Tryst Hospitality, a leader in luxury LGBTQ+ travel and nightlife, is bringing a new boutique gay hotel to Chicago’s historic Northalsted neighborhood. The proposed property, The Tryst Chicago, promises to combine high-end design, community focus, and a lively nightlife hub in the heart of the city’s iconic queer village.
Community-Focused Planning
Tryst Hospitality has filed initial plans with the City of Chicago and is launching a series of community discussions as part of the planning and zoning process. Meetings are scheduled with local organizations including the Northalsted Planning and Zoning Council, Northalsted Business Alliance, East Lakeview Neighbors, and a public Zoom session with Alderman Jason Lawson. Community feedback will play a key role in shaping the project, which remains in its early stages.
“Northalsted is one of the most vibrant queer neighborhoods in the world,” said Tristan Schukraft, founder and CEO of Tryst Hospitality. “It deserves a hotel that feels as alive as the community itself. We want this to be a place locals embrace and travelers can’t wait to experience: a hub for culture, nightlife, and connection.”
A Rooftop View of Luxury
The Tryst Chicago is proposed for 3350–3352 North Halsted Street, the former home of DS Tequila, which Tristan acquired in 2024. The five-story property will feature 21 boutique rooms, public spaces designed for gathering, a restaurant and nightclub, and a rooftop pool.
The rooftop pool and bar will be fully enclosed, offering year-round use while minimizing noise for neighbors. Other design considerations include improved alley circulation and a scaled architectural footprint that complements the streetscape without obstructing views.
Mindful, Intimate Luxury
Unlike large-scale hotels, The Tryst Chicago is envisioned as an intimate, design-forward boutique property. Sustainability and community impact are central: the hotel plans to eliminate single-use plastics, provide refillable water stations, and partner with local LGBTQ+ nonprofits and minority-owned businesses. Chicago-based NEWLOOK Design | Build + Development is leading the architecture and design.
Tryst Hospitality emphasizes accessibility in its approach to luxury. For comparison, room rates at The Tryst Puerto Vallarta start in the low $200s. “True luxury isn’t just about high thread counts or flashy pools,” Schukraft said. “It’s about being yourself and waking up surrounded by a community that welcomes you.”
Expanding a Global LGBTQ+ Vision
The Tryst brand has established properties in queer destinations around the globe, including Puerto Vallarta, Fire Island, Rio de Janeiro, Wilton Manors, Provincetown, and San Juan. With The Tryst Chicago, the company aims to bring the same community-driven approach to one of the Midwest’s most celebrated queer neighborhoods.
As planning continues, Tryst Hospitality will maintain communication with community leaders and neighbors, sharing updated renderings, timelines, and design refinements. Early previews and project updates are available via @trysthotels on social media.
For those ready to experience a Tryst property today, reservations can be made at trysthotels.com.
