Lesbian, gay, transgender, queer, bisexual — however you identify, you’ll feel right at home in Chicago. Our city is known for embracing diversity and inclusion, from our world-famous Pride celebrations to establishing the country’s first official gay neighborhood. And while the whole city exudes a welcoming vibe, there are a couple of neighborhoods and places you shouldn’t miss.

Make a beeline for Boystown

Kit Kat Lounge & Supper Club

Boystown is the oldest official recognized LGBTQ+ neighborhood in the country. The area’s proud history is on display with the Legacy Walk, which commemorates notable LGBTQ+ heroes and historic events. The walk is a great way to tour the community — make sure to stop into the many great eateries, friendly bars, vintage stores, and unique boutiques along the way.

Come June, you’ll find Boystown at the heart of the city’s annual Pride Month celebrations, which include two days of LGBTQ+ pride, music, and drag shows at Chicago Pride Fest, and culminates with the famed Chicago Pride Parade, a spectacular procession held on the last Sunday of June.

A couple of the many spots that capture the casual, funky, and fun spirit of the neighborhood include the original Chicago Diner, which puts animal rights and environmentalism front and center, while serving up tasty vegetarian and vegan food; sassy, swanky Kit Kat Lounge & Supper Club, where dinner is served with a tableside drag show; and Wood, an explosion of smoky wood-fired flavor that’s earned a Michelin Bib Gourmand award.

At night, check out leather-theme nights at laid-back Cell Block, drag shows and dance parties at Hydrate, and slushy drinks and show-tune nights at Sidetrack. Boystown classics like The Closet and Roscoe’s Tavern are also local favorites.

When it comes to shopping, don’t miss casual men’s wear boutique CRAM Fashion, hard-to-find queer works at Unabridged Bookstore, and works by local LGBTQ+ artists at the Leigh Gallery.

Shop local in Andersonville

Andersonville is known for it’s deep Swedish roots, array of eclectic independent businesses, and their welcoming, diverse LGBTQ+ community.

Women & Children First is where Andersonville’s “shop local” ethos and progressive inclusivity intersect. The bookstore is a Chicago institution, with more than 30,000 books by and about women. They also host an exciting array of public events, like book launches, poetry readings, and author conversations. 

On Clark Street, you’ll find a stretch of locally owned restaurants and bars that always bustling with visitors and locals. Hamburger Marys is a great stop for burgers, and don’t miss their under-the-radar upstairs venue. Mary’s Attic features a packed schedule of events like drag queen bingo, cabaret performances, diva brunches, and more.

If you’re looking to take home a unique piece of Chicago, explore the Andersonville Galleria. This multi-level labyrinth is where dozens of local artisans sell their handcrafted ware. Or check out Foursided, an LGBTQ-owned gem that stocks tons of cute and modern gifts and home decor.

If you’re in the neighborhood during June’s Pride Month, make sure you stop by Midsommarfest. The annual festival celebrates the community’s heritage with Swedish food, local artisans, and a Pride stage where you can catch performances from drag divas and Broadway stars.

Go under-the-radar in Rogers Park

This welcoming lakefront enclave is home to a fascinating slice of LGBTQ+ history. The Gerber/Hart Library and Archives in Rogers Park is the largest circulating collection of LGBTQ books and historical items in the Midwest. Their rotating exhibits cover everything from local drag icons to queer sports groups.

Also in Rogers Park, the Leather Archives & Museum is where you can learn everything you’ve ever wanted to know about the leather lifestyle. The adults-only museum celebrates the history of leather and fetishism across sexual orientations.

Also in Rogers Park, the Glenwood Avenue Arts District boasts a highly innovative theatre scene that includes the likes of Babes with Blades Theatre Company, which uses stage combat to place women and their stories center stage; BoHo Theatre, which examines human relationships through the filters of truth, beauty, freedom, and love; boldly original The Factory Theater; and song-and-dance impresarios Theo Ubique Cabaret Theater.

Throughout Rogers Park, you’ll also find sculpture gardens, beaches, parks, a world of global cuisine, and a few Frank Lloyd Wright gems like the stunning Emil Bach House.

Live it up in Uptown

Big Chicks
Big Chicks

If you love bars, live music, and nightlife, you’ll love Uptown. Sip cocktails on the patio at Big Chicks, an LGBTQ restaurant-bar-gallery in one, with great weekly specials and a super-welcoming vibe. Soak in some history and hear jazz greatness happen at Prohibition-era Green Mill. And experience drag queen artistry at The Baton Show Lounge, one of Chicago’s long-standing loves.

You can also catch a show at the Pride Arts Center, which presents queer theatre, movies, and comedy that resonates with all audiences. Mix in some Art Deco and Prairie School beauties; authentic Asian, Ethiopian, Lebanese, and Indian eateries and grocery stores; beautiful beachfront parks; and the hidden gem that is Graceland Cemetery, and you’ll find it hard not to linger in Uptown.

Party at LGBTQ+ festivals

Northalsted Market Days

Chicago is defined by many great things, and festivals is definitely one of them. June’s Chicago Pride Festival, one of the largest annual gay pride festivals in the country, and Chicago Pride Parade, which attracts an estimated one million spectators, are among the summer’s stars. Other great Pride Month events include Pride in the Park, Chicago Dyke March, Andersonville Midsommar Fest, Back Lot Bash, and Navy Pier Pride.

Another festival worth planning a trip around: Boystown’s Northalsted Market Days every August. This weekend-long party celebrates LGBTQ+ life and community with all-day live music, unique vendors, arts and crafts, food and drink, DJs, and dancing at the largest street festival in the Midwest.

In September, the Reeling Film Festival showcases LGBTQ+ films and filmmakers, with the mission of counteracting the misrepresentation and stereotyping of LGBTQ+ people in mainstream media. FYI: This is the second longest-running film festival of its kind in the world.