Subway: Red to Chicago(312) 440-1500 theallertonhotel.com/dining_lounge.html41.895154 -87.623928 701 N Michigan Ave (at Huron St) Magnificent Mile, Chicago
4pm–midnightAverage cocktail: $10
Venturing into the famous “Tip Top Tap” building (a.k.a. the Allerton Hotel), we expected to find a bar that hearkens back to the “good old days”: jazz quintets doing Armstrong, flappers dancing the Charleston…that sort of thing. But in fact, this is a quiet, sophisticated spot where one can have a cocktail by himself, and if not relive the old days, at least think about them in peace.