An LGBTQ-focused nightlife and hospitality company that acquired a Northalsted bar in 2024 now plans to redevelop the site into a luxury gay hotel, aiming to expand its footprint in one of the country’s most prominent LGBTQ neighborhoods according to Crain’s Chicago.
Tryst Hospitality has submitted preliminary plans to the City Council to build a five-story, 21-room Tryst Chicago hotel at 3350–3352 N. Halsted St., according to the company. The site was formerly home to DS Tequila, a bar and patio purchased by a Tryst-affiliated venture with initial plans to convert it into a nightclub. The company has since shifted direction and now intends to demolish the existing building and construct a boutique hotel, joining other Tryst properties operating or planned in destinations including Puerto Vallarta, Puerto Rico, Brazil, New York, Florida, and Provincetown, Massachusetts.
The proposal underscores Northalsted’s status as a major tourism draw. The annual Chicago Pride Festival and Parade in the neighborhood attract more than 100,000 attendees each year, according to Choose Chicago.
“Northalsted is one of the most dynamic queer villages in the world, and it deserves a luxury gay hotel that matches its energy,” said Tristan Schukraft, founder and CEO of Tryst Hospitality. “We want to create a place where people stay in the neighborhood—not just visit—while offering a space that serves locals, welcomes travelers, and becomes a hub for LGBTQ culture and nightlife.”
The project will require City Council approval to rezone the property. Tryst said it has begun community outreach with neighborhood groups and 44th Ward Ald. Bennett Lawson.
A Tryst spokesperson declined to disclose the project’s estimated cost but said construction would likely take about 18 months. An entity led by Schukraft purchased the DS Tequila property for $3.1 million, according to Cook County records.
Schukraft launched Tryst Hospitality in 2024 as a luxury hotel brand focused on LGBTQ travelers in major global destinations. He previously founded Mistr, a telemedicine platform specializing in HIV prevention, and ID90, an online ticketing company.
Chicago recorded a record 11.9 million hotel room nights last year, according to Choose Chicago, up from 11.6 million in 2024. Overall visitation reached 55.3 million people in 2024—an increase of 6.5% year over year, though still below the city’s pre-pandemic peak of 61.6 million visitors in 2019.
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