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Caribbean Islands

$108+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 April 4, 2025.

Round-trip from

$310
(American Airlines)

One-way from

$108
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$474
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. 1% potential increase in price ($7 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 April 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 April 4, 2025.

This American Airlines deal was found by Cheapflights users on 4/3. 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 11/105:19 pmMSN - SJU
2 stops20h 16mAmerican Airlines
Wed 11/125:55 amSJU - MSN
2 stops17h 29mAmerican Airlines
Deal found 4/3$255
This Delta deal was found by Cheapflights users on 4/4. 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 5/31:24 pmMSN - SJU
2 stops8h 51mDelta
Sat 5/101:55 pmSJU - MSN
2 stops10h 26mDelta
Deal found 4/4$369
This United deal was found by Cheapflights users on 4/4. 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.
Sat 5/31:05 pmMSN - SJU
1 stop9h 49mUnited Airlines
Fri 5/91:05 amSJU - MSN
2 stops13h 47mUnited Airlines
Deal found 4/4$382
This American Airlines deal was found by Cheapflights users on 4/4. 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 9/17:21 amMSN - AUA
1 stop7h 04mAmerican Airlines
Wed 9/101:00 pmAUA - MSN
1 stop9h 28mAmerican Airlines
Deal found 4/4$401
This American Airlines deal was found by Cheapflights users on 4/3. 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 5/136:13 amMSN - PUJ
1 stop7h 27mAmerican Airlines
Tue 5/203:16 pmPUJ - MSN
1 stop17h 45mAmerican Airlines
Deal found 4/3$455
This American Airlines deal was found by Cheapflights users on 4/3. 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 5/104:10 pmNAS - MSN
1 stop7h 44mAmerican Airlines
Deal found 4/3$469
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/229:48 amMSN - SDQ
2 stops14h 53mMultiple Airlines
Wed 11/58:30 amSDQ - MSN
1 stop10h 58mMultiple Airlines
Deal found 4/4$482
This American Airlines deal was found by Cheapflights users on 4/3. 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 4/264:22 pmMSN - MBJ
1 stop16h 48mAmerican Airlines
Fri 5/212:25 pmMBJ - MSN
1 stop9h 49mAmerican Airlines
Deal found 4/3$491
This Delta deal was found by Cheapflights users on 4/4. 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 4/116:10 amMSN - MBJ
1 stop7h 23mDelta
Wed 5/71:02 pmMBJ - MSN
1 stop8h 11mDelta
Deal found 4/4$513
This United deal was found by Cheapflights users on 4/4. 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.
Sat 5/38:05 amMSN - NAS
1 stop5h 54mUnited Airlines
Fri 5/95:00 pmNAS - MSN
2 stops20h 12mUnited Airlines
Deal found 4/4$533
This American Airlines deal was found by Cheapflights users on 4/3. 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 4/146:37 amMSN - SDQ
2 stops15h 03mAmerican Airlines
Fri 4/1812:15 pmSDQ - MSN
2 stops12h 05mAmerican Airlines
Deal found 4/3$539
This United Airlines deal was found by Cheapflights users on 4/4. 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 7/175:26 pmMSN - GCM
2 stops19h 04mUnited Airlines
Tue 7/221:35 pmGCM - MSN
2 stops22h 08mUnited Airlines
Deal found 4/4$542

Cheapflights Fare Finder

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 April 4, 2025.
Use the filters below to find and compare flights from Madison to Caribbean Islands that are best for you.

Fly from

Madison

Fly to

Caribbean Islands

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 5/3

11:28 am-5:00 am

1 stop16h 32m

San Juan Luis Munoz Marin Intl

Sat 5/10

3:50 pm-11:45 pm

1 stop8h 55m

$310

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 5/3

1:24 pm-11:15 pm

2 stops8h 51m

San Juan Luis Munoz Marin Intl

Sat 5/10

1:55 pm-11:21 pm

2 stops10h 26m

$369

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 5/3

8:05 am-11:57 pm

2 stops14h 52m

San Juan Luis Munoz Marin Intl

Fri 5/9

1:05 am-1:52 pm

2 stops13h 47m

$382

MadisonOranjestad

MSN - AUA

MSNAUA

Madison Truax Field

Mon 9/1

7:21 am-3:25 pm

1 stop7h 04m

Oranjestad Reina Beatrix

Wed 9/10

1:00 pm-9:28 pm

1 stop9h 28m

$401

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Tue 5/13

6:13 am-2:40 pm

1 stop7h 27m

Punta Cana

Tue 5/20

3:16 pm-8:01 am

1 stop17h 45m

$455

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Sat 5/3

4:22 pm-9:28 am

1 stop16h 06m

Nassau Intl

Sat 5/10

4:10 pm-10:54 pm

1 stop7h 44m

$469

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 4/26

4:22 pm-9:10 am

1 stop16h 48m

Montego Bay Sangster Intl

Fri 5/2

12:45 pm-10:44 pm

1 stop9h 59m

$491

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Sat 5/3

8:05 am-2:59 pm

1 stop5h 54m

Nassau Intl

Fri 5/9

5:00 pm-12:12 pm

2 stops20h 12m

$533

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Mon 4/14

6:37 am-10:40 pm

2 stops15h 03m

Santo Domingo Las Americas

Fri 4/18

12:15 pm-11:20 pm

2 stops12h 05m

$539

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 7/17

5:26 pm-12:30 pm

2 stops19h 04m

George Town Owen Roberts Intl

Tue 7/22

1:35 pm-11:43 am

2 stops22h 08m

$542

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/4

Showing 1-10 of 30 results
1
2
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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.

Cheapflights Insights

Everything you need to know about your flight from Madison to Caribbean Islands

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 December is currently the most expensive (average of $336). 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 April 4, 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 April 4, 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
7,899 reviews

Crew

8.5

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.9

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
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.9

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
1,753 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.9

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
8,618 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.9

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
7,899 reviews

Crew

8.5

Food

7.3

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.9

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 American Airlines, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from Delta and United 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 - Nassau 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 December is currently the most expensive (average of $336). 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 Islands

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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$670FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$330Average$635FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$358Average$687FlexibilityNo cancel feeOn-time69%

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