If you were planning to spend Pride Month somewhere fun, fabulous and full of flavor (rainbow and otherwise), you wouldn’t be alone in choosing Chicago. According to Airbnb’s 2025 travel data, the Windy City is one of the top trending Pride Month destinations among Gen Z and Millennial travelers, with searches spiking 37% over last year’s numbers.
Chicago joins the ranks of other buzzworthy Pride cities like Boston, Bogotá and Cologne, all seeing a swell in bookings as younger generations plan trips around parades, parties and unforgettable experiences. The data tracks bookings for late June, just in time for the city’s big Pride festivities, including the iconic Chicago Pride Parade, which draws nearly a million people annually.
And it's not just about marching. Airbnb has also spotlighted “The Animated Tour of Chicago” as one of the standout experiences travelers are booking while in town. The creative walking tour, hosted by local artist and animator O.J., blends history, city landmarks and vibrant visuals into a delightfully nerdy cultural deep dive. Think Schoolhouse Rock meets Chicago Architecture Center—with original art, humor and just the right dash of weird. Reviews call it “10/10,” “super fun” and “an incredible, inspiring start to the trip.”
Pride-seekers can also take advantage of Airbnb’s expanding menu of local services, from in-home yoga to prepared meals, all geared toward helping visitors make the most of their stay no matter their budget or itinerary.
Chicago’s place on the list makes sense: The city boasts a thriving LGBTQ+ community, legendary nightlife and plenty of rainbow-splashed events throughout the month. But it’s also a city of neighborhoods—each offering something different, whether you’re brunching in Boystown, gallery-hopping in Pilsen or cruising the lakefront on a Divvy bike with a drag queen-led tour (yes, that exists).
If you're still hunting for a last-minute Pride trip that delivers on both substance and sparkle, Chicago just might be calling your name, with a deep dish in one hand and a parade flag in the other.