Hey Chicagoland Singles!
(To see the entire list of events, click here)
Welcome back to another edition! I have to say, I’m still riding the high from the Chicago Air and Water Show this past weekend. Between the jets flying over the lake, packed beaches, and everyone actually being outside enjoying summer, Chicagoland was very much alive. And somehow, we’re already heading into another stacked week of singles events.
There’s a little bit of everything this week, including rooftop mixers, speed dating, arcade nights, salsa dancing on the beach, and plenty more. But I have to spotlight one event in particular: Single N Minglin Presents: Therapy for the Heart ❤️, this Saturday, August 22 at Privilege Restaurant Bar. It’s my Hidden Gem of the Week. More details on that one below.
And always, my favorite part, let’s jump 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.
Monday, August 17
Ivy Dating | Ivy App: Bringing Dating Back to Real Life — August 17 • 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.
ThrowbackDating | How to Date Over 50, Masterclass Series - Dress to Impress: A Men's Style Guide for Dating Over 50 (VIRTUAL) (Ages 50+) — August 17 @7:00 PM • Google Meets, Chicago
Wednesday, August 19
On Love Xperiences | Singles Party 35ish-50 Crowd @ Kennedy Rooftop (Ages 35-50) — August 19 @5:30 PM - 8:00 PM • Kennedy Rooftop, Chicago, IL
West Town Social Club | Singles & Social Folks Rooftop Mixer @ Aire Rooftop — August 19 @6:30 PM - 9:00 PM • Aire Rooftop Bar Chicago, Chicago, IL
West Town Social Club | Singles & Social Folks Rooftop Mixer @ Aire Rooftop — August 19 @6:30 PM - 9:00 PM • Aire Rooftop Bar Chicago, Chicago, IL
The City Social | Chicago Social Hour: Speed Dating For Ages 25-35 (Ages 25-35) — August 19 @6:30 PM - 9:30 PM • Park & Field, Chicago, IL
Fun Events | Chicago Singles Speed Dating Game Night (Ages 25-39) — August 19 @7:00 PM - 9:00 PM • Barcocina Lakeview, Chicago, IL
Intelligent Singles Network | Intelligent Singles Mixer at the Four Seasons Hotel in Chicago! — August 19 @7:00 PM - 10:00 PM • Adorn Bar & Restaurant (Four Seasons Hotel), Chicago, IL
CitySwoon | Speed Dating Chicago | CitySwoon® | 47-62 years | at Aire Rooftop Bar (Ages 47-62) — August 19 @7:30 PM • Aire Rooftop Bar, Chicago
Thursday, August 20
Let's Do Fun Things | Singles, Sun, and Salsa — August 20 @6:30 PM - 9:00 PM • Whispers on Oak Street Beach, Chicago, IL
Jigsaw Dating | Singles Arcade Night 30-45, August 20th - Chicago (Ages 30-45) — August 20 @7:00 PM • Dave and Busters, Rosemont
Chicago First Dates | Singles w/ Advanced Degrees (Ages Women 33-45, Men 35-48) — August 20 @7:00 PM • Marriott Residence Inn - The Loop, Chicago
Chicago First Dates | Singles Ages 30s & 40s - In-Person Speed Dating (Ages Women 33-45, Men 35-48) — August 20 @7:00 PM • Marriott Residence Inn - The Loop, Chicago
Hot Potato Hearts | Speed Dating — August 20 @7:00 PM • Central Park Bar, Chicago
Thursday Dating | Thursday | Love Notes: Live Music, Cocktails and Romance — August 20 @7:30 PM • Grapes & Grains Piano Bar Cocktail Lounge, Chicago, IL
Saturday, August 22
Hindu Vivah | Zoom Event | US/Canada Raised (Ages Female 26-46, Male 28-48) — August 22 @11:00 AM - 1:00 PM • Online, Online
Showdown Game Experiences | Love Games — August 22 @2:00 PM - 4:00 PM • Guthries Tavern, Chicago, IL
Break The Ice Social Events LLC | Singles Social Mixer Libertyville, IL Bar Crawl Starting at Morgan's — August 22 @6:30 PM • Morgan's - Saturday, August 22, 2026 at Morgan's Bar & Grill, Libertyville
Jigsaw Dating | Sunset Speed Dating 30-45, August 22nd - Chicago (Ages 30-45) — August 22 @7:00 PM • The Original Mother's, Chicago
