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Caribbean Islands

$113+ Cheap flights from Madison (MSN) to Caribbean Islands

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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
mai 2 — mai 91
sáb 5/2
sáb 5/9
1 adult, Economy
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Cheap flight deals from Madison to Caribbean Islands

Cheapest flights from Madison to Caribbean Islands
Explore the most affordable flight options available from Madison to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 2, 2026.

This United Airlines deal was found by Cheapflights users on 3/31. 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.
ter 10/279:44 am
MSN
-
SJU
2 stops10h 38m
United Airlines
ter 11/34:52 pm
SJU
-
MSN
1 stop9h 20m
United Airlines
Deal found 3/31$226
This American Airlines deal was found by Cheapflights users on 3/31. 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.
seg 10/198:25 pm
MSN
-
SJU
1 stop16h 20m
American Airlines
qua 10/285:25 am
SJU
-
MSN
1 stop14h 33m
American Airlines
Deal found 3/31$326
This American Airlines deal was found by Cheapflights users on 3/31. 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.
qua 4/2211:35 am
MSN
-
SJU
1 stop8h 16m
American Airlines
qua 4/297:25 am
SJU
-
MSN
1 stop17h 30m
American Airlines
Deal found 3/31$331
This American Airlines deal was found by Cheapflights users on 3/31. 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 9/58:26 pm
MSN
-
MBJ
1 stop16h 05m
American Airlines
sáb 9/1212:43 pm
MBJ
-
MSN
1 stop10h 40m
American Airlines
Deal found 3/31$352
This American Airlines deal was found by Cheapflights users on 3/30. 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.
qua 9/26:00 am
MSN
-
SJU
2 stops11h 15m
American Airlines
seg 9/73:50 pm
SJU
-
MSN
1 stop17h 25m
American Airlines
Deal found 3/30$356
This American Airlines deal was found by Cheapflights users on 3/30. 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.
qui 5/148:24 pm
MSN
-
MBJ
2 stops17h 01m
American Airlines
qui 5/212:08 pm
MBJ
-
MSN
2 stops17h 41m
American Airlines
Deal found 3/30$357
This Delta deal was found by Cheapflights users on 3/31. 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 9/65:45 am
MSN
-
SJU
1 stop9h 50m
Delta
qua 9/167:00 am
SJU
-
MSN
2 stops10h 36m
Delta
Deal found 3/31$358
This American Airlines deal was found by Cheapflights users on 3/31. 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.
sex 12/43:55 pm
MSN
-
MBJ
1 stop17h 17m
American Airlines
qui 12/102:30 pm
MBJ
-
MSN
1 stop19h 49m
American Airlines
Deal found 3/31$358
This American Airlines deal was found by Cheapflights users on 3/28. 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.
sex 5/81:20 pm
MSN
-
SJU
1 stop6h 55m
American Airlines
sáb 5/97:25 am
SJU
-
MSN
1 stop17h 30m
American Airlines
Deal found 3/28$361
This American Airlines deal was found by Cheapflights users on 4/1. 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.
qui 4/166:20 am
MSN
-
MBJ
1 stop7h 55m
American Airlines
qui 4/3010:17 am
MBJ
-
MSN
1 stop13h 38m
American Airlines
Deal found 4/1$364
This American Airlines deal was found by Cheapflights users on 3/30. 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.
qui 4/231:05 pm
MSN
-
SJU
1 stop8h 00m
American Airlines
qua 4/291:31 pm
SJU
-
MSN
2 stops10h 57m
American Airlines
Deal found 3/30$366
This Delta deal was found by Cheapflights users on 4/1. 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.
seg 4/206:22 pm
MSN
-
MBJ
2 stops18h 41m
Delta
sex 5/812:51 pm
MBJ
-
MSN
2 stops21h 25m
Delta
Deal found 4/1$367

Find flight deals from Madison to Caribbean Islands

Keep the following information in mind while searching for Madison to Caribbean Islands flight deals. Data was last updated abril 2, 2026.

