$216 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 12/6. 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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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
$521United Airlines
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Tue, Feb 24 - Thu, Mar 5
United Airlines Logo
7:00 am - 6:25 pmMFR-SJU
31h 25m3 stops
United Airlines Logo
8:10 am - 9:23 pmSJU-MFR
17h 13m2 stops
$567United Airlines
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Mon, Dec 8 - Tue, Dec 9
United Airlines Logo
5:00 am - 6:25 pmMFR-SJU
9h 25m1 stop
United Airlines Logo
2:05 am - 1:23 pmSJU-MFR
15h 18m2 stops
$588United Airlines
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Mon, Dec 8 - Tue, Dec 9
United Airlines Logo
5:00 am - 10:22 pmMFR-SJU
13h 22m2 stops
United Airlines Logo
2:05 am - 1:23 pmSJU-MFR
15h 18m2 stops
$591United Airlines
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Tue, Feb 24 - Wed, Mar 4
United Airlines Logo
7:00 am - 4:36 pmMFR-SJU
29h 36m2 stops
United Airlines Logo
2:05 am - 5:41 pmSJU-MFR
19h 36m2 stops
$603United Airlines
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Fri, Jan 16 - Sun, Jan 25
American Airlines Logo
4:47 pm - 10:48 amMFR-SJU
14h 01m2 stops
American Airlines Logo
6:00 am - 7:38 pmSJU-MFR
17h 38m2 stops
$618American Airlines
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Tue, Nov 25 - Sat, Nov 29
Multiple Airlines Logo
6:37 pm - 5:21 pmMFR-SJU
18h 44m3 stops
Multiple Airlines Logo
6:00 am - 9:03 pmSJU-MFR
19h 03m3 stops
$1,056Multiple Airlines
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Tue, Nov 25 - Sat, Nov 29
Multiple Airlines Logo
6:37 pm - 8:27 pmMFR-SJU
21h 50m2 stops
Multiple Airlines Logo
6:00 am - 9:03 pmSJU-MFR
19h 03m3 stops
$1,067Multiple Airlines
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Tue, Nov 25 - Sat, Nov 29
American Airlines Logo
1:45 pm - 6:10 amMFR-SJU
12h 25m2 stops
American Airlines Logo
6:25 am - 5:18 pmSJU-MFR
14h 53m2 stops
$1,128American 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 $280, prices are generally cheapest when you fly direct.

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Good to know

Low seasonJune
Cheapest flight$216
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 11049 reviews
8.0Crew
7.5Boarding
6.4Food
7.2Comfort
6.9Entertainment
Airline reviews

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

10.0 ExcellentAnonymous, Nov 2025MIA - LAX
Read more American Airlines reviews

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We were very rushed by a staff member at the gate when transferring from American Airlines to Fijian. Then the plane stayed put for ages anyhow! The plane was delayed and my bag sent to San Francisco instead of Fiji

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Medford (MFR)