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.


Lonely Planet's must-see attractions

Nearby Chicago attractions

1. Center on Halsted

0.41 MILES

The mod, glassy Center on Halsted is the Midwest's largest LGBT community center. It's mostly a social service organization for locals, but visitors can…

2. Wrigley Field

0.48 MILES

Built in 1914, Wrigley Field – aka the Friendly Confines – is the second-oldest baseball park in the major leagues. It’s home to the Chicago Cubs and…

3. Gallagher Way

0.54 MILES

It's impossible to get any closer to Wrigley Field without actually crossing the stadium's threshold, making this newly developed plaza (formerly a…

4. Alta Vista Terrace

0.73 MILES

Chicago’s first designated historic district is worthy of the honor. Developer Samuel Eberly Gross re-created a block of London row houses on Alta Vista…

5. Wrightwood 659

0.98 MILES

Fans of modern architecture shouldn't miss Chicago's newest gallery, designed by Pritzker Prize–winner Tadao Ando. Walk past the facade of the former…

6. Graceland Cemetery

1.06 MILES

The final resting place for some of the biggest names in Chicago history, including architects Louis Sullivan and Ludwig Mies van der Rohe and retail…

7. Hutchinson Street District

1.12 MILES

Homes here were built in the early 1900s and represent some of the best examples of Prairie School architecture in Chicago. Many residences – including…

8. Biograph Theater

1.15 MILES

In 1934 the ‘lady in red’ betrayed notorious bank robber John Dillinger (aka Public Enemy Number One) at this theater, which used to show movies. FBI…