$383 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 12/13. 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

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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Flight Deals

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
5:23 pm - 12:58 pmMFR-SJU
15h 35m2 stops
Delta Logo
3:10 pm - 11:59 pmSJU-MFR
12h 49m2 stops
$431Delta
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Tue, Feb 24 - Wed, Mar 4
United Airlines Logo
5:02 am - 12:36 amMFR-SJU
15h 34m2 stops
United Airlines Logo
2:05 am - 5:41 pmSJU-MFR
19h 36m2 stops
$521United Airlines
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Fri, Jan 23 - Sun, Feb 1
United Airlines Logo
6:00 am - 10:22 pmMFR-SJU
12h 22m2 stops
United Airlines Logo
8:10 am - 9:02 pmSJU-MFR
16h 52m2 stops
$543United Airlines
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Mon, Nov 10 - Thu, Nov 13
United Airlines Logo
6:36 pm - 1:17 pmMFR-SJU
14h 41m2 stops
United Airlines Logo
2:05 am - 1:23 pmSJU-MFR
15h 18m2 stops
$585United Airlines
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Fri, Jan 23 - Sun, Feb 1
United Airlines Logo
5:00 am - 6:25 pmMFR-SJU
9h 25m1 stop
United Airlines Logo
8:10 am - 9:02 pmSJU-MFR
16h 52m2 stops
$641United Airlines
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Mon, Nov 17 - Fri, Nov 21
Delta Logo
6:00 am - 12:35 pmMFR-GCM
27h 35m2 stops
Delta Logo
1:50 pm - 11:00 amGCM-MFR
24h 10m2 stops
$661Delta
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Mon, Nov 10 - Thu, Nov 13
American Airlines Logo
3:00 pm - 3:18 pmMFR-SKB
20h 18m2 stops
American Airlines Logo
4:28 pm - 1:59 pmSKB-MFR
25h 31m2 stops
$1,033American Airlines
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Sun, Nov 9 - Thu, Nov 13
American Airlines Logo
3:00 pm - 3:18 pmMFR-SKB
20h 18m2 stops
American Airlines Logo
4:28 pm - 1:59 pmSKB-MFR
25h 31m2 stops
$1,082American Airlines
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Mon, Dec 22 - Mon, Dec 29
American Airlines Logo
3:12 pm - 9:35 amMFR-SJU
14h 23m2 stops
American Airlines Logo
5:24 am - 8:20 pmSJU-MFR
18h 56m2 stops
$1,425American Airlines
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Mon, Dec 22 - Sun, Dec 28
American Airlines Logo
3:12 pm - 9:35 amMFR-SJU
14h 23m2 stops
American Airlines Logo
1:30 am - 1:59 pmSJU-MFR
16h 29m2 stops
$1,524American Airlines
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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 $272, prices are generally cheapest when you fly direct.

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Good to know

Low seasonJune
Cheapest flight$383
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 70% lower on average.
Flight from Medford to San Juan Airport

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 airline 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.
7.2
American AirlinesOverall score based on 11033 reviews
6.4Food
7.5Boarding
6.9Entertainment
7.2Comfort
8.0Crew
Airline reviews

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

10.0 ExcellentMax, Oct 2025DCA - SAV
Read more American Airlines reviews

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

The only thing to like was that we eventually got to our destination

Delayed delayed delayed and no offer for food or vouchers

Disliked having to wait a little longer to disembark from the plan when we landed in London

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Medford (MFR)

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