Gay Things To Do in Chicago

Written by JosephOctober 4, 2021

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Chicago is one of the most inclusive cities in the country, with a long and vibrant LGBTQ+ history.

The Windy City is an absolute must-visit for any gay traveler. Brimming with culturally and architecturally rich neighborhoods, gorgeously designed parks, and long stretches of scenic lakefront, this city of nearly 3 million boasts a host of pleasures for gay travelers of all stripes.

Gay Chicago might not be your first thought when considering gay hotspots in the USA where you can just be yourself, but after you have immersed yourself in the frenzied energy of the Boystown gaybourhood you will soon be wondering how the Windy City managed to keep its fabulousness under wraps for so long….

In the bustling downtown, historical theater marquees and landmark skyscrapers compete with thriving cafes and boutiques to garner attention from tourists. In the warm and humid summer months, sun-worshippers gather at the popular lakefront spots spanning the city’s shores, including North Avenue Beach, Montrose Beach, and Kathy Osterman Beach, a beautiful gay beach on the north side. With glamourous old hotels, world-renowned restaurants, and speakeasy-style cocktail bars practically on every corner, Chicago never fails to impress, whether it’s your first time here or your hundredth.

If you’re a professional shopper or even a professional window-shopper, then you definitely don’t want to miss the Magnificent Mile, located in the shadows of the city’s most iconic skyscrapers. This stretch of commercial indulgence is a marvel for shopaholics; you’ll find an avenue lined with 460 different stores to feed your material cravings, and over 220 delicious restaurants to enjoy. This retail district should quell all of your shopping addictions, but if you’re looking for more, head over to Wicker Park or Bucktown for some out-of-this-world funky boutique shops and discount stores.

Queer-Friendly Neighborhoods

One thing I love about queer life in Chicago is how so many faces and voices are being recognized. In the past, you’d go to Boystown and it seemed like it was mostly just a place for gay white guys. Today so many more people seem to have a larger presence in queer life in Chicago—people of color, femmes, trans men and women, genderqueer and more. And what’s beautiful to me is everywhere you go in Chicago, queers are there. Even though many of us still live in gay-heavy ‘hoods, we’re not ghettoized anymore and live everywhere — and the city, for the most part, is open and accepting.


Despite the name, Boystown is Chicago’s largest inclusive LGBTQ+ neighborhood with bars, shops, restaurants, gyms, theaters, a historical legacy walk with rainbow-clad demarcations along Halsted Street and the Center on Halsted, the city’s large LGBTQ+ center. The annual Pride parade and festival take place here each June as does Market Days, one of the country’s largest street fairs. Gays started moving here in the 1960s and ‘70s and it officially became a gay village in 1997, the first in country.


Set on the Far North Side centered along Clark Street between Winnemac and Irving Park, this former Swedish enclave started attracting more gays and lesbians in the late 1980s, especially with the opening of Women & Children First Bookstore. Today, Andersonville is a lively, colorfully-mixed neighborhood with fantastic restaurants and bars like AnteprimaLittle Bad WolfReplay and Marty’s Martini Bar. There are beautiful homes and easy access to Hollywood Beach, a.k.a. the gay beach, just a few blocks to the east.

Wicker Park

While not really considered an official LGBTQ+ neighborhood, Wicker Park (and Bucktown and Logan Square for that matter) is very gay friendly, as evidenced by the large number of queer folk who live in that part of the city. This area is a hub of creativity, excellent nightlife, live music bars, galleries, theaters, and so much more.

Chicago is one of the most inclusive cities in the country, with a long and vibrant LGBTQ+ history. If you’re planning on meeting hot guys this weekend around Chicago, make sure to download our favorite gay dating apps like Gay Dating Solutions and My Gay Match.

My Gay Match is a new gay dating site that focuses on matching gay men not only on demographic information but a unique personality measure developed by a psychologist. All members are personally confirmed and carefully screened by their staff to prove that they are real. If you’re looking to find a warm and meaningful connection with interesting and caring singles this is the site for you. The gay dating website is currently offering a free 30-day trial.

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