
Cheap Flights to Caribbean from $80 (2025/2026)
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Santo Domingo
Flights
How Much Does it Cost To Fly To Caribbean?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
BWI
Baltimore Washington Intl. Thurgood Marshall
SJU
Luis Munoz Marin Intl.
$160 Roundtrip, just found
$160
Roundtrip
just found
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
$169 Roundtrip, found 3 days ago
$169
Roundtrip
found 3 days ago
BWI
Baltimore Washington Intl. Thurgood Marshall
PUJ
Punta Cana Intl.
$244 Roundtrip, just found
$244
Roundtrip
just found
BWI
Baltimore Washington Intl. Thurgood Marshall
SDQ
Las Americas Intl.
$250 Roundtrip, found 2 days ago
$250
Roundtrip
found 2 days ago
BWI
Baltimore Washington Intl. Thurgood Marshall
MBJ
Sir Donald Sangster Intl.
$266 Roundtrip, found 5 days ago
$266
Roundtrip
found 5 days ago
JFK
John F. Kennedy Intl.
AUA
Queen Beatrix Intl.
$281 Roundtrip, found 21 hours ago
$281
Roundtrip
found 21 hours ago
BWI
Baltimore Washington Intl. Thurgood Marshall
STI
Cibao Intl.
$284 Roundtrip, found 5 days ago
$284
Roundtrip
found 5 days ago
JFK
John F. Kennedy Intl.
PUJ
Punta Cana Intl.
$285 Roundtrip, found 4 hours ago
$285
Roundtrip
found 4 hours ago
Origin | Destination | Travel Dates | Flights From* |
---|---|---|---|
EWR | San Juan | November 15 to November 19 | $138 |
FLL | Montego Bay | September 1 to September 5 | $214 |
LGA | Santiago de los Caballeros | September 9 to September 16 | $253 |
EWR | Montego Bay | September 2 to September 6 | $260 |
BOS | Santiago de los Caballeros | September 8 to September 16 | $285 |
FLL | Oranjestad | September 6 to September 13 | $297 |
EWR | Nassau | September 15 to September 20 | $310 |
PHL | Piarco | September 7 to September 23 | $433 |
JFK | West End | September 8 to September 12 | $453 |
JFK | West End | September 8 to September 12 | $453 |
LHR | San Juan | November 3 to November 18 | $691 |
LGW | Piarco | September 19 to October 5 | $738 |
LHR | Kingston | September 29 to October 6 | $810 |
BKK | Punta Cana | September 22 to September 29 | $1,596 |
BKK | Piarco | October 5 to November 5 | $1,633 |
Origin | Destination | Travel Dates | Flights From* |
---|---|---|---|
MIA | Santiago de los Caballeros | August 24 to September 11 | $321 |
MIA | Nassau | August 23 to August 30 | $328 |
MIA | Oranjestad | August 24 to August 28 | $331 |
EWR | Santiago de los Caballeros | August 24 to September 21 | $348 |
JFK | San Juan | August 24 to August 26 | $355 |
EWR | Santo Domingo | August 22 to September 4 | $380 |
EWR | Montego Bay | August 24 to September 6 | $386 |
BOS | Montego Bay | August 23 to August 30 | $403 |
PHL | Punta Cana | August 24 to September 2 | $407 |
BOS | Santo Domingo | August 24 to September 2 | $409 |
BOS | Santiago de los Caballeros | August 23 to September 25 | $442 |
BOS | Kingston | August 24 to September 4 | $532 |
BOS | Piarco | August 22 to September 24 | $574 |
YYZ | Nassau | August 24 to August 26 | $769 |
BKK | Montego Bay | August 24 to August 30 | $2,661 |
Best Caribbean Flight and Hotel Packages
Price found within the past 48 hours. Click for updated prices.



Travelers ❤️ These Caribbean 🏨

Hotel El Convento
100 Cristo St, San Juan
Stay at this 4.5-star luxury hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Pan American Pier are located nearby.
8.8/10 Excellent! (1,005 reviews)
"So kind. Thanks!"
Reviewed on Aug 15, 2025

British Colonial - Nassau
Number One Bay St, Nassau
Stay at this 4-star beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 8 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Junkanoo Beach and Cable Beach are located nearby.
8.6/10 Excellent! (1,888 reviews)
"Antonya at the front desk was excellent"
Reviewed on Aug 14, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street, San Juan, Puerto Rico
Stay at this 4-star business-friendly hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Pan American Pier are located nearby.
9/10 Wonderful! (1,095 reviews)
"Everything from staff to rooms and shopping was great."
Reviewed on Aug 15, 2025
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The Reef at Atlantis
Paradise Beach Drive, Paradise Island, New Providence
Stay at this 4.5-star luxury resort in Paradise Island. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Junkanoo Beach and Cable Beach are located nearby.
8.8/10 Excellent! (1,405 reviews)
"Everything was great . But would love to to have some fish or shrimp without paying a fortune ."
Reviewed on Aug 16, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
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