$534 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 5/3. 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

Sun, May 3 - Wed, May 6
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
7:20 am - 9:31 pm
SJU
-
MFR
17h 11m
2 stops
$534United Airlines
Sun, May 3 - Tue, May 5
United Airlines Logo
6:36 pm - 2:44 pm
MFR
-
SJU
17h 08m
2 stops
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m
2 stops
$554United Airlines
Mon, Apr 13 - Thu, Apr 16
United Airlines Logo
5:00 am - 12:30 pm
MFR
-
GCM
29h 30m
2 stops
United Airlines Logo
1:50 pm - 11:48 am
GCM
-
MFR
23h 58m
2 stops
$582United Airlines
Tue, Jun 2 - Mon, Jun 8
United Airlines Logo
6:35 pm - 12:04 pm
MFR
-
SJU
14h 29m
2 stops
United Airlines Logo
1:00 am - 12:04 pm
SJU
-
MFR
14h 04m
2 stops
$592United Airlines
Sun, May 3 - Wed, May 6
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:40 pm - 9:31 pm
SJU
-
MFR
10h 51m
1 stop
$610United Airlines
Sun, May 3 - Wed, May 6
United Airlines Logo
6:36 pm - 5:38 pm
MFR
-
SJU
20h 02m
3 stops
United Airlines Logo
7:20 am - 9:31 pm
SJU
-
MFR
17h 11m
2 stops
$616United Airlines
Sun, May 3 - Wed, May 6
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:40 pm - 9:31 pm
SJU
-
MFR
10h 51m
1 stop
$620United Airlines
Tue, Jun 2 - Mon, Jun 8
United Airlines Logo
6:35 pm - 12:04 pm
MFR
-
SJU
14h 29m
2 stops
United Airlines Logo
1:00 am - 12:04 pm
SJU
-
MFR
14h 04m
2 stops
$624United Airlines
Mon, Jun 29 - Wed, Jul 1
American Airlines Logo
5:15 am - 11:59 pm
MFR
-
SJU
15h 44m
2 stops
American Airlines Logo
10:29 am - 11:44 pm
SJU
-
MFR
16h 15m
2 stops
$684American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
1:39 pm - 11:25 am
MFR
-
GCM
19h 46m
2 stops
American Airlines Logo
12:10 pm - 11:24 pm
GCM
-
MFR
13h 14m
2 stops
$826American 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.

How long does a flight from Medford to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest route to Caribbean from Medford is to San Juan, which takes 9h 38m.

Good to know

Low seasonJune
Cheapest flight$534
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 9428 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

Everything was on time and service on the flight was great!

10.0 ExcellentAsha, Mar 2026
MIA - IAH
Read more United Airlines reviews

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It’s always a great time flying with united airlines.

Good flight. Efficient boarding and competent flight crew. No problems until we arrived at our destination gate. We were early so there was an aircraft at the gate that had to move before we could pull in. Then, due to the type of aircraft we flew, the cabin door could not be opened until some luggage from the cargo bay was offloaded to preserve center of gravity characteristics. So, that further delayed deplaning. Despite being 20 minutes early on landing, we ended up being 5 to 10 minutes late after all the delays.

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

There was no WiFi available, there were mechanical problems with the plane and we landed at C 124, then the gate was switched to A 26, then all the way back to C126! For a 75 yo woman traveling alone, this was a difficult journey, indeed!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports