Find cheap flights to Caribbean Islands

Find cheap flights to Caribbean Islands

Round-trip
Economy
Boston (BOS)
Caribbean Islands
Fri 2/26
Fri 3/5
Any month
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Latest Caribbean Islands Flight Deals

San Juan
Nonstop from $227
Nonstop from $129
Saint Thomas Island
1 stop from $234
1 stop from $296
Punta Cana
Nonstop from $347
1 stop from $331
Oranjestad
1 stop from $343
2+ stops from $387
Montego Bay
Nonstop from $400
1 stop from $389
Santo Domingo
Nonstop from $214
Nonstop from $212

Good to know

Low season

August Best time to beat the crowds with an average 5% drop in price.

High season

December Most popular time to fly with an average 13% increase in price.

Average price round-trip

$390 (avg. price over the last 2 weeks)

Good deal round-trip

$129 or less

Good deal one-way

$74 or less

Top tips for finding cheap flights to Caribbean Islands

  • Looking for cheap airfare to Caribbean Islands? 25% of our users found tickets to Caribbean Islands for the following prices or less: From Miami $126 one-way - $189 round-trip, from Philadelphia $174 one-way - $247 round-trip, from Los Angeles $207 one-way - $289 round-trip
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly to Caribbean Islands is August.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Caribbean Islands flight deals.

FAQs - booking Caribbean Islands flights

Which airlines have a flexible cancellation policy for flights to Caribbean Islands due to COVID-19?

Which airlines apply social distancing measures on flights to Caribbean Islands due to COVID-19?

How long is the flight to Caribbean Islands?

What is the cheapest flight to Caribbean Islands?

Which airlines fly to Caribbean Islands?

What are the most popular destinations in Caribbean Islands?

How does KAYAK’s flight Price Forecast tool help me choose the right time to buy?

Top airlines flying to Caribbean Islands

Scores according to KAYAK customer reviews

5.7
Frontier
Overall score based on 39,502 reviews
6.4
Boarding
5.4
Comfort
6.8
Crew
4.6
Entertainment
4.7
Food
Airline reviews

Pros: "Check in was"

Pros: "Nothing"
Cons: "Smoother ride to location"

Cons: "Nothing because everything is good."

Pros: "En realidad nada porque desde los empleados hasta las azafatas del avión brindan muy pésimo servicio"
Cons: "Todo Check in Empleados Meriendas Entretenimiento"

Cons: "Frontier is usually good, not this flight. Dirty and packed full, not clean at all."

Cons: "Covid prevention methods need to be fixed ASAP, I don't trust Frontier with my health safety. Everyone was cramped in the plane and there was not any space betweem seats like other airlines. The app did not work to pay for carryon and I had to pay $60 in the front desk."

Cons: "The check in/bag drop process is terrible. Took 45 min. No explanation. No help."

Cons: "First time on Frontier, not a bad experience even though some of the comforts are not there. But the price is good if you need no frills"

Pros: "That was fun"
Cons: "The food in the airplane"

Pros: "Prompt, professional, and smooth landing. Very friendly staff"

Cons: "Great flight, boarding in Newark on Saturday, a nightmare getting through long security line."

Pros: "The crew of the flight was good but the seat are no comfortable."
Cons: "Comfortable seats."

Pros: "Everything was perfect flight on time the baggage very fast and the flight was just 3:30 minutes smoother than u can ask!"

Pros: "Nothing. Maybe the leg room."
Cons: "Everything. Delayed due to frontier poor logistics. Bad updates by staff (ie none), rude gate attendants and rude flight attendants throughout. We did make it an hour late and bags arrived but this felt like a banana republic airline."

Pros: "Once again everyone was so wonderful and helpful"
Cons: "Lower luggage cost. I spent $110 additional on this trip since since I wasn't well informed (my fault)"

Cons: "No entertainment or food, the worst plan ride ever"

Pros: "Nothing"
Cons: "Everything"

Pros: "Nothing"
Cons: "Staff crabage"

Pros: "Fast easy boarding, friendly helpful staff"
Cons: "There was more kids sitting on their parents lap than I’ve ever seen before and it made a very chaotic noisy flight"

Pros: "The crew was great, the chairs are uncomfortable."
Cons: "For the price it’s great."

