$542 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 10/3. 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

Sat, Oct 3 - Wed, Oct 7
Delta Logo
5:21 pm - 12:13 pm
MFR
-
SJU
15h 52m
2 stops
Delta Logo
7:00 am - 11:12 pm
SJU
-
MFR
19h 12m
2 stops
$542Delta
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
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:25 pm - 1:20 pm
MFR
-
SJU
16h 55m
2 stops
Delta Logo
7:30 am - 11:22 pm
SJU
-
MFR
18h 52m
2 stops
$689Delta
Wed, May 6 - Sun, May 10
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
$691United Airlines
Sat, Oct 3 - Tue, Oct 6
United Airlines Logo
2:03 pm - 3:42 pm
MFR
-
SJU
22h 39m
3 stops
United Airlines Logo
1:00 am - 11:34 am
SJU
-
MFR
13h 34m
2 stops
$705United Airlines
Wed, May 6 - Sat, May 9
United Airlines Logo
6:36 pm - 12:34 pm
MFR
-
SJU
14h 58m
2 stops
United Airlines Logo
1:00 am - 1:01 pm
SJU
-
MFR
15h 01m
2 stops
$720United Airlines
Sat, Oct 3 - Wed, Oct 7
United Airlines Logo
2:03 pm - 12:34 pm
MFR
-
SJU
19h 31m
3 stops
United Airlines Logo
2:00 pm - 11:34 am
SJU
-
MFR
24h 34m
3 stops
$723United Airlines
Wed, May 6 - Sun, May 10
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
$726United Airlines
Thu, Jun 4 - Thu, Jun 11
American Airlines Logo
1:24 pm - 1:35 pm
MFR
-
GCM
22h 11m
2 stops
American Airlines Logo
2:42 pm - 12:50 pm
GCM
-
MFR
24h 08m
2 stops
$734American Airlines
Tue, May 5 - Sun, May 10
United Airlines Logo
5:00 am - 11:50 pm
MFR
-
SJU
15h 50m
2 stops
United Airlines Logo
1:40 pm - 9:31 pm
SJU
-
MFR
10h 51m
1 stop
$736United 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.

Find deals

Good to know

Low seasonMarch
Cheapest flight$542
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 9643 reviews
7.7Boarding
8.1Crew
7.1Entertainment
7.3Comfort
6.6Food
Airline reviews

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

10.0 ExcellentAnonymous, Apr 2026
LAX - FRA
Read more United Airlines reviews

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

They told us yesterday APR21st that they were cleaning the plane and we got delayed. After that they said they didn't had any crew for the flight so they cancelled the flight till next day.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Flight itself excellent, but delayed so missed connection & got to destination 2 hrs later

The flight crew on this leg of my trip was very friendly and pleasant. Every one of them was humorous, as well as helpful and accommodating. This group was BY FAR the best crew I’ve flown with. They deserve kudos.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was delayed from take off because only one runway was operational in San Francisco.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Really hard landing... as in slammed into the runway then hit the brakes really hard ...

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Medford (MFR)