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The ultimate LGBTQ+ guide to Chicago – from visiting the first US ‘gaybourhood’ to dining like a queen

Simon Calder’s Travel

“Let’s cross the street to see Freddie”. The street in question is North Halstead Street, and ‘Freddie’ is none other than Freddie Mercury, his boyish face shining in the scorching Chicago sun. “After him, I’ll show you where Sylvia and Marsha are, so you can say hello.”

This is how my guide Victor Salvo introduces me to Chicago’s Legacy Walk, his magnum opus, and the first open-air museum celebrating LGBT+ culture in the world.

Chicago may have clung to its “Second City” moniker fiercely, but when it comes to queer history and communities, the city is second to none.

Believe it or not, not all “firsts” in LGBT+ history are linked to New York. Not only is Northalsted (historically named “Boystown”) the first official ‘gaybourhood’ in the US, Chicago is also where the first Pride March took place on 27 June 1970, a day before the Christopher Street Liberation March in NYC that would shake the world awake.

Rory on Chicago's Legacy Walk

Rory on Chicago’s Legacy Walk (Rory Buccheri)

“Everybody always talks about New York or San Francisco, whereas Chicago has always been, in some respects, a flyover city”, Victor explains. “But because people in Chicago have historically been overlooked, they’ve developed their own attitude towards getting things done.”

The Walk, 25 years in the making, is the result of that attitude.

Once just steel pylons rooted on busy North Halsted Street, today the 20 rainbow pillars form a monument to remember queer people who left a mark, from politics and medicine, to sports and entertainment. Well-known or obscure, each person gets a bronze portrait and plaque telling their story, as well as recognising those who contributed to put them there, including organisations and individuals sponsoring their place on the Walk.

Read more: 15 emerging LGBT+ travel hotspots to discover in 2025, from Osaka to Medellin

As Victor and I walk from pillar to pillar, the tarmac under our feet is steaming hot, a result of 38C weather, construction works and the city preparing for its pride festivals: the three main ingredients of a “Chicago summer”, he tells me. Road repairs and street parades are both things Chicagoans save for when their freezing winters are over.

And LGBT+ celebrations are a big part of the city coming back to life in summer. There’s Pride Fest…

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