$424 Find Cheap Flights from Medford to Caribbean - 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 departing on 12/4. 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.
Flight Deals
Cheap Flights from Medford to Caribbean
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysNonstop only
Weekend trip
Sort by: Cheapest
Christiansted, U.S. Virgin Islands
21h 33m4 stops
from $595per person
Oranjestad, Aruba
19h 34m4 stops
from $694per person
Freeport, The Bahamas
16h 08m5 stops
from $1,160per person
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
Thu, Jan 28 - Fri, Feb 5
1:30 pm - 10:38 amMFR Medford-SJU San Juan Luis Munoz Marin Intl
17h 08m2 stops Phoenix Sky Harbor Intl Miami
10:32 am - 11:31 pmSJU San Juan Luis Munoz Marin Intl-MFR Medford
16h 59m2 stops Miami Phoenix Sky Harbor Intl
$528American Airlines
Thu, Jan 7 - Sat, Jan 16
1:30 pm - 10:38 amMFR Medford-SJU San Juan Luis Munoz Marin Intl
17h 08m2 stops Phoenix Sky Harbor Intl Miami
7:22 am - 7:30 pmSJU San Juan Luis Munoz Marin Intl-MFR Medford
16h 08m2 stops Miami Phoenix Sky Harbor Intl
$543American Airlines
Sat, Oct 31 - Tue, Nov 10
5:01 am - 9:22 pmMFR Medford-SJU San Juan Luis Munoz Marin Intl
13h 21m2 stops Denver Intl Washington, D.C. Dulles Intl
8:05 am - 9:18 pmSJU San Juan Luis Munoz Marin Intl-MFR Medford
17h 13m2 stops Washington, D.C. Dulles Intl Denver Intl
$558United Airlines
Sat, Oct 31 - Tue, Nov 10
5:01 am - 5:25 pmMFR Medford-SJU San Juan Luis Munoz Marin Intl
9h 24m1 stop Denver Intl
2:21 pm - 9:18 pmSJU San Juan Luis Munoz Marin Intl-MFR Medford
10h 57m1 stop Denver Intl
$558United Airlines
Sat, Oct 31 - Tue, Nov 10
5:01 am - 5:25 pmMFR Medford-SJU San Juan Luis Munoz Marin Intl
9h 24m1 stop Denver Intl
8:05 am - 9:18 pmSJU San Juan Luis Munoz Marin Intl-MFR Medford
17h 13m2 stops Washington, D.C. Dulles Intl Denver Intl
$558United Airlines
Sat, Jan 23 - Sat, Feb 6
1:31 pm - 3:04 pmMFR Medford-STX Christiansted Henry Rohlsen
21h 33m2 stops Phoenix Sky Harbor Intl Miami
3:51 pm - 12:55 pmSTX Christiansted Henry Rohlsen-MFR Medford
25h 04m2 stops Miami Phoenix Sky Harbor Intl
$595American Airlines
Fri, Jan 8 - Sat, Jan 16
1:30 pm - 9:38 amMFR Medford-SJU San Juan Luis Munoz Marin Intl
16h 08m2 stops Phoenix Sky Harbor Intl Miami
7:22 am - 7:30 pmSJU San Juan Luis Munoz Marin Intl-MFR Medford
16h 08m2 stops Miami Phoenix Sky Harbor Intl
$608American Airlines
Tue, Oct 13 - Sat, Oct 17
5:25 pm - 12:05 pmMFR Medford-SJU San Juan Luis Munoz Marin Intl
15h 40m2 stops Seattle/Tacoma Intl New York John F Kennedy Intl
7:15 am - 11:18 pmSJU San Juan Luis Munoz Marin Intl-MFR Medford
19h 03m2 stops Atlanta Hartsfield-Jackson Seattle/Tacoma Intl
$676Delta
Tue, Oct 13 - Fri, Oct 16
5:00 am - 5:38 pmMFR Medford-SJU San Juan Luis Munoz Marin Intl
9h 38m1 stop Denver Intl
1:00 am - 11:50 amSJU San Juan Luis Munoz Marin Intl-MFR Medford
13h 50m2 stops Newark San Francisco
$676United Airlines
Sat, Feb 6 - Tue, Feb 16
6:00 am - 12:36 amMFR Medford-SJU San Juan Luis Munoz Marin Intl
14h 36m2 stops San Francisco Newark
8:25 am - 9:10 pmSJU San Juan Luis Munoz Marin Intl-MFR Medford
16h 45m2 stops Chicago O'Hare Intl Denver Intl
$693United Airlines
Recent one-way flight deals from Medford to Caribbean
Fri, Dec 4
7:30 am - 2:40 pmMFR Medford-CUR Willemstad Hato Int.
