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Caribbean Islands

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

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — SJU
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Medford to Caribbean Islands

Keep the following information in mind while searching for Medford to Caribbean Islands flight deals. Data was last updated September 16, 2025.

Round-trip from

$431
(Delta)

Popular in

December

Cheapest in

June

Average price

$796
From Medford to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($181 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($59 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Medford to Caribbean Islands

Cheapest flights from Medford to Caribbean Islands
Explore the most affordable flight options available from Medford to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Delta deal was found by Cheapflights users on 9/14. 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 34mDelta
Wed 12/103:20 pmSJU - MFR
2 stops12h 39mDelta
Deal found 9/14$431
This United Airlines deal was found by Cheapflights users on 9/14. 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 12/86:35 pmMFR - SJU
2 stops14h 14mUnited Airlines
Wed 12/102:25 pmSJU - MFR
1 stop11h 04mUnited Airlines
Deal found 9/14$521
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/142:22 pmMFR - GCM
2 stops18h 58mAmerican Airlines
Tue 10/2112:10 pmGCM - MFR
2 stops27h 05mAmerican Airlines
Deal found 9/14$638
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 10/116:00 amMFR - SJU
2 stops14h 54mAmerican Airlines
Mon 10/207:00 pmSJU - MFR
2 stops21h 15mAmerican Airlines
Deal found 9/16$663
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 10/45:30 amMFR - GCM
2 stops27h 52mAmerican Airlines
Thu 10/98:25 amGCM - MFR
2 stops17h 28mAmerican Airlines
Deal found 9/14$683
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/17:24 pmMFR - SJU
2 stops14h 14mAmerican Airlines
Tue 12/98:20 amSJU - MFR
2 stops15h 51mAmerican Airlines
Deal found 9/14$688
This Delta deal was found by Cheapflights users on 9/14. 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 11/1712:41 pmMFR - GCM
2 stops20h 54mDelta
Fri 11/211:50 pmGCM - MFR
2 stops24h 11mDelta
Deal found 9/14$701
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 10/115:00 amMFR - SJU
2 stops15h 57mUnited Airlines
Mon 10/202:00 pmSJU - MFR
1 stop10h 06mUnited Airlines
Deal found 9/16$790
This United Airlines deal was found by Cheapflights users on 9/14. 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 12/16:36 pmMFR - SJU
2 stops22h 50mUnited Airlines
Tue 12/92:25 pmSJU - MFR
1 stop11h 04mUnited Airlines
Deal found 9/14$793
This American Airlines deal was found by Cheapflights users on 9/13. 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 9/13$812
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/302:40 pmMFR - GCM
2 stops18h 45mAmerican Airlines
Sat 10/412:10 pmGCM - MFR
2 stops27h 18mAmerican Airlines
Deal found 9/15$854
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/305:43 amMFR - GCM
2 stops32h 22mMultiple Airlines
Sat 10/44:00 pmGCM - MFR
1 stop21h 25mMultiple Airlines
Deal found 9/15$989

Cheapflights Fare Finder

 
Customize your flight search to find flights from Medford to Caribbean Islands 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 September 16, 2025.
Use the filters below to find and compare flights from Medford to Caribbean Islands that are best for you.

Fly from

Medford

Fly to

Caribbean Islands

Route

Depart

Return

Price

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 2/24

5:21 pm-1:07 pm

2 stops15h 46m

San Juan Luis Munoz Marin Intl

Thu 3/5

7:00 am-11:09 pm

2 stops20h 09m

$431

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Mon 12/8

5:23 pm-12:57 pm

2 stops15h 34m

San Juan Luis Munoz Marin Intl

Wed 12/10

3:20 pm-11:59 pm

2 stops12h 39m

$431

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Wed 2/4

5:00 am-6:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Thu 2/12

2:25 pm-9:23 pm

1 stop10h 58m

$521

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Sun 2/8

5:00 am-6:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Fri 2/13

2:25 pm-9:23 pm

1 stop10h 58m

$568

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

$568

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 2/10

5:00 am-6:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Fri 2/13

2:25 pm-9:23 pm

1 stop10h 58m

$568

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 2/24

5:10 am-6:25 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Thu 3/5

5:50 pm-12:10 pm

2 stops22h 20m

$634

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Tue 10/14

2:22 pm-11:20 am

2 stops18h 58m

George Town Owen Roberts Intl

Tue 10/21

12:10 pm-1:15 pm

2 stops27h 05m

$638

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Sat 10/4

5:30 am-11:22 am

2 stops27h 52m

George Town Owen Roberts Intl

Thu 10/9

8:25 am-11:53 pm

2 stops17h 28m

$683

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-11:01 am

2 stops24h 11m

$701

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 16 results
1
2

Best time to book a flight from Medford to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Find hourly flight availability from Medford to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Medford to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated September 16, 2025.
See what other customers who have flown with Alaska Airlines and American Airlines from Medford to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from Medford to Caribbean Islands. 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 Islands?

    If you book a flight to Caribbean Islands from Medford, you will be flying from Medford, which is the city’s only airport. Medford (MFR) is located 3.0 mi from the center of Medford.

  • How long is the flight from Medford to Caribbean Islands?

    Departing from Medford to Caribbean Islands will take you 15h 46m. Airlines will cover a distance of 3687 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    While some choose either Medford - George Town Owen Roberts Intl or Medford - Havana Jose Marti Intl, Medford - San Juan Luis Munoz Marin Intl is the most popular route from Medford to Caribbean Islands.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Medford to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Medford to Caribbean Islands (average of $254). Flying from Medford to Caribbean Islands in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 4 airlines flying from Medford to Caribbean Islands

Discover the top 4 airlines that operate flights from Medford to Caribbean Islands. 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$202Average$580FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$484Average$649FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$499Average$678FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$574Average$688FlexibilityNo cancel feeOn-time69%

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