$336 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 6/14. 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 24% 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

Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
6:35 am - 9:59 pm
MFR
-
SJU
12h 24m
2 stops
American Airlines Logo
11:55 am - 9:54 pm
SJU
-
MFR
12h 59m
2 stops
$522American Airlines
Mon, May 4 - Wed, May 6
American Airlines Logo
2:08 pm - 11:31 am
MFR
-
GCM
19h 23m
2 stops
American Airlines Logo
12:00 pm - 11:04 pm
GCM
-
MFR
13h 04m
2 stops
$534American Airlines
Fri, May 1 - Fri, May 8
Delta Logo
5:28 pm - 12:52 pm
MFR
-
SJU
16h 24m
2 stops
Delta Logo
7:05 am - 11:42 pm
SJU
-
MFR
19h 37m
2 stops
$542Delta
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:25 pm - 12:01 pm
MFR
-
SJU
15h 36m
2 stops
Delta Logo
7:30 am - 11:22 pm
SJU
-
MFR
18h 52m
2 stops
$579Delta
Mon, May 4 - Wed, May 6
United Airlines Logo
6:36 pm - 12:30 pm
MFR
-
GCM
15h 54m
2 stops
United Airlines Logo
1:35 pm - 1:01 pm
GCM
-
MFR
25h 26m
2 stops
$654United Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
6:35 am - 9:59 pm
MFR
-
SJU
12h 24m
2 stops
American Airlines Logo
11:55 am - 11:44 pm
SJU
-
MFR
14h 49m
2 stops
$659American Airlines
Fri, May 1 - Thu, May 7
United Airlines Logo
6:36 pm - 5:38 pm
MFR
-
SJU
20h 02m
3 stops
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m
2 stops
$665United Airlines
Mon, May 4 - Wed, May 6
United Airlines Logo
2:07 pm - 12:30 pm
MFR
-
GCM
20h 23m
2 stops
United Airlines Logo
1:35 pm - 11:47 am
GCM
-
MFR
24h 12m
2 stops
$674United Airlines
Fri, May 1 - Thu, May 7
United Airlines Logo
6:36 pm - 5:38 pm
MFR
-
SJU
20h 02m
3 stops
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m
2 stops
$680United Airlines
Fri, Jun 5 - Sun, Jun 14
Delta Logo
5:25 pm - 4:33 pm
MFR
-
SJU
20h 08m
2 stops
Delta Logo
2:04 pm - 11:57 pm
SJU
-
MFR
12h 53m
2 stops
$694Delta
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.

What is the cheapest month to fly from Medford to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Medford to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Medford to Caribbean is July, when tickets cost $589 (return) on average. On the other hand, the most expensive months are March and February, when the average cost of round-trip tickets is $2,196 and $1,286 respectively.

Good to know

Low seasonMarch
Cheapest flight$336
Best time to beat the crowds but there is an average 142% increase in price.
Most popular time to fly and prices are also 30% 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 9552 reviews
8.1Crew
7.7Boarding
7.3Comfort
7.1Entertainment
6.6Food
Airline reviews

All good flight was 35 minutes early when arriving in Edinburgh

10.0 ExcellentJohn, Apr 2026
EWR - EDI
Read more United Airlines reviews

All good flight was 35 minutes early when arriving in Edinburgh

Flights were on time actually early service was good and crew cheerful

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

Boarding was again a "free for all". We were boarding group 4, and almost the entire plane was able to board before us. It's a shame that someone who follows the rules, gets the short end of the stick. Not fair.

Flight left on time, arrived early, pleasant staff provided water, coffee, etc. access to bathrooms was reasonable and were well maintained. blankets were available, lots of entertainment options. LUGGAGE SERVICE WAS GREAT. I got my one checked bag quickly and was able to make a bus connection for a 2 hour bus ride saving me from waiting another 1.5 hours.

The boarding process was straightforward. One pertinent observation regarding all boarding procedures is that if an individual requires assistance or possesses a special status and is part of preboarding, it is advisable to limit the number of passengers who can preboard with them, rather than the entire, sometimes large, companion groups. The seats are uncomfortable, and the entertainment options are significantly inferior compared to other airlines. During the snack service, I requested an additional bag of snacks, but my request was denied. Initially, the flight attendant agreed to my request.becoming a strange accurate moment. The flight duration was four hours.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports