742 West Addison

Located on the east side of the Lakeview neighborhood just south of Wrigleyville, Boystown is the center of LGBTQ life in Chicago, and was the first officially recognized “gay village” in the country. The neighborhood is known for its nightlife: Dozens of clubs, bars, and restaurants — like neighborhood mainstays Roscoe, Elixir, and Hydrate — stretch down Halsted Avenue, and Broadway hosts a variety of trendy shops and dining establishments. It’s easy to go out, but it’s also easy to stay in: Boystown’s iconic brownstones are beautiful, and can offer a perfect home base for the area’s annual Pride Parade, which draws over 800,000 people every June.