$542 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 - 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
$542American Airlines
Sat, Sep 26 - Tue, Sep 29
United Airlines Logo
2:03 pm - 11:57 am
MFR
-
SJU
18h 54m
3 stops
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m
2 stops
$632United Airlines
Tue, Jul 28 - Tue, Aug 4
United Airlines Logo
6:35 pm - 12:34 pm
MFR
-
SJU
14h 59m
2 stops
United Airlines Logo
1:40 pm - 9:16 pm
SJU
-
MFR
10h 36m
1 stop
$639United 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
$669American Airlines
Tue, Jul 28 - Tue, Aug 4
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
$709United Airlines
Mon, Nov 2 - Thu, Nov 5
United Airlines Logo
6:00 am - 4:30 pm
MFR
-
GCM
31h 30m
2 stops
United Airlines Logo
5:45 pm - 1:09 pm
GCM
-
MFR
22h 24m
2 stops
$756United Airlines
Fri, Jun 5 - Mon, Jun 15
American Airlines Logo
6:35 am - 9:58 pm
MFR
-
SJU
12h 23m
2 stops
American Airlines Logo
12:57 am - 3:14 pm
SJU
-
MFR
17h 17m
2 stops
$796American Airlines
Wed, Jun 3 - Wed, Jun 10
American Airlines Logo
6:35 am - 9:59 pm
MFR
-
SJU
12h 24m
2 stops
American Airlines Logo
5:30 am - 3:14 pm
SJU
-
MFR
12h 44m
2 stops
$801American Airlines
Thu, Jul 16 - Fri, Jul 24
American Airlines Logo
4:34 pm - 9:45 am
MFR
-
SJU
14h 11m
2 stops
American Airlines Logo
12:58 am - 3:14 pm
SJU
-
MFR
17h 16m
2 stops
$866American Airlines
Tue, Aug 25 - Fri, Aug 28
United Airlines Logo
5:00 am - 8:38 pm
MFR
-
SJU
12h 38m
2 stops
United Airlines Logo
7:00 am - 9:16 pm
SJU
-
MFR
17h 16m
3 stops
$867United 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 $316, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonMarch
Cheapest flight$542
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 9684 reviews
8.1Crew
7.7Boarding
6.6Food
7.3Comfort
7.1Entertainment
Airline reviews

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

6.0 GoodAnonymous, May 2026
DEN - ORD
Read more United Airlines reviews

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)

I liked that my son and I were reseated next to each other (we had different bookings). I liked that it was a directg flight and mostly on time. I liked that you provided pillows and blankets. Flight attendants were generally courteous. The messaging through wifi did not work well. The food was not good. Seats are very narrow and I felt slightly claustraphobic in the window seat.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

Some crew were unfriendly or in some cases just straight up rude.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Medford (MFR)