Foolproof Tips for Winter Trips

By Wendy Perrin
11/19/2014 8:23:49 AM

Winter can be a tricky time to travel, what with holidays that bring insane fares, traffic-snarling snowstorms, and overhead bins stuffed fuller than a Christmas goose. But this winter is looking to be trickier than usual. Flights are fewer-which means deals will be tougher to find, planes will be full, and, should bad weather cause your flight to be canceled, it will be harder than ever to find seats on another plane. At the same time, pockets of value have cropped up in unexpected places, and new digital tools offer better solutions to age-old problems. Here's how I'm planning to skate through winter:

Credit: CN Traveler

1. Snag the deals

Sneak away between Thanksgiving and Christmas.

December 3 through December 16 will be the best window for bargains at warm- weather resorts, which are relatively empty between the holidays. Think Arizona, the Caribbean, Florida, Hawaii, or Mexico. For early-season ski deals, look to the Canadian Rockies, which has relatively good snow in early December, or to places with world-class snowmaking, such as Vail.

Book Presidents' Day weekend, which is also Valentine's day weekend, in early December.

"Airlines won't start to lower their January and February 2014 fares until late November," says airfare expert Rick Seaney, founder of, "so the perfect time to shop for Presidents' Day week- end airfares will be the first couple of weeks in December."

Escape to the sun in mid-January.

Unless you're going to a popular ski destination such as Aspen or Vail, "the cheapest time of year to fly within the Northern Hemisphere is the last three weeks of January and the first two weeks of February," says Seaney. Most airfares are 45 percent cheaper than peak summer rates. Go to Hawaii or Australia in late January and you'll pay well under half what you'd pay at Christmas."

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2. Ace the holidays

Hone your airfare searches.

The least expensive times to fly during the Christmas/New Year's window are, of course, Christmas Day and New Year's Day, as well as late afternoon and evening on Christmas Eve and New Year's Eve. Other dates for low fares differ from city to city, depending on when school lets out, and can vary wildly, from $1,000 one day to $400 the next. It can be tough to determine which days have the lowest fares to and from your destination, so do a one-way airfare search rather than a round-trip search. In other words, if you're trying to determine whether it's least expensive to fly on December 20, 21, or 22, a one-way search for each of those dates will tell you.

Try alternate airports.

If you can't find affordable fares to your Florida destination-say, Miami or Orlando-look at flights into Tampa or Fort Lauderdale, which are much less expensive over Christmas/New Year's. As for California, consider flying into Los Angeles-an almost always affordable hub-and driving to San Diego.

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