$221 Find Cheap Flights from Medford to Caribbean Islands

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 Islands departing on 4/5. 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

Mon, Apr 27 - Wed, May 6
Delta Logo
5:28 pm - 12:52 pm
MFR
-
SJU
16h 24m
2 stops
Delta Logo
7:15 am - 11:30 pm
SJU
-
MFR
19h 15m
2 stops
$452Delta
Wed, Apr 15 - Tue, May 5
United Airlines Logo
5:00 am - 11:50 pm
MFR
-
SJU
15h 50m
2 stops
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m
2 stops
$462United Airlines
Wed, Apr 15 - Wed, May 6
United Airlines Logo
5:00 am - 11:50 pm
MFR
-
SJU
15h 50m
2 stops
United Airlines Logo
1:40 pm - 9:31 pm
SJU
-
MFR
10h 51m
1 stop
$479United Airlines
Sun, May 24 - Tue, May 26
United Airlines Logo
6:25 pm - 12:04 pm
MFR
-
SJU
14h 39m
2 stops
United Airlines Logo
1:00 am - 12:04 pm
SJU
-
MFR
14h 04m
2 stops
$540United Airlines
Mon, Mar 2 - Wed, Mar 4
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
$542United 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
$547United Airlines
Sun, May 24 - Tue, May 26
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:00 am - 12:04 pm
SJU
-
MFR
14h 04m
2 stops
$567United Airlines
Tue, Jul 28 - Mon, Aug 10
United Airlines Logo
2:07 pm - 5:29 am
MFR
-
SJU
12h 22m
2 stops
United Airlines Logo
2:05 am - 11:34 am
SJU
-
MFR
12h 29m
2 stops
$582United Airlines
Mon, Mar 2 - Wed, Mar 4
United Airlines Logo
6:25 pm - 12:49 pm
MFR
-
SJU
14h 24m
2 stops
United Airlines Logo
8:30 am - 9:18 pm
SJU
-
MFR
16h 48m
2 stops
$629United Airlines
Tue, Jul 28 - Mon, Aug 10
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
2:05 am - 11:34 am
SJU
-
MFR
12h 29m
2 stops
$653United Airlines
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 $274, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonJune
Cheapest flight$221
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 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 9276 reviews
7.7Boarding
7.1Entertainment
7.3Comfort
8.1Crew
6.6Food
Airline reviews

Check-in and in-flight staff were better than average. The seat was a fair size but too hard and not enough padding. The cushion/pillow provided is poor (thin and seems to be disposable ,it provides no effective cushioning or support). Food was OK-ish but no choice of inflight snacks and no easy place to get drinks other than water (I could ask for juice by intruding into the staff area at the back of the plane) Entertainment was very good actually. Overall better than I expected from a US-based airline (sorry!) but compared to ANA or Singapore it was so-so. (I live in Japan so they are my comparative airlines)

6.0 GoodMike, Feb 2026
LAX - NRT
Read more United Airlines reviews

Check-in and in-flight staff were better than average. The seat was a fair size but too hard and not enough padding. The cushion/pillow provided is poor (thin and seems to be disposable ,it provides no effective cushioning or support). Food was OK-ish but no choice of inflight snacks and no easy place to get drinks other than water (I could ask for juice by intruding into the staff area at the back of the plane) Entertainment was very good actually. Overall better than I expected from a US-based airline (sorry!) but compared to ANA or Singapore it was so-so. (I live in Japan so they are my comparative airlines)

Everything was on time Will use united again for sure

Plane outlets in my row not working to charge phone. Staff response was, well it should be. Plug into seed for volume not working well. Had to find the sweet spot for plug in or it would shut off and on.

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Fine not above and beyond as I had a connection that was delayed due to maintenance

The power at the seat didn't work and the seat itself was difficult to adjust - this was a business class seat. Flight attendant gave me miles to compensate. The attendant was very professional and on top of his game the entire flight.

Terrible. Our first time back on United for 10 years, the seats in Polaris class are small and uncomfortable. They have squished too many people in to get more $$$. The staff are not friendly and not wanting to accommodate. I asked for two salads rather than a main meal and was advised no we wont do that. Then asked what I would like for breakfast and given something else anyway. I will not be flying United International anytime soon.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Medford (MFR)