What the Castro is to San Francisco, Boystown is to the Windy City. The mecca of queer Chicago (especially for men), the streets of Boystown are full of rainbow flags and packed with bars, shops and restaurants catering to residents of the gay neighborhood.
Halsted St is the main vein. Rainbow-colored pylons rise up along the road marking the district. Look closely and you'll see each pillar has placards on it telling the stories of different LGBTQ history makers or events. They span about a half-mile stretch between Melrose and Grace Sts and are known collectively as the Legacy Walk.