Find cheap flights from Medford to Caribbean Islands

Find cheap flights from Medford to Caribbean Islands

Round-trip
Economy
Medford (MFR)
Caribbean Islands
Fri 11/27
Fri 12/4
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Good to know

Low season

November Best time to beat the crowds with an average 11% drop in price.

High season

December Most popular time to fly with an average 6% increase in price.

Average price round-trip

$658 (avg. price over the last 2 weeks)

Good deal round-trip

$529 or less

Good deal one-way

$229 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.
  • On average*, there is no price difference when choosing to fly in the morning or the evening on this flight route.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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Top 3 airlines serving Medford to Caribbean Islands

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,795 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Delay with boarding"

Pros: "Mal servicio; compre un tickets que no permitía escoger los asientos y nos seleccionó la última fila en cada vuelo. La diferencia entre ser priority y regula es bien marcada"
Cons: "Mejor trato a todo pasajero; se reconoce las ventajas de estar en primera clase pero el servicio debe ser excelente"

Pros: "The crew was not overly friendly"

Pros: "Movies"
Cons: "Comfort. Jetblue offers betwee seats ne apacing betqeen rows"

Pros: "I needed extra space because of my pregnancy, but didn't realize I couldn't upgrade my seat online or at check in. I was advised to tell the Boarding attendants I needed extra space and they promptly changed my seat and let me preboard. I'm so grateful and I had a wonderful flight back home. I was also very sick, so it was a relief knowing I could rest comfortably before arriving home to my children."

Pros: "Seats too small"
Cons: "Crappie entertainment. Never figured out how to login on phone,"

Pros: "Great crew"

Cons: "Delta is top notch!"

Pros: "Nice service"

Pros: "Love it"

Cons: "In the last months I have travel 3 times , this is the first with Delta. I can say it has been the best experience I had. Good entertainment, the access to texting and the variety of snacks make superior this airline."

Pros: "Crew was awesome. Very friendly."
Cons: "I’m 6 foot tall and I found my seat space feeling crowded. I found myself wishing for just 2 more inches of legroom. It feels that airplanes are being built for quantity of passengers, not quality of flight."

Pros: "Crew was very fast but not enough during boarding and people had brought oversized carry on luggage to the gate requiring stowing. We had checked a carry-on at check in and paid $30 while several people got theirs stowed for free which seemed unfair."
Cons: "The charging for checked luggage has created a situation that was unfair for all travellers and ultimately made the plane’s departure late. This policy drives people to bring too much luggage into the cabin, putting at risk the safety of others and delays."

Pros: "The gate agent in Medford for delta was awesome"

Pros: "The friendliness of the passengers and most of the crew."
Cons: "One of the younger female flight attendants was rude . She was collecting trash and took my neighbor’s (aisle seat) trash but wouldn’t take mine. I tapped her elbow to show that I had trash, she looked at me but didn’t take it. She returned and still refused until I exclaimed. She rolled her eyes."

Cons: "I feel like all the problems the aircraft had it should've been repaired before trying to use it, upon boarding they told us the left engine had to be started from an external source, as a new flyer that was terrifying to hear"

Pros: "The crew was totally understanding with the huge delay."
Cons: "The communication from Delta on the delay."

Cons: "Cabin was cold enough to store meat. Entertainment system was poor at best. And, of course, the seats were too small and uncomfortable. Time to start looking at other airlines."

Cons: "Worst transatlantic flight in 40 years. Filthy old seats and mine had a wet ironed stain. The seat in front of me was broken and reclined into my lap. That made the screen for entertainment unusable. The reading lights didn’t work. The toilets were a mess and never serviced."

Cons: "I was flying standby. I checked the list on line and my name was number 5. I get to the gate and there’s just a handful of customers. The agent said there was enough seats for the standbys I wait and wait for my name to be called but no luck. My name wasn’t cleared yet. Finally I was the next to last one to get a seat. The gate agent who didn’t ask for my name tells me I was all the down at the bottom of the list. While I am glad that I got on I wish I knew what method is use to get your name on the stand by list?"

Cons: "Cabin was too hot since the very beginning. Even in first class."

