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Madison

$190+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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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 August 20, 2025.

Round-trip from

$337
(American Airlines)

One-way from

$190
(Delta)
From Caribbean Islands to Madison Truax Field
Search Deals
One-way flight from Caribbean Islands to Madison Truax Field
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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 August 20, 2025.

This American Airlines deal was found by Cheapflights users on 8/18. 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 12/226:40 amSJU - MSN
1 stop10h 28mAmerican Airlines
Tue 1/1311:43 amMSN - SJU
1 stop9h 57mAmerican Airlines
Deal found 8/18$390
This American Airlines deal was found by Cheapflights users on 8/18. 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 8/223:30 pmSJU - MSN
1 stop8h 57mAmerican Airlines
Sun 8/248:14 pmMSN - SJU
1 stop16h 51mAmerican Airlines
Deal found 8/18$419
This American Airlines deal was found by Cheapflights users on 8/18. 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 10/302:00 pmMBJ - MSN
1 stop9h 36mAmerican Airlines
Mon 12/18:12 pmMSN - MBJ
1 stop16h 02mAmerican Airlines
Deal found 8/18$502
This American Airlines deal was found by Cheapflights users on 8/18. 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 8/283:50 pmSJU - MSN
1 stop9h 09mAmerican Airlines
Mon 9/17:16 amMSN - SJU
2 stops9h 59mAmerican Airlines
Deal found 8/18$579
This United Airlines deal was found by Cheapflights users on 8/18. 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 10/22:33 pmNAS - MSN
1 stop9h 00mUnited Airlines
Thu 10/912:26 pmMSN - NAS
2 stops48h 24mUnited Airlines
Deal found 8/18$613
This Delta deal was found by Cheapflights users on 8/18. 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.
Sun 12/213:13 amSJU - MSN
2 stops12h 39mDelta
Tue 1/139:26 amMSN - SJU
2 stops12h 23mDelta
Deal found 8/18$759
This United Airlines deal was found by Cheapflights users on 8/18. 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 8/211:05 amSJU - MSN
2 stops19h 04mUnited Airlines
Sun 8/246:30 amMSN - SJU
1 stop7h 14mUnited Airlines
Deal found 8/18$962
This United Airlines deal was found by Cheapflights users on 8/18. 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 8/271:05 amSJU - MSN
2 stops16h 42mUnited Airlines
Mon 9/16:30 amMSN - SJU
1 stop7h 14mUnited Airlines
Deal found 8/18$1,011

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 August 20, 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

Mon 12/22

6:40 am-3:08 pm

1 stop10h 28m

Madison Truax Field

Tue 1/13

11:43 am-11:40 pm

1 stop9h 57m

$390

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 2/12

7:20 am-2:05 pm

1 stop8h 45m

Madison Truax Field

Thu 2/19

11:22 am-4:55 am

1 stop15h 33m

$468

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 10/30

2:00 pm-11:36 pm

1 stop9h 36m

Madison Truax Field

Mon 12/1

8:12 pm-1:14 pm

1 stop16h 02m

$502

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Thu 10/2

2:33 pm-1:50 pm

2 stops24h 17m

Madison Truax Field

Thu 10/9

12:26 pm-1:50 pm

2 stops48h 24m

$613

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sun 12/21

3:13 am-1:52 pm

2 stops12h 39m

Madison Truax Field

Tue 1/13

9:26 am-11:49 pm

2 stops12h 23m

$759

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 2/11

2:05 am-1:48 pm

2 stops13h 43m

Madison Truax Field

Thu 2/19

2:25 pm-8:55 pm

1 stop28h 30m

$805

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 9/5

2:20 pm-10:14 pm

1 stop8h 54m

$190

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 9/5

6:10 am-9:10 pm

2 stops16h 00m

$230

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sat 8/30

6:00 am-10:13 pm

2 stops17h 13m

$236

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 8/27

6:00 am-4:45 pm

2 stops11h 45m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 18 results
1
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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, January is the cheapest month in which you can book a flight from Caribbean Islands to Madison (average of $338). Flying from Caribbean Islands to Madison in March is currently the most expensive (average of $422). 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 August 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Madison as you normally would.

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 August 20, 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
10,000 reviews

Overall

7.2

Comfort

7.2

Entertainment

6.9

Crew

8.0

Food

6.5

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Comfort

7.2

Entertainment

6.9

Crew

8.0

Food

6.5

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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 10h 28m. The time it takes to get you to your destination can typically vary by up to 13h 49m. 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 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, January is the cheapest month in which you can book a flight from Caribbean Islands to Madison (average of $338). Flying from Caribbean Islands to Madison in March is currently the most expensive (average of $422). 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

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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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$506FlexibilityNo cancel feeOn-time71%

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