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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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
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Cheap 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 diciembre 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/10. 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.
sáb. 12/133:12 pmMSN - PUJ
2 stops18h 43mAmerican Airlines
lun. 12/155:21 pmPUJ - MSN
1 stop8h 19mAmerican Airlines
Deal found 12/10$438
This American Airlines deal was found by Cheapflights users on 12/11. 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.
mar. 12/308:10 pmMSN - SJU
1 stop6h 50mAmerican Airlines
vie. 1/92:31 pmSJU - MSN
2 stops10h 09mAmerican Airlines
Deal found 12/11$479
This Delta deal was found by Cheapflights users on 12/10. 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.
mié. 12/105:38 amMSN - MBJ
1 stop7h 35mDelta
dom. 12/143:38 pmMBJ - MSN
1 stop7h 48mDelta
Deal found 12/10$503
This American Airlines deal was found by Cheapflights users on 12/10. 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.
mié. 12/106:09 amMSN - MBJ
2 stops8h 40mAmerican Airlines
dom. 12/1411:12 amMBJ - MSN
2 stops11h 36mAmerican Airlines
Deal found 12/10$513
This American Airlines deal was found by Cheapflights users on 12/11. 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.
mar. 12/1612:18 pmMSN - SJU
1 stop7h 51mAmerican Airlines
sáb. 12/276:00 amSJU - MSN
1 stop15h 40mAmerican Airlines
Deal found 12/11$539
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/215:40 amMSN - MBJ
1 stop14h 01mDelta
dom. 12/282:55 pmMBJ - MSN
1 stop8h 14mDelta
Deal found 12/11$580
This American Airlines deal was found by Cheapflights users on 12/10. 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.
jue. 12/187:00 amMSN - SJU
1 stop13h 05mAmerican Airlines
jue. 1/81:24 pmSJU - MSN
2 stops11h 16mAmerican Airlines
Deal found 12/10$602
This American Airlines deal was found by Cheapflights users on 12/11. 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.
jue. 12/187:00 amMSN - SJU
1 stop13h 05mAmerican Airlines
jue. 12/256:00 amSJU - MSN
1 stop13h 42mAmerican Airlines
Deal found 12/11$632
This United Airlines deal was found by Cheapflights users on 12/9. 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.
mié. 12/106:30 amMSN - SJU
1 stop7h 10mUnited Airlines
mié. 12/105:50 pmSJU - MSN
2 stops22h 01mUnited Airlines
Deal found 12/9$634
This American Airlines deal was found by Cheapflights users on 12/10. 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.
mié. 12/312:30 pmMSN - STT
2 stops19h 35mAmerican Airlines
sáb. 1/106:39 pmSTT - MSN
2 stops18h 04mAmerican Airlines
Deal found 12/10$641
This eDestinos deal was found by Cheapflights users on 12/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/222:56 pmMSN - SJU
3 stops32h 43mMultiple Airlines
vie. 1/92:29 amSJU - MSN
2 stops17h 07mMultiple Airlines
Deal found 12/10$646
This American Airlines deal was found by Cheapflights users on 12/10. 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.
lun. 12/229:51 amMSN - SJU
2 stops10h 14mAmerican Airlines
vie. 12/262:44 pmSJU - MSN
1 stop11h 15mAmerican Airlines
Deal found 12/10$662

Find flight deals from Madison to Caribbean

Keep the following information in mind while searching for Madison to Caribbean flight deals. Data was last updated diciembre 12, 2025.

Round-trip from

$235
(United Airlines)

One-way from

$118
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$617
From Madison Truax Field to Caribbean
Search Deals
One-way flight from Madison Truax Field to Caribbean
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 diciembre 12, 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. 2/10

8:15 am-9:26 pm

2 stops11h 11m

San Juan Luis Munoz Marin Intl

mar. 2/17

2:05 am-11:58 am

2 stops11h 53m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

jue. 1/29

7:25 am-8:50 pm

2 stops11h 25m

San Juan Luis Munoz Marin Intl

mar. 2/3

7:00 am-4:20 pm

1 stop11h 20m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 1/27

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

vie. 1/30

2:05 am-11:51 am

2 stops11h 46m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

lun. 1/26

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

jue. 1/29

2:05 am-11:51 am

2 stops11h 46m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dom. 1/25

2:56 pm-6:11 am

2 stops13h 15m

San Juan Luis Munoz Marin Intl

vie. 1/30

8:35 am-2:52 pm

1 stop8h 17m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

jue. 1/29

7:00 am-10:26 pm

1 stop13h 26m

San Juan Luis Munoz Marin Intl

jue. 2/5

6:00 am-12:46 pm

1 stop8h 46m

$268

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dom. 1/11

3:48 pm-6:11 am

2 stops12h 23m

San Juan Luis Munoz Marin Intl

mié. 1/21

8:10 am-5:47 pm

2 stops11h 37m

$312

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mié. 1/21

6:30 am-9:26 pm

2 stops12h 56m

San Juan Luis Munoz Marin Intl

mié. 1/28

8:35 am-2:52 pm

1 stop8h 17m

$325

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 1/20

6:30 am-9:26 pm

2 stops12h 56m

San Juan Luis Munoz Marin Intl

sáb. 1/24

7:45 am-9:05 pm

2 stops15h 20m

$325

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 1/20

6:30 am-9:26 pm

2 stops12h 56m

San Juan Luis Munoz Marin Intl

jue. 1/22

8:35 am-2:52 pm

1 stop8h 17m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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, November is the cheapest month in which you can book a flight from Madison to Caribbean (average of $113). 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 diciembre 12, 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 25% 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 diciembre 12, 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
8,007 reviews

Food

7.3

Boarding

8.1

Comfort

7.9

Overall

7.9

Entertainment

7.9

Crew

8.5

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
8,007 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Boarding

8.1

Comfort

7.9

Overall

7.9

Entertainment

7.9

Crew

8.5

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
9,095 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Boarding

8.1

Comfort

7.9

Overall

7.9

Entertainment

7.9

Crew

8.5

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
11,050 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Boarding

8.1

Comfort

7.9

Overall

7.9

Entertainment

7.9

Crew

8.5

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 9h 02m. Fly via United Airlines, 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 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 - Saint Thomas Island Cyril E King.

  • 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 $113). 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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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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$225Average$756FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$257Average$664FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$269Average$669FlexibilityNo cancel feeOn-time71%

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