Pros: "The counter assistant change my seats and my wife and me seat together"
Cons: "Hot cabin"

Pros: "Although our flight was fully booked. The crewmembers on this flight was professional, friendly and efficient. We boarded quickly and took off on time. We even arrived ahead of schedule. Each passenger was given free headphones and complimentary beverages and snacks. I love Delta they are a cut above the rest. They are constantly striving to put the customers needs and wants top priority"
Cons: "Tight seats need more legroom"

Cons: "I will avoid middle seat from now on"

Pros: "The workers."
Cons: "The selection on an incorrect plane that didn't fit the docking port"

Pros: "Arrived early. Got a beverage & snack which is becoming rarer with American carriers. Video selection was very good. Staff was nice and attentive. Overall a good flight at a reasonable price."
Cons: "Narrow corridor to seats"

Pros: "Everything escept the seat that was too small. I also had problems with the entertainment when trying to see movies."
Cons: "Seats too small ant could not watch Movies beacause the screen was defective."

Pros: "I bought my ticket about 3 months ago. At my check-in at AMS they said that! DELTA now charges for the 1st bag. Total (unpleasant) surprise. Will I be charged on my RETUTN FLIGHT?"
Cons: "I bought my ticket about 3 months ago. At my check-in at AMS they said that! DELTA now charges for the 1st bag. Total (unpleasant) surprise. Will I be charged on my RETUTN FLIGHT?"

Cons: "Flight was delayed over 1hr."

Pros: "A great flight overall. Delta provided a lot of entertainment options. Flight attendants were very friendly."
Cons: "I don’t like that we had to pay for our checked bag."

Pros: "Buen entretenimiento."

Cons: "La incomodidad de los asientos además que la escala fue de más de 6 horas y fuimos los últimos en abordar. Para colmo los asientos fueron los últimos de la fila y ni siquiera eran reclinables. Creo que deben tomar en consideración a las personas que estamos tantas horas en la escala y permitirles abordar primero además de darles asientos más cómodos más aún si hemos comprado los boletos con tanto tiempo de anticipación."

Pros: "Well, the seats and the lavatories are smaller than ever. And I am quite petite."

Pros: "Itwas fast and easy."
Cons: "Nothing. Everyrhing was good."

Pros: "Excelente"

Pros: "Not sure who thought every passenger is 5'6 but for the rest of us, the seat pitch is ridiculously close. Like knees to the seat in front close. I'm 5'10 and I was very uncomfortable the entire flight."
Cons: "See above"

Pros: "Entertainment is very good"
Cons: "Send my carry on bag, outside."

Pros: "Late delay notification"
Cons: "Called the airline directly to verify the status of flight within 24hrs and everything was on schedule according to them. Even tho the airport at San Juan have not night arrivals due to the effects of Hurricane Maria, and on previous days the same flight had been moved to a morning schedule for that reason. I was notified of the delay within hours of departure of the connecting flight."

Cons: "Small plane"

Pros: "Great help from gate agent when a delay in connecting flight would have missed the last flight. Agent put a great new agent it together better than the original."
Cons: "Delta is the best"

Pros: "The flight left on time and we got in 15 minutes before the scheduled time. Awesome service from gate to gate."
Cons: "I didn't like that I had to pay for my bags and still purchase food on plane. The price for ticket is already overpriced to begin with. Fuel is cheaper, the planes burn less fuel due to updated design and still the tickets are three times the cost of five years ago. No one should have to pay for bags period. Show that you really care."

Pros: "Entertainment, food having only two seats on our side of aisle."
Cons: "Leg room"

Pros: "Comfortable aircraft with tv in the seats"
Cons: "Huge delay on my flight and most other flights from LaGuardia that day, lack of information on reasons for the delays ."

Pros: "The flight itself was fairly quick."
Cons: "We were late by 4hours and they kept changing the times. I wish they would have set it to one time like the other airlines. The seating is uncomfortable and there was no entertainment."

Pros: "Movie selection"

Pros: "Service and friendliness was awesome."
Cons: "No drinks served, sorry flight."

Pros: "Food was OK. Crew was very friendly"
Cons: "No Entertainment for a 4 hour flight. Plane was very old."

Pros: "Although I am a vegetarian, It was nice Delta was serving sandwiches."

Pros: "newer aircraft; good entertainment options; large overhead storage compartments"
Cons: "cramped passenger space"

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 was great!"

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: "Poor service"

Pros: "I loved everything. No complaints. American airlines is one of the best airlines I have flown with."

