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Caribbean Islands

$132+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Nov 19 — Nov 261
1 adult
Tue 11/19
Tue 11/26
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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 November 14, 2024.

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 November 14, 2024.

This American Airlines deal was found by Cheapflights users on 11/13. 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.
Sun 12/85:30 amMSN - SJU
2 stops9h 52mAmerican Airlines
Wed 12/114:40 pmSJU - MSN
2 stops9h 16mAmerican Airlines
Deal found 11/13$364
This Delta deal was found by Cheapflights users on 11/13. 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.
Sat 12/149:39 amMSN - SJU
2 stops13h 20mDelta
Tue 12/177:30 amSJU - MSN
2 stops11h 56mDelta
Deal found 11/13$389
This American Airlines deal was found by Cheapflights users on 11/13. 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 12/1011:41 amMSN - PUJ
1 stop22h 09mAmerican Airlines
Mon 12/165:50 pmPUJ - MSN
1 stop8h 06mAmerican Airlines
Deal found 11/13$482
This United Airlines deal was found by Cheapflights users on 11/13. 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.
Sun 12/87:00 amMSN - SJU
1 stop6h 38mUnited Airlines
Tue 12/102:05 amSJU - MSN
2 stops12h 01mUnited Airlines
Deal found 11/13$484
This Mytrip deal was found by Cheapflights users on 11/14. 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 12/116:05 pmMSN - PUJ
2 stops19h 43mMultiple Airlines
Wed 12/184:50 pmPUJ - MSN
3 stops26h 51mMultiple Airlines
Deal found 11/14$530
This United Airlines deal was found by Cheapflights users on 11/14. 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 12/117:00 amMSN - PUJ
2 stops8h 35mUnited Airlines
Wed 12/185:25 pmPUJ - MSN
2 stops27h 45mUnited Airlines
Deal found 11/14$568
This American Airlines deal was found by Cheapflights users on 11/14. 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 12/111:22 pmMSN - STT
2 stops20h 45mAmerican Airlines
Wed 12/184:30 pmSTT - MSN
1 stop9h 26mAmerican Airlines
Deal found 11/14$577
This American Airlines deal was found by Cheapflights users on 11/14. 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 12/144:19 pmMSN - SXM
2 stops20h 11mAmerican Airlines
Fri 12/203:33 pmSXM - MSN
1 stop9h 15mAmerican Airlines
Deal found 11/14$589
This American Airlines deal was found by Cheapflights users on 11/14. 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 12/74:19 pmMSN - AUA
1 stop17h 56mAmerican Airlines
Tue 12/172:55 pmAUA - MSN
1 stop23h 09mAmerican Airlines
Deal found 11/14$646
This Delta deal was found by Cheapflights users on 11/14. 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.
Sat 12/146:30 amMSN - MBJ
1 stop7h 08mDelta
Wed 12/183:29 pmMBJ - MSN
1 stop7h 37mDelta
Deal found 11/14$649
This American Airlines deal was found by Cheapflights users on 11/14. 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 12/236:21 amMSN - GCM
1 stop7h 44mAmerican Airlines
Sat 12/2812:55 pmGCM - MSN
1 stop11h 31mAmerican Airlines
Deal found 11/14$657
This Mytrip deal was found by Cheapflights users on 11/14. 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.
Sat 12/146:05 pmMSN - SXM
3 stops42h 25mMultiple Airlines
Fri 12/203:25 pmSXM - MSN
2 stops19h 35mMultiple Airlines
Deal found 11/14$684

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/28

11:14 am-11:45 pm

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Thu 1/30

4:25 pm-10:39 pm

1 stop8h 14m

$264

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 2/17

3:35 pm-5:00 am

1 stop11h 25m

San Juan Luis Munoz Marin Intl

Fri 2/21

2:25 pm-10:45 pm

1 stop10h 20m

$289

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/28

8:12 am-10:22 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Tue 1/28

2:05 am-11:54 am

2 stops11h 49m

$348

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 1/29

9:48 am-2:10 pm

3 stops26h 22m

San Juan Luis Munoz Marin Intl

Wed 2/5

9:26 pm-6:16 pm

2 stops22h 50m

$391

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Wed 1/22

6:30 am-5:11 pm

1 stop8h 41m

Punta Cana

Tue 1/28

2:50 pm-9:03 pm

1 stop8h 13m

$473

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sat 2/1

6:27 pm-3:55 pm

2 stops19h 28m

Punta Cana

Thu 2/6

1:30 pm-11:55 pm

2 stops12h 25m

$478

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Mon 1/13

7:10 am-1:45 pm

1 stop5h 35m

Nassau Intl

Fri 1/17

12:32 pm-11:55 pm

1 stop12h 23m

$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

6:31 pm-10:29 am

2 stops17h 58m

$498

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 1/10

5:30 am-2:23 pm

1 stop7h 53m

Montego Bay Sangster Intl

Fri 1/17

1:50 pm-11:55 pm

1 stop11h 05m

$519

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Wed 12/11

6:05 pm-3:48 pm

2 stops19h 43m

Punta Cana

Wed 12/18

4:50 pm-5:41 pm

3 stops26h 51m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 37 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 $335). 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 November 14, 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 November 14, 2024.
See what other customers who have flown with Delta, American Airlines and United 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
8,788 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

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
8,788 reviews
Delta
8.0
Very good
8,788 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

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
1,948 reviews
Delta
8.0
Very good
8,788 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

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
9,194 reviews
Delta
8.0
Very good
8,788 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

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
8,788 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

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
8,198 reviews
Delta
8.0
Very good
8,788 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

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 American Airlines, with whom users have recently found tickets for as low as $132. However, be on the lookout for offers from United 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 - Saint Thomas Island Cyril E King 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 $335). 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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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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$234Average$275FlexibilityNo cancel feeOn-time62%
DeltaCheapest$279Average$662FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$339Average$639FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$396Average$641FlexibilityNo cancel feeOn-time69%
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