Cheap Flights to Caribbean

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Flight deals we found

These prices are lower than our typical predictions for similar flights.
65% less than typical
US$389
Roundtrip per traveler
Sunday, 19 May - Sunday, 26 May
UnitedUnited
6h 29m
6:00am
12:29pm
CMH
1 stop • 1h 12m in IAD
SJU
Found 7 hours ago
65% less than typical
US$381
Roundtrip per traveler
Thursday, 16 May - Thursday, 23 May
American AirlinesAmerican Airlines
8h 30m
8:35am
5:05pm
CMH
1 stop • 3h 18m in CLT
SJU
Found 16 hours ago
55% less than typical
US$338
Roundtrip per traveler
Saturday, 25 May - Thursday, 30 May
UnitedUnited
11h 2m
10:22am
9:24pm
CMH
1 stop • 5h 45m in IAD
SJU
Found 3 hours ago
60% less than typical
US$385
Roundtrip per traveler
Saturday, 27 Jul - Wednesday, 31 Jul
DeltaDelta
9h 49m
6:00am
3:49pm
CMH
1 stop • 4h 50m in ATL
PUJ
Found 19 hours ago
40% less than typical
US$723
Roundtrip per traveler
Friday, 24 May - Monday, 27 May
American AirlinesAmerican Airlines
6h 25m
6:00am
12:25pm
CMH
1 stop • 59m in PHL
PUJ
Found 4 hours ago
65% less than typical
US$305
Roundtrip per traveler
Monday, 2 Sep - Thursday, 5 Sep
American AirlinesAmerican Airlines
8h 40m
8:15am
3:55pm
CMH
1 stop • 4h 11m in CLT
MBJ
Found 19 hours ago
60% less than typical
US$333
Roundtrip per traveler
Wednesday, 14 Aug - Sunday, 18 Aug
UnitedUnited
7h 40m
6:45am
1:25pm
CMH
1 stop • 1h 36m in IAH
MBJ
Found 4 hours ago
60% less than typical
US$339
Roundtrip per traveler
Monday, 1 Jul - Monday, 15 Jul
UnitedUnited
8h 10m
6:00am
1:10pm
CMH
1 stop • 2h 23m in EWR
MBJ
Found 12 hours ago
70% less than typical
US$362
Roundtrip per traveler
Thursday, 29 Aug - Friday, 20 Sep
DeltaDelta
30h
7:00am
1:00pm
+1
CMH
1 stop • 23h 2m in JFK
AUA
Found 2 hours ago

Featured airlines

Featured Airlines: American Airlines, United Airlines, Delta, Spirit, JetBlue, Frontier, Air India, Hawaiian Airlines and Qatar Airways

Top Cities to Visit in Caribbean

Are last-minute flights to the Caribbean cheaper?

Yes. Booking your plane tickets to the Caribbean at the last minute could save you some cash, but it's important to remain flexible. Researching different routes, travel dates, airlines and fare types can help you score a cheap ticket. It's also a good idea to set up a price alert for your preferred route so you can snap up a great deal when you see one.

What are the most popular months to visit the Caribbean?

December through April is often regarded as the best time to visit the Caribbean. It's when temperatures are mild, rainfall is minimal and humidity is at its lowest. This is the region's tourism peak season, meaning airfares are generally higher. Travelers tend to avoid the months of June to November, which is the hurricane season. But you'll still find places that are rarely affected by this, including Aruba, Barbados, Curaçao and Trinidad and Tobago. If you want to avoid the crowds and land bargain Caribbean flight deals, try the shoulder seasons of May to June and November to December. A combination of fewer tourists and great weather promises an idyllic Caribbean getaway.

Which airlines fly to the Caribbean?

This exciting vacation destination is served by a number of leading airlines. American Airlines, JetBlue Airways and United Airlines are among the more popular carriers that will get you from the United States to your island paradise. Enter your departure dates and destination into Expedia to see a complete list of airlines offering affordable tickets around the region.

What are some of the best places to visit in the Caribbean?

Whether you want to kick back on white sand beaches, try watersports in crystalline waters, tour historic monuments or dance to the rhythms of calypso, the Caribbean has an adventure for everyone. Delve into the region's fascinating past at places like the UNESCO-listed Old San Juan, Puerto Rico and the Dutch town of Willemstad in Curaçao. Or, take the plunge at Dunn's River Falls, Jamaica and Stingray City, Cayman Islands. With an aquarium, casino, private beaches and a waterpark, there's fun for all ages at Atlantis Paradise Island, Bahamas. Be sure to also explore some of the Caribbean's most impressive natural attractions. The Pitons, St Lucia and The Baths, British Virgin Islands are just the start of the wonders spread throughout the archipelago.

What are some of the Caribbean's most popular airports to fly into?

Grantley Adams International Airport (BGI), Luis Muñoz Marin International Airport (SJU) and Sangster International Airport (MBJ) are among the most popular airports to fly into. You'll find flights to these terminals and other Caribbean destinations from major cities located across the United States.

Caribbean Flights Information

Airlines serving
Roundtrip price
*Available to One Key members.