Summer Happy Hour at Cindy's Rooftop

Golden hour, skyline views, and good company... this is summer in Chicago at its best.

Join us at Cindy's Rooftop for a Summer Happy Hour above the Chicago Athletic Association Hotel, with one of the city's most iconic views. Think panoramic sightlines of Millennium Park, Lake Michigan, and the skyline... a refreshing breeze... and easy conversation with members who are actually worth meeting. Come solo, come curious, and let the evening do the rest.

Drinks and apps are on your own, so grab what you're craving and settle in.

Event Details

Date: Thursday, August 20th, 2026

Time: 4:30 PM – 6:00 PM

Location: Cindy's Rooftop, 12 S Michigan Ave, Chicago

Admission (Basic Members): $30 — your ticket into a vetted community of singles who are actually worth meeting. Drinks and apps on your own.

Admission (Inner Circle Members): $10. Drinks and apps on your own.

Parking: Valet available at the hotel entrance on Michigan Ave. For a more affordable option, we recommend booking ahead at Millennium Park Garage or using SpotHero.

Meeting Location: Enter at the Chicago Athletic Association (12 S Michigan) and take the 3rd elevator to the Rooftop. Meet us on the terrace - there is a bar out there.

A Quick Note on the Bill: Some venues can't split checks... so if that's the case, don't worry, Megan's got you covered. She'll take care of the full bill, and you can simply pay her back your portion (tax and gratuity included) with cash or Venmo. Easy and stress-free!

For singles in their 50s and 60s

This is a Throwback Dating community event. Not a member yet? Apply to join — we'd love to meet you.