The Cheapest Places to Fly This Winter and Still Have an Amazing Vacation

Only suckers travel during peak season. Here are five great winter vacations you can take for under $350 for a round-trip flight.

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Dec 14 2018, 6:30pm

A fisherman with his haul on Boca Chica beach in the Dominican Republic, at left, and the Walking Man Robot sculpture in Deep Ellum, Dallas, Texas, at right. Photos by Getty Images

Once you’ve unwrapped all the presents and downed all the holiday Champagne, you might feel a little blue during the cold winter months from January to early March. One way to snap out of that post-holiday funk is by taking a trip during one of the cheapest travel times of the year.

“If you're flying from the US in the winter, you're likely to find flights to destinations both domestic and international down by as much as 20 to 30 percent from peak season,” says Liana Corwin, travel expert at Hopper. A round-trip ticket to Portland, Oregon may cost well over $300 on average in during peak travel times, for example, but if you wait until February to visit you can fly for $227 on average, according to travel search site Skyscanner. The same rule applies for international tickets. A $700 round-trip flight to Barcelona in June goes for just $450 in January.

Juanillo Beach Punta Cana DR, photo by Jane-Sweeney / Getty Images
Get out of the cold and onto a warm beach this winter. Flights to the Dominican Republic in the winter are a good deal and you can enjoy places like Juanillo Beach in Punta Cana, pictured above. Photo by Jane Sweeney / Getty Images

Winter travel also means cheaper lodging and a better chance of scoring a free upgrade on your flight or hotel room. What’s more, you’ll spend less time waiting in line and more time seeing the sights sans the selfie stick swarm.

Just don’t make the mistake of booking at the last minute. To get the lowest airfare, Skyscanner’s Allie Cheatam recommends purchasing international flights as early as possible and domestic tickets at least eight weeks prior to departure. If you miss the window, you still might be able to score a deal. “Mid to late January still looks to be one of the cheapest time to book travel,” Cheatam said.

To help you find the best deals, Hopper monitored fares from every US airport to determine the average round-trip cost to the following winter destinations. The five destinations below are not only our favorites, but also offer some of the biggest savings during the coldest months.

Dallas: $139 v. $269 during peak months

Dallas may be insufferable in the summer, but in winter, temperatures hover between 45 and 65 degrees. In addition to warm weather and cowboys, Dallas has a killer arts scene. Home to the country’s largest contiguous arts district, you’ll want to end your arty tour at the Dallas Museum of Art (free admission!). On Fridays and weekends, search out picnic provisions at the open-air Dallas Farmers Market, then dine al fresco at the Main Street Garden Park (10 minute walk). If you arrive during a cold spell, hole up in Adair’s Saloon, where there’s free live music, nightly; happy hour specials; and burgers for under $8.

Boston: $183 v. $329 during peak months

Bully Boy Distillers Estate Gin on the packaging line at the distillery in Boston. Photo by Boston Globe / Getty Images
Bully Boy Distillers' Estate Gin on the packaging line at the distillery in Boston. Photo by Boston Globe / Getty Images

There’s no way around it: Winter in Boston is cold. Pack an extra layer and get over it–after all, you’re saving around $140. Fuel up at Santarpio’s Pizza (cash only), then take the T to the King’s Chapel where $7 gets you a tour of the chapel’s crypt and a lesson in 18th century burial traditions. If all else fails, an afternoon of $9 draft cocktails at the Bully Boy Distillers will warm you up. If you like Boston sports (or even Boston sports fans), Celtics tickets start at $40.

Santa Ana, Orange County: $209 v. $302 during peak months

Beachfront homes on Balboa Island, Orange County. Photo by Richard Cummins / Getty
Beachfront homes on Balboa Island, Orange County. Photo by Richard Cummins / Getty Images

It might not be peak season, but you can still get a taste of The O.C. lifestyle (without Summer Roberts’ allowance) once your flight lands at John Wayne Airport. Check out the tide pools at Crystal Cove State Park and hike the three-mile El Moro Canyon trail, then wash it all down with a malt from the iconic Ruby’s Shake Shack. If you’ve got an extra $26 bucks, book the whale-watching cruise from Newport Beach to glimpse the seasonal grey whale migration, then board the ferry to Picante Martin’s on Balboa Island for a giant plate of cheap Mexican food.

Santo Domingo, Dominican Republic: $299 v. $575 during peak months

Fisherman in Boca Chica, Dominican Republic. Photo by Maria Bobrova / Getty Images
A fisherman on Boca Chica beach in the Dominican Republic shows off his catch. Photo by Maria Bobrova / Getty Images

The capital city of the DR is one of the Caribbean’s most historic cities, but we’re guessing you’re going for the beach. Boca Chica is 13 minutes from the airport and has accomodations for well under $50 a night (an extra $20 gets you this beachfront spot). If you’re looking to avoid spring breakers, keep heading east and you’ll reach Guayacanes, a quiet beach town 25-minutes from the airport. Nosh on tostones (twice-fried plantains) at Salitre and bring friends so you can book this airy 4-person house on the beach.

Rome: $340 v. $1,112 during peak months

Dusk on the Tiber River in Rome. Photo by Getty Images / Roberto Moiola Sysaworld

Dusk on the Tiber River in Rome. Photo by Roberto Moiola / Sysaworld / Getty Images

Rome an ancient city heavy on culture. You can walk through the Forum, the heart of the ancient Roman empire; stuff your face with lamb, pasta, and artichoke (the latter comes in season in January); and peer up at Michelangelo’s work in the Sistine Chapel.

If the weather’s right, download the oBike app and explore via city bike. Hustle to the Colosseum (get there by 8:15 a.m. to avoid a line) before cruising north to the Trevi Fountain. Reward yourself with a panna cotta gelato from Melograno across from the fountain. If you don’t have a SIM card or international data, oBike will be impossible, so book a bike rental from Rome for You ($10 for 4 hours).

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