NOW CLOSED...Formerly: Hailed as Chicago's most popular cocktail-hour bar for the professional gay community, this campy piano bar is downtown's only upscale gay bar. Music begins at 5:30 p.m. Tuesday to Friday, giving you something to drink to. And the sipping won't have to end anytime soon: The music continues until 1 a.m., 1:30 a.m. on Saturday.
A budding singer yourself? Beckie Menzie has hosted Gentry's downtown open mic night since 1989 (there's also a Halsted location).