$381 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 7/6. 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

Mon, Sep 14 - Fri, Sep 18
United Airlines Logo
6:28 pm - 2:44 pm
MFR
-
SJU
17h 16m
2 stops
United Airlines Logo
1:00 am - 12:02 pm
SJU
-
MFR
14h 02m
2 stops
$542United Airlines
Mon, Sep 14 - Sat, Sep 19
United Airlines Logo
6:28 pm - 11:57 am
MFR
-
SJU
14h 29m
2 stops
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m
2 stops
$571United Airlines
Mon, Sep 14 - Sat, Sep 19
United Airlines Logo
6:28 pm - 2:44 pm
MFR
-
SJU
17h 16m
2 stops
United Airlines Logo
2:00 pm - 9:08 pm
SJU
-
MFR
10h 08m
1 stop
$660United Airlines
Mon, Sep 14 - Sat, Sep 19
United Airlines Logo
6:28 pm - 2:44 pm
MFR
-
SJU
17h 16m
2 stops
United Airlines Logo
2:00 pm - 9:08 pm
SJU
-
MFR
10h 08m
1 stop
$662United Airlines
Mon, Sep 14 - Sat, Sep 19
United Airlines Logo
6:28 pm - 2:44 pm
MFR
-
SJU
17h 16m
2 stops
United Airlines Logo
2:00 pm - 9:08 pm
SJU
-
MFR
10h 08m
1 stop
$663United Airlines
Mon, Sep 14 - Sat, Sep 19
United Airlines Logo
6:28 pm - 11:57 am
MFR
-
SJU
14h 29m
2 stops
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m
3 stops
$674United Airlines
Mon, Aug 31 - Wed, Sep 2
United Airlines Logo
2:07 pm - 11:57 am
MFR
-
SJU
18h 50m
3 stops
United Airlines Logo
7:00 am - 5:58 pm
SJU
-
MFR
13h 58m
2 stops
$699United Airlines
Mon, Aug 31 - Wed, Sep 2
United Airlines Logo
2:07 pm - 3:42 pm
MFR
-
SJU
22h 35m
2 stops
United Airlines Logo
7:00 am - 5:58 pm
SJU
-
MFR
13h 58m
2 stops
$771United Airlines
Mon, Aug 31 - Wed, Sep 2
United Airlines Logo
5:00 am - 11:50 pm
MFR
-
SJU
15h 50m
2 stops
United Airlines Logo
7:00 am - 5:58 pm
SJU
-
MFR
13h 58m
2 stops
$774United Airlines
Fri, Jul 10 - Mon, Jul 20
American Airlines Logo
6:08 am - 10:59 pm
MFR
-
SJU
13h 51m
2 stops
American Airlines Logo
10:35 am - 10:02 pm
SJU
-
MFR
14h 27m
2 stops
$796American 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.

What is the cheapest month to fly from Medford to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Medford to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Medford to Caribbean is January, when tickets cost $411 (return) on average. On the other hand, the most expensive months are March and July, when the average cost of round-trip tickets is $2,196 and $946 respectively.

Find deals

Good to know

Low seasonMarch
Cheapest flight$381
Best time to beat the crowds but there is an average 123% increase in price.
Most popular time to fly and prices are also 35% 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 9901 reviews
8.1Crew
7.3Comfort
6.6Food
7.7Boarding
7.1Entertainment
Airline reviews

The flight was delayed from take off because only one runway was operational in San Francisco.

2.0 MediocreMartin, Apr 2026
EUG - SFO
Read more United Airlines reviews

The flight was delayed from take off because only one runway was operational in San Francisco.

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

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

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

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

We had a 90 minute delay due to equipment failure that was detected just before we took off. United rebooked my connecting flight.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

This was a Lufthansa flight. Disappointing main meal. Very rough over Canada and arrival at FRA. IFE was almost unusable.

Poor seating comfort, seat cushion too thin, very uncomfortable. My luggage didi not make the flight due to equipment change. At least. United had it delivered the next day. I was without my toilet items for one day.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Medford (MFR)