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Caribbean

$128+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
fev 27 — mar 61
sex 2/27
sex 3/6
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 janeiro 28, 2026.

This United Airlines deal was found by Cheapflights users on 1/26. 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.
ter 2/246:30 am
MSN
-
SJU
2 stops12h 56m
United Airlines
qua 3/48:30 am
SJU
-
MSN
1 stop7h 37m
United Airlines
Deal found 1/26$256
This Delta deal was found by Cheapflights users on 1/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 4/86:00 am
MSN
-
SJU
1 stop7h 15m
Delta
qua 4/156:15 am
SJU
-
MSN
1 stop11h 02m
Delta
Deal found 1/26$304
This American Airlines deal was found by Cheapflights users on 1/27. 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.
ter 4/146:10 am
MSN
-
SJU
2 stops13h 41m
American Airlines
ter 4/217:25 am
SJU
-
MSN
1 stop16h 36m
American Airlines
Deal found 1/27$319
This American Airlines deal was found by Cheapflights users on 1/27. 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.
seg 4/208:25 pm
MSN
-
SJU
1 stop16h 43m
American Airlines
qua 4/294:30 pm
SJU
-
MSN
1 stop8h 25m
American Airlines
Deal found 1/27$324
This United Airlines deal was found by Cheapflights users on 1/26. 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.
sáb 2/285:44 pm
MSN
-
SJU
2 stops10h 27m
United Airlines
ter 3/32:05 am
SJU
-
MSN
2 stops11h 48m
United Airlines
Deal found 1/26$325
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 4/86:00 am
MSN
-
SJU
1 stop7h 15m
Delta
sáb 5/27:15 am
SJU
-
MSN
2 stops15h 00m
Delta
Deal found 1/27$338
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 4/216:30 am
MSN
-
SJU
2 stops13h 54m
United Airlines
ter 4/281:00 am
SJU
-
MSN
2 stops11h 38m
United Airlines
Deal found 1/27$346
This United Airlines deal was found by Cheapflights users on 1/26. 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.
dom 3/13:53 pm
MSN
-
SJU
2 stops12h 18m
United Airlines
qui 3/58:30 am
SJU
-
MSN
1 stop7h 32m
United Airlines
Deal found 1/26$350
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 3/246:00 am
MSN
-
SJU
1 stop7h 15m
Delta
sex 4/177:30 am
SJU
-
MSN
2 stops11h 19m
Delta
Deal found 1/27$352
This Faresmojo deal was found by Cheapflights users on 1/26. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 2/195:38 am
MSN
-
SJU
1 stop6h 54m
JetBlue
qui 2/267:30 am
SJU
-
MSN
1 stop10h 47m
JetBlue
Deal found 1/26$356
This American Airlines deal was found by Cheapflights users on 1/27. 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.
ter 3/38:09 am
MSN
-
SJU
2 stops11h 25m
American Airlines
qua 3/111:23 pm
SJU
-
MSN
2 stops11h 12m
American Airlines
Deal found 1/27$359
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 4/226:36 pm
MSN
-
SJU
1 stop13h 11m
Multiple Airlines
qua 4/296:30 am
SJU
-
MSN
1 stop12h 26m
Multiple Airlines
Deal found 1/27$361

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 janeiro 28, 2026.

Round-trip from

$256
(United Airlines)

One-way from

$128
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$409
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. 7% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 janeiro 28, 2026.
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

sáb 4/11

6:00 am-2:15 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

ter 5/5

2:34 pm-10:27 pm

1 stop8h 53m

$256

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

qua 4/8

6:00 am-2:15 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

qua 4/15

6:15 am-4:17 pm

1 stop11h 02m

$304

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

ter 3/3

5:38 am-2:32 pm

1 stop6h 54m

San Juan Luis Munoz Marin Intl

qua 3/11

7:00 am-9:06 pm

2 stops15h 06m

$304

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

seg 3/16

7:00 am-10:58 pm

2 stops14h 58m

San Juan Luis Munoz Marin Intl

qui 4/9

11:59 pm-11:04 am

1 stop12h 05m

$324

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

ter 3/24

6:00 am-2:15 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

sex 4/17

6:15 am-5:49 pm

2 stops12h 34m

$352

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dom 4/5

6:00 am-2:15 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

qua 4/29

2:34 pm-10:27 pm

1 stop8h 53m

$371

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

seg 4/13

7:00 am-8:24 pm

2 stops12h 24m

San Juan Luis Munoz Marin Intl

sex 4/17

6:15 am-5:49 pm

2 stops12h 34m

$386

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

ter 4/7

6:30 am-9:24 pm

2 stops13h 54m

San Juan Luis Munoz Marin Intl

sex 5/1

7:40 am-3:00 pm

1 stop8h 20m

$389

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

qui 2/19

6:30 am-3:22 pm

1 stop7h 52m

Nassau Intl

ter 2/24

12:55 pm-8:15 pm

1 stop8h 20m

$404

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

ter 4/14

11:33 am-8:51 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

sex 5/8

11:59 pm-11:04 am

1 stop12h 05m

$408

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 46 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 $378). 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

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 janeiro 28, 2026.
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
8,123 reviews

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Comfort

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
8,123 reviews
Delta
7.9
Good
8,123 reviews

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Comfort

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
9,212 reviews
Delta
7.9
Good
8,123 reviews

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Comfort

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
11,201 reviews
Delta
7.9
Good
8,123 reviews

Boarding

8.1

Entertainment

7.8

Food

7.2

Overall

7.9

Crew

8.5

Comfort

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 15m. Fly via Delta, American Airlines, or United Airlines 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 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 $113). Flying from Madison to Caribbean in June is currently the most expensive (average of $378). 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 janeiro 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$214Average$755FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$257Average$620FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$663FlexibilityNo cancel feeOn-time71%

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