San Juan, Puerto Rico
When a bunch of new flights are added to a destination, you're more likely to score a deal on short notice, says Jessica Casano-Antonellis of Kayak.com.
Last year JetBlue opened a new terminal in San Juan and added more direct flights from its D.C. hub. There are about three times the number of flights from New York City to San Juan as there are to Jamaica; recently you could find a New York City to San Juan fare in mid-March for $281 vs. a flight to Jamaica for $411.
Why go: San Juan has options for culture and nature lovers alike. Visit the colorful buildings of Old San Juan, soak up the rays on Isla Verde beach, or explore the El Yunque rain forest an hour out of the city (be sure to stop by the food stalls at Luquillo for authentic local cuisine).
Want a side trip? Hop a flight to St. Croix via Jet-Blue's partnership with Cape Air for just $59.
Sample deal: The city has a range of lodging, and it's not tough to find discounts, says Travelzoo's Saglie. The Sheraton Old San Juan Hotel & Casino has rooms for $140 a night in April, vs. an average of $154 for hotels in all of San Juan.
If you know when to go, you can visit four great towns without paying sky-high prices.
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