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Caribbean

$235+ Cheap flights from Madison (MSN) to Caribbean

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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
1 adult, Economy
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Cheap flight deals from Madison to Caribbean

Keep the following information in mind while searching for Madison to Caribbean flight deals. Data was last updated April 3, 2025.

Round-trip from

$310
(American Airlines)

One-way from

$235
(United Airlines)

Popular in

December

Cheapest in

August

Average price

$474
From Madison Truax Field to Caribbean
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One-way flight from Madison Truax Field to Caribbean
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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

Cheapest flights from Madison to Caribbean
Explore the most affordable flight options available from Madison to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 3, 2025.

This American Airlines deal was found by Cheapflights users on 4/2. 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 8/246:52 amMSN - SJU
1 stop15h 08mAmerican Airlines
Thu 9/43:58 pmSJU - MSN
2 stops19h 23mAmerican Airlines
Deal found 4/2$255
This United Airlines deal was found by Cheapflights users on 4/1. 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 5/142:27 pmMSN - SJU
1 stop8h 27mUnited Airlines
Sat 5/177:45 amSJU - MSN
1 stop8h 32mUnited Airlines
Deal found 4/1$378
This American Airlines deal was found by Cheapflights users on 4/2. 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 8/224:34 pmMSN - NAS
1 stop15h 55mAmerican Airlines
Wed 8/272:40 pmNAS - MSN
1 stop7h 44mAmerican Airlines
Deal found 4/2$424
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.
Fri 9/54:32 pmMSN - AUA
1 stop17h 53mAmerican Airlines
Wed 9/105:25 pmAUA - MSN
1 stop17h 56mAmerican Airlines
Deal found 4/3$426
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/1$455
This United Airlines deal was found by Cheapflights users on 4/2. 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 4/136:30 amMSN - PUJ
1 stop7h 35mUnited Airlines
Wed 4/161:50 pmPUJ - MSN
1 stop8h 38mUnited Airlines
Deal found 4/2$469
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/1$491
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 American Airlines deal was found by Cheapflights users on 4/2. 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.
Thu 7/175:30 pmMSN - GCM
2 stops17h 50mAmerican Airlines
Tue 7/2212:10 pmGCM - MSN
2 stops11h 04mAmerican Airlines
Deal found 4/2$542
This United Airlines deal was found by Cheapflights users on 4/2. 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.
Sat 5/36:30 amMSN - NAS
1 stop7h 29mUnited Airlines
Fri 5/95:00 pmNAS - MSN
2 stops29h 28mUnited Airlines
Deal found 4/2$543
This American Airlines deal was found by Cheapflights users on 4/2. 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.
Thu 6/58:16 pmMSN - STT
2 stops18h 44mAmerican Airlines
Wed 6/1111:29 amSTT - MSN
2 stops12h 49mAmerican Airlines
Deal found 4/2$554
This Delta deal was found by Cheapflights users on 4/2. 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 4/106:10 amMSN - SJU
1 stop6h 51mDelta
Wed 4/167:15 amSJU - MSN
2 stops10h 22mDelta
Deal found 4/2$562

Cheapflights Fare Finder

Customize your flight search to find flights from Madison to Caribbean 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 3, 2025.
Use the filters below to find and compare flights from Madison to Caribbean that are best for you.

Fly from

Madison

Fly to

Caribbean

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 8/24

5:40 pm-3:00 pm

2 stops20h 20m

San Juan Luis Munoz Marin Intl

Thu 9/4

11:55 am-10:21 am

2 stops23h 26m

$255

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 5/14

2:27 pm-11:54 pm

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Sat 5/17

7:45 am-3:17 pm

1 stop8h 32m

$378

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Fri 8/22

4:34 pm-9:29 am

1 stop15h 55m

Nassau Intl

Wed 8/27

2:40 pm-9:24 pm

1 stop7h 44m

$424

MadisonOranjestad

MSN - AUA

MSNAUA

Madison Truax Field

Fri 9/5

4:32 pm-11:25 am

1 stop17h 53m

Oranjestad Reina Beatrix

Wed 9/10

5:25 pm-10:21 am

1 stop17h 56m

$426

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

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sun 4/13

6:30 am-3:05 pm

1 stop7h 35m

Punta Cana

Wed 4/16

1:50 pm-9:28 pm

1 stop8h 38m

$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

12:25 pm-10:14 pm

1 stop9h 49m

$491

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

5:30 pm-11:20 am

2 stops17h 50m

George Town Owen Roberts Intl

Tue 7/22

12:10 pm-11:14 pm

2 stops11h 04m

$542

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Sat 5/3

3:58 pm-1:50 pm

2 stops20h 52m

Nassau Intl

Fri 5/9

5:00 pm-12:12 pm

2 stops20h 12m

$543

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 32 results
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Best time to book a flight from Madison to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean (average of $254). Flying from Madison to Caribbean 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 CB?

Find hourly flight availability from Madison to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 3, 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 as you normally would.

Rainfall in Caribbean by month

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

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

Temperature in Caribbean by month

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

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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated April 3, 2025.
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

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
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

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
1,754 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

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
8,619 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

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
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

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.
Air Canada
7.0
Good
9,028 reviews
Delta
8.0
Very good
7,897 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

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. 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?

    Most people fly from Madison Truax Field (MSN) if they book a flight from Madison to Caribbean. Madison Truax Field is conveniently located just 5.4 mi from Madison’s city center.

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

    The most popular flight routes from Madison to Caribbean are Madison Truax Field - San Juan Luis Munoz Marin Intl, Madison Truax Field - Punta Cana and Madison Truax Field - Montego Bay Sangster Intl.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison to Caribbean 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?

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

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

Discover the top 3 airlines that operate flights from Madison to Caribbean. 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 3, 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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