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LGBTQ+ Owned Businesses in Chicago

Posted on June 25
Kayleigh Padar

Kayleigh Padar

A group of five people walking down a street side by side. They are holding rainbow balloons that spell out "PRIDE"

Chicago’s Pride Parade in 2025. (Kayleigh Padar)

Seeing Chicago’s vibrant queer community come out in full force as the whole city launches into summertime always reminds me why I love living here.

I’m especially looking forward to the Pride Parade on Sunday. This year is particularly special because it falls on my birthday! I can’t think of a better way to celebrate than putting some glitter on my face and soaking up thousands of people’s sheer joy.

I’ve rounded up some of my favorite LGBTQ+ owned businesses that keep Chicago bright and colorful all year long. For even more recommendations, check out City Cast Chicago contributor Anna DeShawn’s lesbian-owned business directory.

Loaves and Witches (Edgewater)

Iced coffee, bagels, and tarot, oh my! This community-centered coffee shop has quickly become a staple in the neighborhood. I swear, every time I walk by, there’s a line out the door. It offers a wide range of pastries, including vegan and gluten-free options, and they create a new zodiac-themed drink every month. The cafe hosts a slew of community events, from crafting meetups to comedy shows to tarot readings.

Open since 1980, it’s one of the city’s oldest LGBTQ+ bookstores and a place that’s easy to get lost in. Its multiple rooms of winding shelves are home to an unparalleled collection of LGBTQ+ literature, plenty of fiction and poetry, and an extensive section on sale. This gallery of photos shows how the bookstore has evolved in the last 45 years.

This vintage shop has been “making Bridgeport weirder since 2022,” with its wide selection of clothing, art, and everything in between. The owners remake, remix, and repair antiques to give new life to timeless treasures. New items drop in-store every week, and you can also buy online.

Dorothy (Ukrainian Village)

On a quest to increase the dwindling number of lesbian bars throughout the country, one queer couple opened a neighborhood cocktail lounge “for every friend of Dorothy.” The subterranean, 70s-inspired speakeasy is known for its arts-focused events, including silent reading nights, open mics, movie nights, and more. It’s a little tricky to find the first time, but don’t let that deter you. Look for the unmarked red door on Chicago Avenue just west of the “2500” painted on the building.

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