Find cheap flights from Medford to Caribbean Islands

Search hundreds of travel sites at once for deals on flights to Caribbean Islands. Bundle your flight + hotel and save!

MFR — Caribbean Islands
Jun 18 — Jun 251
Round-trip
1 adult
Economy
0 bags
From?
To?
Sat 6/18
Sat 6/25

Good to know

Low season

December

High season

December

Average price round-trip

$689

Good deal round-trip

$433

Good deal one-way

$295
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 6% increase in price.
(avg. price over the last 2 weeks)
or less
or less

Top tips for finding cheap flights to Caribbean Islands

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Caribbean Islands is August.
  • Morning departure is around 31% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Caribbean Islands flights

Top airlines flying Medford to Caribbean Islands

Scores according to KAYAK customer reviews
7.2
American AirlinesOverall score based on 47665 reviews
7.5Boarding
7.1Comfort
7.9Crew
6.9Entertainment
6.7Food
Airline reviews

Just perfect

Read more about American Airlines

Just perfect

It was a 10

For a delayed flight, and one that most choose because of the amenities, no one apologized for the lack of amenities. A simple, “we are truly sorry” announced to everyone would have gone miles. Instead, the crew kept trying to almost conceal the total lack of available entertainment and even feign like it might “sort of work” until the last minute. I was traveling with my life partner, who intended upon and did work the whole flight (despite zero internet, even for the little time avail that we are aware of when traveling to/from PR), but also with a just turned 6 year old who had been looking forward to using “his own” screen for the last 2 weeks. Underwhelming to say the least. The crew’s apathy didn’t help.