Date Faster | Naperville Singles Mixer 2026 — August 22 @7:00 PM - 9:00 PM • The Can Bar Naperville, Naperville, IL
Ermantourage Sports | Dinner with New Friends: Chicago | Single Parents Edition (Ages Single Parents) — August 22 @7:00 PM - 10:00 PM • Restaurant of the Week, Chicago, IL
CitySwoon | Speed Dating Chicago | CitySwoon® | 32-44 years | at Aire Rooftop Bar (Ages 32-44) — August 22 @7:30 PM • Aire Rooftop Bar, Chicago
Chicago First Dates | Singles Ages 20s & 30s - Online Speed Dating (Ages Women 24-36, Men 25-37) — August 22 @8:00 PM • Online, Online
Single N Minglin LLC | Single N Minglin Presents: Therapy for the Heart ❤️ — August 22 @8:00 PM - 1:00 AM • Privilege Restaurant Bar, Chicago, IL
Sunday, August 23
NomadÉire | Love Without Borders: Virtual Speed Dating — August 23 @12:00 PM - 2:00 PM • Online, Online
Pitch Your Peeps Queer Slide Deck Match Making | Pitch Your Peeps: QUEER Slide Deck Match Making @ Two Hearted Queen (Ages 35+) — August 23 @2:00 PM • Two Hearted Queen, Chicago, IL
Break The Ice Social Events LLC | Singles Social Mixer Brookfield, WI Bar Louie — August 23 @5:00 PM • Bar Louie - Brookfield, Brookfield
Event Management | Chicago Speed Dating Mixer (Ages 29-40) — August 23 @5:00 PM - 11:30 PM • 216 N Wabash Ave, Chicago, IL
Shuffle Dating | Speed Dating (Queer Men) (Ages 30-44) — August 23 @7:00 PM • The Dandy Crown, Chicago, IL
Hidden Gem of the Week
Therapy for the Heart, hosted by Single N Minglin.
Single N Minglin are a singles events organization that runs events in Chicago, and was created to bring real energy, real people, and real connection back to dating. Single N Minglin is more than a speed dating event. It’s a movement for singles who are ready to step outside, be seen, and connect with purpose.
A blurb from the event page:
Join us for Therapy for the Heart, a unique and intentional dating experience that blends meaningful conversation with real opportunities to connect. Before the speed dating begins, we’re bringing together a dynamic panel of relationship experts, matchmakers, therapists, and everyday people to have an honest, engaging discussion about modern love.
Date, Time, Location: August 22 @8:00 PM - 1:00 AM • Privilege Restaurant Bar, Chicago, IL
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:
Kat | Single & here to Mingle in Mundelein ~Smokin' Jack's BBQ (Ages 20s, 30s & 40s) — August 26 @7PM - 9PM • Smokin' Jack's BBQ, Mundelein, IL
South Asian Socials | South Asian Singles Mixer for Marriage-Minded Professionals (Ages 25-45) — August 27 @6:00 PM - 9:00 PM • Barcocina Lakeview, Chicago, IL
Quirk Events | Board Game Speed Dating - Big Star Wrigleyville (Ages 20s-30s) — August 27 @7:00 PM - 9:00 PM • Big Star Wrigleyville, Chicago, IL
The Social Market Collective Events | Neon Nights Singles Social (Ages 25-40) — August 28 @7:00 PM - 10:00 PM • Valley Ridge Golf Course, Antioch, IL
Meet Sweet | Singles Water Balloon Fight at Hollywood Beach! — August 29 @12:00 PM - 1:00 PM • Kathy Osterman Beach, Chicago, IL
EarlyBurdz | Chicago Art Date Night: 30s/40s (Ages 30s-40s) — August 29 @4:00 PM • Chicago, IL
Media Naranja | Tacos and Loteria: A Dating Event for Singles — August 30 @1:00 PM - 3:00 PM • Lalo's on Maxwell, Chicago, IL
ThrowbackDating | Skyline Singles Soirée (Ages 50+) — September 10 @6:30 PM • Avli on the Park, North Field Boulevard Chicago
Wable | Unmasked - Neurodivergent/ADHD/Autistic Speed Dating & Friending — September 17 @6:00 PM - 8:00 PM • 4014 N Rockwell St, Chicago, IL
(To see the entire list of events, 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!
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