Roscoe'sBoystown | Website
No doubt, this Boystown spot is one of Chicago's best-known gay bars. On weeknights, it's a place to unwind after a hard day's work. Come here to shoot a game of pool or grab a sandwich at the bar's summertime sidewalk cafe (or eat inside during the winter). On weekends, get ready for a fun change of pace: The six bars and big dance floor are in full swing. Between shaking it, take a breather on the outdoor garden patio.