Cons: "For the price, you cannot go wrong. Would recommend and travel again with this airline."

Cons: "People should be restrained from jamming entrance to aircraft BEFORE their zone is called."

Cons: "Never happened, the flight was cancelled and never rebooked."

Cons: "The flight was delayed, it was a mess."

Cons: "Boarding"

Pros: "Great flught for the price."
Cons: "Can’t complain."

Cons: "Good"

Cons: "Tremenda porquería horrendo"

Pros: "Crew was amazing, I love that they had tablets to take the order instead of driving the cart up and down the aisle."
Cons: "Paid fifty dollars for more leg room and it basically felt like basic seats that I’ve flown with such as spirit and American Airlines"

Pros: "Yes"
Cons: "Food"

Cons: "Everything was good. It’s was a nice travel... safety and puntual. I like that... the only things I think they may could be better is the airplane seat. And they don’t have television."

Pros: "Me cobraron por bulto de mano lo que lo encuentro inlógico porque con ese bulto viaje a Philadelphia y al volver me vienen a cobrar $60 no tiene sentido"
Cons: "Como comenté anterior Me cobraron por bulto de mano lo que lo encuentro inlógico porque con ese bulto viaje a Philadelphia y al volver me vienen a cobrar $60 no tiene sentido deben mejorar y no cojer a la gente de boba eso no se hace primera y última vez que viajo por Frontier"

Pros: "On time, new comfortable plane."
Cons: "Entertainment?"

Pros: "No issues"

Pros: "Price"
Cons: "Hardest most uncomfortable seats, ever!"

Pros: "SEAT was comfortable"
Cons: "Service"

Pros: "Price on the flight to ket"
Cons: "Sits are really uncomfortable, staff wasn't courteous and boarding process was a mess"

Pros: "Estaba todo bien."
Cons: "Pero no me gusto q havia mucha turbulencia. Y mis photos queria esplotar."

Cons: "The crew were not welcoming or friendly. One of them (blond, curly hair) was mean and disrespectful to everyone. She had an attitude all the time. Just the opposite of my flight from SJU to ATL. Other than that, the flight was on time, etc."

Pros: "Good"

Pros: "Very inexpensive even with buying extra legroom on the way back"
Cons: "Very little legroom in standard seats"

Pros: "They to entertain like the other airlines"
Cons: "Getting home safe"

Pros: "We had an uneventful flight"
Cons: "Didn’t depart until 1055 pm. One hour later than scheduled"

Cons: "Las 2 horas de retraso del vuelo."

Cons: "The seats are very uncomfortable"

Pros: "Everything went well. No issues at all."
Cons: "Deplaning is slow. Should consider a rear deplaning procedure from back doors into tarmac and into terminal."

Pros: "Nice service. Exceptionally new plane about a year old to the month."
Cons: "Need to ask people to prepare to deplane. Perhaps use rear door to expedite process"

Pros: "Great service."
Cons: "Limited food"

Pros: "The flight was Very puntual, clean and nice personal in the round trip. I will recomend to my friends and I will flight again soon."
Cons: "Nothing"

Pros: "Nothing was enjoyable except the price, but JetBlue it ten times better for only a tiny bit more."
Cons: "The cabin was out of control. People were running around, cursing, not wearing masks. The crew did nothing about it. The seats were wildly uncomfortable. There was no food, no entertainment, no comfort. I will not be flying Spirit again unless they're my only option."

Pros: "La experiencia en general ha sido muy buena. Solo que en las ocasiones que te sucede una emergencia no tienes derecho de cancelar, no se le otorga al menos un crédito y ni siquiera te pueden asistir mediante servicio al cliente."
Cons: "Necesitaba cancelar mi vuelo por razones de salud y se me informó que no me podían asistir a través del servicio al cliente. Ya que ellos no podían hacerlo."

Pros: "Plane was clean."

Cons: "They charge me more for bags"

Cons: "Then confort and they not have food for the passenger"

Pros: "Very tired trip. Nothing I like."

Pros: "Fair price"
Cons: "Comfort"

Cons: "Service skills it seems not to be part of the employee profiles. Unfortunately they all have the same lack of empathy and rudeness"

Cons: "Everything"

Cons: "Everything. Staff was completely unhelpful with relaying information regarding delays."

