$271 Find Cheap Flights from Medford to Caribbean Islands - Compare and Save

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 9/15. 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

Thu, Oct 1 - Wed, Oct 14
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:00 am - 12:02 pm
SJU
-
MFR
14h 02m
2 stops
$597United Airlines
Mon, Oct 19 - Tue, Oct 20
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
$637United Airlines
Mon, Oct 19 - Tue, Oct 20
United Airlines Logo
2:07 pm - 11:57 am
MFR
-
SJU
18h 50m
3 stops
United Airlines Logo
1:00 am - 12:02 pm
SJU
-
MFR
14h 02m
2 stops
$642United Airlines
Fri, Jul 3 - Mon, Jul 6
American Airlines Logo
4:34 pm - 11:04 am
MFR
-
SJU
15h 30m
2 stops
American Airlines Logo
12:58 am - 3:14 pm
SJU
-
MFR
17h 16m
2 stops
$736American Airlines
Fri, Jul 10 - Mon, Jul 20
American Airlines Logo
1:23 pm - 9:45 am
MFR
-
SJU
17h 22m
2 stops
American Airlines Logo
7:25 am - 10:02 pm
SJU
-
MFR
17h 37m
2 stops
$804American Airlines
Fri, Jul 3 - Tue, Jul 7
United Airlines Logo
6:35 pm - 2:44 pm
MFR
-
SJU
17h 09m
2 stops
United Airlines Logo
1:40 pm - 9:16 pm
SJU
-
MFR
10h 36m
1 stop
$817United Airlines
Fri, Jul 10 - Mon, Jul 20
American Airlines Logo
1:23 pm - 9:45 am
MFR
-
SJU
17h 22m
2 stops
American Airlines Logo
7:25 am - 10:02 pm
SJU
-
MFR
17h 37m
2 stops
$861American 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
7:25 am - 10:02 pm
SJU
-
MFR
17h 37m
2 stops
$932American 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
11:54 am - 10:02 pm
SJU
-
MFR
13h 08m
2 stops
$936American Airlines
Fri, Jul 10 - Sun, Jul 19
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
2:05 am - 10:59 pm
SJU
-
MFR
23h 54m
2 stops
$971United 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 $341, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonMarch
Cheapest flight$271
Best time to beat the crowds but there is an average 125% 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 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 9868 reviews
6.6Food
7.3Comfort
7.7Boarding
8.1Crew
7.1Entertainment
Airline reviews

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

4.0 OkayPrincess, Jun 2026
IAH - SAV
Read more United Airlines reviews

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

The boarding process on the departure from LA was rather slow even though I was in Group 1. For first class, I was not expecting to have to pay for Wi-fi but I did and then the wi-fi was spotty. The entree was surprisingly good and so that was a pleasant surprise. However, once I got to Houston, it was terrible. Unfortunately there was bad weather but the constant gate changes for my connecting flight was difficult to manage due to having to navigate back and forth between different terminals.

We used Kayak to reserve our tickets and specifically checked the luggage option which was a more expensive option. When we arrived at the terminal we had to pay an extra $90 per suitcase for the three passengers. This has been a pattern for the past 3 years. Why charge for a more expensive luggage option, and the ticket price not include luggage?

They delayed the flight 3 hours because it wasn't full they moved us to 5 different gates probably the worst airline ever not even spirit is this bad.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Checking bag at terminal was horrible. No agents to check us in and only 1 kiosk working. Boarding went ok. Crew onboard was very scattered rained. Missed our row while serving and then didn’t see them hardly again.

Crew was amazing, takeoff wonderful. The bathroom was disgusting from before takeoff the odor made the flight uncomfortable as you could smell the bathroom from the center of the plane where we were sitting. Smelled like raw sewage. My daughter was throwing up as we landed due to the smell and horrible turbulence as we approached Newark.

Airline tickets are not cheap. You expect reliable competent service. Thanks to canceled flights and botched transfers we arrived at our destination two days late. This is not acceptable

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

The entertainment they offer could use some games, and maybe they could add some cookies to the snack menu. And the automated messages are a bit repetitive. But it was comfortable temperature wise and the seats were comfortable. The crew is very polite and helpful

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Medford (MFR)