By Stirling Kelso
November 19, 2015
Skating in Chicago, where there are bargains to be had on an urban holiday vacation.
Skating in Chicago, where there are bargains to be had on an urban holiday vacation.

If you haven’t made your plans to go over the river and through the woods this holiday season, it’s not too late. With these tips, you might even find some great bargains.


This is a great time to take the family on an urban adventure. “Because most travelers think of resort destinations for the holidays,” says Jon Gray, HomeAway’s chief revenue officer, “prices in cities tend to drop.” In San Francisco, two- and three-bedroom listings (all rated four or five stars by HomeAway users) during Christmas week average $219. Similar places in Chicago go for $293. Even warm-weather cities can be a bargain. Last Christmas, hotels in San Diego averaged $136 a night, 33% less than in the summer, according to Trivago; L.A. hotels cost $185, about 9% less than during the summer.

New Year's Eve in Seattle, where you can find the excitement of New York without the crowds--or the expense.


Want to get away for New Year’s? Skip crowded, ball-dropping New York City (where rooms average $432, according to STR) and try Celebrate San Antonio, a free festival of spicy food, live music, and riverside pyrotechnics. Hotel rooms average $174 a night. In Seattle, the fireworks burst over the Space Needle, and hotels go for $190 a night, according to


To snag a hefty airfare deal, you usually have to book months in advance, but there are ways to save on late bookings too, says Adam Goldstein, co-founder and CEO of Hipmunk. The key: Fly when most people won’t. For instance, don’t go on Dec. 23, when prices are 5% to 6% higher than those on Dec. 24, Goldstein suggests. And flying Dec. 21 (a Monday) can lead to a savings of up to 30%, according to fare predictor Hopper. Traveling on New Year’s Eve or Jan. 1 may save you 25% on what it would cost a few days later.

The Hilton Aruba, where rates are 45% less before Christmas week.
Courtesy of the Hilton


If you’re set on a popular tropical getaway, going between Thanksgiving and Christmas can pay off. Orlando is the most popular Christmas destination for Americans, according to Orbitz, but rooms at the plush Waldorf Astoria Orlando start at $199 from Dec. 8 to 21. The price on Dec. 22: $369. In Aruba, rooms at the 355-room Hilton Aruba start at $199 a night before Dec. 23, 45% less than Christmas-week rates. You’ll find deals between Christmas and New Year’s too: $71 a night on average in Las Vegas, and $89 in New Orleans on

Read next: 6 Hacks for Booking Last-Minute Holiday Travel