Sidetrack

Sidetrack is the mecca of gay Chicago, a sprawling 15,000-square-foot video bar that's been the beating heart of Boystown since 1982 and is regularly named the best gay bar in Chicago, the most popular bar in Illinois, and one of the top gay bars in the country. Spanning eight storefronts across two levels, it unfolds into six distinct rooms plus a fabulous rooftop deck, each with its own vibe, and it's famous for its slick video mix of pop, dance, and camp specialty programming, above all the legendary Show Tunes nights (Musical Mondays, TGIFridays and Sunday Funday) where the whole crowd sings along. Add its cult frozen cocktails, weekend dancing till late, Drag Race viewing parties in season, and a genuinely diverse, all-ages crowd, and you have a place that's never had a cover and never lost its crown. If you visit just one gay bar in Chicago, make it this one.