Midweek Speed Dating 2.0 in West Loop | Cityswoon | Ages 38-52

Speed Dating 2.0 returns to La Bella Trattoria in West Loop!

Ditch the apps and meet real singles in person at La Bella Trattoria 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

La Bella Trattoria is a bold, stylish, and lively Italian restaurant in the Chicago Loop, known for traditional and Italian-American pizza, pasta, seafood, and cocktails. It's a popular spot near downtown attractions for any meal, happy hour, or pre-theater dining.


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.