10 Most Affordable Places to Travel in the U.S. This Winter, According to Kayak

Wedged between the holidays and spring’s arrival, January and February often get overlooked—but they might just be the best months for travel. In most destinations across the country, you can expect fewer crowds, a more relaxed pace, and excellent deals on airfare and lodging.

But don’t just take it from us: “Early in the new year—January and February—is a fantastic time to travel to beat the winter blues and score affordable options,” says Sarah Kennedy, Kayak’s travel and trends expert. “The destinations we found to be most affordable offer a little something for everyone: warm weather for the snowbirds, easy access to ski mountains for the adventurers.”

To find where travelers can stretch their dollars the absolute furthest this winter, Kayak analyzed flight and hotel searches made between March 15 and Sept. 15, 2025, for trips departing and checking in between Jan. 2 and Feb. 28, 2026. The results reveal U.S. destinations that deliver big on experience without breaking the bank—most with combined flight and hotel costs under $500.

Chicago, Illinois

View of the Chicago metro.

Christopher Larson/Travel + Leisure

Combined flight and hotel cost: $426

Embrace the cold weather in the Windy City: Winter travelers will enjoy fewer crowds and easier reservations at popular restaurants and attractions—just be sure to bundle up, as Chicago’s famous chill is part of its charm. For a culture-fueled getaway, go museum-hopping through world-class organizations like the Art Institute of Chicago, the Field Museum, and the Griffin Museum of Science and Industry. Alternatively, lace up your skates at Millennium Park, Maggie Daley Park, or Navy Pier, go sledding at Soldier Field, and try your hand at curling on the rooftop of The Gwen Hotel. For a warm reprieve, snag a table at the oh-so-cozy Armitage Alehouse, where you’ll find crackling fireplaces and hearty British-inspired fare.

Minneapolis, Minnesota

The Minnesota State Capitol surrounded by snow.

Chris Bacarella/Travel + Leisure

Combined flight and hotel cost: $435

This Midwestern city has so much to offer—from world-class arts and dining to its famously friendly locals—and while winter here may not be for the faint of heart, it’s part of what makes Minneapolis magical. Stroll through the Minneapolis Institute of Art or the Walker Art Center, shop the Mall of America, or explore the scenic trails around the Chain of Lakes by snowshoe or cross-country ski. Cheers to a fun-filled winter trip with a craft brew at Surly Brewing Co. or Indeed Brewing, and dig into the city’s famed “Juicy Lucy” (an ooey-gooey cheese-stuffed burger, not to be confused with a typical cheeseburger) at Matt’s Bar or The 5-8 Club.

Washington, D.C.

A snowy dawn at the U.S. Capitol in Washington D.C.

John Baggaley/Getty Images

Combined flight and hotel cost: $445

In winter, D.C. trades its usual bustle for a quieter kind of charm. The museums are easier to wander (read: way less crowded), the marble monuments glow against a pale sky and fresh blanket of snow, and the National Gallery of Art’s Sculpture Garden transforms into one of the city’s most scenic skating spots. Duck into one of the Smithsonian museums to warm up between strolls along the National Mall, or cozy up with a piping-hot cup of coffee at Baked & Wired. For something heartier, slurp a steaming bowl of ramen at Daikaya before heading back out into the refreshing night air.

Boston, Massachusetts

View of the Boston skyline.

Yale Goodman/Travel + Leisure

Combined flight and hotel cost: $464

Boston in winter feels like stepping into a real-life snow globe, with its powder-dusted cobblestone streets and glistening frozen harbor. Defrost inside one of the art-filled halls at the Museum of Fine Arts and Isabella Stewart Gardner Museum, or pack a jacket, hat, and scarf and wander through Snowport, where you can sip cocoa, shop artisan goods, and savor the season. Then, slip into Neptune Oyster and chase a bit of summer with lobster rolls and a crisp glass of white, or lean into the season with mulled wine at La Famiglia Giorgio’s Ristorante.

Baltimore, Maryland

Aerial view of the Washington Monument in Baltimore.

Greg Pease/Getty Images

Combined flight and hotel cost: $471

Trade the summer crowds for a serene escape in Baltimore this winter, when the city’s historic waterfront takes on a glow all its own. Winter on the Waterfront brings a festive energy with ice skating, pop-up markets, and seasonal lights that twinkle across the harbor. Take advantage of the off-season lull and explore Baltimore’s best museums unhurriedly, from The Walters Art Museum to the American Visionary Art Museum. Best of all, winter also marks peak oyster season, when the Chesapeake’s cold waters yield their sweetest, briniest catch. Enjoy the bounty at Thames Street Oyster House or linger over other local staples like hot crab soup and golden crab cakes as snow flurries drift past the harbor.

New York, New York

Aerial view of the New York City skyline.

Don Eim/Travel + Leisure

Combined flight and hotel cost: $491

The Big Apple feels unexpectedly laidback when the holiday crowds have disappeared and spring visitors haven’t yet arrived. And while it’s true that the city never sleeps, winter slows its rhythm just enough for travelers looking to experience a quieter side of the five boroughs. The Bank of America Winter Village at Bryant Park keeps the season lively with ice skating, open-air bars, and pop-up shops tucked beneath a skyline that seems even more defined in the cold. Wander through MoMA or The Met without the usual lines, snag tickets to a Broadway show or two for lower prices, and settle in for indulgent afternoon tea—and perhaps a bottle of bubbly— at top spots like The Plaza or The Whitby Hotel.

Raleigh, North Carolina

A mural in downtown Raleigh.

Stephanie Pollak/Travel + Leisure

Combined flight and hotel cost: $523

In Raleigh, winter means brisk mornings and clear, sunny afternoons. Take advantage of the mild temps and wander through the oak-lined streets downtown, browse local art at CAM Raleigh or the North Carolina Museum of Art, and sample inventive Southern cooking at Poole’s Diner. As night falls, grab a seat at one of the city’s cozy craft breweries or rooftop spots like Urban Oak or The Willard, and watch the sunset stretch across the skyline.

Tampa, Florida

Water Street in downtown Tampa.

Michela Sieman/Travel + Leisure

Combined flight and hotel cost: $533

Trade the snow for sand and sun with a trip to Tampa, where you’ll be within easy driving distance to some of the Sunshine State’s best beaches, including Clearwater and St. Petersburg. In Tampa proper, stroll the 2.6-mile-long Riverwalk, where Winter Village at Curtis Hixon Park brings skating and pop-up shops to the waterfront. Just steps away lies the Tampa Museum of Art, which showcases contemporary and classical works in a striking glass-and-steel building along the river.