re: Must Eats in Chicago

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I am also looking at which bars/lounges to go have some drinks at as well.

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Violet Hour is outstanding. Technically, it's a "speakeasy," though very well-known and one of the better cocktails you'll find in the Midwest. It's across the street from Big Star (awesome patio space) and its door is hidden on a giant mural. Dimly-lit inside with one true rule: don't be an a-hole and bring someone that could be construed as one.

I live in Chicago, though originally from Madison, Wisconsin. Hard to beat an Old Fashioned (whiskey or bourbon) from Wisconsin and I'm pretty picky with my choices. Best Old Fashioned I've found in the city is at Gilt Bar, which is down in River North.

For other upscale cocktail bars, I highly recommend Barrelhouse Flat in Lincoln Park. Extensive cocktail list.

For rooftop bars/lounges further into the City, head to London House, Rock Bottom, J. Parker, Cindy's, and Joy District. I can provide some recommendations further north or west, too.

Not sure how old you are, but you'll see a young professional crowd at the bars in Old Town lining Wells. As a recent graduate myself, this is where I typically find myself. There are quite a few "upscale" sports bars.

If you head west of the interstate, over into the Wicker Park area, there are an abundance of great bars on Division, west of Milwaukee.