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Madison

$118+ Cheap flights from Caribbean 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Jan 28 — Feb 41
Wed 1/28
Wed 2/4
1 adult, Economy
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Cheap flight deals from Caribbean to Madison

Best flights from Caribbean to Madison
Discover carefully curated flight deals from Caribbean to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 29, 2025.

This United Airlines deal was found by Cheapflights users on 12/28. 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 1/277:45 amSJU - MSN
2 stops12h 02mUnited Airlines
Wed 2/410:45 amMSN - SJU
2 stops9h 37mUnited Airlines
Deal found 12/28$235
This American Airlines deal was found by Cheapflights users on 12/28. 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 1/277:00 amSJU - MSN
1 stop11h 20mAmerican Airlines
Wed 2/47:20 amMSN - SJU
1 stop12h 19mAmerican Airlines
Deal found 12/28$235
This Delta deal was found by Cheapflights users on 12/28. 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 1/274:30 pmSJU - MSN
1 stop8h 20mDelta
Sun 2/17:00 amMSN - SJU
2 stops11h 58mDelta
Deal found 12/28$235
This Delta deal was found by Cheapflights users on 12/28. 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 1/274:30 pmSJU - MSN
1 stop8h 20mDelta
Tue 2/311:15 amMSN - SJU
1 stop7h 43mDelta
Deal found 12/28$235
This American Airlines deal was found by Cheapflights users on 12/28. 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 1/277:00 amSJU - MSN
1 stop11h 20mAmerican Airlines
Tue 2/311:29 amMSN - SJU
1 stop8h 10mAmerican Airlines
Deal found 12/28$235
This United Airlines deal was found by Cheapflights users on 12/28. 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 1/277:45 amSJU - MSN
2 stops10h 59mUnited Airlines
Tue 2/38:15 amMSN - SJU
2 stops12h 07mUnited Airlines
Deal found 12/28$235
This American Airlines deal was found by Cheapflights users on 12/28. 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 1/257:00 amSJU - MSN
1 stop11h 20mAmerican Airlines
Sun 2/111:23 amMSN - SJU
1 stop9h 03mAmerican Airlines
Deal found 12/28$301
This United Airlines deal was found by Cheapflights users on 12/28. 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 4/281:00 amSJU - MSN
2 stops10h 11mUnited Airlines
Tue 5/56:30 amMSN - SJU
2 stops13h 08mUnited Airlines
Deal found 12/28$325
This American Airlines deal was found by Cheapflights users on 12/28. 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 4/2911:59 pmSJU - MSN
1 stop12h 05mAmerican Airlines
Tue 5/56:10 amMSN - SJU
2 stops10h 56mAmerican Airlines
Deal found 12/28$307
This United Airlines deal was found by Cheapflights users on 12/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/242:05 amSJU - MSN
2 stops14h 02mUnited Airlines
Sat 2/282:48 pmMSN - SJU
2 stops13h 23mUnited Airlines
Deal found 12/26$368

Find flight deals from Caribbean to Madison

Keep the following information in mind while searching for Caribbean to Madison flight deals. Data was last updated December 29, 2025.

Round-trip from

$235
(Delta)

One-way from

$118
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$461
From Caribbean to Madison Truax Field
Search Deals
One-way flight from Caribbean to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($97 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 December 29, 2025.
Use the filters below to find and compare flights from Caribbean to Madison that are best for you.

Fly from

Caribbean

Fly to

Madison

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 1/27

7:45 am-5:47 pm

2 stops12h 02m

Madison Truax Field

Wed 2/4

10:45 am-10:22 pm

2 stops9h 37m

$235

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 1/27

7:00 am-4:20 pm

1 stop11h 20m

Madison Truax Field

Wed 2/4

7:20 am-9:39 pm

1 stop12h 19m

$235

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 1/27

4:30 pm-10:50 pm

1 stop8h 20m

Madison Truax Field

Sun 2/1

7:00 am-8:58 pm

2 stops11h 58m

$235

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 1/27

4:30 pm-10:50 pm

1 stop8h 20m

Madison Truax Field

Tue 2/3

11:15 am-8:58 pm

1 stop7h 43m

$235

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 1/27

7:00 am-4:20 pm

1 stop11h 20m

Madison Truax Field

Tue 2/3

11:29 am-9:39 pm

1 stop8h 10m

$235

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 1/27

7:45 am-4:44 pm

2 stops10h 59m

Madison Truax Field

Tue 2/3

8:15 am-10:22 pm

2 stops12h 07m

$235

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sun 1/25

7:00 am-4:20 pm

1 stop11h 20m

Madison Truax Field

Sun 2/1

11:23 am-10:26 pm

1 stop9h 03m

$301

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 4/29

11:59 pm-11:04 am

1 stop12h 05m

Madison Truax Field

Tue 5/5

6:10 am-6:06 pm

2 stops10h 56m

$307

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 4/28

1:00 am-10:11 am

2 stops10h 11m

Madison Truax Field

Tue 5/5

6:30 am-8:38 pm

2 stops13h 08m

$325

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 2/24

2:05 am-2:07 pm

2 stops14h 02m

Madison Truax Field

Sat 2/28

2:48 pm-6:11 am

2 stops13h 23m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

Showing 1-10 of 25 results
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Best time to book a flight from Caribbean to Madison

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

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

Currently, September is the cheapest month in which you can book a flight from Caribbean to Madison (average of $113). Flying from Caribbean to Madison in July is currently the most expensive (average of $289). 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 CB to MSN?

Find hourly flight availability from Caribbean 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 December 29, 2025.

It’s typically best to fly out from Caribbean to Madison in the evening. Doing so could potentially save you 33% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 December 29, 2025.
See what other customers who have flown with Delta and American Airlines from Caribbean to Madison have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,014 reviews

Entertainment

7.9

Overall

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,014 reviews
Delta
7.9
Good
8,014 reviews

Entertainment

7.9

Overall

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,072 reviews
Delta
7.9
Good
8,014 reviews

Entertainment

7.9

Overall

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Caribbean 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?

    If you book a flight to Madison from Caribbean, you will be flying to Truax Field, which is the city’s only airport. Madison Truax Field (MSN) is located 5.4 mi from the center of Madison.

  • How long is the flight from Caribbean to Madison?

    United Airlines, American Airlines, and Delta can get you from Caribbean to Madison in just under 8h 20m. Your travel time can differ by up to 3h 42m. The distance from Caribbean to Madison is about 2180 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $112. American Airlines flights start at $132 while deals on United Airlines start at $140 one-way.

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

    The most popular route from Caribbean to Madison is San Juan Luis Munoz Marin Intl - Madison Truax Field. You may also consider Montego Bay Sangster Intl - Madison Truax Field or Nassau Intl - Madison Truax Field.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Madison?

    Currently, September is the cheapest month in which you can book a flight from Caribbean to Madison (average of $113). Flying from Caribbean to Madison in July is currently the most expensive (average of $289). 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 to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Caribbean to Madison

Discover the top 2 airlines that operate flights from Caribbean 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 December 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$550FlexibilityNo cancel feeOn-time71%
DeltaCheapest$449Average$495FlexibilityNo cancel feeOn-timeN/A

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