Speed Dating Chicago | In-Person | Cityswoon | Ages 40-55

*New Venue Alert!*
Ditch the apps and meet real singles in person at Roanoke in West Loop.
Join a big room of singles and get around 8 of your best live-selected, mini-dates!
Meet like-minded singles face to face in a relaxed, fun and social atmosphere.
Spots are limited, booking is essential.
How it works:
- Quick check-in on your phone. No nametags, matchcards, pens or fuss.
- Loads of singles in the room. Our platform finds your best matches for each round of mini-dates.
- Friendly, professional hosts guide the night.
- Balanced mix of men & women so the event flows naturally.
- Stay and mingle afterwards, most people do!
Why you'll love Smart Speed Dating:
- Relaxed, social vibe, perfect if you're coming solo (most do!).
- Great venues, great people, and actual conversations.
- Over 95% of attendees meet someone they're attracted to, and 90% get at least one mutual match!
- 10+ years of successful CitySwoon events and millions of dates!
Learn more about CitySwoon and our unique events on the
FAQ page.
The Venue
Roanoke, an upscale American restaurant in Chicago's Loop, offers artisan comfort food, signature rotisserie, seasonal salads, and craft cocktails. Located at 135 W. Madison Street, it provides a warm setting for lunch, dinner, or drinks, plus flexible event space and elevated New American cuisine.
All our venues are carefully selected for great vibes and atmosphere.
Tickets are non-refundable.
You can cancel 7 days out and receive a credit or transfer.
A $19 late cancellation/no-show fee applies if you cancel within 24 hours of the event.
See Terms & conditions for details.
Ready to meet your match? Grab your ticket today, spots go fast!

NB: A fully completed CitySwoon profile, complete with a profile photo where your face is clearly visible, is required to fully participate in any CitySwoon event.

Event Venue & Nearby Stays

Roanoke Restaurant, 135 West Madison Street, Chicago, United States

Concerts, fests, parties, meetups - all the happenings, one place.

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