After 14 years as a Market Days and Pride staple, the former D.S. Tequila corner on Halsted is being lined up for a very different kind of late night. Plans are in motion for The Tryst Chicago, a five-story, 21-room boutique hotel aimed at LGBTQ+ travelers, complete with a restaurant, indoor nightclub venue and enclosed rooftop pool. If it goes through, it would tuck overnight lodging directly into the Boystown nightlife strip, a move that is still pretty rare on North Halsted.
In a news release on GlobeNewswire, Tryst Hospitality said the project would occupy 3350–3352 N. Halsted St. The Tryst Chicago is pitched as an intimate, design-forward property, with 21 guest rooms spread across five stories plus a rooftop pool, restaurant and nightclub venue. The company says it already owns the site and released early renderings, along with a promise to bring neighbors into the conversation as the proposal advances.
Tristan Schukraft, founder and CEO of Tryst Hospitality, wants the hotel to change how visitors use the neighborhood. It should “give people a reason to stay in the neighborhood, not just pass through it,” he told CBS Chicago. According to CBS, Tryst has submitted plans to the city and already started community meetings, including a public Zoom session with Ald. Bennett Lawson and local residents. City filings, CBS reports, show the new building fitted between Roscoe’s Tavern and adjacent storefronts.
The company has also said it plans to prioritize eco-conscious practices and partnerships with local LGBTQ+ organizations and minority-owned businesses, FOX 32 Chicago reports. FOX 32 also notes the project is in early planning and zoning stages, so the height, layout and mix of uses could still shift as neighbors and city officials weigh in.
Tryst’s growing footprint
Tryst Hotels bills itself as a luxury, queer-focused boutique brand and lists Chicago among several “coming soon” destinations on its website, alongside new properties in Puerto Vallarta and San Juan, according to Tryst Hotels. The company has been expanding into well-known LGBTQ+ markets and ties its hospitality work to nightlife programming and community partnerships, per Tryst’s own materials. In other words, the hotel is meant to feel less like a generic chain outpost and more like an extension of the neighborhood’s existing scene.
What stands on Halsted now
D.S. Tequila Co., which held down the Halsted address for 14 years, closed in November 2023. The building historically included apartments above the restaurant, and longtime regulars considered the spot a fixture of Market Days and Pride celebrations. For many, seeing its two-story facade come down for a hotel would mark a noticeable shift in how that stretch of Halsted looks and feels.
Renderings and neighboring proposals
Renderings released with Tryst’s announcement depict a new five-story structure replacing the current two-story storefront and the small single-story addition behind it, a change that would require demolition, CBS Chicago reports. CBS also notes that Tryst’s proposal is one of two hotel projects moving through the Northalsted corridor. The Backbeat Hotel is planned a few blocks to the south and aims to open in the coming years, adding even more rooms to the area if both projects clear city review.
Neighbors and next steps
Tryst Hospitality says it will keep meeting with neighbors as the plan winds its way through Chicago’s planning and zoning process, giving residents and community leaders multiple chances to review designs and raise concerns, according to FOX 32 Chicago. The company has not floated a target opening date. How fast things move will come down to city approvals, any design revisions that emerge from community feedback and the usual realities of construction scheduling. More public meetings are expected in the coming months as new filings land at City Hall.
Why it matters
Dropping a hotel onto Halsted could turn some event crowds from one-night bar crawlers into multi-night guests, which in turn could boost restaurants, shops and late-night venues during big weekends like Pride and Market Days, as well as on slower, off-season nights. For Tryst, and for neighborhood advocates watching closely, the pitch is that a resident hotel can deepen Northalsted’s cultural and economic life while anchoring nightlife in a single, locally engaged operator, according to Tryst Hotels. Whether the final design lives up to that promise will be decided in community rooms, zoning hearings and, eventually, by the guests who check in.
