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Caribbean Islands

$201+ 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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 January 21, 2025.

Round-trip from

$260
(Frontier)

One-way from

$201
(United Airlines)
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 January 21, 2025.

This Frontier deal was found by Cheapflights users on 1/21. 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 1/21$260
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/1111:43 amMSN - SJU
2 stops10h 21mAmerican Airlines
Wed 2/128:05 amSJU - MSN
1 stop17h 45mAmerican Airlines
Deal found 1/21$270
This Delta deal was found by Cheapflights users on 1/21. 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 2/251:23 pmMSN - SJU
2 stops8h 23mDelta
Tue 3/117:45 amSJU - MSN
2 stops13h 37mDelta
Deal found 1/21$300
This United deal was found by Cheapflights users on 1/21. 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 2/116:30 amMSN - SJU
2 stops12h 58mUnited Airlines
Tue 2/112:05 amSJU - MSN
2 stops15h 03mUnited Airlines
Deal found 1/21$360
This Delta deal was found by Cheapflights users on 1/20. 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 4/36:10 amMSN - PUJ
1 stop8h 56mDelta
Thu 4/103:32 pmPUJ - MSN
1 stop8h 28mDelta
Deal found 1/20$505
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/113:20 pmMSN - PUJ
2 stops19h 00mAmerican Airlines
Tue 2/185:45 pmPUJ - MSN
2 stops19h 30mAmerican Airlines
Deal found 1/20$509
This Delta deal was found by Cheapflights users on 1/21. 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 2/195:42 amMSN - NAS
1 stop9h 19mDelta
Tue 2/253:06 pmNAS - MSN
1 stop7h 26mDelta
Deal found 1/21$515
This American Airlines deal was found by Cheapflights users on 1/20. 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 4/24:21 pmMSN - STT
1 stop17h 29mAmerican Airlines
Tue 4/84:50 pmSTT - MSN
2 stops18h 12mAmerican Airlines
Deal found 1/20$519
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/196:01 amMSN - NAS
2 stops12h 24mAmerican Airlines
Tue 2/2512:35 pmNAS - MSN
2 stops9h 28mAmerican Airlines
Deal found 1/21$519
This American Airlines deal was found by Cheapflights users on 1/20. 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 12/27:14 amMSN - GCM
1 stop7h 41mAmerican Airlines
Wed 12/101:40 pmGCM - MSN
1 stop11h 01mAmerican Airlines
Deal found 1/20$525
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/224:13 pmMSN - MBJ
1 stop17h 02mAmerican Airlines
Wed 2/2611:55 amMBJ - MSN
1 stop12h 10mAmerican Airlines
Deal found 1/20$541
This United Airlines deal was found by Cheapflights users on 1/21. 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 3/191:05 pmMSN - NAS
2 stops23h 28mUnited Airlines
Mon 3/2412:55 pmNAS - MSN
1 stop8h 01mUnited Airlines
Deal found 1/21$579

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

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

Sun 3/16

2:44 am-2:59 pm

1 stop13h 15m

$260

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/11

11:43 am-11:58 pm

1 stop10h 15m

San Juan Luis Munoz Marin Intl

Wed 2/12

8:05 am-11:50 pm

1 stop17h 45m

$270

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/25

1:23 pm-11:46 pm

2 stops8h 23m

San Juan Luis Munoz Marin Intl

Tue 3/11

7:45 am-8:22 pm

2 stops13h 37m

$300

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/11

6:30 am-9:28 pm

2 stops12h 58m

San Juan Luis Munoz Marin Intl

Tue 2/11

2:05 am-3:08 pm

2 stops15h 03m

$360

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Thu 4/3

6:10 am-4:06 pm

1 stop8h 56m

Punta Cana

Thu 4/10

3:32 pm-11:00 pm

1 stop8h 28m

$505

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Tue 2/11

3:20 pm-12:20 pm

2 stops19h 00m

Punta Cana

Tue 2/18

5:45 pm-11:15 am

2 stops19h 30m

$509

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Wed 2/19

5:42 am-4:01 pm

1 stop9h 19m

Nassau Intl

Tue 2/25

3:06 pm-9:32 pm

1 stop7h 26m

$515

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Wed 4/2

5:30 am-4:31 pm

2 stops10h 01m

Saint Thomas Island Cyril E King

Tue 4/8

4:50 pm-11:17 am

2 stops19h 27m

$519

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Wed 2/19

6:01 am-7:25 pm

2 stops12h 24m

Nassau Intl

Tue 2/25

12:35 pm-9:03 pm

2 stops9h 28m

$519

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 2/22

4:13 pm-10:15 am

1 stop17h 02m

Montego Bay Sangster Intl

Wed 2/26

11:55 am-11:05 pm

1 stop12h 10m

$541

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 42 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 $378). 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 January 21, 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 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 January 21, 2025.
See what other customers who have flown with Frontier, Delta and American Airlines 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
8,521 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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
1,858 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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
8,985 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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
8,521 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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
8,635 reviews
Delta
8.0
Very good
8,521 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

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 United Airlines, with whom users have recently found tickets for as low as $201. However, be on the lookout for offers from American Airlines and Delta, 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 - Saint Thomas Island Cyril E King, 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 $378). 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

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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$176Average$272FlexibilityNo cancel feeOn-time62%
DeltaCheapest$264Average$694FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$332Average$631FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$396Average$659FlexibilityNo cancel feeOn-time69%
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