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Caribbean Islands

$207+ Cheap flights from Madison (MSN) to Caribbean Islands

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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Dec 24 — Dec 311
Tue 12/24
Tue 12/31
1 adult, Economy
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Cheap flight deals from Madison to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Caribbean Islands (zzEPX). 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 19, 2024.

Round-trip from

$264
(American Airlines)

One-way from

$207
(Frontier)
From Madison Truax Field to Caribbean Islands
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One-way flight from Madison Truax Field to Caribbean Islands
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Find flight deals from Madison to Caribbean Islands

Cheapest flights from Madison to Caribbean Islands
Explore the most affordable flight options available from Madison to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 19, 2024.

This American Airlines deal was found by Cheapflights users on 12/18. 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 12/216:19 amMSN - SJU
1 stop16h 07mAmerican Airlines
Mon 12/305:18 amSJU - MSN
2 stops13h 12mAmerican Airlines
Deal found 12/18$629
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/185:25 pmMSN - SJU
1 stop20h 13mUnited Airlines
Wed 12/252:10 pmSJU - MSN
1 stop10h 50mUnited Airlines
Deal found 12/17$745
This Delta deal was found by Cheapflights users on 12/19. 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 12/235:47 amMSN - GCM
1 stop7h 45mDelta
Sat 12/284:21 pmGCM - MSN
1 stop7h 24mDelta
Deal found 12/19$883
This United Airlines deal was found by Cheapflights users on 12/18. 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.
Mon 12/235:23 pmMSN - GCM
2 stops22h 02mUnited Airlines
Sat 12/286:00 pmGCM - MSN
2 stops28h 13mUnited Airlines
Deal found 12/18$919
This American Airlines deal was found by Cheapflights users on 12/19. 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 12/235:18 pmMSN - GCM
2 stops17h 42mAmerican Airlines
Sat 12/284:05 pmGCM - MSN
1 stop7h 58mAmerican Airlines
Deal found 12/19$938
This Mytrip deal was found by Cheapflights users on 12/17. 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.
Wed 12/189:40 amMSN - SJU
3 stops34h 50mMultiple Airlines
Tue 12/242:32 amSJU - MSN
1 stop16h 53mMultiple Airlines
Deal found 12/17$978
This Delta deal was found by Cheapflights users on 12/17. 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 12/247:00 amMSN - SJU
1 stop6h 50mDelta
Tue 12/313:33 pmSJU - MSN
1 stop7h 10mDelta
Deal found 12/17$986
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/305:18 pmMSN - MBJ
1 stop15h 57mAmerican Airlines
Sat 1/42:20 pmMBJ - MSN
1 stop10h 06mAmerican Airlines
Deal found 12/17$1,047
This United Airlines deal was found by Cheapflights users on 12/18. 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 12/275:00 amMSN - MBJ
2 stops32h 00mUnited Airlines
Wed 1/13:20 pmMBJ - MSN
2 stops32h 10mUnited Airlines
Deal found 12/18$1,071
This American Airlines deal was found by Cheapflights users on 12/18. 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 12/2710:53 amMSN - UVF
2 stops25h 57mAmerican Airlines
Tue 12/313:50 pmUVF - MSN
2 stops24h 39mAmerican Airlines
Deal found 12/18$1,109
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Mon 12/236:20 amMSN - AUA
1 stop8h 20mUnited Airlines
Sun 12/293:00 pmAUA - MSN
1 stop8h 13mUnited Airlines
Deal found 12/17$1,137
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/235:18 pmMSN - AUA
2 stops21h 27mAmerican Airlines
Sun 12/295:45 pmAUA - MSN
2 stops19h 27mAmerican Airlines
Deal found 12/17$1,209

Find flights from Madison to Caribbean Islands within your budget

Customize your flight search to find flights from Madison to Caribbean Islands 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 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/21

10:38 am-12:04 am

2 stops11h 26m

San Juan Luis Munoz Marin Intl

Thu 1/23

12:50 pm-11:50 pm

2 stops13h 00m

$263

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/21

12:40 pm-12:36 am

2 stops9h 56m

San Juan Luis Munoz Marin Intl

Wed 1/22

2:05 am-11:54 am

2 stops11h 49m

$354

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 1/26

6:40 pm-12:57 am

3 stops28h 17m

San Juan Luis Munoz Marin Intl

Fri 1/31

10:16 am-9:08 am

3 stops24h 52m

$403

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 3/10

3:59 pm-1:49 am

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Mon 3/17

5:45 am-2:59 pm

1 stop10h 14m

$414

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Sat 3/1

11:14 am-1:08 pm

2 stops23h 54m

Santo Domingo Las Americas

Sun 3/9

2:59 pm-2:59 pm

1 stop25h 00m

$417

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 1/18

5:46 pm-12:10 pm

2 stops17h 24m

Montego Bay Sangster Intl

Fri 1/24

1:16 pm-9:08 am

2 stops20h 52m

$484

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Thu 1/23

4:16 pm-11:40 am

1 stop17h 24m

Punta Cana

Tue 1/28

5:40 pm-10:12 am

1 stop18h 32m

$493

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Sun 2/2

4:16 pm-11:50 am

1 stop17h 34m

Saint Thomas Island Cyril E King

Mon 2/10

12:30 pm-11:50 pm

1 stop13h 20m

$508

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/25

10:58 am-11:46 pm

2 stops10h 48m

San Juan Luis Munoz Marin Intl

Mon 3/3

4:10 pm-10:42 pm

1 stop8h 32m

$524

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Fri 3/7

6:15 am-5:35 pm

1 stop9h 20m

Saint Thomas Island Cyril E King

Wed 3/12

2:00 pm-10:30 pm

1 stop9h 30m

$532

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 43 results
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Best time to book a flight from Madison to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

What is the cheapest month to book a flight from Madison to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $254). Flying from Madison to Caribbean Islands in March is currently the most expensive (average of $334). 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 EPX?

Find hourly flight availability from Madison to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 19, 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 Islands as you normally would.

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated December 19, 2024.
See what other customers who have flown with American Airlines, United Airlines and Frontier from Madison to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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
8,600 reviews
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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
1,879 reviews
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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
9,048 reviews
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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
8,600 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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
8,391 reviews
Delta
8.0
Very good
8,600 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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 Islands. 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 Islands?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Caribbean Islands. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • What are the cheapest airlines to fly from Madison to Caribbean Islands one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $207. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Madison to Caribbean Islands for a low price.

  • What are the most popular routes from Madison to Caribbean Islands?

    While some choose either Madison Truax Field - Punta Cana or Madison Truax Field - Montego Bay Sangster Intl, Madison Truax Field - San Juan Luis Munoz Marin Intl is the most popular route from Madison to Caribbean Islands.

  • Can I find deals for flights from Madison to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Madison to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Caribbean Islands.

  • Can I find deals for business class flights from Madison to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Madison to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $254). Flying from Madison to Caribbean Islands in March is currently the most expensive (average of $334). 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.

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Alternative routes for Madison to Caribbean Islands

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 Islands

Discover the top 4 airlines that operate flights from Madison to Caribbean Islands. 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 19, 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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