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$132+ 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
Dec 30 — Jan 61
Mon 12/30
Mon 1/6
1 adult, Economy
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Cheap flight deals from Madison to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 25, 2024.

Round-trip from

$228
(Frontier)

One-way from

$132
(American Airlines)
From Madison Truax Field to Caribbean
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One-way flight from Madison Truax Field to Caribbean
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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 December 25, 2024.

This Delta deal was found by Cheapflights users on 12/25. 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.
Mon 12/306:15 amMSN - SJU
1 stop7h 22mDelta
Tue 1/74:25 pmSJU - MSN
1 stop8h 14mDelta
Deal found 12/25$530
This American Airlines deal was found by Cheapflights users on 12/25. 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 12/2811:45 amMSN - SJU
1 stop10h 10mAmerican Airlines
Wed 1/15:18 amSJU - MSN
2 stops11h 11mAmerican Airlines
Deal found 12/25$657
This United deal was found by Cheapflights users on 12/25. 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.
Mon 12/305:23 pmMSN - SJU
2 stops10h 49mUnited Airlines
Mon 1/62:05 amSJU - MSN
2 stops15h 03mUnited Airlines
Deal found 12/25$900
This Mytrip deal was found by Cheapflights users on 12/25. 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.
Fri 12/271:50 pmMSN - SJU
3 stops30h 40mMultiple Airlines
Tue 12/312:32 amSJU - MSN
1 stop16h 53mMultiple Airlines
Deal found 12/25$964
This Delta deal was found by Cheapflights users on 12/24. 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 12/2711:17 amMSN - MBJ
1 stop8h 34mDelta
Wed 1/12:28 pmMBJ - MSN
1 stop7h 11mDelta
Deal found 12/24$1,109
This American Airlines deal was found by Cheapflights users on 12/24. 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 12/276:00 amMSN - MBJ
1 stop7h 20mAmerican Airlines
Wed 1/16:04 pmMBJ - MSN
2 stops17h 19mAmerican Airlines
Deal found 12/24$1,129
This Delta deal was found by Cheapflights users on 12/24. 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 12/255:47 amMSN - STT
1 stop8h 25mDelta
Thu 1/23:01 pmSTT - MSN
1 stop8h 23mDelta
Deal found 12/24$1,138
This Delta deal was found by Cheapflights users on 12/25. 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.
Thu 12/265:47 amMSN - GCM
1 stop7h 45mDelta
Sat 1/44:21 pmGCM - MSN
1 stop7h 24mDelta
Deal found 12/25$1,223
This Mytrip deal was found by Cheapflights users on 12/24. 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.
Fri 12/271:50 pmMSN - MBJ
3 stops22h 55mMultiple Airlines
Wed 1/12:38 pmMBJ - MSN
3 stops28h 03mMultiple Airlines
Deal found 12/24$1,249
This United Airlines deal was found by Cheapflights users on 12/24. 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.
Thu 12/265:00 amMSN - GCM
2 stops34h 25mUnited Airlines
Sat 1/46:00 pmGCM - MSN
2 stops18h 40mUnited Airlines
Deal found 12/24$1,308
This United deal was found by Cheapflights users on 12/24. 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.
Wed 12/256:19 amMSN - STT
1 stop7h 21mMultiple Airlines
Thu 1/28:39 amSTT - MSN
2 stops15h 51mMultiple Airlines
Deal found 12/24$1,462
This American Airlines deal was found by Cheapflights users on 12/25. 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.
Thu 12/264:55 pmMSN - GCM
2 stops18h 05mAmerican Airlines
Sat 1/42:50 pmGCM - MSN
1 stop28h 10mAmerican Airlines
Deal found 12/25$1,611

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 December 25, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 2/15

11:14 am-12:47 am

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Fri 2/21

10:43 pm-10:14 am

1 stop13h 31m

$228

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/25

6:01 am-5:29 pm

2 stops9h 28m

San Juan Luis Munoz Marin Intl

Tue 3/11

5:00 am-2:26 pm

2 stops10h 26m

$264

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/4

12:40 pm-12:36 am

2 stops9h 56m

San Juan Luis Munoz Marin Intl

Mon 3/3

2:05 am-2:56 pm

2 stops14h 51m

$322

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 2/2

11:14 am-11:46 pm

1 stop10h 32m

San Juan Luis Munoz Marin Intl

Wed 3/5

7:30 am-4:28 pm

1 stop10h 58m

$347

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 1/6

3:50 pm-3:19 pm

2 stops21h 29m

San Juan Luis Munoz Marin Intl

Tue 1/14

8:40 pm-5:06 pm

2 stops22h 26m

$378

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Wed 1/22

6:30 am-4:35 pm

1 stop8h 05m

Punta Cana

Tue 1/28

5:40 pm-10:12 am

1 stop18h 32m

$493

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Wed 4/2

6:05 am-4:31 pm

2 stops9h 26m

Saint Thomas Island Cyril E King

Tue 4/8

1:40 pm-10:49 pm

1 stop10h 09m

$508

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Tue 2/4

7:10 am-1:45 pm

1 stop5h 35m

Nassau Intl

Tue 2/11

12:19 pm-9:10 pm

1 stop9h 51m

$513

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Sun 2/2

6:00 am-3:05 pm

1 stop7h 05m

Santo Domingo Las Americas

Sun 2/9

5:00 am-7:02 pm

2 stops16h 02m

$528

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 2/25

6:20 am-2:50 pm

1 stop7h 30m

Montego Bay Sangster Intl

Tue 3/4

1:35 pm-11:22 pm

1 stop10h 47m

$539

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/24

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 $380). 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 December 25, 2024.

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 December 25, 2024.
Delta
8.0
Very good
8,580 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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

Delta
8.0
Very good
8,580 reviews
Delta
8.0
Very good
8,580 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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

LATAM Airlines
7.5
Good
1,867 reviews
Delta
8.0
Very good
8,580 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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

United Airlines
7.4
Good
9,006 reviews
Delta
8.0
Very good
8,580 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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
8,580 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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

Air Canada
7.0
Good
8,426 reviews
Delta
8.0
Very good
8,580 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

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 $132. Users have also found prices from $145 and $179 on Frontier and Delta, 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 - Saint Thomas Island Cyril E King 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 March is currently the most expensive (average of $380). 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 December 25, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$234Average$272FlexibilityNo cancel feeOn-time62%
DeltaCheapest$284Average$695FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$335Average$643FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$358Average$645FlexibilityNo cancel feeOn-time69%
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