What's it really like?
When gay travelers consider visiting the USA, cities like San Francisco, Palm Springs, and New York immediately spring to mind. However, gay Chicago should also be high on the list. There’s plenty for gays to see and do in the Windy City.
Chicago hosts several gay-themed events every year. First, there’s the Pride Festival weekend at the end of June, held in Boystown. It features music stages, vendors, food, and a vibrant parade.
Chicago is also the home of Mr. International Leather, and it has been since 1979. It’s held every year over Memorial Day Weekend in October.
Six Flags Great America theme park north of Chicago hosts Out in the Park, an annual gay night held every September.
If you happen to be in Chicago near Christmas, head to Sidetrack Bar in Boystown to experience the annual Chicago’s Most Fabulous Santa Speedo Run. Participants get into the festive spirit dressed as Santa—but with a twist: they wear red speedos instead of pants! It’s a wild and fun race down the main street of Boystown, showcasing the playful and inclusive spirit of gay Chicago.
For other tourist adventures, Chicago is situated on Lake Michigan, and there are numerous attractions and activities on the river.
There’s no ‘best’ time to visit Chicago as it’s an all-year destination. Summer is the peak season, so expect crowds and high hotel prices. Spring and Fall are excellent times to visit as the climate is more moderate. Christmas in Chicago is magical as there’s snow, and Millenium Park becomes an ice rink. In Winter, hotel prices are at their lowest.
Boystown, the oldest officially recognized gay Chicago neighborhood in the United States. It’s one giant strip along N Halsted Street in Northalsted. A few bars are on the surrounding streets, but you could bar hop up and down the main drag all night.
Happy hours starts at 5 pm, perfectly timed for the after-work crowd. Whether you’re into twink, drag, bear bars, cocktail lounges, or dive bars, there’s something for every gay man in this vibrant neighborhood.
The second Chicago gayborhood is Andersonville, which is Boystown adjacent. This is the home of the more chilled bars—as well as Chicago’s premier go-go bar, Atmosphere.
For those of you looking for something more non-scene, sprinkled around the city in Uptown and Rogers Park, you’ll find other gay venues.
Today, with your phone overflowing with dating apps, finding a new guy in any city is a breeze—almost too easy, right? But let’s be real, the thrill of bumping into someone new offline? Priceless. And guess what? Gay Chicago spices it up with a classic gay bathhouse right in the heart of Boystown.
For those whose interests are strictly therapeutic, Thai Lotus Bodywork in the CBD offers non-erotic massages. It’s the perfect spot to unwind without any unexpected plot twists!
Although Chicago doesn’t yet have any gay-owned or operated hotels, gays are warmly welcomed everywhere in Chicago. As the city hosts several gay events each year, hotels across the city vie for the pink dollar. It’s estimated that 7.5% of the population identifies as LGBTQI, ensuring a friendly and inclusive atmosphere wherever you stay.
Travelers can choose from luxury brands like Sofitel and JW Marriott, mid-range options like Radisson Blu, or budget-friendly hostels near Boystown. While a few hotels are located in the Boystown gayborhood of Northalsted, most are in the downtown area known as The Loop, putting you close to major tourist attractions.
Tours.
Unleash your creativity at this BYOB spray paint workshop in Chicago's Uptown. Guided by local artists, learn graffiti techniques, stencil application, and create your own canvas to take home. No prior experience needed; just bring your favorite drink and enjoy the vibrant atmosphere.
Embark on a 2-hour guided Segway adventure through Chicago's scenic lakefront and Museum Campus. After a brief orientation, glide past Grant Park's Buckingham Fountain, Shedd Aquarium, The Field Museum, and Soldier Field. Suitable for ages 12 and up; helmets and training included.
Discover Chicago's architectural gems on a 90-minute river cruise, offering unobstructed views of iconic landmarks like Marina City and the Wrigley Building. Learn insider stories about the city's top attractions from expert guides aboard comfortable vessels with indoor and outdoor seating.
Taste the unique flavors of the Chicago's Loop District, savoring iconic dishes like deep-dish pizza and Italian beef sandwiches. Along the way, admire landmarks such as the Willis Tower and the Rookery building. Choose between small-group or private tour options for a personalized experience.
Delve into Chicago's rich LGBTQ+ history on this immersive bus tour. Explore vibrant neighborhoods like Boystown and Andersonville, visit landmarks such as the Jane Addams Hull-House Museum, and uncover the city's pioneering LGBTQ+ movements, all while enjoying iconic Windy City sights.
Travel around Chicago's iconic sites on a leisurely bike tour through Museum Campus, Grant Park, and Millennium Park. Enjoy the city skyline, learn about public art and history, and capture unforgettable images of the Windy City.
Gays and the Law
Chicago has been at the forefront of gay rights since as far back as the 1920s. During the 1960s, Chicago was well-known as one of the first US cities to establish gay rights organizations. In 1973, The Center on Halsted, a major LGBTQ+ community center, opened its doors and is still there to this day.
In 2013, same-sex marriage became legal in Illinois, and in 2019, Lori Lightfoot became the first Black woman and an openly gay person to become Mayor of Chicago, further cementing the city’s reputation as a progressive stronghold for the LGBTQ+ community. Boystown remains the vibrant center for LGBTQ+ life in gay Chicago, symbolizing the city’s strong sense of acceptance and community.
Getting Tested
The AIDS Foundation of Chicago, in conjunction with the Center on Halsted, offers HIV and STI testing. It can also provide PrEP refills and emergency PEP. Most health practitioners in the city can also prescribe PEP.
Local Neighhorhoods
Chicago, home to Boystown, the US’s first officially recognized gay district, is a cornerstone of gay Chicago. It’s primarily one street, N Halsted, in the Northalsted suburb. Apart from the Center on Halsted, which provides community services to LGBTQIs, there are 11 gay bars, clubs, and a bathhouse.
There’s a smaller gayborhood known as Andersonville to the north of Boystown. It’s a quaint suburb with antique shops, boutiques, and four gay venues, including the city’s only go-go bar.
As most of the city’s hotels are located in The Loop, there’s one gay bar, just across the river called Second Story, only a few minutes away in a taxi.
Wish you were here?
Sign up for our newsletter and discover travel experiences you’ll really want to try.
The Gay Passport is your complete Gay Travel Guide. Looking to Drink, Play or Sleep we have reviews to help. Award-winning & Updated 2025.
