–49 years | at Bar Moxy (Ages 35–49) — November 5 @7:30 PM • Bar Moxy, Chicago
Shuffle Dating | Shuffle Dating Chicago – District Brew Yards (Ages 30–40) — November 5 @ 7:00 PM • District Brew Yards, West Loop (Chicago)
Thursday, November 6
The Shaka Club | Singles Only: Early/Mid-20s Happy Hour (River North) (Ages Early/Mid-20s) — November 6 @7:00 PM • Parlay River North, 112 W Hubbard St, Chicago
Quirk Events | Board Game Speed Dating – Big Star Wrigleyville (Ages 20s & 30s) — November 6 @7:00 PM • Big Star Wrigleyville, Chicago
Thursday Dating | Thursday | AI Matchmaking Singles Mixer | River North — November 6 @7:30 PM • Hubbard Inn, Chicago
Chicago First Dates | Single Professionals, 40s & 50s (Ages Women 43–55, Men 45–58) — November 6 @7:00 PM • Moretti’s Ristorante & Pizzeria – Edison Park, Chicago
MyCheekyDate | Speed Dating @ Untitled Supper Club — Chicago (Ages 24–36) (Ages 24–36) — November 6 @7:00 PM • Untitled Supper Club, Chicago
meet irl | Curated Speed Dating @ Hopsmith (Ages 22–32) — Nov 6 @6:30 PM • Hopsmith, Chicago
Intelligent Singles Network | Intelligent Singles Mixer in Chicago — Nov 6 @7:00 PM • Tre Denari, Chicago
Shuffle Dating | Speed Dating @ The Albion Manor (Ages 35–45) — Nov 6 @7:00 PM • The Albion Manor, Chicago
Friday, November 7
meet irl | Singles Basketball Social — Nov 7 @6:30 PM • Wintrust Arena, Chicago
Flirty Friday at Anthem Ale House | Flirty Friday – Naperville Singles Mixer — November 7 @ 8:00 PM • Anthem Ale House, Naperville (IL)
Saturday, November 8
Jigsaw Dating | Coffee Shop Speed Dating, November 8th – Chicago (Ages 25–45+) — November 8 @3:00 PM • Coffee Shop Speed Dating, Chicago
Jigsaw Dating | Singles Trivia Night, November 8th – Chicago (Ages 25–45+) — November 8 @7:00 PM • Hubbard Inn, Chicago
MyCheekyDate | Saturday Night Speed Dating @ Time Out Market Chicago — Chicago (Ages 25–39) (Ages 25–39) — November 8 @7:30 PM • Time Out Market Chicago, Chicago
Break The Ice Social Events LLC | Singles Social Mixer – McHenry DC Cobbs — November 8 @ 6:30 PM • DC Cobbs, McHenry (IL)
ChicagoCrawls.com | Chicago Singles Bar Crawl – Welcome Shots at Every Bar! — November 8 @9:00 PM • Wrigleyville’s BEST Bars (TBA), Chicago
Sunday, November 9
MyCheekyDate | Speed Dating @ Recess — Chicago (Ages 32–44) (Ages 32–44) — November 9 @6:00 PM • Recess, Chicago
Shuffle Dating | Shuffle Dating Chicago – The Dandy Crown (Ages 27–34) — November 9 @ 4:00 PM • The Dandy Crown, River West (Chicago)
Break The Ice Social Events | Singles Social Mixer @ Cooper’s Hawk — Nov 9 @6:00 PM • Cooper’s Hawk Winery & Restaurant, South Barrington
Events Next Week:
Break The Ice Social Events LLC | Singles Social Mixer Schaumburg Fox & Hound — November 11 @6:30 PM • Fox & Hound, Schaumburg
The Shaka Club | Fulton Market Singles: Late 20s/30s Happy Hour (Ages Late 20s–30s) — November 12 @7:00 PM • Punch Bowl Social, 310 N Green St, Chicago
CitySwoon | Speed Dating Chicago | CitySwoon® | 38–52 years | at Carnivale (Ages 38–52) — November 12 @7:30 PM • Carnivale, Chicago
