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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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
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 octubre 29, 2025.

Round-trip from

$235
(Delta)

One-way from

$118
(Delta)

Popular in

March

Cheapest in

September

Average price

$420
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 ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/96:30 amMSN - SJU
2 stops12h 56mUnited Airlines
mar. 12/168:10 amSJU - MSN
1 stop7h 51mUnited Airlines
Deal found 10/28$257
This American Airlines deal was found by Cheapflights users on 10/28. 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.
mar. 12/912:18 pmMSN - SJU
1 stop7h 51mAmerican Airlines
mar. 12/165:56 pmSJU - MSN
1 stop7h 44mAmerican Airlines
Deal found 10/28$268
This American Airlines deal was found by Cheapflights users on 10/27. 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.
sáb. 12/611:00 amMSN - SJU
2 stops21h 09mAmerican Airlines
mar. 12/98:20 amSJU - MSN
1 stop17h 20mAmerican Airlines
Deal found 10/27$295
This American Airlines deal was found by Cheapflights users on 10/27. 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.
mar. 12/95:00 amMSN - SJU
2 stops15h 09mAmerican Airlines
lun. 12/155:56 pmSJU - MSN
1 stop7h 44mAmerican Airlines
Deal found 10/27$301
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/183:46 pmMSN - SJU
2 stops12h 25mUnited Airlines
jue. 12/258:10 amSJU - MSN
1 stop7h 44mUnited Airlines
Deal found 10/28$325
This American Airlines deal was found by Cheapflights users on 10/28. 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.
mié. 12/1010:20 amMSN - SJU
1 stop11h 32mAmerican Airlines
lun. 12/152:36 pmSJU - MSN
2 stops11h 04mAmerican Airlines
Deal found 10/28$331
This American Airlines deal was found by Cheapflights users on 10/27. 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.
lun. 12/88:05 amMSN - SJU
1 stop12h 04mAmerican Airlines
mar. 12/165:56 pmSJU - MSN
1 stop7h 44mAmerican Airlines
Deal found 10/27$340
This Frontier deal was found by Cheapflights users on 10/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/78:00 pmMSN - SJU
2 stops17h 19mFrontier
jue. 11/137:30 amSJU - MSN
2 stops13h 45mFrontier
Deal found 10/26$366
This American Airlines deal was found by Cheapflights users on 10/27. 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.
vie. 12/512:18 pmMSN - SJU
1 stop7h 51mAmerican Airlines
mié. 12/108:20 amSJU - MSN
1 stop17h 20mAmerican Airlines
Deal found 10/27$382
This United Airlines deal was found by Cheapflights users on 10/27. 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.
lun. 11/36:30 amMSN - PUJ
1 stop7h 32mUnited Airlines
sáb. 11/812:56 pmPUJ - MSN
2 stops9h 39mUnited Airlines
Deal found 10/27$416
This Delta deal was found by Cheapflights users on 10/27. 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.
jue. 12/115:38 amMSN - NAS
1 stop9h 05mDelta
jue. 12/181:19 pmNAS - MSN
1 stop10h 07mDelta
Deal found 10/27$445
This American Airlines deal was found by Cheapflights users on 10/29. 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. 11/37:00 amMSN - PUJ
1 stop7h 27mAmerican Airlines
sáb. 11/85:30 pmPUJ - MSN
1 stop8h 29mAmerican Airlines
Deal found 10/29$452

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 octubre 29, 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

7:00 am-11:44 pm

2 stops14h 44m

San Juan Luis Munoz Marin Intl

mié. 1/28

4:30 pm-10:40 pm

1 stop8h 10m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 1/20

5:22 pm-10:48 am

2 stops15h 26m

San Juan Luis Munoz Marin Intl

mié. 1/28

6:00 am-3:27 pm

2 stops11h 27m

$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

lun. 12/15

2:05 am-11:44 am

2 stops11h 39m

$257

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 12/9

6:13 am-10:09 pm

2 stops13h 56m

San Juan Luis Munoz Marin Intl

mar. 12/16

8:20 am-11:40 pm

1 stop17h 20m

$268

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 3/10

6:30 am-2:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

mar. 3/10

1:05 am-1:52 pm

2 stops13h 47m

$320

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

mar. 1/27

2:05 am-2:52 pm

2 stops14h 47m

$325

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

jue. 12/18

3:46 pm-6:11 am

2 stops12h 25m

San Juan Luis Munoz Marin Intl

jue. 12/25

8:10 am-1:54 pm

1 stop7h 44m

$325

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

jue. 12/11

5:38 am-3:43 pm

1 stop9h 05m

Nassau Intl

jue. 12/18

1:19 pm-10:26 pm

1 stop10h 07m

$445

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

mié. 2/18

8:00 am-7:52 pm

2 stops10h 52m

Nassau Intl

mar. 2/24

12:09 pm-10:51 pm

2 stops11h 42m

$449

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

jue. 12/11

6:13 am-8:12 pm

2 stops12h 59m

Nassau Intl

jue. 12/18

3:38 pm-11:59 pm

2 stops9h 21m

$449

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 60 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, October is the cheapest month in which you can book a flight from Madison to Caribbean (average of $143). 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 octubre 29, 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 octubre 29, 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
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,999 reviews
Delta
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,992 reviews

Comfort

7.9

Overall

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 12h 07m. 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, October is the cheapest month in which you can book a flight from Madison to Caribbean (average of $143). 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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$225Average$634FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$260Average$643FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$269Average$649FlexibilityNo cancel feeOn-time71%

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