$206 Find Cheap Flights from Medford to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Medford to Caribbean Islands departing on 10/29. 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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Cheap Flights from Medford to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town2 stops$549
George Town
George Town2 stops$549

Book Cheap Medford to Caribbean Islands 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 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
3:25 pm - 11:44 pmSJU-MFR
12h 19m2 stops
$411Delta
Find Deal
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
$463Delta
Find Deal
Mon, Dec 8 - Wed, Dec 10
United Airlines Logo
5:00 am - 6:25 pmMFR-SJU
9h 25m1 stop
United Airlines Logo
2:25 pm - 9:29 pmSJU-MFR
11h 04m1 stop
$501United Airlines
Find Deal
Mon, Nov 17 - Fri, Nov 21
Delta Logo
5:55 am - 12:37 pmMFR-GCM
27h 42m2 stops
Delta Logo
2:02 pm - 10:55 amGCM-MFR
23h 53m2 stops
$549Delta
Find Deal
Mon, Dec 1 - Mon, Dec 15
United Airlines Logo
6:36 pm - 4:30 pmMFR-GCM
18h 54m2 stops
United Airlines Logo
5:45 pm - 12:09 pmGCM-MFR
21h 24m2 stops
$568United Airlines
Find Deal
Wed, Oct 29 - Sun, Nov 2
Delta Logo
5:24 pm - 11:56 amMFR-SJU
15h 32m2 stops
Delta Logo
7:00 am - 4:44 pmSJU-MFR
13h 44m2 stops
$595Delta
Find Deal
Thu, Oct 30 - Sun, Nov 2
Delta Logo
5:15 am - 9:59 pmMFR-SJU
13h 44m2 stops
Delta Logo
7:00 am - 4:44 pmSJU-MFR
13h 44m2 stops
$605Delta
Find Deal
Thu, Jan 15 - Mon, Jan 26
American Airlines Logo
3:25 pm - 11:45 amMFR-SJU
16h 20m2 stops
American Airlines Logo
6:50 pm - 12:58 pmSJU-MFR
22h 08m2 stops
$712American Airlines
Find Deal
Mon, Nov 10 - Thu, Nov 13
American Airlines Logo
3:00 pm - 2:39 pmMFR-SKB
19h 39m2 stops
American Airlines Logo
3:39 pm - 1:54 pmSKB-MFR
26h 15m2 stops
$812American Airlines
Find Deal
Mon, Dec 22 - Sun, Dec 28
Alaska Airlines Logo
1:20 pm - 5:05 amMFR-SJU
11h 45m2 stops
Alaska Airlines Logo
1:30 am - 8:11 pmSJU-MFR
22h 41m2 stops
$1,604Alaska Airlines
Find Deal
Booking Insights

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 $397, prices are generally cheapest when you fly direct.

Good to know

Low seasonJune
Cheapest flight$206
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 75% lower on average.
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
7.0Entertainment
8.1Boarding
7.1Food
8.5Crew
Airline reviews

All went smoothly. Only one delay departing Seattle of around 30 minutes.

8.0 ExcellentAnonymous, Aug 2025EUG - SEA
Read more Alaska Airlines reviews

All went smoothly. Only one delay departing Seattle of around 30 minutes.

I like the friendliness of the staff. The food choices were OK. I wish there was more options. The entertainment through the movie portal was alright.

First time flying with Alaska, and it went great. Thank you for a great experience flying to PDX.

There was a very drunk man behind me who kept talking loudly to no one in particular. He was slurring his words and at times he didn’t know where we were going or whether or not we landed. He was also loudly using a lot of profanity. The attendants didn’t seem to notice or care and in fact continued to serve him alcohol. He was allowed to purchase 4 little bottles.

We did not realize there wasn't any food apart from a small packet of pretzels - I dropped one and nearly cried.

I recently flew with Alaska Airlines on a trip to Oregon and had a very frustrating experience that I hope the airline can learn from. I purchased upgraded seats with extra legroom for my flight, paying the additional fees for the comfort and space. During my trip planning, I called customer service to inquire about their pet travel policies and conditions, as I was considering bringing my dogs. However, I ultimately decided NOT to bring my pets and never authorized or confirmed any pet travel arrangements. Despite this, Alaska Airlines took it upon themselves to change my seat assignment without any notification or contact. When I arrived for my flight, I discovered that my paid upgrade had been downgraded to a regular seat - presumably because they assumed I would be traveling with pets based on my inquiry call. I hope Alaska Airlines will improve their communication processes and ensure that customer inquiries don’t automatically trigger booking changes without explicit customer authorization. Better staff training on distinguishing between inquiries and actual bookings would prevent this type of situation in the future. While I appreciate that the airline tries to accommodate pet travelers, making assumptions and changes without customer consent is poor service that needs to be addressed.

It was a good flight, short so there was no food or water service

The customer service personnel were excellent. We had pre-ordered two meals but they could only provide one of them; they substituted the meal with a snack at no charge. Flight was on-time.

The friendliest flight attendants at flight 2276 from Portland to YVR August 3

Both flights delayed while the crew blamed it on local festivities instead of the truth of not having enough staff.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

Great flight. No issues at all. I still think boarding could be more efficient but otherwise, a good experience.

Pretty good. The food was just mediocre, the boarding and crew were good.

The comfort of the seats was great, the crew eased my child’s anxieties and the fact that I had full cans of my beverage choice was great.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

Sat on the ground in Cincinnati for 50 minutes before deplaning

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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