A couple of weeks ago I went to Webster's Wine Bar with a girlfriend for a long overdue catch-up session. This is one of my all time favorite places in the city. The atmosphere is quaint and relaxed, and they have great small plates and a huge wine selection. You can also generally always get a reservation, or even just walk in, so it's a good place to go for a laid back night, in which you won't be rushed. And if you want to make a night out of it, go across the street to see a movie before or after your wine.
This place is owned by the same people as Bluebird and
Telegraph. They also have a lot of fun special events; I am on their email list and there are always things happening that I actually want to go to (but have yet to do so). Although this isn't a must-go place in Chicago if you're here from out of town, if you are local, it should be on your list.
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