The Gwen Hotel's fifth-floor terrace has ditched quiet hotel-bar vibes for full holiday spectacle, turning into a pop-up that marries an iceless curling rink with twinkle lights, fire pits, and strong seasonal cocktails. Guests can reserve an hour on the synthetic lanes, sip boozy hot chocolate or mulled wine, and take in skyline views above the Magnificent Mile while they play. It is very much designed for those "do it for the photo" winter nights out.
FOX 32 Chicago's "Tasting Chicago" spotlighted the setup on Dec. 12, giving viewers a look at the terrace in motion. As shown on FOX 32 Chicago, the segment walks through the curling action, the holiday-heavy decor, and the signature winter drinks, and notes how the hotel is leaning into festive programming to keep the rooftop buzzing through the colder months.
The hotel is branding the whole thing "Gwen's Winter Curl & Chill," billing it as curling sessions followed by "boozy hot chocolate, spiced mulled wine, and handcrafted signature cocktails," according to the venue's event details. The rooftop program layers in a rotating menu of seasonal small plates and plenty of heat lamps so guests can stay parked on the terrace instead of retreating indoors. As outlined by Upstairs at The Gwen, the goal is a mashup of game night and après-ski bar, only with Chicago's skyline standing in for mountain peaks.
Reservations are highly recommended for curling. OpenTable lists Gwen's Winter Curl & Chill as running Nov. 22, 2025, through March 8, 2026, with a $25 per person admission that covers one hour on the iceless rink, a firepit table and a seasonal treat. That fee does not include food or drinks, which are all ordered à la carte. Weekend and peak holiday slots tend to disappear quickly.
What To Expect
The curling surface is synthetic, designed to mimic the sweep-and-slide feel without actual ice, and staff surround the area with heat lamps and fire pits so players and onlookers are not shivering between shots. The rooftop is strung with twinkle lights, framed with photo-friendly backdrops, and anchored by a bar program built around warming cocktails overseen by the hotel's culinary team. Gwen's site notes that each curling booking includes access to a dedicated firepit table for the full length of the session.
Practical Info & Booking
The experience is one of several winter rooftop setups promoted around the city, and the official tourism site groups The Gwen with other heated terraces and holiday pop-ups. Choose Chicago advises booking early for winter rooftop programs, especially around major holidays and weekends. To lock in a specific time on the rink, guests can reserve through the hotel's reservation tools or via OpenTable.
Where It Fits In Chicago’s Holiday Scene
The Gwen's curling-and-cocktails concept slots neatly into the wave of immersive holiday bars and themed rooftops that have taken over Chicago's winter calendar in recent years. In its seasonal roundup, Time Out Chicago highlights similar pop-ups that lean into bold decor, over-the-top themes and plenty of social media moments. The Gwen's version keeps the festive energy but skews a bit more polished, offering an activity-forward night out that still feels upscale.
Because slots tighten up during the core holiday stretch, anyone set on curling with a skyline backdrop should plan ahead. Reservations and current availability are listed on OpenTable, which confirms the hour-long session format and the per-person fee. Expect to cover the session charge plus whatever food and drinks you decide to tack on at the rooftop bar.