Shuffle Dating | Singles Mixer @ The Albion Manor (Ages 25–32) — November 13 @7:00 PM • The Albion Manor, Chicago
Chicago First Dates | Singles Ages 20s & 30s – In-Person Speed Dating (Ages Women 24–38, Men 25–39) — November 13 @7:00 PM • Moretti’s Ristorante & Pizzeria – Edison Park, Chicago
Break The Ice Social Events | Singles Social Mixer @ Spartan Ale House — Nov 14 @6:30 PM • Spartan Ale House, Naperville
meet irl x Boppn | The Great Singles Scavenger Hunt! — Nov 15 @3:00 PM • The Dawson, Chicago
Jigsaw Dating | Coffee Shop Speed Dating 40+, November 15th – Chicago (Ages 40+) — November 15 @3:00 PM • The Avondale Coffee Club, Chicago
Tantra Speed Date | Tantra Speed Date® – Chicago (Meet Singles Speed Dating) — November 15 @ 5:30 PM • Moksha Yoga Center, Wicker Park
Break The Ice Social Events LLC | Singles Social Mixer St. Charles Alley 64 — November 15 @6:30 PM • Alley 64, St. Charles
Jigsaw Dating | Singles Happy Hour 40+, November 15th – Chicago (Ages 40+) — November 15 @7:00 PM • Joy District, Chicago
MyCheekyDate | Saturday Night Speed Dating @ Tabu — Chicago (Ages 25–39) (Ages 25–39) — November 15 @7:30 PM • Tabu, Chicago
Meet IRL | Curated Speed Dating at Half Acre Beer Co | 30s + Early 40s (Ages 30s & early 40s) — November 16 @11:00 AM • Half Acre Beer Co, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Oak Lawn Cooper’s Hawk — November 16 @1:00 PM • Cooper’s Hawk Winery & Restaurant, Oak Lawn
Shuffle Dating | Singles Mixer @ The Dandy Crown (Ages 27–34) — November 16 @4:00 PM • The Dandy Crown, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Oak Park Cooper’s Hawk — November 16 @6:00 PM • Cooper’s Hawk, Oak Park
MyCheekyDate | Speed Dating @ Tabu — Chicago (Ages 36–48) (Ages 36–48) — November 16 @6:00 PM • Tabu, Chicago
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And a Sneak Peek into a Few Events Coming Up in the following weeks:
Break The Ice Social Events LLC | Singles Social Mixer Oak Brook, IL Wonderverse — November 18 @6:30 PM • Wonderverse, Oak Brook
Shuffle Dating | Singles Mixer @ The Parlour at Park & Oak (Ages 41–53) — November 19 @6:30 PM • The Parlour at Park & Oak, Glen Ellyn
The Shaka Club | West Town Singles: Late 30s/40s Happy Hour (Ages Late 30s–40s) — November 21 @7:30 PM • Barcocina West Town, 1814 W Chicago Ave, Chicago
The Feels | The Feels Chicago, edition 5: a mindful singles event— November 24 @ 6:30–9:30 PM • Chicago
Meet IRL | Singles Volunteer Evening | Ages 35+ (Ages 35+) — November 25 @6:00 PM • The Parlor, 3325 West Wrightwood Avenue, Chicago
CitySwoon | Thanksgiving Eve Speed Dating @ City Winery (Ages 29–49) — Nov 26 @7:30 PM • City Winery – West Loop, Chicago
Meet IRL | Queer Singles Basketball Social (Ages 21+. Queer Singles Only) — December 4 @7:30 PM • Wintrust Arena, Chicago
Throwback Dating | Singles In Service: Holiday Gift Wrapping with Kids Above All (Ages 40+) — Dec 7 @1:00 PM • Kids Above All’s Better Life Distribution Center, Des Plaines
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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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