Chicago Joins New York Orlando Phoenix Las Vegas San Diego and More as Must-Visit US Destinations for Road Trippers This Holiday Season

Published on December 9, 2025

Chicago is now alongside New York, Orlando, Phoenix, Las Vegas, San Diego, and other top U.S. cities as a must-visit stop for road trippers this holiday season. The city’s iconic winter charm, vibrant holiday festivities, and world-renowned attractions make it a perfect destination for travelers seeking a mix of culture, cuisine, and seasonal magic. From the festive lights on the Magnificent Mile to ice skating at Millennium Park and indulging in the city’s renowned dining scene, Chicago offers an unforgettable holiday experience. With its central location and a wide range of accommodations, Chicago is an essential stop on any holiday road trip.

Hilton’s 2026 Trends Report reveals that 71% of travelers are planning to embark on road trips for their next vacation, fueling growing interest in U.S. destinations. A review of Hilton’s search data for stays between December 21, 2025, and January 4, 2026, highlights some of the top spots road trippers are eyeing this holiday season.

Top Trending Holiday Season Destinations in the U.S.

1. New York City
   Where to Stay: Tempo by Hilton New York Times Square offers the perfect spot to celebrate the New Year in style. Guests can enjoy exclusive access to a private viewing area for the iconic Times Square Ball Drop, paired with gourmet bites, top-shelf cocktails, and a live DJ. It’s a premier way to ring in 2026 in the heart of the city.
2. Orlando, Florida
   Where to Stay: Hilton Orlando transforms the holiday experience with its Hot Chocolate Bomb Bar, a whimsical mobile cart offering customizable treats. With a lazy river, tropical pools, and easy access to world-famous theme parks, this vibrant resort is a family-friendly holiday haven that turns traditions into lasting memories.
3. Phoenix, Arizona
   Where to Stay: Embassy Suites by Hilton Phoenix Biltmore offers a warm desert retreat perfect for the holidays. The spacious two-room suites are located in the city’s upscale shopping and dining district. Guests can enjoy festive breakfasts and evening receptions, along with easy access to Arizona Biltmore and Camelback Mountain.
4. Las Vegas, Nevada
   Where to Stay: Waldorf Astoria Las Vegas offers a sophisticated escape above the glittering Strip. With luxurious rooms, a world-class spa, and Michelin-star dining, this oasis of calm provides an elevated holiday experience. It’s the ideal destination for those seeking glamour and relaxation amid the excitement of Las Vegas.
5. Chicago, Illinois
   Where to Stay: Hilton Chicago provides a nostalgic Midwestern road trip stopover. Guests can reserve “The Kevin” experience, which includes a whole cheese pizza, an ADA-approved toothbrush, and ice cream delivery. Overlooking Grant Park and Lake Michigan, this iconic hotel combines comfort and classic charm.
6. San Diego, California
   Where to Stay: Hotel del Coronado, Curio Collection by Hilton, offers a legendary beachfront resort experience. From its iconic red turrets to its dazzling holiday lights and beachfront ice rink, The Del transforms into a coastal winter wonderland, bringing festive magic to the Pacific coast.
7. Anaheim, California
   Where to Stay: Hampton Inn & Suites Anaheim Resort Convention Center provides comfort and convenience for road trippers. Offering spacious rooms and complimentary hot breakfast, this family-friendly hotel ensures that travelers are refueled and ready to enjoy the holiday magic of Southern California.
8. Los Angeles, California
   Where to Stay: Conrad Los Angeles offers modern luxury in the heart of downtown. Guests can indulge in festive dining at restaurants from Chef José Andrés, relax at the rooftop pool with city views, and celebrate the season surrounded by art, culture, and sophistication.
9. Fort Lauderdale, Florida
   Where to Stay: Beach House Fort Lauderdale, a Hilton Resort, provides a beachfront retreat with ocean-view suites and full kitchens. Guests can unwind on the wraparound pool deck, enjoy festive seaside dining, and relax in upgraded suites with additional space—all amid tropical holiday décor and the sounds of the Atlantic.

Chicago joins New York, Orlando, Phoenix, Las Vegas, San Diego, and more as a must-visit destination this holiday season, offering a unique blend of festive charm, iconic attractions, and unforgettable experiences for road trippers.

These top trending destinations reflect a blend of classic holiday charm, festive events, and unique experiences, making them the perfect stops for travelers hitting the road this holiday season. Whether you’re looking to celebrate New Year’s in the heart of Times Square or unwind by the Pacific Ocean, these Hilton properties are set to provide unforgettable memories for road trippers across the U.S.