$431 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 2/24. 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

Tue, Feb 24 - Thu, Mar 5
American Airlines Logo
5:25 am - 11:32 pm
MFR
-
SJU
14h 07m2 stops
American Airlines Logo
8:30 am - 11:59 pm
SJU
-
MFR
19h 29m2 stops
$431American Airlines
Tue, May 5 - Wed, May 6
United Airlines Logo
6:34 pm - 1:45 pm
MFR
-
SJU
16h 11m2 stops
United Airlines Logo
1:00 am - 11:47 am
SJU
-
MFR
13h 47m2 stops
$516United Airlines
Tue, May 5 - Wed, May 6
United Airlines Logo
2:09 pm - 12:34 pm
MFR
-
SJU
19h 25m3 stops
United Airlines Logo
1:00 am - 11:47 am
SJU
-
MFR
13h 47m2 stops
$521United Airlines
Tue, Apr 7 - Tue, Apr 14
United Airlines Logo
6:34 pm - 12:34 pm
MFR
-
SJU
15h 00m2 stops
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m2 stops
$543United Airlines
Mon, Jan 26 - Thu, Jan 29
United Airlines Logo
6:25 pm - 1:15 pm
MFR
-
GCM
15h 50m2 stops
United Airlines Logo
2:50 pm - 9:02 pm
GCM
-
MFR
33h 12m2 stops
$597United Airlines
Tue, May 5 - Thu, May 7
United Airlines Logo
5:10 am - 5:38 pm
MFR
-
SJU
9h 28m1 stop
United Airlines Logo
1:40 pm - 9:10 pm
SJU
-
MFR
10h 30m1 stop
$633United Airlines
Tue, Apr 7 - Wed, Apr 15
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m1 stop
United Airlines Logo
1:40 pm - 9:26 pm
SJU
-
MFR
10h 46m1 stop
$654United Airlines
Tue, Apr 7 - Wed, Apr 15
United Airlines Logo
2:03 pm - 2:44 pm
MFR
-
SJU
21h 41m3 stops
United Airlines Logo
7:20 am - 9:26 pm
SJU
-
MFR
17h 06m2 stops
$718United Airlines
Mon, Dec 22 - Mon, Dec 29
United Airlines Logo
6:34 pm - 6:25 pm
MFR
-
SJU
19h 51m2 stops
United Airlines Logo
3:46 pm - 1:25 pm
SJU
-
MFR
25h 39m2 stops
$1,205United Airlines
Mon, Dec 22 - Mon, Dec 29
United Airlines Logo
12:50 pm - 4:36 pm
MFR
-
SJU
23h 46m2 stops
United Airlines Logo
7:45 am - 10:57 pm
SJU
-
MFR
19h 12m2 stops
$1,366United Airlines
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 $309, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonJune
Cheapest flight$431
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 71% 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 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.
7.4
United AirlinesOverall score based on 9095 reviews
7.1Entertainment
7.7Boarding
6.6Food
8.1Crew
7.3Comfort
Airline reviews

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

10.0 ExcellentMichele, Dec 2025
RSW - ORD
Read more United Airlines reviews

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

United have really come back. Airport and boarding process is clear and good, app and information also very good

They charged a fee for 1st bag checked. Others in same party were free.

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Medford (MFR)