$414 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 4/5. 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

Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Mon, Apr 20 - Tue, Apr 28
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
7:20 am - 11:14 pm
SJU
-
MFR
18h 54m
2 stops
$483United Airlines
Mon, Apr 20 - Tue, Apr 28
American Airlines Logo
2:08 pm - 9:13 am
MFR
-
SJU
16h 05m
2 stops
American Airlines Logo
7:00 pm - 2:57 pm
SJU
-
MFR
22h 57m
2 stops
$499American Airlines
Sun, May 3 - Wed, May 6
United Airlines Logo
6:36 pm - 2:44 pm
MFR
-
SJU
17h 08m
2 stops
United Airlines Logo
7:40 am - 11:31 pm
SJU
-
MFR
18h 51m
2 stops
$534United Airlines
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:25 pm - 1:11 pm
MFR
-
SJU
16h 46m
2 stops
Delta Logo
7:00 am - 11:13 pm
SJU
-
MFR
19h 13m
2 stops
$559Delta
Mon, Apr 13 - Thu, Apr 16
United Airlines Logo
2:12 pm - 12:45 pm
MFR
-
GCM
20h 33m
3 stops
United Airlines Logo
1:50 pm - 11:48 am
GCM
-
MFR
23h 58m
2 stops
$562United Airlines
Sun, May 3 - Wed, May 6
United Airlines Logo
2:07 pm - 5:38 pm
MFR
-
SJU
24h 31m
3 stops
United Airlines Logo
7:40 am - 11:31 pm
SJU
-
MFR
18h 51m
2 stops
$611United Airlines
Sun, May 3 - Tue, May 5
United Airlines Logo
2:07 pm - 5:38 pm
MFR
-
SJU
24h 31m
3 stops
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m
2 stops
$629United Airlines
Mon, Apr 13 - Thu, Apr 16
United Airlines Logo
2:12 pm - 12:45 pm
MFR
-
GCM
20h 33m
2 stops
United Airlines Logo
1:50 pm - 11:48 am
GCM
-
MFR
23h 58m
2 stops
$630United Airlines
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:25 pm - 1:11 pm
MFR
-
SJU
16h 46m
2 stops
Delta Logo
7:00 am - 11:13 pm
SJU
-
MFR
19h 13m
2 stops
$636Delta
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
$640United 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 ($452) and Delta ($559).

Good to know

Low seasonJune
Cheapest flight$414
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 9408 reviews
7.7Boarding
6.6Food
7.3Comfort
7.1Entertainment
8.1Crew
Airline reviews

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.

2.0 MediocreMichael, Mar 2026
RSW - IAH
Read more United Airlines reviews

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!

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports