Thank the rainbow gods it’s Pride Month, a chance to celebrate love in all forms and connect with like-minded community. Some people travel for Pride if their city doesn’t host large-scale festivities, and renting an Airbnb to share makes the journey even more special. To that end, Airbnb has released a list of the top trending Pride Month destinations this year, based on searches by Gen Z and millennial users.
Younger travelers like those born between 1981 and 1996 (a.k.a. Millennials) and between 1997 and 2012 (Gen Z) have been looking online for the best cities to celebrate Pride Month, with search interest surging from 20-percent last year to 90-percent in June 2025. In the U.S., the cities seeing the most trending interest are Chicago, Illinois and Boston, Massachusetts, beating LGBT-friendly hubs like New York and San Francisco. And internationally, the cities of Cologne, Germany; Bogotá, Colombia; and Mexico City, Mexico are also seeing a huge uptick in interest.
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Why these two American cities? Chicago was where the country's first gay rights organization (the Society for Human Rights) was founded in the 1920s; half a century later, the city's annual Pride Parade began as a protest march in 1970 after the significant Stonewall Riots in New York City, where people protested the police raid on a gay club called the Stonewall Inn. Today, Chicago's Pride Parade brings out more than a million people to cheer and celebrate. The larger Pride festivities last all month around Chicagoland, with concerts, street festivals and dance parties.
And Boston, of course, has its own historical LGBTQ+ bonafides: its own Pride parade, which debuted in 1971, was the first in all of New England. This year's observances, centered on the ever-resilient theme of "Here to Stay," include an epic parade, rainbow flag raising, live music and performances from both drag kings and queens.