Hey Chicagoland Singles!

(To see the entire list of events, click here)

Virgo Season is off to a hot start (literally 🥵) and the singles events calendar is back in full form. There are over 130 events in the next month alone in Chicagoland.

There are two events I want to spotlight this week: (1) Skyline Singles Soirée hosted by Throwback Dating at Avli on the Park. This event is for those in their 50s & 60s. And (2) the Singles Skeeball League hosted by S3 at Sluggers. This is a 5-week league starting this Thursday. Both events are my Hidden Gems of the Week. More details below.

Whether you’re a Virgo or not—and whether you love Virgos or don’t—there’s definitely a singles event for you! I know it, and your couch knows it. Give those cushions a night off, put on something nice, and go meet someone who might just be worth leaving the house for!

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, September 7

  • Ivy Dating | Ivy App: Bringing Dating Back to Real Life — September 7 • 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.

Tuesday, September 8

Wednesday, September 9

Thursday, September 10

Friday, September 11

Saturday, September 12

Sunday, September 13

Hidden Gem Events of the Week

This week’s Hidden Gems: Skyline Singles Soirée by Throwback Dating and Singles Skeeball League hosted by S3.

Skyline Singles Soirée

Hosted by Throwback Dating, which was founded by Megan Wessels. Throwback Dating is a curated community of active, open-hearted singles in their 50s and 60s who are genuinely ready to meet someone.

From the event page:

An exclusive rooftop mixer for singles in their 50s and 60s. Set against the backdrop of a breathtaking Chicago sunset, this one-of-a-kind event brings together a curated, upscale crowd of like-minded, socially active singles ready to enjoy conversation, laughter, and possibility.

Date, time, location: September 10, 2026, 6:30 PM, Avli on the Park, Chicago

Singles Skeeball League

Hosted by S3 (Simply Social Sports) League, a recreational sports league community in Chicago, which has hosted over 1400 leagues over the past 17+ years.

Blurb from the event page:

  • 7 skeeball games per night in a match!

  • S3 buys half of all players in each match a shot with a post-game raffle!

  • FREE batting cages (up to 2 tokens per night)

Date, time, location: September 10, 2026 to October 15, 2026. Starting at 6:50 PM, Sluggers in Wrigleyville

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:

(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!

And for more, subscribe to Where’s Your Boo?

Keep Reading

View more
caret-right
© 2026 Where's Your Boo?.
beehiivPowered by beehiiv