$431 Find Cheap Flights from Medford to Caribbean

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Medford to Caribbean departing on 2/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Book Cheap Medford to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Medford to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Medford to Caribbean

Tue, Feb 24 - Thu, Mar 5
American Airlines Logo
4:30 pm - 11:55 am
MFR
-
SJU
15h 25m2 stops
American Airlines Logo
8:30 am - 11:59 pm
SJU
-
MFR
19h 29m2 stops
$431American Airlines
Tue, May 5 - Wed, May 6
United Airlines Logo
6:34 pm - 1:45 pm
MFR
-
SJU
16h 11m2 stops
United Airlines Logo
1:00 am - 11:47 am
SJU
-
MFR
13h 47m2 stops
$516United Airlines
Tue, Feb 24 - Thu, Mar 5
United Airlines Logo
5:02 am - 12:36 am
MFR
-
SJU
15h 34m2 stops
United Airlines Logo
2:25 pm - 9:33 pm
SJU
-
MFR
11h 08m1 stop
$521United Airlines
Mon, Jan 26 - Thu, Jan 29
United Airlines Logo
6:25 pm - 1:15 pm
MFR
-
GCM
15h 50m2 stops
United Airlines Logo
2:50 pm - 1:19 pm
GCM
-
MFR
49h 29m2 stops
$597United Airlines
Tue, May 5 - Thu, May 7
United Airlines Logo
5:10 am - 5:38 pm
MFR
-
SJU
9h 28m1 stop
United Airlines Logo
1:40 pm - 9:10 pm
SJU
-
MFR
10h 30m1 stop
$633United Airlines
Mon, Jan 26 - Thu, Jan 29
United Airlines Logo
2:00 pm - 1:15 pm
MFR
-
GCM
20h 15m2 stops
United Airlines Logo
2:50 pm - 9:02 pm
GCM
-
MFR
33h 12m2 stops
$648United Airlines
Sun, May 24 - Sat, May 30
United Airlines Logo
6:34 pm - 1:45 pm
MFR
-
SJU
16h 11m2 stops
United Airlines Logo
1:05 am - 11:34 am
SJU
-
MFR
13h 29m2 stops
$747United Airlines
Sun, May 24 - Sat, May 30
United Airlines Logo
5:10 am - 5:30 pm
MFR
-
SJU
9h 20m1 stop
United Airlines Logo
1:05 am - 11:34 am
SJU
-
MFR
13h 29m2 stops
$786United Airlines
Sun, May 24 - Sun, May 31
United Airlines Logo
2:03 pm - 12:04 pm
MFR
-
SJU
19h 01m3 stops
United Airlines Logo
4:55 pm - 11:34 am
SJU
-
MFR
21h 39m2 stops
$830United Airlines
Sat, Mar 28 - Sat, Apr 4
American Airlines Logo
3:14 pm - 9:00 am
MFR
-
SJU
14h 46m2 stops
American Airlines Logo
1:30 am - 2:34 pm
SJU
-
MFR
16h 04m2 stops
$935American Airlines
Booking Insights

KAYAK's insights & trends for Medford to Caribbean flights

Get data-powered insights and trends into flights from Medford to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines fly non-stop between Medford and Caribbean?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Medford to Caribbean.

There are 2 airlines that fly nonstop from Medford to Caribbean. They are Delta and United Airlines. The cheapest airline for this route is Delta, with the best round-trip deal found costing $202 and arriving in San Juan Luis Munoz Marin Intl Airport (SJU). On average, Delta offers the best prices for nonstop flights between Medford and Caribbean.

Which airlines provide the cheapest flights from Medford to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Medford to Caribbean were found on American Airlines ($431) and United Airlines ($516).

Good to know

Low seasonJune
Cheapest flight$431
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 71% lower on average.
Flight from Medford to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Medford to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Medford to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Medford to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Medford to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Medford to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Medford to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Medford to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Medford to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost $869 on average. Morning departures are around 8% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $941.

Reviews of the top airlines flying from Medford to Caribbean

 
Need help choosing which airline to fly with from Medford to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8009 reviews
8.1Boarding
8.5Crew
7.9Comfort
7.3Food
7.9Entertainment
Airline reviews

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

10.0 ExcellentVenkata Krishna, Dec 2025
ATL - SDF
Read more Delta reviews

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

United have really come back. Airport and boarding process is clear and good, app and information also very good

They charged a fee for 1st bag checked. Others in same party were free.

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports