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$158+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$225
(American Airlines)

One-way from

$164
(American Airlines)

Popular in

December

Cheapest in

November

Average price

$515
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. 2% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/12. 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.
Sat 8/302:20 pmMSN - SJU
1 stop7h 29mAmerican Airlines
Fri 9/54:42 pmSJU - MSN
2 stops17h 23mAmerican Airlines
Deal found 6/12$225
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 9/96:30 amMSN - SJU
1 stop7h 14mUnited Airlines
Sat 9/131:25 pmSJU - MSN
2 stops9h 58mUnited Airlines
Deal found 6/12$260
This Delta deal was found by Cheapflights users on 6/12. 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.
Fri 8/295:40 amMSN - SJU
1 stop9h 56mDelta
Sat 9/67:30 amSJU - MSN
2 stops15h 28mDelta
Deal found 6/12$295
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Fri 9/57:48 amMSN - PUJ
1 stop6h 37mAmerican Airlines
Wed 9/104:25 pmPUJ - MSN
1 stop7h 45mAmerican Airlines
Deal found 6/10$376
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 12/36:27 amMSN - MBJ
1 stop5h 43mAmerican Airlines
Tue 12/93:50 pmMBJ - MSN
1 stop8h 51mAmerican Airlines
Deal found 6/10$441
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 7/157:16 amMSN - NAS
1 stop5h 09mAmerican Airlines
Tue 7/226:30 pmNAS - MSN
1 stop17h 16mAmerican Airlines
Deal found 6/12$469
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Fri 7/43:50 pmMSN - PUJ
2 stops19h 50mUnited Airlines
Tue 7/81:50 pmPUJ - MSN
1 stop8h 06mUnited Airlines
Deal found 6/12$480
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/276:40 amMSN - NAS
1 stop7h 19mUnited Airlines
Sun 8/34:01 pmNAS - MSN
1 stop7h 29mUnited Airlines
Deal found 6/11$489
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 10/227:00 amMSN - SDQ
2 stops9h 52mDelta
Wed 11/54:15 pmSDQ - MSN
1 stop8h 19mDelta
Deal found 6/10$519
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 12/24:53 pmMSN - GCM
2 stops17h 53mAmerican Airlines
Mon 12/88:30 amGCM - MSN
2 stops13h 56mAmerican Airlines
Deal found 6/12$552
This Delta deal was found by Cheapflights users on 6/12. 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.
Tue 8/265:40 amMSN - NAS
1 stop6h 54mDelta
Sat 8/303:05 pmNAS - MSN
1 stop8h 57mDelta
Deal found 6/12$555
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/286:25 pmMSN - SJU
2 stops23h 54mMultiple Airlines
Tue 7/12:36 amSJU - MSN
1 stop8h 03mMultiple Airlines
Deal found 6/10$558

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 June 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

Sat 9/27

6:30 am-2:44 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Tue 9/30

1:05 am-11:45 am

2 stops11h 40m

$225

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 8/25

6:19 am-10:49 pm

1 stop15h 30m

San Juan Luis Munoz Marin Intl

Sat 9/6

4:45 pm-11:10 pm

1 stop7h 25m

$290

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Fri 8/29

5:40 am-4:36 pm

1 stop9h 56m

San Juan Luis Munoz Marin Intl

Sat 9/6

7:30 am-9:58 pm

2 stops15h 28m

$295

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Fri 9/5

7:48 am-3:25 pm

1 stop6h 37m

Punta Cana

Wed 9/10

4:25 pm-11:10 pm

1 stop7h 45m

$376

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 12/3

6:27 am-1:10 pm

1 stop5h 43m

Montego Bay Sangster Intl

Tue 12/9

3:50 pm-11:41 pm

1 stop8h 51m

$441

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Tue 7/15

7:16 am-1:25 pm

1 stop5h 09m

Nassau Intl

Tue 7/22

6:30 pm-10:46 am

1 stop17h 16m

$469

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Fri 7/4

3:50 pm-12:40 pm

2 stops19h 50m

Punta Cana

Tue 7/8

1:50 pm-8:56 pm

1 stop8h 06m

$480

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Sun 7/27

6:40 am-2:59 pm

1 stop7h 19m

Nassau Intl

Sun 8/3

4:01 pm-10:30 pm

1 stop7h 29m

$489

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Wed 10/22

7:00 am-5:52 pm

2 stops9h 52m

Santo Domingo Las Americas

Wed 11/5

4:15 pm-10:34 pm

1 stop8h 19m

$519

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 12/2

4:53 pm-11:46 am

2 stops17h 53m

George Town Owen Roberts Intl

Mon 12/8

8:30 am-9:26 pm

2 stops13h 56m

$552

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 40 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 June is currently the most expensive (average of $339). 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 June 12, 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 June 12, 2025.
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
LATAM Airlines
7.5
Good
1,785 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,531 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 cheapest airlines to fly from Madison to Caribbean one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $164. Users have also found prices from $181 and $235 on Delta and United Airlines, respectively.

  • 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 - Oranjestad Reina Beatrix and Madison Truax Field - Montego Bay Sangster Intl.

  • 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 June is currently the most expensive (average of $339). 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$683FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$329Average$651FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$330Average$639FlexibilityNo cancel feeOn-time71%

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