$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 10/20. 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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Flight Deals

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$628
George Town
George Town2 stops$628

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 - 12:57 pmMFR-SJU
15h 34m2 stops
Delta Logo
3:20 pm - 11:59 pmSJU-MFR
12h 39m2 stops
$431Delta
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Mon, Dec 8 - Wed, Dec 10
United Airlines Logo
6:35 pm - 12:49 pmMFR-SJU
14h 14m2 stops
United Airlines Logo
2:25 pm - 9:29 pmSJU-MFR
11h 04m1 stop
$521United Airlines
Find Deal
Wed, Feb 4 - Fri, Feb 13
United Airlines Logo
5:00 am - 6:25 pmMFR-SJU
9h 25m1 stop
United Airlines Logo
2:25 pm - 9:23 pmSJU-MFR
10h 58m1 stop
$568United Airlines
Find Deal
Mon, Feb 9 - Tue, Feb 10
United Airlines Logo
5:00 am - 6:25 pmMFR-SJU
9h 25m1 stop
United Airlines Logo
2:25 pm - 9:02 pmSJU-MFR
10h 37m1 stop
$591United Airlines
Find Deal
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
$615United Airlines
Find Deal
Mon, Nov 17 - Fri, Nov 21
American Airlines Logo
5:20 am - 8:28 pmMFR-GCM
12h 08m2 stops
American Airlines Logo
9:00 am - 11:04 pmGCM-MFR
17h 04m2 stops
$628American Airlines
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Tue, Oct 14 - Tue, Oct 21
American Airlines Logo
2:22 pm - 11:20 amMFR-GCM
18h 58m2 stops
American Airlines Logo
12:10 pm - 1:15 pmGCM-MFR
27h 05m2 stops
$638American Airlines
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Tue, Sep 30 - Sat, Oct 4
Multiple Airlines Logo
5:43 am - 4:05 pmMFR-GCM
32h 22m2 stops
Multiple Airlines Logo
4:00 pm - 11:25 amGCM-MFR
21h 25m1 stop
$989Multiple Airlines
Find Deal
Sat, Oct 4 - Thu, Oct 9
Multiple Airlines Logo
6:00 am - 3:30 pmMFR-GCM
31h 30m1 stop
Multiple Airlines Logo
7:00 am - 11:16 amGCM-MFR
30h 16m2 stops
$1,072Multiple Airlines
Find Deal
Thu, Feb 5 - Mon, Feb 16
Alaska Airlines Logo
5:45 am - 10:14 pmMFR-SJU
12h 29m2 stops
Alaska Airlines Logo
4:25 pm - 3:00 pmSJU-MFR
26h 35m2 stops
$1,464Alaska 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 $277, prices are generally cheapest when you fly direct.

Good to know

Low seasonJune
Cheapest flight$216
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 73% 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
8.1Boarding
7.1Food
7.8Comfort
8.5Crew
7.1Entertainment
Airline reviews

Didn't buy food and did not use entertainment as these were not the purpose of my flight.

10.0 ExcellentAnonymous, Sep 2025PDX - MCI
Read more Alaska Airlines reviews

Didn't buy food and did not use entertainment as these were not the purpose of my flight.

Website could be better with faster access to specific flight information and boarding pass once reservation is made. Not a fan of no seat selection on line. I had to consult gate agent each time to change seats on flights with lots of open seats. This cannot possibly be cost effective for airline. On plus side, Alaska seat legroom seemed larger than American. ns

Staff inside Portland terminal were rude, made us fell rushed and not at all accommodating to seniors. For this alone I will probably never booked from them again.

It was fine—the seats are not very comfortable and the aisles are very narrow. Nothing different from other airlines

I booked a round trip. I ordered a lunch going and a lunch for the return but got both lunches going. Could have been my error. Both lunches were good.

Well the flight being delayed multiple time really was frustrating. But the crew and flight was good.

generally good. No snacks or drinks on the flight 3379 from Portland to San Jose, CA. Sad.

Everything except for the lack of a choice of the snack provided was great.

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.

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

Everything you need to know for your flight to Caribbean Islands

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