NORTHALSTED — A new luxury boutique hotel designed to serve LGBTQ+ travelers is in the planning stages for a prime location on Halsted Street in Northalsted, a historic hub for Chicago’s LGBTQ+ community. The proposed development, led by Tryst Hospitality and NewLook Development, would transform the former DS Tequila site at 3352 N. Halsted St. into a multi-story hotel featuring a restaurant, event space, and rooftop with two pools, a terrace, and a retractable roof.

Revitalizing a Historic Site

The project would replace the existing structures on the site and use a combination of steel, brick, and glass for its design. If approved, it would mark the first ground-up hotel built under the Tryst brand, which currently operates luxury LGBTQ+-focused properties in locations such as Puerto Vallarta, Fire Island, and Rio de Janeiro.

The proposed hotel would be the second luxury boutique hotel catering to LGBTQ+ guests on Halsted Street. Last March, City Council approved a six-story, 51-room hotel at 3257 N. Halsted St., formerly the location of Yoshi’s Cafe, a block south of the proposed Tryst Chicago site.

Tristan Schukraft, founder and CEO of Tryst Hospitality, first became interested in the hotel business after visiting Puerto Rico and envisioning a beachfront property on a prime piece of real estate. Schukraft, who also founded the telemedicine and HIV prevention care company MISTR, has been an entrepreneur since his teenage years and has since focused on acquiring and rehabbing legacy gay institutions across the Americas.

Preserving Gay Institutions

According to Schukraft, the inspiration for the Tryst name came from a hotel of the same name that once stood near the Puerto Rico property where he first had the idea for his hotel business. The original Tryst Hotel had been a famous gay establishment before it was converted to a straight hotel.

“It sits right in front of the gay beach, and it showed me how when one key institution in a neighborhood disappears, gay life disappears with it,” Schukraft said. “There used to be a big tea party here every Sunday and the beach would be packed. But the hotel disappeared, a nightclub closed, and the whole scene changed.”

Schukraft has since taken it upon himself to preserve and revitalize gay institutions, including The Abbey in Los Angeles and Circo in Puerto Rico. He described the effort as a mission driven by the importance of these spaces for the LGBTQ+ community.

“These places are really important for the community,” he said. “There aren’t a lot of people stepping up to acquire these places.”

Chicago’s Vibrant LGBTQ+ Scene

The proposed Tryst Chicago would be the first new build under the Tryst brand, with other projects in Puerto Vallarta, Rio de Janeiro, Provincetown, and Fire Island being redeveloped properties. Schukraft was drawn to Northalsted because of the neighborhood’s vibrant LGBTQ+ culture and its appeal as a destination for both visitors and locals.

“Chicago has a really vibrant LGBTQ+ scene,” Schukraft said. “You have places like Wilton Manors, West Hollywood, Boystown, and Oak Lawn in Dallas, and Northalsted is definitely one of the premier neighborhoods.”

He noted the ability for visitors to walk between bars, restaurants, and entertainment venues in Northalsted, which he said makes the district feel like a true destination. “There’s a big need for one, and I’m excited to bring that to Chicago,” he said.

The proposed hotel would include signature elements such as 24-hour room service, happy hours, drag brunch on Sundays, and rooftop pool parties. The idea for a Chicago location began taking shape after Schukraft started visiting the city regularly, especially for Market Days, one of the country’s largest LGBTQ+ street festivals.

“I’ve been going to Chicago for many years, especially for Market Days, and one thing that always bothered me was there was no hotel in the neighborhood,” Schukraft said. The concept became more concrete after he purchased the former DS Tequila property in 2024.

Because of the size and scope of the project, the development would require approval from the city as a Planned Development, a zoning designation typically used for larger projects that allows developers to negotiate specific design and density details with the city. Ald. Bennett Lawson (44th) is now collecting feedback from neighbors and community members about the proposal.

Neighbors can share their thoughts with the alderperson’s office by emailing [email protected] or calling 773-525-6034. Construction can’t begin until the project is approved by City Council.