Pros: "Nothing to like about Spirit"
Cons: "Everything. It's not a secret"

Cons: "Good"

Pros: "Nothing"
Cons: "Everything"

Cons: "Good"

Pros: "ticket price"
Cons: "baggage charges. carryon fees, outregous"

Cons: "Loud children"

Pros: "Nothing."
Cons: "All."

Pros: "The comfort"
Cons: "The employer not speak spanish"

Cons: "Too much information/forms while checking in and have to pay for luggage which is expensive."

Pros: "Nothing!!"
Cons: "Nothing"

Cons: "delayed"

Cons: "Luggage Charges are outrageous"

Pros: "Kind attendants"
Cons: "Too many "hidden" and extra costs"

Pros: "Very bad"
Cons: "Nothing"

Cons: "The space of the seat and that know we have to pay for our luggage"

Cons: "Turbulence"

Pros: "Nothing"
Cons: "All. Price too high for kind of service"

Cons: "It's too bad. When I buy the ticket you must showing them. I never know about that. Why I need pay over$50 a small baggage?"

Pros: "I was impressed with the professionalism and the space on the plane. The staff was great, I am looking forward to flying again."
Cons: "I didn't like to delay."

Pros: "Nothing"

Cons: "Invalid ticket from online check in when going through security. Unclear boarding process"

Pros: "nothing"
Cons: "bag fees boarding pass fees"

Pros: "Plane wing tip said howdy. Few was great"
Cons: "Looking back it was what I expected. Great for short flights"

Pros: "Nothing!!!"
Cons: "All"

Pros: "Landed early"
Cons: "-"

Cons: "Getting dinging for bags at the gate, $50 a bag each way?!? Wasn't explicit ok Kayaks website and very financially cumbersome. Not cool."

Cons: "To many money for bags"

Pros: "Fantastic cree"
Cons: "No entertainment, not even an outlet to plug my headphones into. That would have been ideal."

Pros: ""Carmen " at the Newark station....calm and very attractive !"
Cons: "Disorganized gate ops"

Pros: "Short and sweet."

Pros: "Just what i need from traveling."

Pros: "I liked the staff. They made it seem easy"
Cons: "The $55 carry on fee that springs up out of nowhere. Not cool"

Pros: "Punctual"

Pros: "Nothing"
Cons: "Every thing what's awful"

Cons: "The service,"

Pros: "It was tough, but I did it. I just reduced what I needed"

Pros: "Excelente!"

Cons: "$50 for each bag. this $100 total extra for the round trip. RIDICULOUS! and NO BEVERAGE! Better have lots of extra cash with Spirit Airlines."

Pros: "Departure and Arrival went smooth. No delays."

Pros: "Food is free"

Read more about Frontier
COVID-19 information

Safety measures for airlines flying to Caribbean Islands

Airlines flying to Caribbean Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights to Caribbean Islands

