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Caribbean

$118+ Cheap flights from Madison (MSN) 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Madison to Caribbean

Keep the following information in mind while searching for Madison to Caribbean flight deals. Data was last updated September 11, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$118
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$353
From Madison Truax Field to Caribbean
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One-way flight from Madison Truax Field to Caribbean
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Highest demand for flights based on searches. 3% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 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 Madison to Caribbean

Cheapest flights from Madison to Caribbean
Explore the most affordable flight options available from Madison 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.
Sat 10/186:00 amMSN - SJU
1 stop7h 11mDelta
Sat 10/257:00 amSJU - MSN
2 stops14h 21mDelta
Deal found 9/10$235
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/910:50 amMSN - SJU
2 stops11h 46mUnited Airlines
Tue 12/168:30 amSJU - MSN
2 stops10h 15mUnited Airlines
Deal found 9/10$255
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.
Wed 10/229:20 amMSN - SJU
2 stops13h 36mDelta
Sat 10/252:22 pmSJU - MSN
2 stops9h 07mDelta
Deal found 9/10$294
This American Airlines deal was found by Cheapflights users on 9/11. 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 11/86:00 amMSN - SJU
2 stops13h 24mAmerican Airlines
Tue 11/117:00 amSJU - MSN
1 stop16h 54mAmerican Airlines
Deal found 9/11$315
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 9/296:40 pmMSN - SJU
2 stops17h 07mAmerican Airlines
Tue 10/75:30 amSJU - MSN
1 stop12h 09mAmerican Airlines
Deal found 9/10$317
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/226:30 amMSN - SJU
1 stop7h 14mUnited Airlines
Fri 10/241:05 amSJU - MSN
2 stops11h 40mUnited Airlines
Deal found 9/10$335
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.
Wed 10/227:40 amMSN - SJU
2 stops13h 30mAmerican Airlines
Sun 10/265:30 amSJU - MSN
1 stop12h 09mAmerican Airlines
Deal found 9/10$350
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:38 pmMSN - PUJ
2 stops17h 57mAmerican Airlines
Tue 10/74:30 pmPUJ - MSN
1 stop7h 26mAmerican Airlines
Deal found 9/9$355
This American Airlines deal was found by Cheapflights users on 9/11. 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 11/14:29 pmMSN - PUJ
2 stops18h 27mAmerican Airlines
Tue 11/45:24 pmPUJ - MSN
2 stops18h 26mAmerican Airlines
Deal found 9/11$358
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.
Fri 10/316:00 amMSN - PUJ
1 stop7h 05mAmerican Airlines
Tue 11/43:02 pmPUJ - MSN
1 stop10h 28mAmerican Airlines
Deal found 9/10$377
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:08 pmMSN - PUJ
1 stop16h 39mAmerican Airlines
Sun 12/145:57 pmPUJ - MSN
1 stop17h 58mAmerican Airlines
Deal found 9/9$383
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/268:25 pmMSN - PUJ
2 stops18h 20mAmerican Airlines
Sun 11/25:47 pmPUJ - MSN
2 stops17h 31mAmerican Airlines
Deal found 9/11$387

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison 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 Madison to Caribbean that are best for you.

Fly from

Madison

Fly to

Caribbean

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

11:43 am-12:05 am

2 stops10h 22m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:45 pm-11:42 pm

2 stops10h 57m

$275

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

11:43 am-12:05 am

2 stops10h 22m

San Juan Luis Munoz Marin Intl

Tue 1/27

4:40 pm-11:42 pm

1 stop9h 02m

$275

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 12/9

8:05 am-8:57 pm

1 stop10h 52m

San Juan Luis Munoz Marin Intl

Tue 12/16

12:49 pm-8:19 pm

2 stops9h 30m

$275

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 12/9

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Tue 12/16

8:10 am-2:01 pm

1 stop7h 51m

$311

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sat 10/4

6:24 pm-2:34 pm

2 stops19h 10m

Punta Cana

Tue 10/7

4:35 pm-10:15 am

2 stops18h 40m

$355

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sat 1/31

4:17 pm-11:50 am

2 stops17h 33m

Punta Cana

Tue 2/3

6:20 pm-10:47 am

2 stops18h 27m

$358

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sat 11/1

4:29 pm-11:56 am

2 stops18h 27m

Punta Cana

Tue 11/4

5:24 pm-9:50 am

2 stops18h 26m

$358

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

6:30 am-9:26 pm

2 stops12h 56m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-2:10 pm

2 stops14h 05m

$365

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 1/12

10:45 am-9:00 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Fri 1/16

2:05 am-2:10 pm

2 stops14h 05m

$365

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 1/31

2:56 pm-6:11 am

2 stops13h 15m

San Juan Luis Munoz Marin Intl

Wed 2/4

2:05 am-2:10 pm

2 stops14h 05m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 52 results
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Best time to book a flight from Madison to Caribbean

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

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

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

What is the cheapest time of day to fly from MSN to CB?

Find hourly flight availability from Madison 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 Madison 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.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Madison to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

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
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

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
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

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
7,960 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

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 Madison 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 Madison to Caribbean?

    Most people fly from Madison Truax Field (MSN) if they book a flight from Madison to Caribbean. Madison Truax Field is conveniently located just 5.4 mi from Madison’s city center.

  • How long is the flight from Madison to Caribbean?

    There are many flights that can get you from Madison to Caribbean in 7h 19m. Fly via American Airlines or Delta to get the fastest option. There are 1418 mi between Madison and Caribbean. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Madison to Caribbean one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $118. Users have also found prices from $158 and $307 on American Airlines and Delta, respectively.

  • What are the most popular routes from Madison to Caribbean?

    The most popular flight routes from Madison to Caribbean are Madison Truax Field - San Juan Luis Munoz Marin Intl, Madison Truax Field - Punta Cana and Madison Truax Field - Oranjestad Reina Beatrix.

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

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

  • How can I find direct flights from Madison to Caribbean?

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

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

    Yes. Cheapflights offers flight deals from Madison 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 Madison to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean (average of $254). Flying from Madison 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 3 airlines flying from Madison to Caribbean

Discover the top 3 airlines that operate flights from Madison 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$254Average$753FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$270Average$642FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$293Average$648FlexibilityNo cancel feeOn-time69%

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