Unique Chicago Dates (No Dinner, No Movie)

Valentine’s Day falling on a Saturday means restaurants will be booked and theaters will be packed. But dinner-and-a-movie is basic anyways. A V-day cop-out if you ask me.

Here are some more unique date recs from the City Cast Chicago team.

Simone, Executive Producer

“Escape room dates help you learn info that's crucial to choosing a partner: How do you solve problems together? How do you both handle pressure? Are you competitive? My boyfriend and I are still together after ‘Escaping the ‘90s’ at The Quandary in Lakeview.”

Emmi, Newsletter Editor — Wait, That’s Me!

“Meet up at the Flaco’s Tacos on Chicago Avenue and get margaritas to go. They come in nifty, sealed bottles and fair warning, they are strong. (I like the hibiscus.) Then take a short stroll to the Museum of Contemporary Art. Hammering interactive Yoko Ono pieces is more fun with a little buzz.”

Rick, Social Media Manager

"A fun grocery store! My love of food extends to a love of ingredients. Pick somewhere new — Seafood City, Patel Bros., or Andy's Deli — and just marvel at the stuff on the shelves. I'd ask my date to pick out something they've never had before and see if I can make a meal for us with it."

Michelle, Producer

"Take a six pack to Chris's Billiards and shoot pool. He pays for the touch tunes, but I queue the songs. Then hit up a listening bar after: Charis in Bridgeport, Dorian's in Wicker Park, or Parachute HiFi in Avondale!"

Jacoby, Host

“One of my favorite date nights of the last few years was rug making at Freestyle Ceramics & Tufting in Bridgeport/Chinatown. I made a Goofy Movie rug (Max as Powerline) and my partner made a Steven Universe rug (Ruby and Sapphire). The staff were nice, helpful, and really cool about us coming back to finish.”

And if you’re still not feeling inspired, plenty more date ideas are linked in our guide to February 💗