Tryst Hospitality has announced plans for The Tryst Chicago, a boutique gay luxury hotel proposed for the US city's Northalsted neighbourhood.

The company has submitted plans to the City of Chicago and will engage with community groups, including East Lakeview Neighbours, Northalsted Business Alliance, and the Northalsted Planning and Zoning Council.

The project is in its early planning phase, prioritising community feedback.

Tryst Hospitality’s planned site is located at 3350–3352 North Halsted Street, formerly DS Tequila. The location was purchased by founder and CEO Tristan Schukraft in 2024.

This proposed project will be a five-storey building, comprising 21 rooms, and amenities such as a restaurant, public spaces and a nightclub.

Features include a fully enclosed rooftop pool and bar, improved alley circulation for reduced congestion. The rooftop enclosure supports all-season use while minimising noise impact.

The Tryst Chicago intends to operate as an intimate boutique hotel focused on eco-conscious practices such as eliminating single-use plastics and partnering with local LGBTQ+ non-profits and minority-owned businesses.

Tryst is collaborating with NEWLOOK Design | Build + Development as project architect.

Tryst Hospitality operates other properties in Puerto Vallarta, Fire Island, Rio de Janeiro, Wilton Manors, Provincetown, and San Juan.

The company will maintain engagement with community leaders as The Tryst Chicago progresses through city processes.

Schukraft said: “Northalsted is one of the most dynamic queer villages in the world, and it deserves a luxury gay hotel that matches its energy. We want to give people a reason to stay in the neighbourhood, not just pass through it, creating a space that belongs to locals, welcomes travellers, and becomes a new hub for gay culture and nightlife.”