$415 Find Cheap Flights from Medford to Caribbean Islands

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 Islands departing on 12/8. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Medford to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Medford to Caribbean Islands, as well as popular online travel agencies
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Best Caribbean Islands Flight Deals from Medford

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town2 stops$678
George Town
George Town2 stops$678

Cheap Flights from Medford to Caribbean Islands

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Medford to Caribbean Islands 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 Islands

Mon, Dec 8 - Wed, Dec 10
Delta Logo
5:21 pm - 12:58 pmMFR-SJU
15h 37m2 stops
Delta Logo
2:26 pm - 11:44 pmSJU-MFR
13h 18m2 stops
$415Delta
Find Deal
Mon, Dec 8 - Wed, Dec 10
American Airlines Logo
3:30 pm - 12:05 pmMFR-SJU
16h 35m2 stops
American Airlines Logo
5:50 am - 7:13 pmSJU-MFR
17h 23m2 stops
$501American Airlines
Find Deal
Mon, Dec 8 - Wed, Dec 10
United Airlines Logo
6:30 pm - 2:40 pmMFR-SJU
16h 10m2 stops
United Airlines Logo
2:25 pm - 9:20 pmSJU-MFR
10h 55m1 stop
$505United Airlines
Find Deal
Mon, Nov 24 - Fri, Dec 5
American Airlines Logo
7:00 am - 2:10 amMFR-SJU
15h 10m2 stops
American Airlines Logo
8:09 am - 7:13 pmSJU-MFR
15h 04m2 stops
$520American Airlines
Find Deal
Mon, Dec 8 - Wed, Dec 10
United Airlines Logo
6:30 pm - 2:40 pmMFR-SJU
16h 10m2 stops
United Airlines Logo
2:25 pm - 11:01 pmSJU-MFR
36h 36m3 stops
$617United Airlines
Find Deal
Thu, Sep 11 - Sun, Sep 14
American Airlines Logo
6:00 am - 11:37 pmMFR-SJU
14h 37m2 stops
American Airlines Logo
7:05 pm - 2:13 pmSJU-MFR
22h 08m2 stops
$625American Airlines
Find Deal
Mon, Dec 8 - Tue, Dec 9
United Airlines Logo
5:10 am - 6:25 pmMFR-SJU
9h 15m1 stop
United Airlines Logo
2:05 am - 11:01 pmSJU-MFR
24h 56m2 stops
$655United Airlines
Find Deal
Mon, Nov 17 - Fri, Nov 21
American Airlines Logo
3:30 pm - 12:00 pmMFR-GCM
17h 30m2 stops
American Airlines Logo
8:30 am - 7:07 pmGCM-MFR
13h 37m2 stops
$678American Airlines
Find Deal
Mon, Nov 24 - Thu, Dec 4
United Airlines Logo
6:00 am - 12:36 amMFR-SJU
14h 36m2 stops
United Airlines Logo
2:05 am - 11:01 pmSJU-MFR
24h 56m2 stops
$703United Airlines
Find Deal
Mon, Nov 17 - Fri, Nov 21
Delta Logo
11:23 am - 12:37 pmMFR-GCM
22h 14m2 stops
Delta Logo
2:02 pm - 10:55 amGCM-MFR
23h 53m2 stops
$710Delta
Find Deal
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KAYAK's insights & trends for Medford to Caribbean Islands flights

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

Can I save money by flying with a layover from Medford to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $418, prices are generally cheapest when you fly direct.


Good to know

Cheapest flight$415
Flight from Medford to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Medford to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands?

    The cheapest time of day to fly to Caribbean Islands 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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Medford to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Medford to Caribbean Islands? 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.
8.0
Alaska AirlinesOverall score based on 10000 reviews
7.8Comfort
8.1Boarding
7.1Entertainment
8.5Crew
7.1Food
Airline reviews

We have always flown with Alaska when we can. As they have great customer service. This trip we had to transfer to Air LINGUS in Denver to go to Dublin. That’s where things went bad! Our checked luggage didn’t arrive. The process to make a claim was way more complicated than it should be. It took 5 days to recover our luggage. The whole time we couldn’t talk to a real person who could tell us anything. The whole time Alaska blamed Air lingus and vis a versa. No one seemed want to help us. That was the worst part.

