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Caribbean

$148+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
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 julio 30, 2025.

Round-trip from

$255
(American Airlines)

One-way from

$148
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$555
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. 1% potential increase in price ($7 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 July 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 julio 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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.
lun. 9/296:20 amMSN - SJU
2 stops10h 55mAmerican Airlines
mar. 10/73:00 pmSJU - MSN
1 stop9h 36mAmerican Airlines
Deal found 7/30$255
This American Airlines deal was found by Cheapflights users on 7/30. 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.
sáb. 10/45:08 pmMSN - PUJ
1 stop17h 34mAmerican Airlines
sáb. 10/113:21 pmPUJ - MSN
1 stop9h 15mAmerican Airlines
Deal found 7/30$376
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/296:30 amMSN - SJU
1 stop7h 14mUnited Airlines
mar. 10/71:30 pmSJU - MSN
1 stop10h 03mUnited Airlines
Deal found 7/29$385
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/201:20 pmMSN - SJU
1 stop7h 40mDelta
mié. 9/247:30 amSJU - MSN
1 stop9h 48mDelta
Deal found 7/28$397
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/285:30 amMSN - PUJ
1 stop8h 01mDelta
mar. 11/44:56 pmPUJ - MSN
1 stop7h 34mDelta
Deal found 7/28$402
This American Airlines deal was found by Cheapflights users on 7/29. 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.
dom. 9/217:10 amMSN - MBJ
1 stop7h 59mAmerican Airlines
mar. 9/303:54 pmMBJ - MSN
2 stops18h 37mAmerican Airlines
Deal found 7/29$477
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/125:43 pmMSN - PUJ
2 stops17h 57mUnited Airlines
vie. 9/194:35 pmPUJ - MSN
2 stops18h 10mUnited Airlines
Deal found 7/29$490
This Delta deal was found by Cheapflights users on 7/29. 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.
vie. 9/125:40 amMSN - GCM
1 stop5h 56mDelta
vie. 9/1912:52 pmGCM - MSN
1 stop10h 07mDelta
Deal found 7/29$499
This American Airlines deal was found by Cheapflights users on 7/29. 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.
vie. 9/126:24 pmMSN - GCM
2 stops17h 01mAmerican Airlines
vie. 9/1912:25 pmGCM - MSN
1 stop10h 45mAmerican Airlines
Deal found 7/29$503
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/176:08 pmMSN - NAS
1 stop21h 17mMultiple Airlines
mar. 9/2312:38 pmNAS - MSN
2 stops29h 50mMultiple Airlines
Deal found 7/28$512
This Delta deal was found by Cheapflights users on 7/30. 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.
mié. 10/225:30 amMSN - SDQ
1 stop7h 11mDelta
mié. 11/53:56 pmSDQ - MSN
1 stop8h 34mDelta
Deal found 7/30$515
This Delta deal was found by Cheapflights users on 7/29. 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.
dom. 12/75:45 amMSN - NAS
1 stop6h 26mDelta
mié. 12/174:50 pmNAS - MSN
1 stop6h 44mDelta
Deal found 7/29$515

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 julio 30, 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

lun. 9/29

6:20 am-6:15 pm

2 stops10h 55m

San Juan Luis Munoz Marin Intl

mar. 10/7

3:00 pm-11:36 pm

1 stop9h 36m

$255

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

sáb. 10/4

5:08 pm-11:42 am

1 stop17h 34m

Punta Cana

sáb. 10/11

3:21 pm-11:36 pm

1 stop9h 15m

$376

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

lun. 9/29

6:30 am-2:44 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

mar. 10/7

1:30 pm-10:33 pm

1 stop10h 03m

$385

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

sáb. 9/20

1:20 pm-10:00 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

mié. 9/24

7:00 am-4:09 pm

2 stops10h 09m

$397

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

mar. 10/28

5:30 am-2:31 pm

1 stop8h 01m

Punta Cana

mar. 11/4

4:56 pm-10:30 pm

1 stop7h 34m

$402

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

dom. 9/21

7:10 am-3:09 pm

1 stop7h 59m

Montego Bay Sangster Intl

mar. 9/30

3:54 pm-10:31 am

2 stops18h 37m

$477

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

vie. 9/12

5:43 pm-12:40 pm

2 stops17h 57m

Punta Cana

vie. 9/19

4:35 pm-9:45 am

2 stops18h 10m

$490

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

vie. 9/12

5:40 am-11:36 am

1 stop5h 56m

George Town Owen Roberts Intl

vie. 9/19

12:52 pm-10:59 pm

1 stop10h 07m

$499

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

vie. 9/12

6:24 pm-11:25 am

2 stops17h 01m

George Town Owen Roberts Intl

vie. 9/19

12:10 pm-9:05 am

2 stops20h 55m

$503

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

mié. 9/17

6:08 pm-4:25 pm

1 stop21h 17m

Nassau Intl

mar. 9/23

12:38 pm-5:28 pm

2 stops29h 50m

$512

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 44 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 julio 30, 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.

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 julio 30, 2025.
Read reviews from past customers who have flown Delta, LATAM Airlines, and United 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
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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
1,822 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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!
WestJet
7.2
Good
2,975 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

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 $148. Users have also found prices from $164 and $222 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 - 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 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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$763FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$269Average$650FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$331Average$662FlexibilityNo cancel feeOn-time69%

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