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Caribbean

$127+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
déc. 17 — déc. 241
mer. 12/17
mer. 12/24
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 novembre 17, 2025.

Round-trip from

$235
(United Airlines)

One-way from

$127
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$548
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. 2% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in November 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 novembre 17, 2025.

This United Airlines deal was found by Cheapflights users on 11/16. 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.
mar. 12/98:15 amMSN - SJU
2 stops12h 07mUnited Airlines
mar. 12/162:10 pmSJU - MSN
1 stop10h 35mUnited Airlines
Deal found 11/16$235
This American Airlines deal was found by Cheapflights users on 11/17. 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.
mar. 12/96:13 amMSN - SJU
2 stops13h 56mAmerican Airlines
mar. 12/1612:49 pmSJU - MSN
2 stops10h 59mAmerican Airlines
Deal found 11/17$268
This American Airlines deal was found by Cheapflights users on 11/15. 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.
mer. 12/106:13 amMSN - SJU
2 stops9h 39mAmerican Airlines
lun. 12/157:00 amSJU - MSN
1 stop16h 55mAmerican Airlines
Deal found 11/15$301
This American Airlines deal was found by Cheapflights users on 11/15. 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.
jeu. 12/1110:20 amMSN - SJU
1 stop11h 32mAmerican Airlines
lun. 12/157:00 amSJU - MSN
1 stop16h 55mAmerican Airlines
Deal found 11/15$390
This American Airlines deal was found by Cheapflights users on 11/15. 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.
mer. 11/198:00 amMSN - SJU
1 stop10h 48mAmerican Airlines
mer. 11/268:00 amSJU - MSN
1 stop17h 51mAmerican Airlines
Deal found 11/15$409
This American Airlines deal was found by Cheapflights users on 11/15. 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.
dim. 12/78:08 pmMSN - PUJ
1 stop16h 39mAmerican Airlines
dim. 12/142:29 pmPUJ - MSN
1 stop20h 50mAmerican Airlines
Deal found 11/15$412
This United Airlines deal was found by Cheapflights users on 11/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 12/116:30 amMSN - SJU
1 stop7h 10mUnited Airlines
dim. 12/142:05 amSJU - MSN
2 stops13h 46mUnited Airlines
Deal found 11/15$418
This United Airlines deal was found by Cheapflights users on 11/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 11/235:38 pmMSN - PUJ
2 stops17h 21mUnited Airlines
jeu. 11/275:20 pmPUJ - MSN
2 stops18h 40mUnited Airlines
Deal found 11/15$426
This Delta deal was found by Cheapflights users on 11/17. 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.
ven. 12/125:38 amMSN - NAS
1 stop9h 05mDelta
mer. 12/171:19 pmNAS - MSN
1 stop10h 07mDelta
Deal found 11/17$445
This American Airlines deal was found by Cheapflights users on 11/17. 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.
ven. 12/124:02 pmMSN - NAS
1 stop18h 04mAmerican Airlines
mer. 12/171:13 pmNAS - MSN
2 stops10h 29mAmerican Airlines
Deal found 11/17$459
This Kiwi.com deal was found by Cheapflights users on 11/15. 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.
mer. 11/196:08 pmMSN - SJU
1 stop28h 16mMultiple Airlines
mar. 11/253:59 amSJU - MSN
1 stop15h 29mMultiple Airlines
Deal found 11/15$468
This Delta deal was found by Cheapflights users on 11/17. 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.
mar. 12/25:38 amMSN - MBJ
1 stop6h 26mDelta
lun. 12/82:29 pmMBJ - MSN
1 stop8h 57mDelta
Deal found 11/17$473

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 novembre 17, 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

mar. 1/20

6:00 am-3:18 pm

1 stop7h 18m

San Juan Luis Munoz Marin Intl

mer. 1/28

7:00 am-4:20 pm

1 stop11h 20m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 12/9

8:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

mar. 12/16

2:10 pm-10:45 pm

1 stop10h 35m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 12/9

10:25 am-11:52 pm

1 stop11h 27m

San Juan Luis Munoz Marin Intl

mar. 12/16

2:36 pm-11:40 pm

2 stops11h 04m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

sam. 1/31

11:23 am-11:59 pm

2 stops10h 36m

San Juan Luis Munoz Marin Intl

jeu. 2/5

5:55 pm-11:41 pm

1 stop7h 46m

$268

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mer. 1/21

7:00 am-11:45 pm

2 stops14h 45m

San Juan Luis Munoz Marin Intl

sam. 1/24

6:15 am-2:05 pm

2 stops9h 50m

$278

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 1/20

11:31 am-11:45 pm

2 stops10h 14m

San Juan Luis Munoz Marin Intl

mer. 1/28

7:30 am-4:17 pm

1 stop10h 47m

$278

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mer. 1/21

7:00 am-11:45 pm

2 stops14h 45m

San Juan Luis Munoz Marin Intl

mer. 1/28

7:30 am-8:54 pm

2 stops15h 24m

$278

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dim. 2/1

8:10 am-11:59 pm

2 stops13h 49m

San Juan Luis Munoz Marin Intl

sam. 2/7

7:00 am-4:20 pm

1 stop11h 20m

$301

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

ven. 1/2

6:17 pm-11:39 am

1 stop15h 22m

San Juan Luis Munoz Marin Intl

mer. 1/21

6:00 am-4:52 pm

2 stops12h 52m

$301

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 1/20

8:15 am-12:36 am

2 stops14h 21m

San Juan Luis Munoz Marin Intl

mar. 1/27

2:05 am-2:10 pm

2 stops14h 05m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/16

Showing 1-10 of 56 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, November is the cheapest month in which you can book a flight from Madison to Caribbean (average of $142). Flying from Madison to Caribbean in June is currently the most expensive (average of $379). 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 novembre 17, 2025.

When flying from Madison to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 27% versus a flight in the evening.

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 novembre 17, 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
7.9
Good
8,008 reviews

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

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
8,008 reviews
Delta
7.9
Good
8,008 reviews

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

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
9,015 reviews
Delta
7.9
Good
8,008 reviews

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

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.
American Airlines
7.2
Good
11,048 reviews
Delta
7.9
Good
8,008 reviews

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

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 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 18m. Fly via American Airlines, United Airlines, or Delta to get the fastest option. There are 2180 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 American Airlines. According to our data, you can fly for as low as $127. Users have also found prices from $224 and $243 on United 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, November is the cheapest month in which you can book a flight from Madison to Caribbean (average of $142). Flying from Madison to Caribbean in June is currently the most expensive (average of $379). 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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Alternative routes for Madison to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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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 novembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$225Average$639FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$260Average$651FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$269Average$650FlexibilityNo cancel feeOn-time71%

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