Pros: "I liked that we got to San Juan safely. The crew on board was very accommodating."
Cons: "Due to the delays, we missed our jumper flight and American refused to compensate. Also, only had two cookies all day from 8:05am until 3:45 pm! No sandwiches as promised. We were delayed approximately 4 hours total. Had to take a taxi ($85) to Fajardo to HOPEFULLY catch last ferry to Culebra. Guess AmericansAirlines doesn’t care if you have to sleep at the dock!"

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: "Boarding process"
Cons: "Delay, no food,"

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: "Can't think of anything good"
Cons: "SEE: Customer Relations request #1-249830721"

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: "There seets are two small. And they dont sell alcohol. That sucks."

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: "Even when the plane was full they managed to help passengers to get seated."
Cons: "If you still flying economy class, why would you have to pay extra for exit row where the seats are the same. Only received pretzel and a cup of drink on a 3 hour flight once."

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."

Pros: "Overall good flight"
Cons: "I did not like the time needed for boarding/ settling in. But that is a factor of people not following instructions. Not the crew."

Cons: "Terrible airport assistance, many unnecessary customs checks, uncomfortable seats, on flight bad service and late flight times."

Pros: "I was going home"
Cons: "Late flight no pilots andt broke my luggage."

Cons: "I didn't like the American airline people who checked my bag. She threw it because I told her nothing was breakable in it."

Cons: "Gg"

Pros: "Everything was on time, no delays."

Pros: "Should have individual tv's like jet blue does. There shoul be a family travel area for people travelin with todlers. better service and better food. Faster luggage pick up."
Cons: "Nothing. Expesive flights, an unprofessional flight attendant name Sarah, fighting with the customers. No entertainment. It was a nightmare"

Pros: "I live the service which make me feel good. Also the flight was very quiet and the crew help me in everything I asked."

Pros: "The great atendance and on time bording"
Cons: "There is no More options of free food included with the ticket fly and it was a longer flight and there wasn't no tv, no entertament"

Pros: "My window seat was all."
Cons: "I didn't get a call about the delay like other passengers, only an email at 7am as I was in line to check in for the 8:25am flight 395. The female crew members, a dark haired woman and a short blond haired woman both would have ignored me if the other two people seated by me did not also try to get their attention. The dark haired woman gave the guy next to me headphones and when I held out my hand she just looked at me and walked away as if she'd been called away. Which she hadn't she came back and started with the row immediately behind us and the guy next to me was nice enough to give me his. Also after nearly waiting 4 hours, 9 minutes before boarding we were given food vouchers and told to "run and hurry" and get food "to go" so most people didn't even bother using the vouchers because of that. I've had better flights with American Airlines, I just didn't know this one would be so poor. Definitely way below average expectations."

Pros: "The crew was helpful and nice."
Cons: "It was delayed a lot."

Pros: "I liked the perfect landing!!"

Pros: "Nothing, The flight didn't happen"
Cons: "Waited for 6.5 hours for the flight to get cancelled and rescheduled for a week later."

Pros: "Friendly & informative captain & crew"
Cons: "Smooth flight, no complaints, A+"

Pros: "Fast and easy boarding"
Cons: "No tv, no , no magazines"

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."

Pros: "Flight attendants were cordial and helpful"
Cons: "Seating in the last row or rows made deplaning very slow."

Pros: "Everything was perfect, the crew was fantastic"
Cons: "Maybe a bit of food."

Cons: "It took to long to board the flight"

Cons: "The airline is horrible.. Poor customer service"

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: "Bien"
Cons: "Bien"

Pros: "Nothing"
Cons: "Horrible phone customer serviceI."

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."

Cons: "No leg room and also a short free movie wouldn't hurt."

Pros: "What I like the most was that it was on time, also the crew was amicable."

Pros: "One flight attendant saw what we were going through and asked if she could do anything but there waany really much she could do for us. So we asked for more cookies which she quickly obliged."
Cons: "We sat in the last row which was uncomfortable because we couldn't recline our seats. My boyfriend had ice spilled on his lap and the beverage cart was bumped into his shoulder and knee three times. There was a passenger that was annoying to us as well as to the crew. She kept getting up and standing in the aisle. She brought food on board that smelled like spoiled cabbage. This same passenger walked to the back where the food and beverages were to serve herself water. Once seen, the flight attendant told her to go back to her seat. My boyfriend's television controller didn't work and he had to use mines. He sat in his seat and had to watch a movie that was in front of my seat. Overall, it was a rough start to his birthday celebration."

