Jonesing for a May Vacay? Here's where to go to score the best deals, based on where you live. 

By Marisa Spyker
May 10, 2019
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Some vacations come together after months of meticulous planning, while others are reserved for holidays or family visits. But there’s a special category of precious PTO that we often reserve for something a little more spontaneous.

For us, these bonus getaways often involve two things: cheap plane tickets and water views. Fortunately, Kayak has made it easy to find both, no matter what city you live in. As part of their 2019 Travel Hacker Awards, the travel booking site has unveiled an easy-to-use search tool designed to uncover the best destinations to score an airfare deal, tailored especially to where you live and the month you’d like to travel.

The tool, which looks at both domestic and international cities, offers insight into which hot spots have experienced significant price dips compared to last year—meaning, if you had your heart set on Tampa or San Francisco or Cancun, now might be the optimal time to book that last-minute long weekend trip.

Related: How To Pack for a Weekend Getaway: 

In May, when beach getaways are top of mind for many travelers, the list of summer-kick-off-worthy destinations with potentially cheap airfare is, thankfully, robust. If you hail from the Sunshine State (and can fly out of Orlando, specifically) your best bet for water views at a bargain is a trip up north to Boston, where average roundtrip flights are going for a scant $134, 24 percent less than last year. Internationally, you can kick off your flip flops at an all-inclusive resort in Santo Domingo, Dominican Republic, where flights are 22 percent less than they were last year (for an average cost of $283).

Up north, if New York is your home airport, consider going west, where flights to San Diego are 19 percent cheaper than last year (average flight cost of $264). Alternatively, if you’re out west already, this could (and should) be the month you drop everything and head to Hawaii—flights to Honolulu from L.A. are 23 percent cheaper than they were in May of 2018.

Convinced yet? Search top destinations and price trends from your home airport here. And if you’re thinking of getting away on Memorial Day specifically, consider heeding Kayak’s advice for scoring the best flights for a bargain by traveling from Saturday through Tuesday.