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$226+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:28 pm
MFR
-
GCM
2 stops16h 32m
Delta
Thu 4/301:25 pm
GCM
-
MFR
2 stops23h 09m
Delta
Deal found 1/28$432
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Wed 2/255:02 am
MFR
-
SJU
2 stops15h 34m
United Airlines
Wed 3/48:05 am
SJU
-
MFR
2 stops17h 13m
United Airlines
Deal found 1/26$517
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:14 am
MFR
-
GCM
2 stops22h 46m
Delta
Thu 4/301:25 pm
GCM
-
MFR
2 stops23h 09m
Delta
Deal found 1/28$547
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:14 am
MFR
-
GCM
2 stops22h 46m
Delta
Fri 5/11:25 pm
GCM
-
MFR
2 stops23h 09m
Delta
Deal found 1/28$588
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 4/95:00 am
MFR
-
SJU
1 stop9h 38m
United Airlines
Fri 4/177:40 am
SJU
-
MFR
2 stops16h 57m
United Airlines
Deal found 1/27$597
This United Airlines deal was found by Cheapflights users on 1/26. 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 3/26:25 pm
MFR
-
GCM
2 stops15h 50m
United Airlines
Thu 3/52:50 pm
GCM
-
MFR
2 stops33h 28m
United Airlines
Deal found 1/26$600
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/252:08 pm
MFR
-
GCM
2 stops21h 03m
American Airlines
Sat 5/211:55 am
GCM
-
MFR
2 stops13h 02m
American Airlines
Deal found 1/28$631
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 5/212:52 pm
MFR
-
GCM
2 stops21h 38m
United Airlines
Sat 5/94:09 pm
GCM
-
MFR
2 stops22h 52m
United Airlines
Deal found 1/27$660
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Thu 4/236:31 pm
MFR
-
GCM
2 stops15h 59m
United Airlines
Mon 5/41:35 pm
GCM
-
MFR
2 stops24h 12m
United Airlines
Deal found 1/28$676
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Sun 4/266:49 am
MFR
-
GCM
2 stops27h 41m
United Airlines
Mon 5/41:35 pm
GCM
-
MFR
2 stops24h 12m
United Airlines
Deal found 1/28$696
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:14 am
MFR
-
GCM
2 stops22h 46m
Delta
Fri 5/11:25 pm
GCM
-
MFR
2 stops23h 09m
Delta
Deal found 1/28$699
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/252:08 pm
MFR
-
GCM
2 stops19h 24m
American Airlines
Mon 5/42:10 pm
GCM
-
MFR
2 stops26h 47m
American Airlines
Deal found 1/28$756

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 January 29, 2026.

Round-trip from

$432
(Delta)

One-way from

$226
(United Airlines)

Popular in

February

Cheapest in

June

Average price

$642
From Medford to Caribbean
Search Deals
One-way flight from Medford to Caribbean
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($105 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($56 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Sun 4/26

5:28 pm-12:00 pm

2 stops16h 32m

George Town Owen Roberts Intl

Thu 4/30

1:25 pm-10:34 am

2 stops23h 09m

$432

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Mon 4/27

5:28 pm-12:00 pm

2 stops16h 32m

George Town Owen Roberts Intl

Thu 4/30

1:25 pm-10:34 am

2 stops23h 09m

$432

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Wed 2/25

5:02 am-12:36 am

2 stops15h 34m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:05 am-9:18 pm

2 stops17h 13m

$517

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Fri 4/24

5:55 am-12:00 pm

2 stops28h 05m

George Town Owen Roberts Intl

Thu 4/30

1:25 pm-10:34 am

2 stops23h 09m

$547

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Sat 4/25

5:55 am-12:00 pm

2 stops28h 05m

George Town Owen Roberts Intl

Thu 4/30

1:25 pm-10:34 am

2 stops23h 09m

$547

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Mon 4/27

5:28 pm-12:00 pm

2 stops16h 32m

George Town Owen Roberts Intl

Fri 5/1

1:25 pm-10:34 am

2 stops23h 09m

$588

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Sun 4/26

11:14 am-12:00 pm

2 stops22h 46m

George Town Owen Roberts Intl

Fri 5/1

1:25 pm-10:34 am

2 stops23h 09m

$588

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Thu 4/9

5:00 am-5:38 pm

1 stop9h 38m

San Juan Luis Munoz Marin Intl

Fri 4/17

7:40 am-9:37 pm

2 stops16h 57m

$597

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Mon 3/2

6:25 pm-1:15 pm

2 stops15h 50m

George Town Owen Roberts Intl

Thu 3/5

2:50 pm-9:18 pm

2 stops33h 28m

$600

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Sat 4/25

2:08 pm-1:11 pm

2 stops21h 03m

George Town Owen Roberts Intl

Sat 5/2

11:55 am-10:57 pm

2 stops13h 02m

$631

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 20 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
No data available for this route at this time. Please check back soon.

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 January 29, 2026.
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
8,127 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Crew

8.5

Entertainment

7.8

Comfort

7.9

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
8,127 reviews
Delta
7.9
Good
8,127 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Crew

8.5

Entertainment

7.8

Comfort

7.9

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
9,215 reviews
Delta
7.9
Good
8,127 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Crew

8.5

Entertainment

7.8

Comfort

7.9

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 $517, Delta can have you in Caribbean from Medford in 15h 34m. 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 - George Town Owen Roberts Intl. You may also consider Medford - San Juan Luis Munoz Marin 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 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$202Average$202FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$574Average$698FlexibilityNo cancel feeOn-time69%

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