Perfect for

A first (or second or third …) date

Start with

The Dorothy Martini. Made with Irish gin, Cocchi Americano, and angostura, this is a martini with a point of view.

Dorothy first opened on Valentine’s Day 2020, perhaps the most ill-timed opening in Chicago. It almost immediately had to close, but in January 2022, owner Zoe Schor — chef of the delightful American restaurant Split-Rail, located above the bar — tried again. This time, it stuck. Dorothy has a midcentury cool feel and lots of cozy nooks to sip lead bartender Caitria Mikesell’s drinks, like the Rocket Science, a Manhattan riff with rye and Jägermeister. And with regular events like speed dating and burlesque shows, Dorothy is a queer bar through and through. 2500 W. Chicago Ave.