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$368+ Cheap flights from Medford (MFR) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Find 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 October 28, 2025.

This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:23 pmMFR - SJU
2 stops15h 35mDelta
Wed 12/103:10 pmSJU - MFR
2 stops12h 49mDelta
Deal found 10/27$431
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/85:00 amMFR - SJU
1 stop9h 25mUnited Airlines
Wed 12/102:25 pmSJU - MFR
1 stop11h 04mUnited Airlines
Deal found 10/27$521
This United Airlines deal was found by Cheapflights users on 10/26. 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 11/106:36 pmMFR - SJU
2 stops14h 41mUnited Airlines
Thu 11/132:05 amSJU - MFR
2 stops15h 18mUnited Airlines
Deal found 10/26$585
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:00 amMFR - GCM
2 stops27h 35mDelta
Fri 11/211:50 pmGCM - MFR
2 stops24h 10mDelta
Deal found 10/26$661
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/125:00 amMFR - SJU
2 stops13h 22mUnited Airlines
Sat 11/152:05 amSJU - MFR
2 stops15h 18mUnited Airlines
Deal found 10/28$744
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Tue 10/282:22 pmMFR - GCM
2 stops20h 48mAmerican Airlines
Sat 11/13:25 pmGCM - MFR
2 stops25h 34mAmerican Airlines
Deal found 10/27$959
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/103:00 pmMFR - SKB
2 stops20h 18mAmerican Airlines
Thu 11/134:28 pmSKB - MFR
2 stops25h 31mAmerican Airlines
Deal found 10/26$1,033
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Sun 11/93:00 pmMFR - SKB
2 stops20h 18mAmerican Airlines
Thu 11/134:28 pmSKB - MFR
2 stops25h 31mAmerican Airlines
Deal found 10/27$1,082
This United Airlines deal was found by Cheapflights users on 10/26. 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 12/226:00 amMFR - SJU
3 stops32h 25mUnited Airlines
Mon 12/297:45 amSJU - MFR
2 stops19h 12mUnited Airlines
Deal found 10/26$1,161
This American Airlines deal was found by Cheapflights users on 10/25. 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 12/223:12 pmMFR - SJU
2 stops14h 23mAmerican Airlines
Mon 12/295:24 amSJU - MFR
2 stops18h 56mAmerican Airlines
Deal found 10/25$1,425

Cheap flight deals from Medford to Caribbean

Keep the following information in mind while searching for Medford to Caribbean flight deals. Data was last updated October 28, 2025.

Round-trip from

$431
(Delta)

One-way from

$383
(Delta)

Popular in

December

Cheapest in

June

Average price

$613
From Medford to Caribbean
Search Deals
One-way flight from Medford to Caribbean
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($229 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($67 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 October 28, 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

Mon 12/8

5:23 pm-12:58 pm

2 stops15h 35m

San Juan Luis Munoz Marin Intl

Wed 12/10

2:08 pm-11:59 pm

2 stops13h 51m

$431

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 2/24

4:47 pm-11:55 am

2 stops15h 08m

San Juan Luis Munoz Marin Intl

Thu 3/5

8:30 am-10:55 pm

2 stops18h 25m

$431

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Mon 12/8

5:00 am-6:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Wed 12/10

2:25 pm-9:29 pm

1 stop11h 04m

$521

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 2/24

5:02 am-6:25 pm

1 stop9h 23m

San Juan Luis Munoz Marin Intl

Wed 3/4

2:05 am-5:41 pm

2 stops19h 36m

$521

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Mon 11/17

12:41 pm-12:35 pm

2 stops20h 54m

George Town Owen Roberts Intl

Fri 11/21

1:50 pm-11:00 am

2 stops24h 10m

$661

MedfordBasseterre

MFR - SKB

MFRSKB

Medford

Mon 11/10

3:00 pm-3:18 pm

2 stops20h 18m

Basseterre Robert Bradshaw Intl

Thu 11/13

4:28 pm-1:59 pm

2 stops25h 31m

$1,033

MedfordBasseterre

MFR - SKB

MFRSKB

Medford

Sun 11/9

3:00 pm-3:18 pm

2 stops20h 18m

Basseterre Robert Bradshaw Intl

Thu 11/13

4:28 pm-1:59 pm

2 stops25h 31m

$1,082

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Fri 12/12

5:00 am-10:22 pm

2 stops13h 22m

$368

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Sat 12/13

5:23 pm-12:58 pm

2 stops15h 35m

$383

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Fri 12/12

5:23 pm-3:54 pm

2 stops18h 31m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 12 results
1
2

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 October 28, 2025.

It’s typically best to fly out from Medford to Caribbean in the afternoon. Doing so could potentially save you 18% 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 October 28, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American 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
7,994 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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, Delta can have you in Caribbean from Medford in 15h 08m. 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 - George Town Owen Roberts Intl or Medford - Havana Jose Marti 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

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Top 3 airlines flying from Medford to Caribbean

Discover the top 3 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$202Average$580FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$499Average$499FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$523Average$648FlexibilityNo cancel feeOn-time69%

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