A luxury LGBTQ+ boutique hotel is being proposed for the former D.S. Tequila site in Northalsted, adding another hospitality project to the neighborhood’s evolving development landscape.
Tryst Hospitality announced plans Feb. 25 for the Tryst Chicago, a five-story, 21-room hotel with a rooftop pool, restaurant and nightclub at 3350-3352 N. Halsted St. The site was previously home to D.S. Tequila before its closure in 2023.
The company submitted initial plans to the city and is beginning community meetings with neighborhood groups and residents as part of the zoning and planning process.
Meetings include discussions with the Northalsted Planning and Zoning Council, the Northalsted Business Alliance, East Lakeview Neighbors and a public Zoom session hosted with Ald. Lawson.
“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 give people a reason to stay in the neighborhood, not just pass through it, creating a space that belongs to locals, welcomes travelers, and becomes a new hub for gay culture and nightlife.”
The project remains in the early planning phase, with community feedback expected to shape design and operations.
The plans call for a small-scale, design-forward property rather than a large hotel development. The hotel would have a fully enclosed rooftop pool and bar intended to reduce noise.
Illinois-based NEWLOOK Design | Build + Development is serving as architect and lead designer.
Tryst Hospitality framed the project as part of a broader strategy to create LGBTQ+-focused hospitality destinations that serve as both travel accommodations and community gathering spaces.
The Northalsted hotel would join a growing network of Tryst properties in LGBTQ+ travel destinations, including Puerto Vallarta and San Juan, with additional hotels planned for Fire Island and Rio de Janeiro.
Schukraft—an entrepreneur whose portfolio spans nightlife, hospitality and health services—has been expanding his footprint in queer cultural hubs. Through Tryst Hospitality, he owns venues including the Abbey Food & Bar and The Chapel in West Hollywood, and has plans to reopen Circo, a well-known nightclub in Puerto Rico that closed several years ago.
In 2023, Schukraft also bought roughly 75% of the Fire Island Pines commercial district, including the Pavilion nightclub, the Blue Whale, the Canteen, retail spaces, docks and the site of the planned Tryst Fire Island hotel.
He is also CEO of the telehealth platform Mistr, which provides HIV prevention and sexual health services and operates a Chicago clinic at 3324 N. Halsted St.
The Tryst Chicago proposal arrives days after another group of developers unveiled the name and updated design for a different hotel planned at 3255 N. Halsted St.
Plans for The Tryst remain in early stages, with additional details—including timelines and refined designs—expected as the project moves through city review and community input.