Cons: "Some of the crew had an attitude and the purchased WiFi did not work"
Pros: "Fast and easy flight"
Cons: "It’s was very good flight"
Cons: "Almost 4 hour delay."
Pros: "Crew was snappy in getting people in plane and checking in carry ons since occupancy had been reached."
Cons: "Lack of adjustable headrest on seat."
Pros: "Crew helped us find new seats on board."
Cons: "American Airlines changed our seats after ticket purchase so that we were not sitting together. We chose seats at check-in in San Francisco so that we could sit together. When we landed in Miami we discovered our seats had been changed yet again and we were seated in different rows, middle seat!"
Pros: "Smooth ride"
Cons: "Feeling of being cramped"
Pros: "Crew was great!"
Cons: "Todo bien"
Pros: "Service from crew was fine"
Cons: "No delay! Got notification that our flight was one half hour earlier. Then boarded aircraft, and it had electrical problems. Delayed. We had to get off. Then board another aircraft."
Pros: "Checking in with my Mum who needs assistance was excellent."
Cons: "Lack of Entertainment."
Pros: "Time of flight"
Cons: "Aircraft had no screen, old, uncomfortable"
Cons: "Crampt space, cold cabin"
Pros: "None"
Cons: "Long delay"
Pros: "Movie options were good."
Cons: "The a/c was not working well and t"
Pros: "The service was excellent and the flight on time. Love American."
Cons: "The seats have been refurbished and if you are a plus size the seats are uncomfortable."
Pros: "Reliability that your flight will not be cancelled. Punctuality."
Cons: "They charge you $125 for a dog in cabin (JetBlue and Southwest near $100, Frontier $75). There is NO benefit, even with this extra amount of money. I was assigned to enter the aircraft in Group 8... I suggest AA the benefit to enter (at least) in Group 5 for people with PAID in cabin dogs."
Pros: "Service"
Cons: "Seats and space"
Cons: "Entertainment via internet could NEVER be really be done complitly. And the flight attendants did not know how to help costumers"
Pros: "Turkey sandwich snd boarding went smoothly"
Cons: "There was no entertainment and since there is no WiFi for most of the flight due to being over water the flight seemed longer than what it actually was."
Cons: "Dallas to San Juan San Juan Dallas American Airlines has the worst seat of any airline flown by us fare almost 2000 dollars for round trip and the seat is small hard uncomfortable even for a short flight this is no business class!!"
Pros: "On time"
Cons: "Cold cabin"
Cons: "The seats are very tight."
Cons: "Last minute cancellation and reschedule if original flight with 20 people hounding the gate for standby status. Craziness. These last minute revisions mist stop"
Pros: "Direct flight"
Cons: "Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats"
Pros: "USB Outlets are nice to have"
Cons: "Nothing was bad on this flight"
Pros: "Schedule was punctual. The entertainment was superb. Good crew. The overhead bins were, for some reason, larger which aided the boarding process."
Cons: "I guess the lack of snack options but that is just the way it is nowadays."
Pros: "The beauty that is Oregon."
Cons: "The fact that AA had an issue with THEIR plane which caused me to miss an already booked connecting flight. I ended up spending SEVEN hours in Phoenix waiting for a different flight to take me back to Tampa. The least AA could do is offer to pay for my supper or even a snack ANYTHING would've been nice. It's called customer service. I understand things happen that are out of our control, I also understand what it is to help make people whole or happy."
Pros: "Nice crew clean airplane"
Cons: "Initial flight was cancelled after 2 hours delay. My next flight was scheduled the earliest possible by AA which was 24 hours later. No transportation,hotel or miles compensation for this. I had work and responsabilities the next day. TThe scheduled trip was supposed to take off at 7:45. Boarding started late and was very slow. My bag fit the meassurements and still was forced to check it (which I did not want to do as I did not want to be waiting an hour for my bag at my arrival as I had work early the next day. In addition there was airplaine traffic as it was "rush hour" instead of flying at 7:45 we departed almost at 9pm!!!! Have to pay for food Quality of tv monitors very poor And in an uncomfortable position No movie options No wifi although stated the aircraft has Non functioning electrical plug"
Pros: "Nothing"
Cons: "Never made it to San Juan to catch my cruise. To top things off I was a ship for two days without my luggage and underwears. Never again!!! Thank you JetBlue!!!"
Cons: "That all the passengers were rechecked at the Gate by TSA without offering any explanation as to why, if it was a domestic flight, why were they requiring ID again. And checking bags."
Pros: "On time smooth"
Pros: "The pilot was a riot, the flight was on time. Again, nothing wrong, nothing special. As it should be (if only we had more leg and seat room, and I am pretty streamline)."
Pros: "Friendly staff. Landed early. Offered a free bag."
Cons: "They moved the flight earlier, which was not fun. And, there were no entertainment centers."
Pros: "Nothing"
Cons: "Super old planes, no had a tv."
Pros: "Puntuality"
Pros: "Crew was good."
Cons: "The television was in the aisle and couldn't be properly seen. Also there was no outlet charger. During boarding, even thou they called by group number, the crew allowed a queue in the front, making it confusing who was in line and who wasn't. Better wait till the end to board that get in that mess"
Cons: "The airline had trouble with the plane. After we waited 3 hrs in the plane they cancel the flight. They offer a hotel but it was very dirty"
Pros: "Nothing. My fight from San Juan to Miami on Friday Oct. 7 was cancelled because of hurricane Matthews, since I didnot buy a roundtrip with AA they did not reimburse or offer me a credit for my returning flight. I contacted AA in two ocassions and both times their personnel were impersonal and even rude to me with the whole situation. I ended up losing $250 because of choosing American Airlines. I will do my best to avoid traveling with American ever again, and I will spread the word, as well. I felt robbed, so unfair."
Cons: "Everything"
Pros: "Friendly polite staff. Plane left and arrived on time."
Cons: "No have owned screen TV"
Pros: "Everything"
Cons: "Nothing"
Pros: "Comfortable seat"
Cons: "Lack of entertainment"
Cons: "One hour delay sitting inside the plane with no pilot!! And to top it off, the air conditioner was off!! Will never fly American ever again."
Cons: "Terrible airport assistance, many unnecessary customs checks, uncomfortable seats, on flight bad service and late flight times."
Cons: "Gg"
Pros: "Everything was on time, no delays."

Great experience

Great and easy flight from Medford to SFO.

