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Caribbean Islands

$86+ 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Madison to Caribbean Islands

Keep the following information in mind while searching for Madison to Caribbean Islands flight deals. Data was last updated February 20, 2025.

Round-trip from

$261
(Frontier)

One-way from

$86
(Frontier)

Popular in

June

Cheapest in

August

Average price

$477
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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Highest demand for flights based on searches. 9% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 20, 2025.

This Frontier deal was found by Cheapflights users on 2/19. 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 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
Mon 3/175:45 amSJU - MSN
1 stop10h 14mFrontier
Deal found 2/19$261
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Sun 8/317:21 amMSN - SJU
1 stop13h 24mAmerican Airlines
Sat 9/63:55 pmSJU - MSN
1 stop6h 33mAmerican Airlines
Deal found 2/19$340
This Delta deal was found by Cheapflights users on 2/20. 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.
Tue 3/117:00 amMSN - SJU
2 stops8h 43mDelta
Wed 3/193:15 pmSJU - MSN
1 stop8h 49mDelta
Deal found 2/20$406
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1111:00 amMSN - SJU
1 stop7h 55mUnited Airlines
Tue 3/181:05 amSJU - MSN
2 stops11h 59mUnited Airlines
Deal found 2/19$412
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/37:15 pmMSN - STT
3 stops39h 23mMultiple Airlines
Tue 4/811:11 amSTT - MSN
2 stops30h 05mMultiple Airlines
Deal found 2/20$424
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/104:20 pmMSN - SJU
3 stops40h 12mMultiple Airlines
Fri 3/143:38 amSJU - MSN
1 stop13h 38mMultiple Airlines
Deal found 2/19$453
This American Airlines deal was found by Cheapflights users on 2/20. 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 4/27:00 amMSN - PUJ
1 stop7h 50mAmerican Airlines
Mon 4/712:18 pmPUJ - MSN
1 stop23h 20mAmerican Airlines
Deal found 2/20$463
This American Airlines deal was found by Cheapflights users on 2/20. 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 11/84:29 pmMSN - STT
1 stop17h 16mAmerican Airlines
Thu 11/134:38 pmSTT - MSN
1 stop6h 46mAmerican Airlines
Deal found 2/20$509
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/254:21 pmMSN - MBJ
1 stop16h 54mAmerican Airlines
Wed 4/210:15 amMBJ - MSN
1 stop13h 28mAmerican Airlines
Deal found 2/20$521
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 4/36:10 amMSN - PUJ
1 stop8h 56mDelta
Thu 4/103:32 pmPUJ - MSN
1 stop8h 28mDelta
Deal found 2/19$535
This American Airlines deal was found by Cheapflights users on 2/20. 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 5/34:22 pmMSN - NAS
1 stop16h 06mAmerican Airlines
Sat 5/1010:29 amNAS - MSN
1 stop6h 24mAmerican Airlines
Deal found 2/20$540
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/46:30 amMSN - NAS
1 stop7h 29mUnited Airlines
Sat 5/104:01 pmNAS - MSN
1 stop6h 27mUnited Airlines
Deal found 2/20$550

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 February 20, 2025.

Fly from

Madison

Fly to

Caribbean Islands

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

Mon 3/17

5:45 am-2:59 pm

1 stop10h 14m

$261

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 4/1

5:30 am-8:20 pm

2 stops13h 50m

San Juan Luis Munoz Marin Intl

Wed 4/9

5:30 am-10:44 pm

1 stop18h 14m

$340

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 3/11

7:00 am-4:43 pm

2 stops8h 43m

San Juan Luis Munoz Marin Intl

Wed 3/19

3:15 pm-11:04 pm

1 stop8h 49m

$406

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 3/11

11:00 am-7:55 pm

1 stop7h 55m

San Juan Luis Munoz Marin Intl

Tue 3/18

1:05 am-12:04 pm

2 stops11h 59m

$412

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Thu 4/3

7:15 pm-11:38 am

3 stops39h 23m

Saint Thomas Island Cyril E King

Tue 4/8

11:11 am-4:16 pm

2 stops30h 05m

$424

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 3/10

4:20 pm-9:32 am

3 stops40h 12m

San Juan Luis Munoz Marin Intl

Fri 3/14

3:38 am-4:16 pm

1 stop13h 38m

$453

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Wed 4/2

7:00 am-3:50 pm

1 stop7h 50m

Punta Cana

Mon 4/7

12:18 pm-10:38 am

1 stop23h 20m

$463

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Wed 4/2

4:21 pm-10:50 am

1 stop17h 29m

Saint Thomas Island Cyril E King

Tue 4/8

5:50 pm-10:38 am

2 stops17h 48m

$509

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 3/25

4:21 pm-9:15 am

1 stop16h 54m

Montego Bay Sangster Intl

Wed 4/2

10:15 am-11:43 pm

1 stop13h 28m

$521

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

$535

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 40 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 $363). 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 February 20, 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 February 20, 2025.
See what other customers who have flown with Delta, LATAM 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
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

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
8,219 reviews
Delta
8.0
Very good
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

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
1,795 reviews
Delta
8.0
Very good
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

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
8,765 reviews
Delta
8.0
Very good
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

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
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

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
8,748 reviews
Delta
8.0
Very good
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

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 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 $86. However, be on the lookout for offers from Delta 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 - 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 $363). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Madison to Caribbean Islands

Discover the top 3 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$713FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$332Average$633FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$377Average$686FlexibilityNo cancel feeOn-time69%
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