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Caribbean

$190+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
May 6 — May 131
Sal 5/6
Sal 5/13
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 Mayıs 1, 2025.

Round-trip from

$225
(American Airlines)

One-way from

$190
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$596
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. 1% potential increase in price ($6 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 May 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 Mayıs 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. 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.
Cmt 9/138:27 pmMSN - SJU
2 stops18h 53mAmerican Airlines
Cmt 9/203:55 pmSJU - MSN
1 stop6h 33mAmerican Airlines
Deal found 4/29$225
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Çar 7/162:35 pmMSN - SJU
1 stop8h 19mUnited Airlines
Sal 7/293:56 pmSJU - MSN
1 stop7h 37mUnited Airlines
Deal found 4/30$389
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cmt 8/26:45 amMSN - SJU
1 stop7h 27mDelta
Cmt 8/94:25 pmSJU - MSN
1 stop8h 02mDelta
Deal found 4/30$405
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Pzt 5/196:13 amMSN - PUJ
1 stop7h 27mAmerican Airlines
Çar 5/283:16 pmPUJ - MSN
1 stop17h 45mAmerican Airlines
Deal found 4/29$455
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Paz 9/215:45 amMSN - SDQ
1 stop7h 02mDelta
Paz 9/283:12 pmSDQ - MSN
1 stop8h 22mDelta
Deal found 4/29$535
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Çar 10/224:33 pmMSN - SDQ
2 stops17h 27mAmerican Airlines
Çar 11/58:55 amSDQ - MSN
2 stops14h 29mAmerican Airlines
Deal found 4/30$539
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Sal 12/27:14 amMSN - GCM
1 stop7h 41mAmerican Airlines
Pzt 12/82:15 pmGCM - MSN
2 stops9h 39mAmerican Airlines
Deal found 5/1$542
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Çar 9/107:17 amMSN - NAS
1 stop5h 08mAmerican Airlines
Paz 9/142:45 pmNAS - MSN
1 stop7h 43mAmerican Airlines
Deal found 4/30$545
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sal 9/305:45 amMSN - STT
1 stop6h 54mDelta
Cmt 10/43:50 pmSTT - MSN
1 stop7h 44mDelta
Deal found 4/30$547
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Cmt 11/84:29 pmMSN - STT
2 stops19h 31mAmerican Airlines
Cmt 11/153:20 pmSTT - MSN
1 stop8h 03mAmerican Airlines
Deal found 4/29$549
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Sal 12/26:38 amMSN - MBJ
1 stop7h 17mAmerican Airlines
Pzt 12/86:00 pmMBJ - MSN
1 stop17h 21mAmerican Airlines
Deal found 4/29$566
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Per 5/85:30 amMSN - NAS
1 stop9h 34mDelta
Pzt 5/123:20 pmNAS - MSN
1 stop8h 41mDelta
Deal found 4/30$575

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 Mayıs 1, 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

Cmt 9/13

8:27 pm-4:20 pm

2 stops18h 53m

San Juan Luis Munoz Marin Intl

Cmt 9/20

3:55 pm-9:28 pm

1 stop6h 33m

$225

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Çar 7/16

2:35 pm-11:54 pm

1 stop8h 19m

San Juan Luis Munoz Marin Intl

Sal 7/29

3:56 pm-10:33 pm

1 stop7h 37m

$389

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Cmt 8/2

6:45 am-3:12 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Cmt 8/9

4:25 pm-11:27 pm

1 stop8h 02m

$405

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Pzt 5/19

6:13 am-2:40 pm

1 stop7h 27m

Punta Cana

Çar 5/28

3:16 pm-8:01 am

1 stop17h 45m

$455

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Paz 9/21

5:45 am-1:47 pm

1 stop7h 02m

Santo Domingo Las Americas

Paz 9/28

3:12 pm-10:34 pm

1 stop8h 22m

$535

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Çar 10/22

4:33 pm-11:00 am

2 stops17h 27m

Santo Domingo Las Americas

Çar 11/5

8:55 am-9:24 pm

2 stops14h 29m

$539

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Pzt 6/16

6:40 pm-11:15 am

2 stops16h 35m

George Town Owen Roberts Intl

Cmt 6/28

3:05 pm-9:20 am

2 stops18h 15m

$542

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Çar 9/10

7:17 am-1:25 pm

1 stop5h 08m

Nassau Intl

Paz 9/14

2:45 pm-9:28 pm

1 stop7h 43m

$545

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Sal 9/30

5:45 am-1:39 pm

1 stop6h 54m

Saint Thomas Island Cyril E King

Cmt 10/4

3:50 pm-10:34 pm

1 stop7h 44m

$547

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sal 6/10

7:05 am-3:35 pm

1 stop7h 30m

Punta Cana

Per 6/19

4:35 pm-10:11 am

2 stops18h 36m

$584

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 25 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, September is the cheapest month in which you can book a flight from Madison to Caribbean (average of $254). Flying from Madison to Caribbean in December is currently the most expensive (average of $336). 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 Mayıs 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Caribbean as you normally would.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 Mayıs 1, 2025.
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
9,245 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • 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 - Nassau Intl and Madison Truax Field - Punta Cana.

  • 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, September is the cheapest month in which you can book a flight from Madison to Caribbean (average of $254). Flying from Madison to Caribbean in December is currently the most expensive (average of $336). 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

Browse thousands of different options on Cheapflights for your next trip

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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 Mayıs 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$691FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$330Average$638FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$331Average$681FlexibilityNo cancel feeOn-time69%

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