HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$431+ Cheap flights from Medford (MFR) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Medford to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Medford to Caribbean

Cheapest flights from Medford to Caribbean
Explore the most affordable flight options available from Medford to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:34 pmMFR - SJU
2 stops19h 51mUnited Airlines
Mon 12/293:46 pmSJU - MFR
2 stops25h 39mUnited Airlines
Deal found 12/10$1,205
This American Airlines deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:20 amMFR - SJU
2 stops14h 39mAmerican Airlines
Mon 12/297:00 amSJU - MFR
2 stops17h 20mAmerican Airlines
Deal found 12/11$1,532

Find flight deals from Medford to Caribbean

Keep the following information in mind while searching for Medford to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$431
(American Airlines)

Popular in

December

Cheapest in

June

Average price

$1,264
From Medford to Caribbean
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($201 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($63 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Medford to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
Use the filters below to find and compare flights from Medford to Caribbean that are best for you.

Fly from

Medford

Fly to

Caribbean

Route

Depart

Return

Price

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 2/24

4:30 pm-11:55 am

2 stops15h 25m

San Juan Luis Munoz Marin Intl

Thu 3/5

8:30 am-11:59 pm

2 stops19h 29m

$431

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 5/5

6:34 pm-1:45 pm

2 stops16h 11m

San Juan Luis Munoz Marin Intl

Wed 5/6

1:00 am-11:47 am

2 stops13h 47m

$516

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 4/7

6:34 pm-12:34 pm

2 stops15h 00m

San Juan Luis Munoz Marin Intl

Wed 4/15

1:40 pm-9:26 pm

1 stop10h 46m

$516

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 2/24

5:02 am-6:25 pm

1 stop9h 23m

San Juan Luis Munoz Marin Intl

Thu 3/5

2:25 pm-9:33 pm

1 stop11h 08m

$521

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Mon 1/26

6:25 pm-1:15 pm

2 stops15h 50m

George Town Owen Roberts Intl

Thu 1/29

2:50 pm-9:02 pm

2 stops33h 12m

$597

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Fri 12/26

5:00 am-6:11 am

2 stops21h 11m

$539

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Fri 12/26

7:05 pm-10:05 pm

3 stops23h 00m

$639

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Best time to book a flight from Medford to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Medford with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Medford to Caribbean

What is the cheapest time of day to fly from MFR to CB?

Find hourly flight availability from Medford to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

It’s typically best to fly out from Medford to Caribbean in the afternoon. Doing so could potentially save you 48% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated December 12, 2025.
Get a feel of what it's like to fly with Delta and United Airlines from Medford to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,007 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,095 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Medford to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Medford to Caribbean?

    Located just 3.0 mi from the city center, Medford (MFR) is the airport most travelers will use when flying to Caribbean from Medford.

  • How long is the flight from Medford to Caribbean?

    For as low as $431, American Airlines can have you in Caribbean from Medford in 14h 07m. There are 3687 mi between Medford and Caribbean. This flight may include one or multiple stops.

  • What are the most popular routes from Medford to Caribbean?

    The most popular route from Medford to Caribbean is Medford - San Juan Luis Munoz Marin Intl. You may also consider Medford - Havana Jose Marti Intl or Medford - George Town Owen Roberts Intl.

  • Can I find deals for flights from Medford to Caribbean that include hotel bookings?

    Yes. In addition to deals on Medford to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Medford to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Medford to Caribbean.

  • Can I find deals for business class flights from Medford to Caribbean?

    Yes. Cheapflights offers flight deals from Medford to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Medford to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Portland to Los Angeles flights
Portland to Las Vegas flights
Portland to John F Kennedy Intl flights
Portland to Sky Harbor Intl flights
Portland to Newark flights
Portland to Honolulu flights
Portland to Ontario flights
Portland to Kahului flights
Portland to Dallas/Fort Worth flights
Portland to Cancún flights
Portland to Orlando flights
Portland to Miami flights
Portland to Hobby flights
Portland to Minneapolis flights
Portland to San Diego flights
Portland to Denver flights
Portland to San Francisco flights
Portland to Palm Springs flights
Portland to LaGuardia flights
Portland to O'Hare Intl flights
Portland to Atlanta flights
Portland to Kailua-Kona flights
Portland to George Bush Intcntl flights
Portland to Heathrow flights
Portland to Narita flights
Portland to Boston flights
Portland to Mexico City flights
Boise to Los Angeles flights
Portland to Santa Ana flights
Portland to Puerto Vallarta flights
Portland to Haneda flights
Boise to Las Vegas flights
Portland to New Orleans flights
Portland to Salt Lake City flights
Portland to Lihue flights
Boise to Sky Harbor Intl flights
Boise to Seattle flights
Portland to Austin flights
Portland to Burbank flights
Portland to San José del Cabo flights
Portland to Cozumel flights
Portland to Tucson flights
Boise to Denver flights
Portland to Tampa flights
Redmond to Seattle flights
Portland to Dulles Intl flights
Portland to Suvarnabhumi flights
Boise to Dallas/Fort Worth flights
Portland to Nashville flights
Boise to O'Hare Intl flights

Top 2 airlines flying from Medford to Caribbean

Discover the top 2 airlines that operate flights from Medford to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$202Average$580FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$574Average$774FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.