$444 Find Cheap Flights from Medford to Caribbean

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 departing on 4/18. 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

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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

Sat, Apr 18 - Fri, Apr 24
United Airlines Logo
5:00 am - 11:50 pm
MFR
-
SJU
15h 50m
2 stops
United Airlines Logo
1:00 am - 11:48 am
SJU
-
MFR
13h 48m
2 stops
$444United Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
1:24 pm - 11:03 am
MFR
-
SJU
18h 39m
2 stops
American Airlines Logo
6:00 am - 9:54 pm
SJU
-
MFR
18h 54m
2 stops
$522American Airlines
Mon, Apr 27 - Thu, Apr 30
United Airlines Logo
6:00 am - 12:30 pm
MFR
-
GCM
28h 30m
2 stops
United Airlines Logo
1:35 pm - 11:47 am
GCM
-
MFR
24h 12m
2 stops
$582United Airlines
Mon, Apr 27 - Thu, Apr 30
United Airlines Logo
2:12 pm - 12:45 pm
MFR
-
GCM
20h 33m
2 stops
United Airlines Logo
1:35 pm - 9:31 pm
GCM
-
MFR
33h 56m
2 stops
$601United Airlines
Sat, Apr 18 - Fri, Apr 24
United Airlines Logo
2:12 pm - 8:38 pm
MFR
-
SJU
27h 26m
3 stops
United Airlines Logo
1:00 am - 11:48 am
SJU
-
MFR
13h 48m
2 stops
$607United Airlines
Sat, Apr 18 - Fri, Apr 24
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:00 am - 11:48 am
SJU
-
MFR
13h 48m
2 stops
$616United Airlines
Fri, Jun 5 - Mon, Jun 15
American Airlines Logo
12:48 pm - 4:25 am
MFR
-
SJU
12h 37m
2 stops
American Airlines Logo
12:44 am - 3:14 pm
SJU
-
MFR
17h 30m
2 stops
$659American Airlines
Sat, Jun 27 - Sat, Jul 4
American Airlines Logo
4:34 pm - 9:39 am
MFR
-
SJU
14h 05m
2 stops
American Airlines Logo
11:54 am - 11:53 pm
SJU
-
MFR
14h 59m
2 stops
$684American Airlines
Mon, Jun 1 - Thu, Jun 11
United Airlines Logo
6:35 pm - 12:34 pm
MFR
-
SJU
14h 59m
2 stops
United Airlines Logo
2:05 am - 12:04 pm
SJU
-
MFR
12h 59m
2 stops
$723United Airlines
Tue, May 5 - Tue, May 12
Multiple Airlines Logo
5:36 pm - 11:31 am
MFR
-
GCM
15h 55m
2 stops
Multiple Airlines Logo
12:00 pm - 1:25 pm
GCM
-
MFR
27h 25m
2 stops
$963Multiple Airlines
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.

Which airlines provide the cheapest flights from Medford to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Medford to Caribbean were found on United Airlines ($444) and American Airlines ($684).

Find deals

Good to know

Low seasonJune
Cheapest flight$444
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 72% lower on average.
Flight from Medford to San Juan

FAQs - booking Caribbean flights

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

    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.

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

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

    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 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?

    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 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

 
Need help choosing which airline to fly with from Medford to Caribbean? 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 9462 reviews
7.3Comfort
8.1Crew
7.1Entertainment
6.6Food
7.7Boarding
Airline reviews

No seat back entertainment. And app had a hard time getting entertainment loaded.

8.0 ExcellentStephanie, Mar 2026
DEN - CUN
Read more United Airlines reviews

No seat back entertainment. And app had a hard time getting entertainment loaded.

ticket agent lady wás very helpful , she arranged wheel chair for my elderly mother

Didn't make the flight because the first leg of my flight was canceled and the next leg was already booked.

My flight was canceled a few hours before boarding. I was rebooked on Copa airlines and missed an important meeting .

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Business class seats felt very cramped compared to other airlines.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Medford (MFR)