$656 Find Cheap Flights from Medford to Caribbean Islands

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 Islands departing on 6/2. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Medford to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Medford to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Book Cheap Medford to Caribbean Islands 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 Islands 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 Islands

Tue, Jun 2 - Sat, Jun 6
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
7:20 am - 10:59 pm
SJU
-
MFR
18h 39m
2 stops
$656United Airlines
Mon, Oct 26 - Thu, Oct 29
United Airlines Logo
2:03 pm - 3:30 pm
MFR
-
GCM
23h 27m
2 stops
United Airlines Logo
4:45 pm - 1:09 pm
GCM
-
MFR
22h 24m
2 stops
$702United 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
6:01 am - 9:54 pm
SJU
-
MFR
18h 53m
2 stops
$731American 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
11:56 am - 9:54 pm
SJU
-
MFR
12h 58m
2 stops
$736American Airlines
Mon, Oct 26 - Thu, Oct 29
United Airlines Logo
6:34 pm - 3:30 pm
MFR
-
GCM
18h 56m
2 stops
United Airlines Logo
4:45 pm - 11:34 am
GCM
-
MFR
20h 49m
2 stops
$756United Airlines
Tue, Jun 2 - Mon, Jun 8
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:00 am - 9:16 pm
SJU
-
MFR
23h 16m
2 stops
$839United Airlines
Fri, Jun 5 - Tue, Jun 16
Delta Logo
5:25 pm - 1:20 pm
MFR
-
SJU
16h 55m
2 stops
Delta Logo
7:05 am - 11:12 pm
SJU
-
MFR
19h 07m
2 stops
$841Delta
Tue, Jun 2 - Mon, Jun 8
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:00 am - 1:00 pm
SJU
-
MFR
15h 00m
2 stops
$856United Airlines
Tue, Jun 2 - Mon, Jun 8
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:00 am - 1:00 pm
SJU
-
MFR
15h 00m
2 stops
$886United Airlines
Fri, Jun 5 - Tue, Jun 16
Delta Logo
5:25 pm - 1:20 pm
MFR
-
SJU
16h 55m
2 stops
Delta Logo
7:05 am - 11:12 pm
SJU
-
MFR
19h 07m
2 stops
$936Delta
Booking Insights

KAYAK's insights & trends for Medford to Caribbean Islands flights

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

Can I save money by flying with a layover from Medford to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $328, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonMarch
Cheapest flight$656
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 Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Medford to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Medford to Caribbean Islands? 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 9733 reviews
8.1Crew
7.3Comfort
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

Late plane. Only one crew on the ground so we b had to wait for Denver flight to come in, board, and depart. At 78 yrs of age I was not pleased trying to get my connection. What really made me angry was the notification you sent me to hurry up or I would miss my connection. Why tell me to hurry up when you got me in late. It was not a good way of treating customers.

6.0 Goodrsillman, May 2026
ACV - SFO
Read more United Airlines reviews

Late plane. Only one crew on the ground so we b had to wait for Denver flight to come in, board, and depart. At 78 yrs of age I was not pleased trying to get my connection. What really made me angry was the notification you sent me to hurry up or I would miss my connection. Why tell me to hurry up when you got me in late. It was not a good way of treating customers.

No complaints other than luggage carousel was incorrectly guiding passengers to the wrong carousel on the screen.

Did not like that we couldn't complete check in on-line without providing pictures of our passports. Worry about identity theft. We had no delays and boarding was handled In an efficient manner.

We were a little disappointed to not be able to complete check in online without uploading pics of passports. Also we have KTN's and they weren't on our boarding passes when we got to security. Had to trek back to counter to have them fix.

Excellent service in Polaris class IAD to ZRH. Arrived rested and well fed after the overnight flight.

My flight time was changed without any notification to me which ruined my time sensitive plans so I ended up completely changing my travel plans and no reimbursement.

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!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Medford (MFR)