High on the 96th floor, overlooking the entire city of Chicago, you and perfect stranger are enjoying a first date. As you breathe in the city and all its beauty, you have to ask yourself: does it get any better than this? There are so many great date places to explore in the Windy City. Whether it’s your first time in the city or you are a true Chicagoan, this is your chance to be adventurous, fun, and show off your talents - after all, you only get one chance at a first impression.  

Can’t Beat That View

The Signature Lounge on the 96th floor of the John Hancock Center is sure to make your date feel special. Although you will want to be staring into each other’s eyes, it might be hard for you to stop gazing out the floor to ceiling windows. At sunset you can enjoy a view of the whole city, with cars and people rushing by. It will be the kind of first date that will take your breath away.


Dude, Let’s Go Bowling

Show off your bowling skills with a night out at Chicago’s 10 Pin bowling alley. You won’t have to settle for soggy nachos and $2 hotdogs though, you know how Chicagoans love their food. This bowling alley has shared tapas plates, a killer martini list and sweet desserts like s’mores and brownie sundaes.


Connect Over Connect Four

There’s nothing wrong with bringing out a little playful competitive on a first date. For a fun time and a cozy spot, try Guthries Tavern, where you can select from over 50 classic and funny oard games. The intimate lamps will set the scene for a perfect first date, just make sure you play the win.


Good for a Laugh

Laughing has been scientifically proven to release feel-good chemicals in the brain that melt stress and tension. And who needs tension on a first date? Chicago has a great comedy club scene, a great place to go on a first date and break the ice. Zanies Comedy Club is always a bag of laughs including some familiar comedians and newbies you’ve never heard of before.


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