These Chicago LGBTQ-owned businesses offer rainbow cakes, colorful coffees and a ‘third space' for all
To properly celebrate Pride Month, you need quite a lot of energy and definitely a lot of cake. Thanks to October Cafe, Jennivee's Bakery and Chicago Sugar Daddy, there are plenty of ways to keep the caffeine tank full and the sweet tooth satisfied while also supporting LGBTQ-owned small businesses in Chicago.
Jennivee's Bakery
If Tiffany's sold cakes instead of diamonds and had a penchant for rainbows, it might be Jennivee's Bakery on Halsted Street. Rainbow pillows perch on a long pink booth and two faux crystal chandeliers dangle over a black and white checkered floor, the base of a spacious dining area that compelled chef and owner Jenni Vee to upgrade to this location from her beloved original storefront nearly a year ago.
'This is the gayest bakery in Chicago,' she said.
Vee immigrated to the United States from Cebu, Philippines, to pursue a career as a physical therapist. In 2017, she pivoted, employing 'pure ambition and a little bit of delusion' to open a bakery in Lakeview and realize a passion for baking she had been nurturing since age 6. Vee ran her original storefront on the other side of the neighborhood for seven years before opening this location last June.
The new space screams French chic turned a little cheeky: The woman in the Renaissance-style painting (ornate frame and all) casts a sly expression across the room, while the smudged mirror on the back wall reflects rainbow flower leis hung from classy light fixtures. A woman's silhouette holds up a cupcake in Vee's lace-trimmed pink logo.
'I wanted it to be fun, feminine, yet cozy and inviting,' Vee said.
Her cakes fit right in. Vee supercharges classic vanilla buttercream with bright colors and edible glitter. The vivid purple of her signature ube cake has new neighbors every month as Vee brainstorms fresh ideas, mostly based on Filipino flavors but with European baking techniques (think a mango buttercream cake).
This month, pride-themed cakes and cupcakes star in the display case. Rainbow sprinkles coat the outside of a large vanilla cake, with eddies of rainbow icing, coated in edible glitter, lining the top. The cupcake version is much the same: vanilla cake with a hefty swirl of multicolored buttercream icing. Vee has also created an edible monument to transgender pride in a lemon cake with strawberry filling. Stripes of baby blue, pink and white icing paint the transgender flag on the outside; cutting into the cake reveals the same pattern within.
The rainbow cupcakes are bestsellers at Jennivee's, but the pink and blue cake is most significant for Vee, a transgender woman herself.
As both business owner and head baker — her black chef's coat is usually powdered with flour, her hands stained with icing — Vee won't have time this June to participate in the Chicago Pride Parade. The parade, however, marches right past her bakery, so she's expecting a barrage of orders.
'The party comes here,' Vee said.
Since upgrading her space, Vee has become accustomed to mayhem: The bakery gets busiest during its later hours, when customers crowd in for cake, gelato and the comfort of a 'third space' like Jennivee's.
Audrey Borden and Michelle Gonzalez wanted to wave a pride flag in an area they thought could use a little more color. The couple opened October Cafe in Norwood Park, where Gonzalez grew up, two years ago in August. The fall-themed coffee shop offers a proudly queer space for those in search of community.
'I feel like that's what was intended for us — to make roots in a place where I grew up, and kind of push against the norms around here,' Gonzalez said. 'It hasn't been easy, but we're making it happen. I'm here — they're gonna hear me, they're gonna see me.'
Borden and Gonzalez do nothing with subtlety: Their pop music bumps through the space, their flavors are varied and loud, and their jack-o'-lantern decorations watch guests from every wall. For June, giant pride flags hang off one wall while a banner of smaller flags decorates another.
Borden and Gonzalez's love for each other, much like their love for October, is easy to spot. They met in 2019 at a 'Queers and Allies' meeting at North Park University, where Borden was a freshman and Gonzalez a junior. They were married in 2023, and Borden is now eight weeks pregnant with 'baby pumpkin.'
On the first of every month, Gonzalez and Borden roll out a new flight of specialty drinks. After the fall flight, which is available year-round, June's rainbow flight is the most popular. It features an orange-yellow mango and peach jasmine tea, a lavender latte, a red strawberry lemonade and a darker purple ube vanilla latte. Insiders know that this flight, like all the rest, is available year-round on October Cafe's secret menu.
In lieu of having a business float at the Chicago Pride Parade — Gonzalez and Borden said it's a hefty fee — October Cafe will host pride bingo June 20, a drag queen story hour June 21, and small business events June 21-22 to highlight other queer-owned businesses.
Everyone who works at this Lakeview bakery is gay.
'It's not a criteria, I swear,' laughed owner and baker James Cox.
But for Pride Month, it is fitting. In September 2021, Cox opened Chicago Sugar Daddy with his partner — in both business and life — Rayan Ibasco. The bakery's name is a callback to their early days as a couple, when Cox would shower Ibasco in sweet baked goods that earned him the moniker 'sugar daddy.'
At the shop, Cox handles everything baking-related while Ibasco files taxes and organizes payroll on top of working another full-time job as an international student recruiter. Ibasco, who grew up in Manila, Philippines, moved to the United States in 2017 and graduated from DePaul University. Cox moved to Chicago to get his degree from the French Pastry School; he earned it in 2007. He was an executive pastry chef at several restaurants and hotels in the Chicago area, and was the general manager at Jennivee's right before opening Sugar Daddy.
Sugar Daddy focuses more on catering and custom orders. Cox bakes a lot of wedding cakes — he's looking at around 200 this year, 60% of which he estimates are for queer weddings. June is the bakery's busiest month, as all sorts of companies, as well as regular customers, order pride-themed goods.
In the bricks-and-mortar, Cox fills the display case with chocolate and marble cupcakes iced with a rainbow swirl of thick Swiss buttercream. He also spruces up a basic sugar cookie with a rainbow watercolor effect and a heart shape.
'Any way to incorporate rainbows,' Cox said.
The trademark at Chicago Sugar Daddy is connection. Ibasco and Cox are both bad at names, but they remember faces and, more importantly, everyone's favorite order. Cox knows what to recommend for the woman who stops in before her hair appointment (chocolate) and the little boy whose grandmother brings him 'to go see James' (the marble cupcake). Ibasco is adamant that Chicago Sugar Daddy never become too corporate.
'We want to continue to be a home away from home forever,' Ibasco said. 'The bakery has been a gateway for us to be closer to the community.'
Cox and Ibasco will continue to spread sweetness to their community on the day of the Chicago Pride Parade — June 29 — when they plan to hand out free slices of rainbow cake.
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