$334 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 6/1. 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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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, Aug 10 - Mon, Aug 17
American Airlines Logo
1:17 pm - 9:43 am
MFR
-
SJU
17h 26m
2 stops
American Airlines Logo
6:00 am - 10:02 pm
SJU
-
MFR
19h 02m
2 stops
$552American Airlines
Sat, Oct 24 - Tue, Oct 27
United Airlines Logo
6:34 pm - 1:40 pm
MFR
-
SJU
16h 06m
2 stops
United Airlines Logo
1:05 am - 1:09 pm
SJU
-
MFR
15h 04m
2 stops
$632United Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
1:24 pm - 9:39 am
MFR
-
SJU
17h 15m
2 stops
American Airlines Logo
7:00 am - 9:54 pm
SJU
-
MFR
17h 54m
2 stops
$669American Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
1:24 pm - 9:39 am
MFR
-
SJU
17h 15m
2 stops
American Airlines Logo
7:00 am - 9:54 pm
SJU
-
MFR
17h 54m
2 stops
$736American Airlines
Mon, Nov 2 - Thu, Nov 5
United Airlines Logo
2:03 pm - 4:30 pm
MFR
-
GCM
23h 27m
3 stops
United Airlines Logo
5:45 pm - 1:09 pm
GCM
-
MFR
22h 24m
2 stops
$756United Airlines
Tue, Jun 2 - Mon, Jun 8
United Airlines Logo
6:35 pm - 12:04 pm
MFR
-
SJU
14h 29m
2 stops
United Airlines Logo
2:05 am - 12:02 pm
SJU
-
MFR
12h 57m
2 stops
$759United Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
6:35 am - 9:59 pm
MFR
-
SJU
12h 24m
2 stops
American Airlines Logo
7:00 am - 9:54 pm
SJU
-
MFR
17h 54m
2 stops
$796American Airlines
Sat, Oct 24 - Wed, Oct 28
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:25 pm - 9:10 pm
SJU
-
MFR
10h 45m
1 stop
$799United Airlines
Sun, Jul 19 - Thu, Jul 23
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:40 pm - 9:16 pm
SJU
-
MFR
10h 36m
1 stop
$804United Airlines
Thu, Jul 16 - Sat, Jul 25
Multiple Airlines Logo
5:58 am - 9:15 pm
MFR
-
GCM
13h 17m
2 stops
Multiple Airlines Logo
4:00 pm - 10:02 pm
GCM
-
MFR
32h 02m
1 stop
$1,195Multiple 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 December, when the average cost of round-trip tickets is $2,196 and $751 respectively.

Find deals

Good to know

Low seasonMarch
Cheapest flight$334
Best time to beat the crowds but there is an average 139% increase in price.
Most popular time to fly and prices are also 30% 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 9711 reviews
7.1Entertainment
8.1Crew
7.7Boarding
6.6Food
7.3Comfort
Airline reviews

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

10.0 ExcellentAnonymous, May 2026
IAD - MUC
Read more United Airlines reviews

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

I didn’t have a seat assignment and my seat was very dirty on the flight from Frankfurt to Budapest.

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Cree was organized and pleasant. Plane had good seating but as it’s a shuttle toilets hadn’t been thoroughly cleaned (eg. bins too full)

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Medford (MFR)