Cocktail Date Ideas | Winter | Chicago

Whether you met on one of the many dating sites/apps, was set up on a blind date or just and old fashioned run in at the grocery store/bar/work/etc, figuring out where to go on the first date is always a challenge. To a certain extent, I appreciate when the guy asks me where I would like to go, but it also puts a lot of pressure on me. I don’t want to go anywhere too fancy, too casual & I want to have the option of actually consuming food should the date go well. Btw, what’s up with Chicago guys not wanting to eat on dates???

Here are some cocktail bars that are first date approved: you can eat, you can drink & you can get the heck out of there quickly if it doesn’t go so well. If you don’t have time to watch the video, just scroll down for the list. Have fun & good luck!

Berkshire Room: By far my favorite cocktail bar in Chicago for a first date or anytime. The cocktails are amazing, the service is impeccable & the space has a lot of history to it

Bar Siena: Yes, there are lights on the tree that reaches the ceiling all year round & it’s so pretty! If the bar downstairs is packed, head up the stairs to a smaller, but equally great bar upstairs.

The Barrelhouse Flat: A go-to when I lived in Lincoln Park. I’m sure the employees were starting to recognize me. The downstairs is nice, but the real magic is upstairs in the lounge area. Dark, cozy & intimate.

Matilda: Be careful when going down the stairs to use the bathroom. Seriously. Hold onto the handrail. Other than that, this is a perfect spot for a first date meet-up.

Up & UP (in the Robey): No matter what, the view is going to be amazing. This bar is on the 13th floor and has views for miles. If things go well, you can take the elevator down to the first floor to the Cafe Robey.

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