2.0 MediocreAnonymous, Jun 2025PDX - DEN
Read more Alaska Airlines reviews

We have always flown with Alaska when we can. As they have great customer service. This trip we had to transfer to Air LINGUS in Denver to go to Dublin. That’s where things went bad! Our checked luggage didn’t arrive. The process to make a claim was way more complicated than it should be. It took 5 days to recover our luggage. The whole time we couldn’t talk to a real person who could tell us anything. The whole time Alaska blamed Air lingus and vis a versa. No one seemed want to help us. That was the worst part.

I'm a platinum member with American Airlines, however, my ticket did not display status and thus I did not board with an early group. I traveled with my two daughters and we were given a row of seats that did not recline. Not the treatment I would have expected for a platinum customer. The flight was also a bit late leaving Portland. Also on my flight to Portland we were not given premium seats. In fact, we were in the last row of the aircraft.

I was at risk of not getting on the flight, as when I presented my boarding pass at the gate, it showed me as not having checked in. I was sent to the desk as the last of the other passengers boarded. The agent there said he could see that I had done all of my part and allowed times recommended, but it showed me as not checked in and he couldn't figure out how to correct it. He actually asked them to hold the flight as he struggled with it. He called for support, someone corrected it, and he printed boarding passes for both flights to reduce further issues. I did get on, and needed to ask someone to exit my seat.

We had a birthday one day off and almost missed the plane Our fault

5 hour delay from Portland to Newark. Boarded and then were told we had to get off and wait five hours for flight. No food vouchers or any other compensation because they said it was an air traffic control issue. Plane is bare minimum like a discount airline. They have free entertainment but you have to get to it on your own device no screens in the seats

Alaska app and website had numerous problems so couldn’t get boarding passes or check seats

Very good. Gate personnel were excellent flight attendants were also able to change my seat at the last minute everyone, courteous, polite, and.

It was horrible. Last minute gate change, delays, more delays and then we had to wait for a stweardess to onboard. No explanation for the wait. No apologies. We got to RDM way past schedule @ 1:30 am!!!! Stressful and exhausting. We'd avoid flying Alaska ever again.

On time, smooth take off and landing, efficient boarding. Gate staff excellent, stewardess grumpy, but civil enough.

No WiFi available. It was too late to order food also. Guy next to me was huge (not fat) so had his shoulder & thigh next to me the whole way. Plane was delayed leaving PDX due to 8 other planes waiting. Not my best Alaska airlines flight.

The flight delay in Dallas created a domino effect that impacted all of the connecting flights. It also increased the number of connections. I missed my flight from Casablanca to Marrakech because of the tight turnaround when landing in Casablanca. . CMN airport was understaffed. Only one person could help while other employees were just watching him. It was an extremely frustrating situation. People were crying and slamming their palms on the counter when speaking to the customer service provider, Allabough (man’s name?). Allabough couldn’t change my flight in the system. simultaneously, I was on the call with America. Airlines customer service rep named Solomon that said he couldn’t change it either. So, I took a ONYA voyages train to from Casablanca to Marrakech to get there on Friday June 26. This was unpredictable trip.

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

This flight never occurred because AA couldn’t get their act together.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

Am still mad at American airlines. You should know it's us travel nurses who are your customers and you treat us like nonsense it's not ok. American airlines took my money, no refund for whatsoever. A trip that was of 466 and I paid 466 and 833 then they chose for me where to sit and refund my seat choices and gave me expensive seats for 79 USD. Kayak doesn't help at all after booking you are on your own. Skyscanner is better

Bad food, small seats that didn’t recline. I thought I was buying a quantas ticket so I feel like I got scammed

This was a horrible experience. For a first class experience, my chair was held together by 3M tape - and I have a photo. The crew weren’t very attentive, somewhat dismissive and forgot my drink and snack, the chair reclined about 3 inches on a 6-hour cross country flight. I was also not informed that there was no lounge available in Newark airport because of renovations, so all around this was one of the worst experiences and I would actively avoid both American and Alaska Air going forward.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Everything you need to know for your flight to Caribbean Islands

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