Winter is a popular time of year for travel. Some travelers are looking to escape the cold, while others are planning ski trips, holiday getaways, or a few days exploring somewhere new.
And if you’re hoping to use points and miles, you’re probably already searching for flights. At least that’s what the data shows.
We looked at PointsYeah search data to see which short-haul international destinations travelers were searching for most from U.S. airports for winter 2026–2027. The results include plenty of familiar beach destinations, but also a few cities that might surprise you.
From Mexico and the Caribbean to Canada and South America, here’s what makes each destination worth considering for a winter getaway.
Cancún, Mexico (CUN)
It’s not hard to see why Cancún is a popular winter destination. Warm weather, beaches, and tons of resorts make it an appealing escape when temperatures drop across much of the U.S.
Or, for much of the year, actually.
Winter also falls during the region’s relatively dry season. Beyond the Hotel Zone, travelers can explore Isla Mujeres, visit Mayan archaeological sites, or head south toward Playa del Carmen and the Riviera Maya.
Cancún is served by a wide range of U.S. airlines, including American, Delta, United, Southwest, and JetBlue.
If you’d rather spend your winter vacation exploring a city than sitting on a beach, Mexico City is another top option.
The Mexican capital has an amazing food scene, world-class museums, and historic architecture. Neighborhoods like Roma Norte and Condesa are packed with restaurants and cafés. Winter brings mild afternoons, cooler evenings, and relatively little rain.
Mexico City also has extensive air connections with the U.S., including service from Aeromexico and several major U.S. carriers.
Aruba has long been a favorite for travelers looking for reliable sunshine, and winter is an especially popular time to visit.
Eagle Beach and Palm Beach are among its biggest attractions, but there’s more to do than sit by the water, such as visiting Arikok National Park or exploring the island’s hiking trails.
Aruba has nonstop flights from several major U.S. airports, particularly along the East Coast. And because the airport offers U.S. preclearance, you can complete immigration formalities before boarding your flight home.
For travelers who want to get away without planning every detail of their trip, Punta Cana should be top of mind.
The region is known for its all-inclusive resorts, many of which bundle accommodations, meals, drinks, and activities into a single price (or award booking, in some cases).
Punta Cana International Airport sees flights from numerous U.S. gateways, so there’s a good chance you can fly your preferred airline to PUJ.
Not everyone wants to escape winter. Vancouver is a great option for travelers who’d rather embrace it.
The city combines excellent restaurants, waterfront neighborhoods, and easy access to the mountains. Grouse Mountain and Cypress Mountain are nearby, and Whistler Blackcomb is roughly two hours away by car. Just don’t expect snow everywhere, as Vancouver’s winters are often rainy at sea level.
Vancouver International Airport is well connected to the U.S., particularly through West Coast gateways and major airline hubs.
Los Cabos offers a different kind of Mexican beach vacation, with desert landscapes, dramatic coastlines, and luxury resorts at the southern tip of Baja California.
Cabo San Lucas is known for its marina and nightlife, while San José del Cabo has a quieter atmosphere, art galleries, and restaurants. Winter is also whale-watching season, with humpback and gray whales migrating through the surrounding waters during this time of year.
Los Cabos International Airport has nonstop service from numerous U.S. cities, particularly in the western half of the country.
Guatemala offers something a little different from the beach destinations on this list.
Many travelers arriving in Guatemala City continue to Antigua, a colonial city surrounded by volcanoes, or head to Lake Atitlán for mountain scenery and lakeside villages. Winter coincides with Guatemala’s dry season, so it’s a great time for hiking and outdoor activities.
La Aurora International Airport has nonstop connections with several U.S. airports. Antigua is generally about an hour or more away by road, depending on traffic.
Punta Cana may attract much of the Dominican Republic’s resort traffic, but Santo Domingo offers a different experience.
The country’s capital is home to a UNESCO-listed Colonial Zone, with centuries-old architecture, lively public squares, restaurants, and museums. And while it isn’t primarily a beach destination, there are coastal areas within driving distance.
Winter brings warm weather and generally less rainfall, while Las Américas International Airport has nonstop flights from several U.S. cities, particularly in Florida and the Northeast.
While much of the U.S. is bundled up for winter, Lima is enjoying summer, with warmer temperatures and more sunshine from December through March.
Peru’s capital is especially appealing for food lovers, with internationally recognized restaurants and neighborhoods like Miraflores and Barranco where you’ll find cafés, galleries, and Pacific Ocean views. Lima can also be a starting point for exploring the rest of Peru, although the Andes experience their rainy season during these months.
Jorge Chávez International Airport has nonstop flights from several major U.S. gateways, including Miami, Atlanta, Houston, and New York.
Grand Cayman rounds out the list with another warm-weather Caribbean getaway.
Seven Mile Beach is the island’s best-known attraction. There, you’ll find clear water, white sand, and plenty of resorts and restaurants. Visitors can also snorkel, dive, visit Stingray City, or explore quieter parts of the island.
Winter brings warm temperatures and generally drier conditions. Owen Roberts International Airport has nonstop flights from several U.S. gateways, making Grand Cayman particularly convenient for travelers departing from the eastern half of the country.
These 10 destinations were among the most searched international destinations from U.S. airports on PointsYeah for winter 2026–2027.
Search interest doesn’t necessarily mean award seats will be available on every date or from every airport. But it does offer a look at where travelers are hoping to put their points and miles to work this winter.
If one of these destinations is on your list, you can use PointsYeah to view award flights across airlines and loyalty programs, search flexible dates, and see what options are available from your preferred departure airport.
Flight Search
Hotel Search
Winter travel dates around Christmas, New Year’s, and school holidays can be especially competitive. Searching as early as possible and checking a range of dates can help you find more options.
It’s also worth considering nearby departure airports, even if that means booking a separate positioning flight to reach your international departure point.
