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$108+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Mar 8 — Mar 151
Sat 3/8
Sat 3/15
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 March 3, 2025.

Round-trip from

$225
(Delta)

One-way from

$108
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$666
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. 0% potential increase in price ($0 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 3, 2025.

This American Airlines deal was found by Cheapflights users on 3/3. 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 4/296:20 amMSN - SJU
2 stops13h 00mAmerican Airlines
Tue 5/67:15 amSJU - MSN
1 stop17h 37mAmerican Airlines
Deal found 3/3$215
This Delta deal was found by Cheapflights users on 3/3. 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 4/2911:00 amMSN - SJU
2 stops11h 15mDelta
Tue 5/62:20 pmSJU - MSN
1 stop7h 01mDelta
Deal found 3/3$225
This Frontier deal was found by Cheapflights users on 3/3. 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.
Mon 3/103:59 pmMSN - SJU
1 stop8h 50mFrontier
Sun 3/162:44 amSJU - MSN
1 stop13h 15mFrontier
Deal found 3/3$317
This United Airlines deal was found by Cheapflights users on 3/3. 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.
Sat 5/33:58 pmMSN - SJU
1 stop6h 56mUnited Airlines
Tue 5/61:05 amSJU - MSN
2 stops12h 07mUnited Airlines
Deal found 3/3$335
This American Airlines deal was found by Cheapflights users on 3/2. 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.
Mon 3/174:21 pmMSN - PUJ
1 stop17h 19mAmerican Airlines
Mon 3/243:50 pmPUJ - MSN
1 stop8h 53mAmerican Airlines
Deal found 3/2$455
This American Airlines deal was found by Cheapflights users on 3/3. 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 4/264:22 pmMSN - MBJ
1 stop16h 48mAmerican Airlines
Fri 5/22:00 pmMBJ - MSN
1 stop8h 14mAmerican Airlines
Deal found 3/3$491
This American Airlines deal was found by Cheapflights users on 3/3. 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 4/22:56 pmMSN - STT
2 stops19h 39mAmerican Airlines
Tue 4/85:50 pmSTT - MSN
2 stops19h 56mAmerican Airlines
Deal found 3/3$509
This American Airlines deal was found by Cheapflights users on 3/2. 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 5/34:22 pmMSN - NAS
1 stop16h 06mAmerican Airlines
Fri 5/910:29 amNAS - MSN
1 stop14h 23mAmerican Airlines
Deal found 3/2$515
This Delta deal was found by Cheapflights users on 3/3. 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 3/186:10 amMSN - PUJ
1 stop6h 55mDelta
Tue 3/252:35 pmPUJ - MSN
1 stop8h 45mDelta
Deal found 3/3$528
This United Airlines deal was found by Cheapflights users on 3/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/116:15 amMSN - NAS
1 stop7h 40mUnited Airlines
Fri 3/143:57 pmNAS - MSN
1 stop7h 33mUnited Airlines
Deal found 3/1$539
This United deal was found by Cheapflights users on 3/3. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/181:05 pmMSN - PUJ
2 stops25h 10mUnited Airlines
Tue 3/2512:00 pmPUJ - MSN
2 stops11h 30mUnited Airlines
Deal found 3/3$549
This Delta deal was found by Cheapflights users on 3/2. 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 8/265:45 amMSN - NAS
1 stop6h 56mDelta
Sat 8/304:50 pmNAS - MSN
1 stop6h 45mDelta
Deal found 3/2$550

Find flights from Madison to Caribbean within your budget

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 March 3, 2025.

Fly from

Madison

Fly to

Caribbean

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 4/29

6:20 am-8:20 pm

2 stops13h 00m

San Juan Luis Munoz Marin Intl

Tue 5/6

7:15 am-11:52 pm

1 stop17h 37m

$215

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 4/29

11:00 am-11:15 pm

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Tue 5/6

2:20 pm-8:21 pm

1 stop7h 01m

$225

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 5/3

3:58 pm-11:54 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Tue 5/6

1:05 am-12:12 pm

2 stops12h 07m

$335

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Mon 3/17

4:21 pm-10:40 am

1 stop17h 19m

Punta Cana

Mon 3/24

3:50 pm-11:43 pm

1 stop8h 53m

$455

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 4/26

4:22 pm-9:10 am

1 stop16h 48m

Montego Bay Sangster Intl

Fri 5/2

2:00 pm-10:14 pm

1 stop8h 14m

$491

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Wed 4/2

2:56 pm-11:35 am

2 stops19h 39m

Saint Thomas Island Cyril E King

Tue 4/8

5:50 pm-12:46 pm

2 stops19h 56m

$509

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Sat 5/3

4:22 pm-9:28 am

1 stop16h 06m

Nassau Intl

Fri 5/9

10:29 am-11:52 pm

1 stop14h 23m

$515

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Tue 3/18

6:10 am-2:05 pm

1 stop6h 55m

Punta Cana

Tue 3/25

2:35 pm-10:20 pm

1 stop8h 45m

$528

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Tue 3/18

1:05 pm-3:15 pm

2 stops25h 10m

Punta Cana

Tue 3/25

12:00 pm-10:30 pm

2 stops11h 30m

$549

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Tue 8/26

5:45 am-1:41 pm

1 stop6h 56m

Nassau Intl

Sat 8/30

4:50 pm-10:35 pm

1 stop6h 45m

$550

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/3

Showing 1-10 of 41 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.

Travel insights for flights from Madison to Caribbean

Get recent, data-driven insights about flights from Madison to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $353). 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 March 3, 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 March 3, 2025.
Delta
8.0
Very good
8,068 reviews

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

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
8,068 reviews
Delta
8.0
Very good
8,068 reviews

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

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.

LATAM Airlines
7.5
Good
1,763 reviews
Delta
8.0
Very good
8,068 reviews

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

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
8,679 reviews
Delta
8.0
Very good
8,068 reviews

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

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
8,068 reviews

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

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
8,829 reviews
Delta
8.0
Very good
8,068 reviews

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

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 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 $108. Users have also found prices from $113 and $153 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 - Montego Bay Sangster Intl and Madison Truax Field - Saint Thomas Island Cyril E King.

  • 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 March is currently the most expensive (average of $353). 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 4 airlines flying from Madison to Caribbean

Discover the top 4 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 March 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$243FlexibilityNo cancel feeOn-time62%
DeltaCheapest$264Average$703FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$332Average$634FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$377Average$665FlexibilityNo cancel feeOn-time69%
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