Pizza, Wine & Conversation: Chicago Date Ideas


This makes for a relaxing evening with lots of conversation and a perfect after work spot. So don’t bring a date who you might be pulling teeth. Everything is within walking distance, even in the winter. I highly suggest doing this on a weekday versus a weekend since the bars I mention are more difficult to get into on a Friday or Saturday. 



Dinner: La Madia – This pizza place is a modern yet intimate, cozy setting and the food is extra delicious. Sit at the amazing wine bar or the cozy lounge chairs by the fire place. Their Pizza Fondue is an absolute MUST. A large, steaming puff of dough is served…rip off a piece and dunk it in the cheesy, tomato sauce fondue for a fantastic treat. You can’t go wrong with any of their pizzas. The bartender is excellent at helping you chose from the wide selection of wines and actually knows what he’s talking about. They also serve their beers in the appropriate beer glasses.

Tip: Sit at the pizza bar and receive a free glass of Prosecco. Also be sure to check out their website for the montlhy $5 glasses of wine (red & white).

Phone: (312) 329-0400

Drinks: If things are going great then head over to the Irish bar called the Kerryman for some more drinks! It’s literally right around the corner and easily walkable.

Tip: Go on a Tuesday for their 1/2 price wine night.

Website: thekerrymanchicago.com

Late Night: It’s that point in the night where you go big or go home. If you chose big, then step it up by walking over to Martini Park a block away. This is in between a bar and a club and the decor is really cool… they even have chandeliers made out of martini glasses! 

Tip: Check out their calendar for live bands that play on stage. Drinks are on the pricier side and there are no deals here usually…

Website: http://www.martinipark.com/chicago/index.php