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Madison

$118+ Cheap flights from Caribbean Islands to Madison (MSN)

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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Find flight deals from Caribbean Islands to Madison

Cheapest flights from Caribbean Islands to Madison
Explore the most affordable flight options available from Caribbean Islands to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2025.

This United Airlines deal was found by Cheapflights users on 10/25. 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 10/296:45 amSJU - MSN
2 stops12h 05mUnited Airlines
Fri 10/3110:35 amMSN - SJU
2 stops9h 47mUnited Airlines
Deal found 10/25$399
This American Airlines deal was found by Cheapflights users on 10/25. 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 11/146:00 amSJU - MSN
2 stops10h 57mAmerican Airlines
Thu 1/156:00 amMSN - SJU
2 stops12h 50mAmerican Airlines
Deal found 10/25$480
This American Airlines deal was found by Cheapflights users on 10/25. 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 12/253:10 pmNAS - MSN
1 stop8h 14mAmerican Airlines
Sat 1/38:10 pmMSN - NAS
1 stop15h 35mAmerican Airlines
Deal found 10/25$480
This United Airlines deal was found by Cheapflights users on 10/25. 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.
Mon 11/172:05 amSJU - MSN
2 stops13h 58mUnited Airlines
Thu 1/156:30 amMSN - SJU
1 stop7h 10mUnited Airlines
Deal found 10/25$509
This United Airlines deal was found by Cheapflights users on 10/25. 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 11/132:05 amSJU - MSN
2 stops14h 49mUnited Airlines
Thu 1/156:30 amMSN - SJU
1 stop7h 10mUnited Airlines
Deal found 10/25$512
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/215:09 pmSJU - MSN
1 stop18h 41mAmerican Airlines
Sun 11/308:12 pmMSN - SJU
2 stops11h 58mAmerican Airlines
Deal found 10/27$572
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/226:00 amSJU - MSN
1 stop19h 59mAmerican Airlines
Sat 11/298:12 pmMSN - SJU
1 stop16h 37mAmerican Airlines
Deal found 10/26$575
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Tue 11/253:59 amSJU - MSN
1 stop15h 29mMultiple Airlines
Sun 11/302:25 pmMSN - SJU
2 stops32h 47mMultiple Airlines
Deal found 10/26$619
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/226:00 amSJU - MSN
1 stop19h 59mAmerican Airlines
Sun 11/301:19 pmMSN - SJU
2 stops19h 53mAmerican Airlines
Deal found 10/27$622
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/276:42 pmSJU - MSN
2 stops22h 02mAmerican Airlines
Sun 11/308:12 pmMSN - SJU
2 stops11h 58mAmerican Airlines
Deal found 10/27$633
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/272:40 pmSXM - MSN
1 stop9h 50mUnited Airlines
Fri 1/210:45 amMSN - SXM
2 stops25h 05mUnited Airlines
Deal found 10/27$642
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/273:28 pmSXM - MSN
2 stops20h 02mAmerican Airlines
Fri 1/28:10 pmMSN - SXM
2 stops17h 54mAmerican Airlines
Deal found 10/27$692

Cheap flight deals from Caribbean Islands to Madison

Keep the following information in mind while searching for Caribbean Islands to Madison flight deals. Data was last updated October 27, 2025.

Round-trip from

$432
(American Airlines)

One-way from

$118
(American Airlines)
From Caribbean Islands to Madison Truax Field
Search Deals
One-way flight from Caribbean Islands to Madison Truax Field
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Madison 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 October 27, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Madison that are best for you.

Fly from

Caribbean Islands

Fly to

Madison

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 11/14

5:59 pm-11:30 pm

1 stop7h 31m

Madison Truax Field

Thu 1/15

11:23 am-11:59 pm

2 stops10h 36m

$480

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Thu 12/25

3:10 pm-10:24 pm

1 stop8h 14m

Madison Truax Field

Sat 1/3

8:10 pm-12:45 pm

1 stop15h 35m

$480

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Mon 11/17

2:05 am-2:03 pm

2 stops13h 58m

Madison Truax Field

Thu 1/15

6:30 am-3:40 pm

1 stop7h 10m

$509

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 11/13

2:05 am-2:54 pm

2 stops14h 49m

Madison Truax Field

Thu 1/15

6:30 am-3:40 pm

1 stop7h 10m

$512

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Fri 3/6

3:35 pm-10:38 pm

1 stop8h 03m

Madison Truax Field

Tue 3/10

6:30 am-3:22 pm

1 stop7h 52m

$515

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 11/18

2:47 pm-11:30 pm

2 stops10h 43m

Madison Truax Field

Thu 1/15

7:25 am-8:50 pm

2 stops11h 25m

$520

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sat 11/22

4:53 pm-10:40 am

2 stops19h 47m

Madison Truax Field

Sun 11/30

8:12 pm-10:10 am

2 stops11h 58m

$572

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Mon 11/24

6:00 am-11:30 pm

2 stops19h 30m

Madison Truax Field

Sun 11/30

1:19 pm-11:12 am

2 stops19h 53m

$572

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 11/21

5:09 pm-9:50 am

1 stop18h 41m

Madison Truax Field

Sun 11/30

8:12 pm-10:10 am

2 stops11h 58m

$572

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 4/23

2:35 pm-9:18 pm

1 stop7h 43m

Madison Truax Field

Sun 4/26

6:49 pm-3:15 pm

2 stops19h 26m

$702

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 27 results
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Best time to book a flight from Caribbean Islands to Madison

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

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

Currently, September is the cheapest month in which you can book a flight from Caribbean Islands to Madison (average of $113). Flying from Caribbean Islands to Madison in July is currently the most expensive (average of $290). 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 EPX to MSN?

Find hourly flight availability from Caribbean Islands to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 27, 2025.

It’s optimal to fly from Caribbean Islands to Madison in the evening. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight in the morning.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated October 27, 2025.
See what other customers who have flown with American Airlines from Caribbean Islands to Madison have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,033 reviews

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
11,033 reviews
American Airlines
7.2
Good
11,033 reviews

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Madison. 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 into for flights to Madison from Caribbean Islands?

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

  • How long is the flight from Caribbean Islands to Madison?

    Airlines like American Airlines and United Airlines fly from Caribbean Islands to Madison in about 7h 31m. The time it takes to get you to your destination can typically vary by up to 6h 27m. Airlines will cover a distance of 2180 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Caribbean Islands to Madison one-way?

    One-way options have recently been found by users for as low as $118 on American Airlines. Other airlines that offer cheap prices include United Airlines from $206 and Delta from $370 one-way.

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

    Most travelers choose San Juan Luis Munoz Marin Intl - Madison Truax Field, Montego Bay Sangster Intl - Madison Truax Field or Nassau Intl - Madison Truax Field when deciding on the best route from Caribbean Islands to Madison.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean Islands to Madison 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 Caribbean Islands to Madison?

    Currently, September is the cheapest month in which you can book a flight from Caribbean Islands to Madison (average of $113). Flying from Caribbean Islands to Madison in July is currently the most expensive (average of $290). 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

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Alternative routes for Caribbean Islands to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Caribbean Islands to Madison

Discover the top airline that operate flights from Caribbean Islands to Madison. 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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$476FlexibilityNo cancel feeOn-time71%

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