Pros: "The flight it self was ok"
Cons: "The back and forth that I went thru between gate to gate and the last minute changes of the schedule"

Pros: "Very organized . On time"

Pros: "Everything! My grandparents needed special assistance with wheelchair and the crew was very helpful! They spoke Spanish and they were able to get a crew member to translate"

Cons: "Last row seats. Nothing of space, man seating next to me in the isle seat couldn't accomodate his legs inside the available space."

Pros: "The United App is a must. Having so many movie and tv options made the flight breeze by."
Cons: "The cabin was so uncomfortably hot. After passing by a second time with the drink cart, there was still another two hours left on our 4.5 hour flight. I hit the button to request a flight attendant, and after 15 minutes, one finally answered. I asked for water, and they stood over me while I drank it so they could trash the cup."

Pros: "Good trip"
Cons: "Nothing"

Pros: "Got $200 voucher for overbooking"
Cons: "Overbooking"

Cons: "I never took this flight since the San Francisco flight got delayed that when I got to the gate to board the Washington flight. The gates closed on my face literally. Awesome trip.! (Sarcasm included)"

Pros: "That flight had no entrainment. So it wasn't bad, just not available on that short flight"

Pros: "Short lines at Medford airport"
Cons: "Small plane"

Cons: "Not enough time between flights!"

Pros: "The crew kept us feeling comfortable"
Cons: "Hated the security check in on the airport because of their lack of staff also hatted the flight we were delayed 3 hours"

Cons: "They did not have TV and no wifi it was terrible. They only gave me a cup of soda nos even a potato chips which other airline do give."

Pros: "Boarding process on time."
Cons: "The waiting time for my connection flight."

Pros: "Nothing"
Cons: "My connecting flight was sent without me- I paid for upgraded seats that I never got, they tried giving me a connector that didn't get back to Baltimore until 1030pm after my day started at 3am for a flight at 5:30am... Then finally got a connecting flight into Virginia and had to drive 2 hours to get my car from Baltimore. Never flying United again."

Pros: "Getting from point a to point b."
Cons: "Lack of good free snacks. Not getting free bag checked."

Pros: "Service"

Cons: "Waitied in the airplane for about an hour till take off. Wasnt offered anything to drink till after."

Pros: "All very happy staff and super professional service."

Cons: "Plane delay so for an hour flight I had to stay at the airport for 3 hours till the next flight. With not even a sorry."

Pros: "Boarding process"
Cons: "No food... Sporadic drinks.. Very cheap service"

Cons: "Not only did we sit on the plane for over an hour before taking off, but on an over four hour flight I was refused water towards the end. When I asked for more than one glass I was rudely told and I quote, "you know what? No. We have other passengers who may want water." Are you kidding me? I sat down feeling scolded and like I asked for something ridiculous. We landed after 2am and most of the passengers were sleeping and I doubt anyone asked for more water since I didn't see the flight attendant move again. Perhaps she was upset that I interrupted her from reading her paper? Extremely displeased with my experience. I"

Pros: "Smiling faces !"

Pros: "No me gusto nada."
Cons: "Fue una experiencia horrible. La tardanza del vuelo fue excesiva. Nadie daba explicacion alguna. NO ofrecieron alojamiento en hotel y solo dieron $10 para comida que daban para muy poco porque los precios son altos."

Cons: "United airlines.. Terrible"

Pros: "Everything was great"
Cons: "Nothing"

Pros: "It was a short fast flight once in the air."
Cons: "Flight was delayed by at least 45 minutes, making me miss my connecting flight. After that I had to wait 7 hours for the next available flight. Also the connecting flight was all the way on the other side of the airport. No one at the airport would help with directions to the next boarding area."

Pros: "Everyone was friendly and smiling. Stewardess made contact with each person , very personable"
Cons: "Forty minute flight delay. Nobody had any real answers"

Cons: "Their system canceled (it auto confused itself) my tickets and we almost lost the flight. Good thing I'm always 4 hours earlier or else their juggling of seats would have been impossible."

Read more about Delta
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

Mandatory masks

Masks required on board, masks provided

Social distancing seating

Middle seats unavailable to book

Pre-flight testing

Testing for antibodies, testing for symptoms

Book cheap flights from Medford to Caribbean Islands

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