27h 10m2 stops San Francisco Newark
$424United Airlines
Thu, Dec 3
1:31 pm - 2:50 pmMFR Medford-CUR Willemstad Hato Int.
21h 19m2 stops Salt Lake City Atlanta Hartsfield-Jackson
$441Delta
Sun, Nov 8
1:28 pm - 2:40 pmMFR Medford-CUR Willemstad Hato Int.
21h 12m2 stops Phoenix Sky Harbor Intl Miami
$448American Airlines
Sun, Dec 6
1:28 pm - 2:39 pmMFR Medford-CUR Willemstad Hato Int.
21h 11m2 stops Phoenix Sky Harbor Intl Miami
$448American Airlines
Sat, Dec 5
5:04 am - 2:19 pmMFR Medford-CUR Willemstad Hato Int.
29h 15m2 stops Phoenix Sky Harbor Intl Charlotte Douglas
$454American Airlines
Mon, Dec 7
5:04 am - 2:19 pmMFR Medford-CUR Willemstad Hato Int.
29h 15m2 stops Phoenix Sky Harbor Intl Charlotte Douglas
$454American Airlines
Sat, Nov 7
1:20 pm - 2:50 pmMFR Medford-CUR Willemstad Hato Int.
21h 30m2 stops Salt Lake City Atlanta Hartsfield-Jackson
$468Delta
Tue, Dec 8
5:04 am - 4:22 pmMFR Medford-CUR Willemstad Hato Int.
31h 18m2 stops Phoenix Sky Harbor Intl Miami
$486American Airlines
Wed, Dec 2
5:04 am - 2:19 pmMFR Medford-CUR Willemstad Hato Int.
53h 15m2 stops Phoenix Sky Harbor Intl Charlotte Douglas
$494American Airlines
Tue, Dec 8
12:43 pm - 3:25 pmMFR Medford-CUR Willemstad Hato Int.
46h 42m3 stops Portland San Francisco Toronto Pearson Intl
$513Multiple Airlines
Recent last minute flight deals from Medford to Caribbean
Thu, Oct 1 - Sat, Oct 3
1:31 pm - 11:40 amMFR Medford-GCM George Town Owen Roberts Intl
20h 09m2 stops Salt Lake City Atlanta Hartsfield-Jackson
1:05 pm - 12:46 pmGCM George Town Owen Roberts Intl-MFR Medford
25h 41m2 stops Atlanta Hartsfield-Jackson Seattle/Tacoma Intl
$5,168Delta
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.
Prices
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Good to know
Low season | October |
|---|---|
High season | January |
FAQs - booking Caribbean flights
Reviews of the top airline flying from Medford to Caribbean
7.4
United AirlinesOverall score based on 10256 reviews
7.3Comfort
6.7Food
7.7Boarding
7.1Entertainment
8.1Crew
Airline reviews
It was serviceable, nothing special but nothing awful on this leg.
8.0 ExcellentMatthew, Aug 2026
It was serviceable, nothing special but nothing awful on this leg.
The flight was delayed from take off because only one runway was operational in San Francisco.
the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.
Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.
The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.
United have really come back. Airport and boarding process is clear and good, app and information also very good
This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.
We had a 90 minute delay due to equipment failure that was detected just before we took off. United rebooked my connecting flight.
Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.
This was a Lufthansa flight. Disappointing main meal. Very rough over Canada and arrival at FRA. IFE was almost unusable.
More options for your flight to Caribbean
Complete your trip to Caribbean with a hotel stay or car rental
Information on your arrival and departure airports
Cabin class types available on flights to Medford
Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from domestic origins to Medford
Flights from all regions of Medford to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.