An excellent small bar and restaurant that I would consider almost a speakeasy in and of itself. It's inside a door that looks like the entrance to a simple apartment building, but downstairs to the left you'll find it. Follow the green neon sign.

From what I understand, they used to have a spot even deeper down called “Dead Plants” with live music on Saturdays, and a heavy speakeasy vibe, but for the past year and a half it hasn’t been active sadly :( I'll make sure to keep you updated here if that changes.

However, the Press Room itself has excellent drinks and gourmet level food, albeit a bit expensive.

I had a drink called the “Hemingway Daquiri” - it had hints of grapefruit, which I was very much digging. Apparently, the founders of the spot really know their food.

They’ve also got a gorgeous private room you can rent out for a dinner of up to 15 or so - Full of old bottles of wine, elegant décor, and behind a big dramatic sliding door. (I rhymed!)

They showed it to me on the DL. ;) I’m gonna try to gather a group and make it happen.

There was maybe 1 table open at 8 on a Friday, so this place is by no means underrated. The cool people know about it, and they flock, so make reservations or show up early.

You can check out the restaurant's website at: http://pressroomchicago.com/

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UPDATE:

Starting November 20th, 2023, there will be a Monday night popup series at The Press Room by a food company called Pochos.

You can learn more here - it looks super fun:

https://www.instagram.com/p/CzsU4f2gHVk/?igshid=NTYzOWQzNmJjMA%3D%3D