Pros: "Crew was very nice!!"
Cons: "Space on seat not comfortable for tall people"
Cons: "Seats could have been better. Very uncomfortable seats"
Cons: "Again, left stranded in SC."
Cons: "Nothing"
Pros: "The crew was helpful and nice."
Cons: "It was delayed a lot."
Pros: "Not much but it was the best price"
Cons: "The space was so tight I couldn't open the lid to my laptop. I had a small personal item, the gate checked my bag, and there was no room for my feet. I just flew Alaska, delta, American,d Lufthansa recently and none of those airlines were as bad. Like a sardine can. I will avoid United at Ll costs."
Cons: "Flight was canceled and there were no other flights that day."
Pros: "Service at business was good. Comfortable chairs and quiet cabin space."
Cons: "The gate experience due to long time between flights getting worst due to a departure delay."
Pros: "Smooth flight into Denver"
Pros: "Comfortable seats with a touch screen with plenty to choose from to entertain. Updates from the cockpit often. Good music as we boarded and exited the plane to set the mood. Very attentive staff. Would love to fly with United again, soon."
Pros: "EWR gate personnel tried to move things along. Seat was roomie and the flight attendants were pleasant. Flight was on time and landed early. No complaints."
Cons: "Long TSA lines at EWR, but they moved."
Pros: "I liked the perfect landing!!"
Pros: "When the lady in the gate saw me almost dying of running all over the airport with my suitcase, she was very nice and comfort me."
Cons: "Nothing"
Pros: "Crew was very nice"
Cons: "Sits are very uncomfortable"
Pros: "All in the prices!!! Accesibility!!!"
Cons: "The prices changes too much!"
Pros: "Nothing"
Cons: "I'm supposed to bring a carry on with me and they don't allowed me this time. They should be strict with other passengers who bring more than a carry on. I was SO MADDD"
Pros: "Services , on time"
Pros: "All the way we had a great atencion from all the crew and airport facility thanks"
Pros: "Seat more comfortable and any entertainment."
Cons: "The seat."
Cons: "Delay?????"
Pros: "Friendly & informative captain & crew"
Cons: "Smooth flight, no complaints, A+"
Pros: "Estaba supuesto ser un viaje barato y puntual"
Cons: "Pero no fue de esa manera yo soy un paciente esquizofrénico y padezco de vipolarida más tengo problema con el azúcar mas padezco de sleeping adnnea.y muchas otras condiciones.y mi vuelo no salió cuando. Tenía que salir.yo vivo en perth ambos y era muy difícil viajar para Mi en tren para luego tener que pasar todo lo que pase.deverian por lo menos recomendarme con algo desierta por todos mis inconvenientes."
Pros: "On time and comfort"
Pros: "Smooth boarding"
Cons: "No entertainment of any sort available unless paying."
Pros: "It was a good flight. The attendants were courteous and accomodating. There was nothing to complain about."
Pros: "Was fast and on time"
Cons: "Pushing back from gate took for ever due to mechanical problems and somebody got sick on the plane so their decision to wait until the person situation got better affected everyone else"
Cons: "Lots of delay, not so friendly flight attendants"
Pros: "very helpful"
Pros: "The service & how comfortable I was."
Cons: "That you have to pay for everything but I guess now a days every airline is doing the same thing."
Cons: "Thr boarding process was a mess, a lot of people didn't even have seats assigned."
Pros: "The personal are very amability"
Pros: "Love the crew!"
Cons: "The delays was horrible!!"
Cons: "I missed my second flight by 10 minutes due to a delay from my first flight and was only refunded a small portion luckily I found a good price with Jet Blue wich worked out better"
Pros: "United personal quickly found our bag location and made the arraingement to send it to us ASAP."
Cons: "The fact that the only bag we checked in with the airline did not arrived in our plane with out any warning what so ever."
Cons: "Overbooked both my flights and I was a last minute addition to the first flight."
Pros: "El viaje de newark a san juan por united fue excelente. Por la linea aerea de American Airlines terriblemente FATAL. Habia un problema con el avion o la torre del vuelo miami hacia san juan PR. Nos ofrecieron estadia en un hotel supuestamente ellos corrian con los gastos ya q se atraso el vuelo y no fue culpa de ningun pasajero segun nos dijo una señorita del counter, resulta ser q el hotel fue el piso del aeropuerto de miami x 8 horas!!! Wow a la verdad q nos vieron la cara de bobos y nos cojieron de bobos tambien. Q trato mas injusto. No volveremos a viajar por AMERICAN AIRLINES asi mismo le dejaremos saber a todo el mundo el trato de esta linea con los pasajeros. Gracias a esto nos agravamos la espalda, costillas. Por culpa de ellos por tratarnos como basura. Eso no se hace!!!! Despues q estabamos sentados en el avion el piloto no llegaba y nos tuvieron q bajar del avion, esperar a que llegara otro piloto para volvernos a montar en el avion!!! Q mala coordinacion!! Esto es una falta de respeto!! Esta linea AMERICAN AIRLINES ES UNA PORQUERIA!!! No volvemos a viajar por esta linea JAMAS!!! Irresponsables!!"
Cons: "Nothing at all !!!! With AMERICAN AIRLINES THE WORST!!! We will NEVER travel by this linea aerea. Son una gran Porqueria!!"
Pros: "Nothing"
Cons: "I'm usually a patient person, but my flight was supposed to leave at 525am and didn't leave until 730. This was the first flight in the morning. We boarded, waiting 30 minutes on the plane, they told us to get off because there were computer issues. Why wasn't that checked before everybody was boarded? Once we got on the plane we had to wait another 30 minutes for the crew to get someone's luggage from under the plane. Why wasn't that done while the computer was getting fixed? I didn't get to Denver until 1040am missed my flight and didn't get to get on my connection until 500pm. In the meantime I called to get on a different flight at 1, but the guy on the phone didn't actually book me a seat. The gate people weren't very nice."
Cons: "It took to long to board the flight"
Cons: "Plane was late then sat on run way for 30 minutes. Over one hour late."
Pros: "Boarding"
Cons: "Excellent"
Pros: "The service since I am handicap"
Pros: "Everything"
Cons: "Comfortable and affordable!"
Pros: "It was a very well ran flight, both fights were what you would expect from an airline service. Overall satisfied."
Pros: "What I like the most was that it was on time, also the crew was amicable."
Pros: "Short lines at Medford airport"
Cons: "Small plane"
Cons: "Not enough time between flights!"
COVID-19 information

