Introducing The Tryst Chicago: A New Era of Gay Luxury in Chicago’s Most Famous LGBTQ+ Neighborhood

Chicago, IL, Feb. 25, 2026 (GLOBE NEWSWIRE) -- Tryst Hospitality, the global leader in luxury LGBTQ+ travel and nightlife, has announced plans for The Tryst Chicago, a new boutique gay luxury hotel proposed for the heart of Chicago’s historic Northalsted neighborhood.

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

Proposed for the site of the former DS Tequila at 3350–3352 North Halsted Street, which Tristan acquired in 2024, The Tryst Chicago would be a five-story, plus rooftop, 21-room boutique hotel featuring thoughtfully designed public spaces, a new restaurant and nightclub venue, and a rooftop pool.

The Tryst Chicago has been designed with sensitivity to its surroundings. Plans include a fully enclosed rooftop pool and bar to mitigate sound, improved alley circulation and operations to reduce congestion, and architectural scale intended to respect the existing streetscape. The rooftop enclosure allows for year-round use while minimizing noise spillover, and the building’s design is intended to respect neighboring properties without blocking views. 

Envisioned as a small, high-touch luxury hotel rather than a large-scale development, The Tryst Chicago is designed to feel intimate, design-forward, and deeply connected to the community. Like all Tryst properties, the hotel will embrace mindful luxury, incorporating eco-conscious design, eliminating single-use plastics, offering refillable water bottles and water stations, and prioritizing partnerships with local LGBTQ+ nonprofits and minority-owned businesses. The Tryst is working with Chicago-based NEWLOOK Design | Build + Development as the architect and lead designer on the project.

While the award-winning Tryst Hotel brand is known for luxury, that does not mean it is out of reach. Room rates at The Tryst Puerto Vallarta start in the low $200s, reflecting Tryst’s belief that true luxury is about more than thread counts or pool parties. It’s about being your true self. It’s about waking up surrounded by the LGBTQ+ community and knowing you’re exactly where you’re supposed to be.

With existing and upcoming hotels in Puerto Vallarta, Fire Island, Rio de Janeiro, Wilton Manors, Provincetown, and San Juan, Tryst Hospitality continues to redefine LGBTQ+ travel by creating high-end, community-driven hospitality experiences in iconic queer destinations around the world.

The Tryst Chicago is in the early stages of development. Tryst Hospitality will continue working closely with community leaders to keep neighbors informed and engaged as the project evolves. Additional details, including timelines and refined designs, will be shared as the project moves through the City process and community feedback is incorporated. For early glimpses, including renderings of the proposed property, follow @trysthotels on social media.

To book your next escape at a current Tryst Hotel, visit trysthotels.com and follow @trysthotels.

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About Tryst Hotels

Tryst Hotels are a collection of luxury boutique hotels that offer an upscale, inclusive experience for guests seeking high-end accommodations with a vibrant, social atmosphere. Part of Tristan Schukraft’s Tryst Hospitality family of LGBTQ+ venues, Tryst Hotels are in some of the world's most popular LGBT destinations, providing guests with unique experiences, exceptional service, and a commitment to community and sustainability. Each property offers a one-of-a-kind stay where you can experience your best self, even on your worst behavior. Book your tryst in Puerto Vallarta, San Juan, Provincetown, Fire Island, Rio de Janeiro, Chicago and Wilton Manors by visiting trysthotels.com. Follow all the poolside glamour and brunchtime drama by following @trysthotels.

About Tryst Hospitality

Tryst Hospitality, founded by Tristan Schukraft, is redefining LGBTQ+ travel and nightlife. Tryst Hotels is the first luxury gay hotel brand, with properties in premier destinations including Fire Island, Rio de Janeiro, Puerto Vallarta, Provincetown, Wilton Manors, Chicago and San Juan. The company also operates iconic venues such as The Abbey in West Hollywood, The Crown & Anchor in Provincetown, Circo Nightclub in San Juan, and The Blue Whale and Pavilion in Fire Island Pines. Beyond hospitality, Schukraft founded MISTR, a leading telehealth platform providing free online access to PrEP and long-term HIV care. Learn more at trysthospitality.com. 

About NEWLOOK design | build + development

NEWLOOK design | build + development operates as an integrated design-build-development partner, overseeing architecture, construction, and project execution from concept thru completion. Known for inventive, refined, experience-driven environments, NEWLOOK’s portfolio encompasses mixed-use, hospitality and luxury residential and commercial projects throughout the region.

Attachments

• The Tryst Chicago would be a five-story, plus rooftop, 21-room boutique hotel featuring thoughtfully designed public spaces, a new restaurant and nightclub venue, and a rooftop pool.
• Envisioned as a small, high-touch luxury hotel rather than a large-scale development, The Tryst Chicago is designed to feel intimate, design-forward, and deeply connected to the community.

Brian Rosman
Tryst Hotels
323.443.7880
pr@trysthospitality.com

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