Mandatory masks

Masks required on board, masks provided on flights to Caribbean Islands

Social distancing seating

Middle seats unavailable to book on flights to Caribbean Islands

Pre-flight testing

Testing for antibodies, testing for symptoms for flights to Caribbean Islands

Book Cheap Caribbean Islands Plane Tickets

Recent round-trip flight deals

4/7
Wed
nonstop
Frontier
4h 10m
EWR - SJU
4/7
Wed
nonstop
Frontier
4h 15m
SJU - EWR
3/16
Tue
nonstop
Frontier
4h 10m
EWR - SJU
3/24
Wed
nonstop
Frontier
4h 15m
SJU - EWR
3/5
Fri
nonstop
Frontier
4h 10m
PHL - SJU
3/24
Wed
nonstop
Frontier
4h 19m
SJU - PHL
4/10
Sat
nonstop
Frontier
4h 10m
EWR - SJU
5/12
Wed
nonstop
Frontier
4h 11m
SJU - EWR
3/9
Tue
nonstop
Multiple Airlines
4h 10m
EWR - SJU
3/13
Sat
nonstop
Multiple Airlines
4h 05m
SJU - EWR
4/6
Tue
nonstop
Frontier
4h 12m
PHL - SJU
4/14
Wed
nonstop
Frontier
4h 18m
SJU - PHL
5/12
Wed
nonstop
Frontier
4h 10m
EWR - SJU
5/26
Wed
nonstop
Frontier
4h 30m
SJU - EWR
3/16
Tue
nonstop
Frontier
4h 10m
EWR - SJU
3/24
Wed
nonstop
Frontier
4h 15m
SJU - EWR
4/11
Sun
nonstop
Multiple Airlines
4h 10m
EWR - SJU
5/11
Tue
nonstop
Multiple Airlines
4h 21m
SJU - EWR
3/21
Sun
nonstop
Multiple Airlines
3h 36m
EWR - SJU
4/7
Wed
nonstop
Multiple Airlines
4h 15m
SJU - EWR
3/16
Tue
nonstop
Multiple Airlines
3h 36m
EWR - SJU
3/24
Wed
nonstop
Multiple Airlines
4h 15m
SJU - EWR
4/17
Sat
nonstop
Multiple Airlines
4h 12m
PHL - SJU
4/19
Mon
nonstop
Multiple Airlines
4h 13m
SJU - PHL
3/21
Sun
nonstop
Spirit Airlines
3h 36m
EWR - SJU
4/12
Mon
nonstop
Spirit Airlines
4h 05m
SJU - EWR
3/13
Sat
nonstop
Spirit Airlines
3h 36m
EWR - SJU
3/18
Thu
nonstop
Spirit Airlines
4h 05m
SJU - EWR
4/24
Sat
nonstop
Spirit Airlines
3h 36m
PHL - SJU
4/27
Tue
nonstop
Spirit Airlines
4h 17m
SJU - PHL
3/9
Tue
nonstop
Spirit Airlines
3h 36m
EWR - SJU
3/17
Wed
1 stop
Spirit Airlines
10h 46m
SJU - EWR
3/2
Tue
1 stop
American Airlines
14h 07m
JFK - SJU
3/3
Wed
1 stop
American Airlines
12h 21m
SJU - JFK
4/3
Sat
2 stops
United Airlines
10h 59m
LGA - SJU
4/7
Wed
1 stop
United Airlines
10h 20m
SJU - LGA
4/10
Sat
nonstop
Delta
3h 52m
JFK - SJU
4/12
Mon
nonstop
Delta
4h 01m
SJU - JFK
3/14
Sun
nonstop
JetBlue
3h 47m
JFK - SJU
3/31
Wed
nonstop
JetBlue
3h 56m
SJU - JFK
Show more results

Recent one-way flight deals

3/21
Sun
nonstop
Frontier
4h 10m
EWR - SJU
3/13
Sat
nonstop
Frontier
4h 12m
PHL - SJU
3/9
Tue
nonstop
Frontier
4h 10m
EWR - SJU
3/6
Sat
nonstop
Frontier
4h 12m
PHL - SJU
5/26
Wed
nonstop
Frontier
4h 22m
EWR - SJU
3/7
Sun
nonstop
Frontier
4h 12m
PHL - SJU
3/15
Mon
nonstop
Frontier
4h 10m
EWR - SJU
4/7
Wed
nonstop
Spirit Airlines
3h 36m
EWR - SJU
5/5
Wed
nonstop
Spirit Airlines
3h 36m
PHL - SJU
5/21
Fri
nonstop
Spirit Airlines
3h 46m
EWR - SJU
3/16
Tue
nonstop
Spirit Airlines
3h 36m
EWR - SJU
3/13
Sat
nonstop
Spirit Airlines
3h 32m
PHL - SJU
3/28
Sun
nonstop
Spirit Airlines
3h 36m
EWR - SJU
3/10
Wed
1 stop
Delta
7h 15m
EWR - SJU
4/10
Sat
nonstop
Delta
3h 52m
JFK - SJU
3/2
Tue
1 stop
American Airlines
15h 55m
JFK - SJU
3/24
Wed
1 stop
United Airlines
12h 13m
EWR - SJU
3/19
Fri
1 stop
Multiple Airlines
17h 32m
ATL - SJU
3/28
Sun
1 stop
Copa Airlines
25h 27m
JFK - AUA
3/5
Fri
nonstop
JetBlue
3h 35m
JFK - SJU
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