$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 2/25. 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
American Airlines Logo
5:13 am - 11:34 pm
MFR
-
SJU
14h 21m
2 stops
American Airlines Logo
1:58 pm - 11:18 pm
SJU
-
MFR
13h 20m
2 stops
$452American Airlines
Mon, Mar 2 - Tue, Mar 3
United Airlines Logo
6:25 pm - 2:40 pm
MFR
-
SJU
16h 15m
2 stops
United Airlines Logo
2:05 am - 5:42 pm
SJU
-
MFR
19h 37m
2 stops
$537United Airlines
Thu, Mar 5 - Tue, Mar 10
United Airlines Logo
6:22 pm - 3:40 pm
MFR
-
SJU
17h 18m
2 stops
United Airlines Logo
7:05 am - 9:18 pm
SJU
-
MFR
17h 13m
2 stops
$572United Airlines
Fri, Apr 10 - Fri, Apr 17
United Airlines Logo
6:31 pm - 12:34 pm
MFR
-
SJU
15h 03m
2 stops
United Airlines Logo
1:40 pm - 9:37 pm
SJU
-
MFR
10h 57m
1 stop
$580United Airlines
Mon, Feb 23 - Wed, Feb 25
United Airlines Logo
5:02 am - 6:25 pm
MFR
-
SJU
9h 23m
1 stop
United Airlines Logo
7:40 am - 10:28 pm
SJU
-
MFR
18h 48m
2 stops
$619United 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 - 10:59 am
GCM
-
MFR
23h 09m
2 stops
$656United Airlines
Mon, Feb 23 - Wed, Feb 25
United Airlines Logo
6:25 pm - 3:40 pm
MFR
-
SJU
17h 15m
2 stops
United Airlines Logo
7:40 am - 10:28 pm
SJU
-
MFR
18h 48m
2 stops
$689United Airlines
Mon, Feb 23 - Wed, Feb 25
United Airlines Logo
5:02 am - 6:25 pm
MFR
-
SJU
9h 23m
1 stop
United Airlines Logo
7:40 am - 10:28 pm
SJU
-
MFR
18h 48m
2 stops
$696United Airlines
Tue, Mar 17 - Tue, Mar 24
United Airlines Logo
5:00 am - 11:36 pm
MFR
-
SJU
15h 36m
2 stops
United Airlines Logo
7:05 am - 10:58 pm
SJU
-
MFR
18h 53m
2 stops
$724United Airlines
Sat, Mar 7 - Sat, Mar 14
United Airlines Logo
2:00 pm - 6:11 am
MFR
-
SJU
12h 11m
2 stops
United Airlines Logo
7:30 am - 9:23 pm
SJU
-
MFR
16h 53m
2 stops
$745United 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 American Airlines ($452) and United Airlines ($537).

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 9250 reviews
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
Airline reviews

Same thing as flight from Pheonix to Newark. Uograded and Promised extra leg room and when I got to the seat it had none.

2.0 MediocrePiers, Feb 2026
EWR - DXB
Read more United Airlines reviews

Same thing as flight from Pheonix to Newark. Uograded and Promised extra leg room and when I got to the seat it had none.

I upgraded my seat and was promised it would be next to the emergency door for extra leg room and they said it was premium plus but it was at the back of the plane...same thing happened from Newark to Dubai

Everything except the food and entertainment. It was a great experience though

Bad food, bad service, cold cabin with no additional blankets when asked for (they told me they don’t provide additional blankets). I’m a frequent traveler and this is one of the worst companies I traveled with (by the way I thought that I booked my ticket with Lufthansa but I didn’t see that the flights were handled by United).

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

The attendant on board was amazing. She should be doing business/first international long haul.

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports