This Lively Lakeside Midwestern Destination Is America's Safest City For LGBTQ+ Travelers In 2025

Where drag brunches meet deep-dish pizzas and rainbow crosswalks connect to lakefront paths, Chicago doesn't just embrace its LGBTQ+ travelers — it's intertwined with them. Among some of its claims to fame for the community, Chicago is home to America's oldest gay neighborhood, preserves queer history in one of the largest LGBTQ-centered libraries, and boasts the biggest yearly Pride celebration in the Midwest (the second-biggest Pride is in Columbus). All of these milestones are a testament to the city's inclusion and protection of its queer people and history.

A study by Misterb&b — an online service for finding LGBTQ-friendly accommodations — proved this, naming Chicago 2025's No. 1 safest city for LGBTQ+ travelers. The study took into account a few factors, namely: how many bookings the location got through the site, state- and city-level protections, PFLAG chapter presence, and the number of FBI-reported hate crimes. Chicago's legal protections for gender-neutral bathrooms, LGBTQ+ parents, and nondiscrimination in the workplace translate to safety and comfort for LGBTQ+ people. Chicago-born and openly gay Illinois Senator Mike Simmons said, "[W]e must remain vigilant and aggressive in ensuring that Illinois is not only a refuge state and a sanctuary state for LGBTQ communities, but that we call out the hatred, punitive legislation, and entirely unnecessary regression that we're seeing," Associated Press reported.

Beyond the accolades, it's Chicago's lived-in pride that makes it a truly resilient and fun LGBTQ+ city, felt by the people who both live in and visit it. As Redditor u/happilyfour said of the city, "[A]cross the board, you see so much open queer life and queer love and queer presence in so many aspects of life here."

If you're looking for an LGBTQ+ neighborhood to stay in Chicago, the first place on your radar will likely be Northalsted, more commonly known by the nickname "Boystown." About a 30-minute drive from O'Hare International Airport, or accessible by the Red and Brown L lines, Boystown is Chicago's oldest and arguably most well-known gayborhood. The neighborhood was officially designated a gay district in 1997 by Chicago's then-mayor, having established itself as a community focal point for activism and queer spaces. Most of the action takes place along its main road, Halsted Street. It's here that you'll find the Legacy Walk, an outdoor LGBTQ history museum, and iconic gay bars.

Further north, a more laid-back but still proudly queer neighborhood is Andersonville, where you'll find a blend of Swedish roots and unmatched food. It was called "one of Chicago's coolest neighborhoods" by National Geographic, and its main thoroughfare, Clark Street, is lined with thrift stores, museums, and queer bars. A staple on Clark Street is the Brown Elephant, a secondhand shop that donates all proceeds to LGBTQ+ healthcare. Another neighborhood highlight is Nobody's Darling. Called "Andersonville's modern LGBTQ icon" by Eater Chicago, it's a cocktail bar owned by two queer Black women. Andersonville's about 30 to 40 minutes by car from the airport, and the closest subway station is Bryn Mawr off the Red line.

Start your morning with coffee at Two Hearted Queen, a queer-owned coffeehouse in Lake View. Another great option if you're staying in Andersonville is A Taste of Heaven, also a queer-owned cafe, which has a stacked breakfast menu. One classic Chicago destination you don't want to miss on a visit is the Art Institute of Chicago. Aside from having a sprawling collection of iconic works, the museum spotlights many queer artists, including Andy Warhol and Felix Gonzalez-Torres. For a taste of Chicago's saucier side, the Leather Archives & Museum is a must-visit in Rogers Park, with a unique collection dedicated to leather and fetish cultures. On Sundays, the city has many spots hosting drag brunches — some of the most legendary are Lips Drag Brunch, hosted at an opulent venue in South Loop, and the Divalicious Brunch at Kit Kat in Boystown.

Come sundown, Chicago's queer nightlife is bountiful. Boystown, no doubt, is the heart of the queer nightlife scene, home to renowned gay nightclubs like Roscoe's Tavern and Sidetrack. It also has some quieter, more intimate bars for sitting and chatting, too, like The North End, a low-key neighborhood dive bar. You don't have to stay in Boystown for nightlife, though. Andersonville has Atmosphere, which Yelp reviewer Erika G. described as "One of the longest running bars on this strip, and I LOVE IT. Every time I go here, it's fun." Andersonville's also home to Farraguts on Clark, a dive bar catered to queer women. Venture beyond the two main gay neighborhoods and you'll find gems like Big Chicks in Uptown, where retro art lines the walls and everyone's invited to the dance floor.