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$216+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$431
(Delta)

One-way from

$216
(Delta)

Popular in

February

Cheapest in

June

Average price

$796
From Medford to Caribbean
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One-way flight from Medford to Caribbean
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Highest demand for flights based on searches. 21% potential increase in price ($216 potential increase over avg. RT price).
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Cheapest flight prices on average. 17% potential price decrease ($118 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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 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 9/10$431
This United Airlines deal was found by Cheapflights users on 9/9. 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 9/9$521
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Sun 12/145:00 amMFR - SJU
1 stop9h 25mUnited Airlines
Sat 12/208:10 amSJU - MFR
2 stops17h 02mUnited Airlines
Deal found 9/8$675
This United Airlines deal was found by Cheapflights users on 9/9. 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 11/155:00 amMFR - SJU
2 stops15h 36mUnited Airlines
Sat 11/222:05 amSJU - MFR
2 stops23h 09mUnited Airlines
Deal found 9/9$783
This American Airlines deal was found by Cheapflights users on 9/10. 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 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 9/10$812

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 September 11, 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

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

Mon 12/8

6:35 pm-12:49 pm

2 stops14h 14m

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

5:10 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

Mon 3/9

2:05 pm-12:45 pm

3 stops20h 40m

George Town Owen Roberts Intl

Sat 3/14

4:30 pm-8:30 pm

2 stops30h 00m

$800

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

$812

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Sat 10/4

5:00 pm-12:13 pm

2 stops16h 13m

$216

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Sat 10/4

2:13 pm-12:34 pm

3 stops19h 21m

$261

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 9/16

5:00 pm-4:20 pm

2 stops20h 20m

$338

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Tue 9/16

5:00 am-11:57 pm

3 stops15h 57m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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 September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Medford to Caribbean as you normally would.

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 September 11, 2025.
Get a feel of what it's like to fly with Alaska Airlines, 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.0

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.
Delta
8.0
Very good
7,960 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

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.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.0

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. 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 46m. 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.

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

    Currently, September is the cheapest month in which you can book a flight from Medford to Caribbean (average of $254). Flying from Medford to Caribbean 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

Discover the top 4 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 September 11, 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$523Average$688FlexibilityNo cancel feeOn-time69%

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