Speed Dating Chicago | In-Person | Cityswoon | Ages 50-65

Find Your Valentine 2026! Join a group of 50+ singles, ditch the apps and meet real singles in person at Carnivale in West Loop a few days before Valentine's Day!
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
In the West Loop at 702 W Fulton Market, Carnivale brings bold Latin-fusion cuisine, vibrant decor and festive energy. With its art-filled space and global-flavour cocktails, it sets a memorable scene for a gathering.

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.

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