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$415+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — SJU
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$415
(United Airlines)

Popular in

December

Cheapest in

June

Average price

$605
From Medford to Caribbean
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($195 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($62 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 29, 2025.

This United Airlines deal was found by Cheapflights users on 7/29. 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 10/155:00 amMFR - SJU
1 stop9h 30mUnited Airlines
Thu 10/301:25 pmSJU - MFR
1 stop10h 49mUnited Airlines
Deal found 7/29$415
This Delta deal was found by Cheapflights users on 7/29. 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 11/145:21 pmMFR - SJU
2 stops17h 55mDelta
Thu 11/207:30 amSJU - MFR
2 stops20h 14mDelta
Deal found 7/29$470
This Mytrip deal was found by Cheapflights users on 7/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/299:51 pmMFR - SJU
3 stops32h 14mMultiple Airlines
Sun 9/73:19 pmSJU - MFR
3 stops26h 28mMultiple Airlines
Deal found 7/27$537
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Thu 10/232:22 pmMFR - SJU
2 stops17h 44mAmerican Airlines
Tue 10/287:45 amSJU - MFR
2 stops19h 14mAmerican Airlines
Deal found 7/27$604
This Delta deal was found by Cheapflights users on 7/28. 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.
Mon 11/176:05 amMFR - GCM
2 stops27h 32mDelta
Fri 11/212:02 pmGCM - MFR
2 stops23h 53mDelta
Deal found 7/28$710
This United Airlines deal was found by Cheapflights users on 7/26. 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 11/176:36 pmMFR - GCM
2 stops18h 54mUnited Airlines
Fri 11/215:45 pmGCM - MFR
2 stops29h 23mUnited Airlines
Deal found 7/26$758
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Mon 11/103:00 pmMFR - SKB
2 stops19h 39mAmerican Airlines
Thu 11/133:39 pmSKB - MFR
2 stops26h 15mAmerican Airlines
Deal found 7/28$812
This American Airlines deal was found by Cheapflights users on 7/28. 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 12/133:30 pmMFR - GCM
2 stops17h 16mAmerican Airlines
Sat 12/274:15 pmGCM - MFR
2 stops23h 39mAmerican Airlines
Deal found 7/28$886

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 July 29, 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

Wed 10/15

5:00 am-5:30 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Thu 10/30

7:10 am-9:14 pm

2 stops17h 04m

$415

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Fri 11/14

5:21 pm-3:16 pm

2 stops17h 55m

San Juan Luis Munoz Marin Intl

Thu 11/20

7:30 am-11:44 pm

2 stops20h 14m

$470

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Fri 8/29

9:51 pm-9:05 am

3 stops32h 14m

San Juan Luis Munoz Marin Intl

Sun 9/7

3:19 pm-2:47 pm

3 stops26h 28m

$537

MedfordSan Juan

MFR - SJU

MFRSJU

Medford

Thu 10/23

2:22 pm-11:06 am

2 stops17h 44m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:45 am-11:59 pm

2 stops19h 14m

$604

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Mon 11/17

6:05 am-12:37 pm

2 stops27h 32m

George Town Owen Roberts Intl

Fri 11/21

2:02 pm-10:55 am

2 stops23h 53m

$710

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Mon 11/17

6:36 pm-4:30 pm

2 stops18h 54m

George Town Owen Roberts Intl

Fri 11/21

5:45 pm-8:08 pm

2 stops29h 23m

$758

MedfordBasseterre

MFR - SKB

MFRSKB

Medford

Mon 11/10

3:00 pm-2:39 pm

2 stops19h 39m

Basseterre Robert Bradshaw Intl

Thu 11/13

3:39 pm-1:54 pm

2 stops26h 15m

$812

MedfordGeorge Town

MFR - GCM

MFRGCM

Medford

Sat 12/13

3:30 pm-11:46 am

2 stops17h 16m

George Town Owen Roberts Intl

Sat 12/27

4:15 pm-12:54 pm

2 stops23h 39m

$886

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 July 29, 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 July 29, 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
8.0
Very good
7,979 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,979 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,979 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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.

  • 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$202Average$580FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$484Average$649FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$499Average$557FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$582Average$705FlexibilityNo cancel feeOn-time69%

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