Hotels with the best indoor rooftops for a winter proposal
With skyline views and signature cocktails, explore some of the country’s best indoor rooftops for planning a winter marriage proposal.
By Alina Dizik | November 13, 2025
Popping the question calls for a stunning backdrop, so set the stage for the ultimate winter proposal at a hotel with an indoor rooftop offering panoramic city views. Add celebratory dining and craft cocktails before retreating to a plush suite or spacious room to cap off an unforgettable night. With high-end amenities, ideal locations, and a bird’s-eye-view of some of the best skylines across the U.S., consider these indoor rooftops for bending down on one knee.
San Francisco
Toast to your big moment at Cityscape Sky Bar, the tallest indoor rooftop bar in San Francisco, with views over the city skyline and bay. Sitting atop Hilton San Francisco Union Square, Cityscape Sky Bar is the perfect place to grab a table before dusk as sunset views set the mood. Artisanal charcuterie boards and cocktails, like the Moonlight Margarita, are sure to impress during this rooftop proposal. Afterward, settle in for the night at the elegant 46-story hotel that’s just two blocks from Union Square, a hub for entertainment, shopping, and dining. The next day, stop by Poached, the hotel’s decadent breakfast buffet, and relax by the heated outdoor pool and whirlpool. Later, check out a show at Curran Theater or explore the exhibits at SFMOMA, the city’s contemporary art museum, which are both located within walking distance.
New York
Looking for a chic way to celebrate your love? Consider Highball, a tucked-away cocktail bar and lounge perched high above the buzz of Times Square. Located in Tempo by Hilton Times Square, cocktails like Hasta La Matcha, a green tea infused tequila concoction, are a favorite for both locals and visitors. Once you’ve asked the big question, spend the weekend celebrating at the hotel, which features amenities like a 24-hour fitness center, shared spaces for socializing, and modern rooms and suites offering city views of the Manhattan skyline with floor-to-ceiling windows. If you and your future spouse have a fur baby, they can come along too, thanks to the pet-friendly accommodations. With world-class museums, Broadway theaters, Central Park, and top dining all within walking distance, it’s the ideal home base for a winter marriage proposal in New York City.
Chicago
A rotating roster of top live DJs, inventive sushi, and plenty of space to enjoy the 27th floor view, make any visit to ROOF on theWit one to remember. Whether you plan for a sunny daytime proposal over lunch, an intimate evening with friends, or want to dance the night away with bottle service after popping the question, ROOF on theWit is the perfect indoor rooftop with dining and cocktails made with the freshest ingredients. Be sure to check out the rest of the amenities at theWit Chicago, a Hilton Hotel, including stylish rooms and suites, a 24-hour fitness center, and a lively theater-inspired lobby. Unwind after the big moment with one of the signature massages offered by Spa@theWit. A central State Street location near the Chicago Riverwalk also means you can easily leave the hotel and go for a romantic stroll to soak up the excitement of your winter marriage proposal.
Alina Dizik
Alina Dizik is a veteran lifestyle journalist, covering travel, real estate, family, work trends, and dining. She lives in Chicago and has previously lived in New York, Europe, and the Middle East. She spends more than two months each year traveling internationally with her husband and two school-age children. Alina has visited more than 50 countries, and her work appears in The Wall Street Journal, BBC, The Cut, The Guardian, and other top publications.
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