Safety measures for airlines flying from Medford to Caribbean Islands

Airlines flying from Medford 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 from Medford to Caribbean Islands

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Medford to Caribbean Islands

Pre-flight testing

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

Flexible cancellations

Waiving of change fees. Search flexible flights from Medford to Caribbean Islands

Book cheap flights from Medford to Caribbean Islands

Recent round-trip flight deals

9/24Sat
2 stopsUnited Airlines
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$485
9/24Sat
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$486
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$505
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$519
9/24Sat
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$520
9/24Sat
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19h 23mSJU-MFR
$534
9/24Sat
2 stopsUnited Airlines
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10/1Sat
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25h 40mSJU-MFR
$539
11/8Tue
2 stopsUnited Airlines
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$540
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11/10Thu
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7/9Sat
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$736
11/8Tue
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3 stopsAmerican Airlines
16h 24mSJU-MFR
$821
10/30Sun
2 stopsAmerican Airlines
21h 21mMFR-SJU
11/4Fri
3 stopsAmerican Airlines
16h 24mSJU-MFR
$864
9/24Sat
2 stopsAmerican Airlines
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10/1Sat
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$878
10/3Mon
3 stopsAmerican Airlines
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10/10Mon
2 stopsAmerican Airlines
20h 57mSJU-MFR
$893
9/24Sat
2 stopsAmerican Airlines
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10/1Sat
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$945
9/24Sat
2 stopsAmerican Airlines
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21h 37mSJU-MFR
$1,004
7/7Thu
2 stopsAmerican Airlines
30h 01mMFR-SKB
7/14Thu
2 stopsAmerican Airlines
33h 50mSKB-MFR
$1,056

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Medford - Caribbean Islands Flights

Departure:

Medford (MFR)United States

Cabin classes:

$337
$387
$13
$9

Browse origins: