$462 Find Cheap Flights from Medford to Caribbean

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 departing on 4/28. 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

Tue, Apr 28 - Mon, May 4
American Airlines Logo
4:24 pm - 10:53 am
MFR
-
SJU
15h 29m
2 stops
American Airlines Logo
11:59 pm - 2:57 pm
SJU
-
MFR
17h 58m
2 stops
$462American Airlines
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:25 pm - 11:58 am
MFR
-
SJU
15h 33m
2 stops
Delta Logo
7:00 am - 11:13 pm
SJU
-
MFR
19h 13m
2 stops
$529Delta
Fri, Apr 17 - Mon, Apr 20
United Airlines Logo
6:31 pm - 1:45 pm
MFR
-
SJU
16h 14m
2 stops
United Airlines Logo
1:00 am - 11:48 am
SJU
-
MFR
13h 48m
2 stops
$584United Airlines
Fri, Apr 17 - Tue, Apr 21
United Airlines Logo
2:12 pm - 12:04 pm
MFR
-
SJU
18h 52m
3 stops
United Airlines Logo
7:40 am - 11:14 pm
SJU
-
MFR
18h 34m
2 stops
$609United Airlines
Sun, Mar 8 - Thu, Mar 12
Delta Logo
5:30 pm - 4:18 pm
MFR
-
SJU
19h 48m
2 stops
Delta Logo
7:30 am - 10:49 pm
SJU
-
MFR
18h 19m
2 stops
$616Delta
Fri, Apr 17 - Tue, Apr 21
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
7:40 am - 11:14 pm
SJU
-
MFR
18h 34m
2 stops
$620United Airlines
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:25 pm - 11:58 am
MFR
-
SJU
15h 33m
2 stops
Delta Logo
7:00 am - 11:13 pm
SJU
-
MFR
19h 13m
2 stops
$629Delta
Wed, Aug 19 - Mon, Aug 24
American Airlines Logo
6:05 am - 11:40 pm
MFR
-
SJU
14h 35m
2 stops
American Airlines Logo
8:00 am - 11:24 pm
SJU
-
MFR
18h 24m
2 stops
$635American Airlines
Sun, Mar 8 - Thu, Mar 12
United Airlines Logo
5:00 am - 5:25 pm
MFR
-
SJU
9h 25m
1 stop
United Airlines Logo
7:30 am - 9:18 pm
SJU
-
MFR
16h 48m
2 stops
$636United Airlines
Tue, Apr 28 - Sun, May 3
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m
2 stops
$653United 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 ($620) and Delta ($629).

Find deals

Good to know

Low seasonJune
Cheapest flight$462
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 9335 reviews
8.1Crew
7.1Entertainment
7.7Boarding
7.3Comfort
6.6Food
Airline reviews

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

10.0 ExcellentElizabeth, Feb 2026
ATL - IAH
Read more United Airlines reviews

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

Overall we had a good experience during our flight from San Francisco to Houston.

Airport terminal was outdated, flight was on a small jet with no wifi

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

it was a very short flight so my expectations were low.

As great a red-eye flight as red-eye flights can be.

Once boarding started it was pretty quick. Food was inedible; cold and salty..

Entertainment kept turning itself off. Gave up on watching a movie.

Both the WIFI and entertainment did not work for 2.5h

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Medford (MFR)