$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
Delta Logo
11:14 am - 12:00 pm
MFR
-
GCM
22h 46m
2 stops
Delta Logo
1:25 pm - 11:52 pm
GCM
-
MFR
12h 27m
2 stops
$534Delta
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
Thu, May 7 - Wed, May 13
United Airlines Logo
6:36 pm - 12:34 pm
MFR
-
SJU
14h 58m
2 stops
United Airlines Logo
1:00 am - 11:47 am
SJU
-
MFR
13h 47m
2 stops
$585United Airlines
Sat, Jun 13 - Wed, Jun 17
Delta Logo
5:34 pm - 12:00 pm
MFR
-
SJU
15h 26m
2 stops
Delta Logo
7:05 am - 11:22 pm
SJU
-
MFR
19h 17m
2 stops
$619Delta
Tue, Jun 2 - Mon, Jun 8
United Airlines Logo
2:11 pm - 12:04 pm
MFR
-
SJU
18h 53m
3 stops
United Airlines Logo
1:00 am - 1:05 pm
SJU
-
MFR
15h 05m
2 stops
$632United Airlines
Thu, May 7 - Thu, May 14
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
$644United Airlines
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
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
1:24 pm - 9:39 am
MFR
-
SJU
17h 15m
2 stops
American Airlines Logo
10:29 am - 11:44 pm
SJU
-
MFR
16h 15m
2 stops
$669American 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.

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 9569 reviews
6.6Food
7.3Comfort
7.1Entertainment
8.1Crew
7.7Boarding
Airline reviews

It's a long flight and I would have liked better snacks between lunch and the arrival meal. It's fine to have fruit and nuts but I really don't like ramen because it's salty junk soup. I'd suggest sandwiches. They're not expensive nor are they hard to store for a long flight. The FA's had a couple of big services and they were super busy preparing, executing and then cleaning up. Then they disappeared.

8.0 ExcellentJesse, Apr 2026
IAH - NRT
Read more United Airlines reviews

It's a long flight and I would have liked better snacks between lunch and the arrival meal. It's fine to have fruit and nuts but I really don't like ramen because it's salty junk soup. I'd suggest sandwiches. They're not expensive nor are they hard to store for a long flight. The FA's had a couple of big services and they were super busy preparing, executing and then cleaning up. Then they disappeared.

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

This was the first flight in the morning. We boarded fine. The cabin door was closed and we were ready to go. We were notified by the Captain that ATC issued and ground stop for 40 minutes. So, without even pushing back from the gate, we were already 40 minutes late. We actually were released to push-back and taxi at 30 minutes. But, some passengers had tight connections and were not going to make their connections. Some passengers asked about the delay and the effect on the connections and were told by the cabin attendant that all flights will be delayed and so they should be OK. However, that was not true. My connecting flight was on time and I arrived at IAH with 21 minutes to make my connection. I did and I'm happy about that, but the flight crew should not have given assurances to the passengers who might have missed their connections.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports