Chicago has long been a safe haven for the LGBTQIA+ community. With strong legal protections, access to affirming care, and a vibrant network of trans-led events and organizations, it continues to be one of the most trans-affirming cities in the country.

This International Transgender Day of Visibility, were spotlighting the trans, nonbinary, and gender-diverse entrepreneurs who are creating welcoming spaces, building community, and keeping Chicago proudly queer — one cupcake, haircut, and vintage find at a time.

Here are some must-visit spots owned and/or led by trans and gender-diverse folks across the city.

Jennivees Bakery

Founded by Jenni Vee (she/her), a proud Filipina trans woman, Jennivees Bakery blends classic American sweets with Filipino flavors, offering a wide selection of specialty cupcakes, cakes, and other treats. In 2024, the bakery expanded into a larger Lakeview location — an adorably aesthetic space that also serves fresh gelato, coffee, and espresso drinks, making it the perfect spot to treat yourself and hang out.

Lakeview, 2925 N. Halsted St.

Rotofugi

Founded in 2004, Rotofugi is a designer toy store and art gallery located on the border of Lincoln Park and Lakeview that has become one of the world’s top destinations for designer toys and pop art collectibles. Owned by genderqueer art curator and video game enthusiast Kirby Kerr (she/her), the shop features a wide selection of vinyl figures, blind box and capsule toys, plush, and a monthly rotating art gallery spotlighting both local and national artists.

Lakeview, 2780 N. Lincoln Ave.

The Dropped Stitch

Tucked into Chicago’s Andersonville neighborhood, The Dropped Stitch is a cozy, local yarn shop founded by trans fiber artist and Jeopardy winner Hannah Wilson (she/her). Hannah used her Jeopardy winnings to open up what she felt was missing in her neighborhood, a yarn shop and community space for fiber artists and those aspiring to learn. The shop is home to a large selection of yarn, crafting tools, and craft kits.

Andersonville, 1524 W. Bryn Mawr Ave.

Fiber artist and Jeopardy winner Hannah Wilson at The Dropped Stitch in AndersonvilleOUTSKIRTS Vintage

OUTSKIRTS Vintage was founded in 2019 by three friends who saw a gap in Chicago’s vintage scene and set out to create a shop for all genders, complete with on-site professional alterations. Now a four-person worker-owned co-op based in Avondale, the team brings together their backgrounds in retail, tailoring, and costume design to offer curated vintage clothing and accessories, custom pieces, and inclusive alterations both in-store and online.

Avondale, 1742 W. Lawrence

Loaves Witches

Calling all queer, sober witches — Loaves and Witches is a trans- and queer-owned microbakery run by best friends Julia Goodmann (she/they) and Lisa Harriman (she/they), who’ve created a cozy, affirming space where community care comes first. Grab a house-made scone, muffin, or vegan treat, sip on a coffee or tea, and explore the tarot decks scattered throughout. It’s the kind of place where you can grab a treat, recharge, and feel right at home — no spells required.

Edgewater, 6034 N Broadway

Flower Power Furnishings at Rad Pop! Vintage Emporium

This trans-owned home goods business is located inside Rad Pop! Vintage Emporium, a “mini antique mall.” Patti Jakab (she/her), owner of Flower Power Furnishings and vendor at Rad! Pop, specializes in handmade and upcycled furniture, colorful glassware, miniatures, and eclectic home goods. If you’re into vintage and quirky finds, Radpop is a must-stop — and one of my personal favorites in Chicago!

Edgewater, 5820 N. Broadway

Explore more: Discover LGBTQ+-friendly bars and clubs throughout Chicago.

Good Boys Dog Grooming

Good Boys is a premium dog grooming salon co-owned by trans husbands, Nick Petravich (he/they) and Arthur Addison (he/him). Arthur and Nick met in Chicago, united by a shared love for dogs and launched their business together in 2020. Nick, an award-winning groomer, leads with creative flair, while Arthur manages the business side with his background in analytics. They offer high-quality grooming services and a safe and inclusive space for all pet parents (and queer and gender-expansive pets!)

Irving Park, 1615 W. Montrose Ave.

More trans-owned, trans-affirming businesses and community spaces

These trans-owned and -allied businesses go above and beyond to support Chicago’s trans community through donations, inclusive hiring, transgender and gender nonconforming (TGNC) events, and by creating safer, more welcoming spaces across the city:

Above the Bar: Trans-owned gym in EdgewaterHan Training: Trans-owned personal training and wellness space in UptownLogan Parlor: Trans-inclusive and affirming hair salon and barber in Logan SquareHex Appeal Hair Studio: Trans-owned, gender-affirming salon in AndersonvilleEli Tea Bar: Queer-owned sober bar and teahouse that hosts TGNC+-centered eventsDorothy Downstairs: Trans-inclusive lesbian cocktail bar that regularly hosts trans masc-centered eventsCalifornia Clipper: Allied-owned neighborhood bar that hosts, Notes on Masculinity, a BIPOC drag king-centered cabaret bi-monthly eventBrave Space Alliance: Black trans-led LGBTQ+ center on Chicago’s South SideChicago Therapy Collective: Trans-led organization working to advance health, equity, and safety for trans and gender-diverse people through therapy, advocacy, and community careGender F*cked Productions: Trans-founded and -led organization creating bold, queer-centered performances and events that uplift trans and nonbinary artistsWomen and Children First Bookstore: Queer-owned feminist bookstoreThis Trans Day of Visibility, let’s celebrate the trans, nonbinary, and gender-diverse folks helping shape the heart of Chicago — not just today, but year-round. Supporting these businesses is a meaningful way to show up for the community and help keep the city safe, welcoming, and affirming for everyone.

Explore more: Discover LGBTQ+ friendly spots in Chicago’s south and west neighborhoods