Holiday destinations for a festive getaway
Whether you’re seeking seasonal dining or outdoor family fun, these five festive cities offer travelers a memorable winter retreat.
By Alina Dizik | October 19, 2023 (Updated October 9, 2025)
The holiday season is the perfect occasion to explore a new destination. From holiday lights and sleigh rides to world-class monuments and curated cocktails, a festive getaway may be exactly what you need this winter. If you’re craving a seasonal adventure, consider these five cities around the world, each filled with holiday cheer.
Find your holiday stay
Toronto
On the shores of Lake Ontario, Toronto is a buzzing winter destination come holiday time. Start your stay with the annual Cavalcade of Lights, a winter-themed festival, complete with an ice-skating rink, live musical performances, and plenty of holiday lights and activities. Make Hilton Toronto your Canadian home base to be in the heart of the city. Within a short distance of the CN Tower and the Royal Ontario Museum, the hotel has spectacular views and easy access to the city’s most famous landmarks. Traveling with kids? Fort York National Historic Site hosts lots of kid-friendly holiday programming like gingerbread baking demonstrations and more. They’ll also love a visit to Casa Loma, a 98-room Gothic Revival castle full of secret passageways.
St. Louis
St. Louis’ revamped downtown is teeming with live music, local breweries, farm-to-table restaurants, and noteworthy landmarks that have a little extra pizazz during the festive season. Gateway Arch Park gets a holiday-themed makeover, with the Winterfest celebration bringing igloos, s’more-making stations, an ice-skating rink, and more — all under the canopy of 7,000 twinkling lights. While you’re there, explore new heights with a four-minute tram ride to the to the top of the iconic Gateway Arch (the tallest monument in the country) for views of downtown St. Louis, the Mississippi River, and Illinois. Don’t miss a minute of the festivities by spending the night at St. Louis Union Station Hotel, Curio Collection by Hilton, located less than a mile from the heart of downtown.
Denver
With nearly 300 days of annual sunshine, ample fresh air, and stellar mountain views, Denver has year-round appeal but especially come wintertime. Get in the festive spirit with a visit to Denver’s Christkindlmarket, a German-style holiday market complete with traditional mulled wine and handcrafted gifts. If you can brave the cold, the city is covered in gorgeous holiday lights like the Denver Botanic Gardens’ Blossoms of Light display and Chatfield Farms’ Trail of Lights. Colorado also offers some of the best ski resorts in the country, many within a few hours of Denver. Take a day trip to hit the peaks for skiing, snowboarding, or relaxing fireside as you enjoy sweeping views of a winter wonderland.
(Photo © Scott Dressel-Martin)
Mexico City
With more than 9 million people calling Mexico City home, a visit during the holiday season means you’re bound to catch locals celebrating in churches, squares, and neighborhood streets. Get a feel for the city by exploring Zocalo, a central area that includes Mexico City’s main square, where you’ll usually find an ice-skating rink, a manmade hill perfect for “sledding,” and a holiday tree. Throughout the season, you’ll bump into parades and find buildings covered in lights and poinsettias. To stay in the center of all the action, make your homebase the hip Hilton Mexico City Reforma, with its sleek, rooftop infinity pool and city views. The primely located hotel is opposite the historic park, Alameda Central, which gets outfitted with its own festive light display come holiday season.
Chicago
The Windy City takes its winter activities seriously, with multiple ice-skating rinks, seasonal decor, and outdoor markets that serve everything from mulled wine to roasted chestnuts. Start the day by exploring Christkindlmarket, a German-style holiday market with shopping, special events, and family-friendly activities drawing crowds to Daley Plaza. Swap a baseball game for ice skating in the historical Wrigley Field. Once the sun sets, visit downtown Chicago’s Lincoln Park Zoo for a spectacular show at ZooLights. This annual family-friendly attraction is free and features more than one million lights to truly capture the wonder of the season.
(Photo courtesy of Lincoln Park Zoo)
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.
Save up to 25% during The Hilton Sale
Whether you’re craving a cozy city break or the thrill of somewhere new, find the perfect holiday stay in top destinations across the United States, Canada, Mexico, and more. Book November 5 through December 15, 2025.
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