Round-trip from

$326
(American Airlines)

One-way from

$113
(Delta)

Popular in

April

Cheapest in

September

Average price

$661
From Madison Truax Field to Caribbean Islands
Search Deals
One-way flight from Madison Truax Field to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($77 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Caribbean Islands 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 abril 2, 2026.
Use the filters below to find and compare flights from Madison to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

qui 4/23

6:20 am-10:05 pm

1 stop14h 45m

San Juan Luis Munoz Marin Intl

qua 4/29

2:42 pm-11:28 pm

1 stop9h 46m

$326

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

sáb 9/5

8:26 pm-12:31 pm

1 stop16h 05m

Montego Bay Sangster Intl

sáb 9/12

12:43 pm-11:23 pm

1 stop10h 40m

$352

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

seg 5/4

6:30 am-3:10 pm

2 stops8h 40m

Montego Bay Sangster Intl

sex 5/8

4:12 pm-11:37 am

2 stops19h 25m

$357

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

qui 5/14

8:24 pm-1:25 pm

2 stops17h 01m

Montego Bay Sangster Intl

qui 5/21

2:08 pm-7:49 am

2 stops17h 41m

$357

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

ter 5/26

11:04 am-8:30 pm

1 stop8h 26m

San Juan Luis Munoz Marin Intl

qua 6/3

6:15 am-9:27 pm

2 stops16h 12m

$358

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dom 4/26

6:00 am-2:44 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

qui 4/30

7:20 am-9:20 pm

2 stops15h 00m

$366

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

sáb 4/25

11:50 am-4:32 am

1 stop15h 42m

San Juan Luis Munoz Marin Intl

ter 4/28

1:31 pm-11:38 pm

2 stops11h 07m

$366

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

ter 5/5

5:30 am-11:29 am

1 stop5h 59m

Montego Bay Sangster Intl

qui 5/7

12:51 pm-8:49 am

2 stops19h 58m

$367

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

seg 4/20

5:30 am-3:17 pm

1 stop9h 47m

Montego Bay Sangster Intl

ter 5/5

4:32 pm-9:01 am

2 stops16h 29m

$367

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

ter 4/21

7:00 am-3:17 pm

2 stops8h 17m

Montego Bay Sangster Intl

qui 5/7

1:18 pm-8:49 am

2 stops19h 31m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 55 resultsSorted by cheapest first
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6

Best time to book a flight from Madison to Caribbean Islands

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

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

Currently, November is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $113). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $359). 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.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated abril 2, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican Airlines from Madison to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,370 reviews

Food

7.2

Comfort

7.9

Crew

8.5

Entertainment

7.8

Boarding

8.1

Overall

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
8,370 reviews
Delta
7.9
Good
8,370 reviews

Food

7.2

Comfort

7.9

Crew

8.5

Entertainment

7.8

Boarding

8.1

Overall

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
9,533 reviews
Delta
7.9
Good
8,370 reviews

Food

7.2

Comfort

7.9

Crew

8.5

Entertainment

7.8

Boarding

8.1

Overall

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
7.1
Good
11,549 reviews
Delta
7.9
Good
8,370 reviews

Food

7.2

Comfort

7.9

Crew

8.5

Entertainment

7.8

Boarding

8.1

Overall

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 Islands. 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 Islands?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Caribbean Islands. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to Caribbean Islands?

    A quick flight from Madison to Caribbean Islands can take about 8h 26m. American Airlines provides one of the quickest options available for as low as $358. There are 2180 mi between Madison and Caribbean Islands. This flight may include one or multiple stops.

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

    While some choose either Madison Truax Field - Punta Cana or Madison Truax Field - Montego Bay Sangster Intl, Madison Truax Field - San Juan Luis Munoz Marin Intl is the most popular route from Madison to Caribbean Islands.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $113). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $359). 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 Islands

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 Islands

Discover the top 3 airlines that operate flights from Madison to Caribbean Islands. 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 abril 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$212Average$592FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$257Average$571FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$652FlexibilityNo cancel feeOn-time71%

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