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Discover Chicago Pride

While planning a group trip to Chicago, be sure to include a visit to Northalsted (formerly known as Boystown), the oldest officially recognized gay neighborhood in the U.S. While there, take a guided tour of The Legacy Walk, a half-mile-long (.8 km) outdoor history museum along Halsted Street that honors the lives and legacy of notables from the LGBTQ+ community. Afterwards, pop into our recommended gay-owned shops, restaurants, and nightspots. There’s plenty for your group to do in Northalsted day or night.

The Legacy Walk
The Legacy Walk

The Legacy Walk

Founder and executive director Victor Salvo unveiled The Legacy Project and Chicago’s Legacy Walk in 2012. His labor of love is now known as the world’s largest LGBTQ-focused historic landmark. Salvo himself leads visitors along Halsted Street, stopping to comment on The Legacy Walk plaques and to talk about The Legacy Project. “I recommend tours because they really are a lot of fun,” Salvo says.

The Northalsted neighborhood will shine even brighter with enhancements to its visitor experience over the next few years. Plans are in the works to refurbish the Halsted streetscape, thanks to a $4 million Illinois state grant. “The Walk is going through a complete rebirth,” notes Salvo.

Along The Legacy Walk are biographies engraved on 40 bronze memorial plaques, mounted on 25-foot-tall (7.6 m) rainbow pylons. The current rainbow pylons were installed in 1998 and are showing their age, Salvo says. As part of the planned improvements, retrofitted pylons will feature interactive pop-up phone prompts to help make The Legacy Walk more accessible. Visitors who are visually impaired will be able to listen to a recording of the biographies engraved on the plaques. And non-English speakers will be able to choose from recordings in up to 12 different languages.

While touring The Legacy Walk, your group will learn about important contributions of LGBTQ+ people, both locally and around the world. Read mini biographies of instantly recognizable figures, including Queen lead singer Freddie Mercury, poet Walt Whitman, artist Frida Kahlo, activist Harvey Milk, astronaut Sally Ride, and composer Cole Porter. Also delve into the Stonewall Riot, Pink Triangle, and Harlem Renaissance, and discover how they influenced culture and equality.

The two newest Legacy Walk dedications, unveiled on Coming Out Day in October 2023, honor gay Major League Baseball player Glenn Burke, sponsored by the Chicago Cubs baseball team, and “The Road to Marriage Equality,” in recognition of the history-making U.S. Supreme Court decision, sponsored by The Highfield Group.

After-tour receptions take place at Drew’s on Halsted, which Salvo describes as a lovely place with cabaret entertainment and delicious food. Bar Crawl package tours are offered, with groups stopping in various Northalsted establishments along the way. Student groups visit youth-friendly places that include Savanna Restaurant and Las Mañanitas Restaurant. It takes approximately four hours for the full tour, or it can be customized to a shorter “greatest hits” version. Schedule a guided tour for groups ranging from six to 25 people through The Legacy Project.

While work takes place on the Halsted Street pylons, visitors will still be able to see all of The Legacy Walk plaques virtually in an online slideshow. In addition, the Legacy Wall is a one-of-a-kind interactive exhibit that travels the country introducing its inclusive curriculum, which is approved by the Illinois Inclusive Curriculum Advisory Council. The Legacy Wall has visited 50 U.S. cities so far, Salvo says, adding that it’s a powerful tool to start and share conversations. Plans farther in the future include the creation of a brick-and-mortar Northalsted visitor center, where retired Legacy Walk plaques will be put on display.

For now, Salvo is proud to be a part of bringing LGBTQ+ tourism to Chicago. “It’s an essential place for visitors,” he notes. “Coming together in a place is extremely important. This will always be a gayborhood.”

Must-visit Northalsted spots

Enhance a Legacy Walk tour with stops for shopping, dining, cocktails, and entertainment in the Northalsted neighborhood. Along the way, look for the many businesses lining The Legacy Walk route.

A couple of blocks (.5 km) from Halsted Street, the 43-year-old Unabridged Bookstore continues to be the neighborhood spot to shop for books of all genres, including LGBTQ+ literature. Carry your purchases in a branded Unabridged Bookstore tote bag. The store supports several causes, including the Equal Justice Initiative, Gerber/Hart Library and Archives, the Chicago Abortion Fund, and Midwest Access Coalition.

An elegant brunch awaits diners at Wood, a six-time Michelin Bib Gourmand recipient noted for its outstanding fare at affordable prices. Choices range from beignets sided with hot chocolate ancho chili dip to French omelets and fried chicken with biscuits. For dinner, the small-plate menu features locally sourced dishes prepared in a wood-fired oven. Spaces are available for group semi-private and private dining.

Kit Kat Lounge & Supper Club
Kit Kat Lounge & Supper Club

Enjoy contemporary American dishes, cocktails, and unforgettable drag performances nightly at the Kit Kat Lounge & Supper Club, a staple in the Northalsted neighborhood. Watch the dazzling Kit Kat Divas perform at dinnertime and during brunch on Saturdays and Sundays. Private parties, with drag entertainment, can be arranged on the patio or in the main dining room.


Toast with a specialty cocktail at Sidetrack, a neighborhood staple since 1982. In 2022, Sidetrack was named the #1 Nightclub in the Best of Gay Cities Awards. Check out theme nights with show tunes, trivia, and dance parties. Listen to personal LGBTQ+ stories told during Outspoken on the first Tuesday evening of each month. For groups, ask about special accommodations both inside and on the outdoor decks.

Dozens of other businesses on Halsted and surrounding streets are members of the Lakeview East Chamber of Commerce and Northalsted Business Alliance, who are happy to share information about things to see and do in the area.

Explore more Chicago LGBTQ+ neighborhoods, tours, and attractions.


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