$226 Find Cheap Flights from Medford to Caribbean

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 departing on 3/2. 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

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Flight Deals

Book Cheap Medford to Caribbean 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 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

Wed, Feb 25 - Wed, Mar 4
United Airlines Logo
5:02 am - 12:36 am
MFR
-
SJU
15h 34m
2 stops
United Airlines Logo
8:30 am - 9:18 pm
SJU
-
MFR
16h 48m
2 stops
$542United Airlines
Wed, Feb 25 - Wed, Mar 4
United Airlines Logo
5:02 am - 12:36 am
MFR
-
SJU
15h 34m
2 stops
United Airlines Logo
8:30 am - 9:18 pm
SJU
-
MFR
16h 48m
2 stops
$600United Airlines
Sun, Feb 15 - Thu, Feb 19
Delta Logo
5:55 am - 11:58 pm
MFR
-
SJU
14h 03m
2 stops
Delta Logo
7:30 am - 11:56 pm
SJU
-
MFR
20h 26m
2 stops
$606Delta
Mon, Mar 2 - Thu, Mar 5
United Airlines Logo
2:00 pm - 1:15 pm
MFR
-
GCM
20h 15m
2 stops
United Airlines Logo
2:50 pm - 10:59 am
GCM
-
MFR
23h 09m
2 stops
$656United Airlines
Mon, Mar 16 - Mon, Mar 23
United Airlines Logo
6:22 pm - 12:15 pm
MFR
-
GCM
15h 53m
2 stops
United Airlines Logo
4:45 pm - 10:59 am
GCM
-
MFR
20h 14m
2 stops
$660United Airlines
Mon, Mar 2 - Thu, Mar 5
United Airlines Logo
6:25 pm - 1:15 pm
MFR
-
GCM
15h 50m
2 stops
United Airlines Logo
2:50 pm - 9:18 pm
GCM
-
MFR
33h 28m
2 stops
$673United Airlines
Wed, Feb 25 - Fri, Feb 27
United Airlines Logo
5:02 am - 12:36 am
MFR
-
SJU
15h 34m
2 stops
United Airlines Logo
2:05 am - 1:19 pm
SJU
-
MFR
15h 14m
2 stops
$742United Airlines
Sun, Feb 15 - Thu, Feb 19
United Airlines Logo
5:02 am - 6:25 pm
MFR
-
SJU
9h 23m
1 stop
United Airlines Logo
2:25 pm - 9:18 pm
SJU
-
MFR
10h 53m
1 stop
$931United Airlines
Mon, Mar 16 - Mon, Mar 23
American Airlines Logo
4:30 pm - 11:05 am
MFR
-
GCM
16h 35m
2 stops
American Airlines Logo
7:45 am - 11:13 pm
GCM
-
MFR
17h 28m
3 stops
$2,692American Airlines
Mon, Mar 16 - Mon, Mar 23
American Airlines Logo
5:14 am - 7:15 pm
MFR
-
GCM
12h 01m
3 stops
American Airlines Logo
7:45 am - 11:13 pm
GCM
-
MFR
17h 28m
3 stops
$3,495American Airlines
Booking Insights

KAYAK's insights & trends for Medford to Caribbean flights

Get data-powered insights and trends into flights from Medford to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Medford to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Medford to Caribbean were found on United Airlines ($542) and Delta ($606).

Good to know

Low seasonJune
Cheapest flight$226
Best time to beat the crowds with an average 8% 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 flights

  • How does KAYAK find such low prices on flights from Medford to Caribbean?

    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.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Medford to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Medford to Caribbean 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?

    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 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?

    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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Medford to Caribbean

 
Need help choosing which airline to fly with from Medford to Caribbean? 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 9222 reviews
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
7.3Comfort
Airline reviews

Although our flight was delayed the overall boarding process was very smooth and the crew was accommodating.

10.0 ExcellentLori, Jan 2026
EWR - BGI
Read more United Airlines reviews

Although our flight was delayed the overall boarding process was very smooth and the crew was accommodating.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports