The Tryst unveils plans for its first gay, boutique hotel in Chicago — and wants local feedback

2026 is shaping up as a very busy year for The Tryst Hospitality brand. The company just announced plans to launch its first luxury LGBTQ+ hotel in Chicago.

The Tryst group is owned by Tristan Schukraft. The gay businessman also owns The Abbey in West Hollywood and PrEP telehealth brand MISTR, among other business ventures.

Last April, it launched The Tryst Puerto Vallarta. In December, we shared news about Tryst’s purchase of the iconic and well-loved Crown & Anchor in Provincetown. It relaunches as a Tryst business this summer. Tryst has also locked down sites for further hotels in Wilton Manors, Rio de Janeiro, and Fire Island Pines.

Early planning stages

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According to a press release issued yesterday, The Tryst Chicago will be a new boutique gay luxury hotel in the heart of Chicago’s historic Northalsted neighborhood.

However, it’s still in its early planning stages.

“Tryst Hospitality has submitted initial plans to the City of Chicago and is beginning a series of community meetings as part of the planning and zoning process,” says the press release. “These include conversations with the Northalsted Planning and Zoning Council, Northalsted Business Alliance, East Lakeview Neighbors, and a publicly hosted Zoom meeting with Alderman Lawson and interested neighbors to review the proposal. The project remains in its early planning phase, with community input central to the process.”

Northalsted — Chicago’s vibrant gayborhood, formerly known as Boystown — is one of America’s most iconic LGBTQ destinations. Anchored by North Halsted Street, it was the first officially recognised gay neighbourhood in the US. Rainbow pylons line the street, setting the tone for a welcoming, celebratory atmosphere. Visitors will find a rich mix of gay bars, clubs, and businesses catering to every taste, alongside the renowned Center on Halsted LGBTQ center.

“Northalsted is one of the most dynamic queer villages in the world, and it deserves a luxury gay hotel that matches its energy,” says Schukraft. “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.”

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21 rooms, rooftop pool and restaurant

Tryst Hospitality acquired the former DS Tequila at 3350–3352 North Halsted Street in 2024. The five-story building is the proposed site for the 21-room Tryst Chicago. It will include a new restaurant, a nightclub venue, and a rooftop pool. The hospitality group is working with Chicago-based NEWLOOK Design | Build + Development as the architect and lead designer on the project.

For now, anyone wanting to keep abreast of the project’s development can follow @trysthotels on social media.

Besides the forthcoming, planned hotels, Tryst Hospitality is also set to open its first gym and wellness spa this summer. Tryst Fitness will open in Puerto Vallarta, Mexico, on the same block at the Tryst Puerto Vallarta hotel.

Related

The Abbey owner, Tristan Schukraft, just bought a prestigious and much-loved Provincetown hotel
The Tryst group wants to become the world’s premier brand of luxury gay hotels.

The world’s first Tryst Fitness gym and spa will open next summer at this gay hotspot
The flagship Tryst Fitness is set to open next summer.

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