$308 Find Cheap Flights from Medford to Caribbean

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 2/25. 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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Flight Deals

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

Wed, Aug 12 - Sat, Aug 22
American Airlines Logo
6:00 am - 11:40 pm
MFR
-
SJU
14h 40m
2 stops
American Airlines Logo
6:00 am - 11:24 pm
SJU
-
MFR
20h 24m
2 stops
$462American Airlines
Sat, Feb 28 - Wed, Mar 4
United Airlines Logo
12:35 pm - 6:11 am
MFR
-
SJU
13h 36m
2 stops
United Airlines Logo
8:05 am - 9:18 pm
SJU
-
MFR
17h 13m
2 stops
$616United 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
$629United Airlines
Mon, Aug 10 - Wed, Aug 19
American Airlines Logo
4:15 pm - 9:42 am
MFR
-
SJU
14h 27m
2 stops
American Airlines Logo
8:00 am - 11:55 pm
SJU
-
MFR
18h 55m
2 stops
$639American Airlines
Sat, Jun 6 - Fri, Jun 12
United Airlines Logo
1:10 pm - 5:29 am
MFR
-
SJU
13h 19m
2 stops
United Airlines Logo
1:00 am - 12:04 pm
SJU
-
MFR
14h 04m
2 stops
$644United Airlines
Sun, May 10 - Mon, May 18
United Airlines Logo
6:36 pm - 12:34 pm
MFR
-
SJU
14h 58m
2 stops
United Airlines Logo
1:40 pm - 9:31 pm
SJU
-
MFR
10h 51m
1 stop
$682United Airlines
Sun, May 10 - Mon, May 18
American Airlines Logo
4:24 pm - 10:53 am
MFR
-
SJU
15h 29m
2 stops
American Airlines Logo
6:45 am - 9:54 pm
SJU
-
MFR
18h 09m
2 stops
$699American 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
$701United Airlines
Mon, Mar 2 - Thu, Mar 5
United Airlines Logo
2:00 pm - 1:15 pm
MFR
-
GCM
20h 15m
2 stops
United Airlines Logo
2:50 pm - 9:18 pm
GCM
-
MFR
33h 28m
2 stops
$723United Airlines
Mon, Mar 2 - Thu, Mar 5
United Airlines Logo
12:35 pm - 1:15 pm
MFR
-
GCM
21h 40m
2 stops
United Airlines Logo
2:50 pm - 9:18 pm
GCM
-
MFR
33h 28m
2 stops
$729United 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 American Airlines ($462) and United Airlines ($616).

Find deals

Good to know

Low seasonJune
Cheapest flight$308
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 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 9296 reviews
7.1Entertainment
6.6Food
7.7Boarding
7.3Comfort
8.1Crew
Airline reviews

Both the WIFI and entertainment did not work for 2.5h

6.0 GoodAnonymous, Feb 2026
HNL - NRT
Read more United Airlines reviews

Both the WIFI and entertainment did not work for 2.5h

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.

Both of my flights arrived early and check in process was smooth

Terrible. No customer service, no food, no drinks on a 6 hour premier economy booking.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Medford (MFR)