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Madison

$133+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap flight deals from Caribbean to Madison

Cheapest flights from Caribbean to Madison
Explore the most affordable flight options available from Caribbean to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.

This American Airlines deal was found by Cheapflights users on 2/10. 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 4/153:19 pm
SJU
-
MSN
1 stop9h 09m
American Airlines
Wed 4/2211:35 am
MSN
-
SJU
1 stop8h 16m
American Airlines
Deal found 2/10$266
This United Airlines deal was found by Cheapflights users on 2/10. 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 am
SJU
-
MSN
2 stops11h 48m
United Airlines
Sun 3/13:53 pm
MSN
-
SJU
2 stops12h 18m
United Airlines
Deal found 2/10$430
This American Airlines deal was found by Cheapflights users on 2/10. 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 7/212:59 am
SJU
-
MSN
1 stop9h 24m
American Airlines
Sun 7/127:00 am
MSN
-
SJU
1 stop16h 17m
American Airlines
Deal found 2/10$442
This American Airlines deal was found by Cheapflights users on 2/11. 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 7/1612:59 am
SJU
-
MSN
1 stop9h 24m
American Airlines
Tue 7/287:02 am
MSN
-
SJU
1 stop14h 49m
American Airlines
Deal found 2/11$443
This deal was found by Cheapflights users on 2/10. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:30 am
SJU
-
MSN
1 stop7h 51m
Frontier
Sun 3/295:46 pm
MSN
-
SJU
1 stop7h 27m
Frontier
Deal found 2/10$458
This American Airlines deal was found by Cheapflights users on 2/11. 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 4/273:20 pm
MBJ
-
MSN
1 stop8h 08m
American Airlines
Thu 6/47:00 am
MSN
-
MBJ
1 stop6h 31m
American Airlines
Deal found 2/11$471
This Faresmojo deal was found by Cheapflights users on 2/10. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/162:35 pm
SJU
-
MSN
1 stop7h 05m
JetBlue
Tue 7/285:45 am
MSN
-
SJU
1 stop6h 48m
JetBlue
Deal found 2/10$476
This American Airlines deal was found by Cheapflights users on 2/10. 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 2/237:00 am
SJU
-
MSN
2 stops10h 42m
American Airlines
Fri 2/278:24 pm
MSN
-
SJU
1 stop7h 00m
American Airlines
Deal found 2/10$510
This United Airlines deal was found by Cheapflights users on 2/9. 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 2/258:30 am
SJU
-
MSN
1 stop8h 27m
United Airlines
Sat 2/285:44 pm
MSN
-
SJU
2 stops10h 27m
United Airlines
Deal found 2/9$520
This American Airlines deal was found by Cheapflights users on 2/10. 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 7/143:40 pm
SJU
-
MSN
2 stops9h 03m
American Airlines
Sun 7/192:22 pm
MSN
-
SJU
1 stop7h 29m
American Airlines
Deal found 2/10$526

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 February 13, 2026.

Round-trip from

$266
(American Airlines)

One-way from

$133
(American Airlines)

Popular in

June

Cheapest in

August

Average price

$435
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. 20% potential increase in price ($111 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 13, 2026.
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

Wed 4/15

3:19 pm-11:28 pm

1 stop9h 09m

Madison Truax Field

Wed 4/22

11:35 am-8:51 pm

1 stop8h 16m

$266

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 4/17

3:56 pm-11:49 pm

1 stop8h 53m

Madison Truax Field

Tue 4/21

10:05 am-8:34 pm

1 stop9h 29m

$266

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 4/17

11:43 am-9:25 pm

2 stops10h 42m

Madison Truax Field

Tue 4/21

9:18 am-8:51 pm

2 stops10h 33m

$329

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 2/24

2:05 am-11:53 am

2 stops11h 48m

Madison Truax Field

Sun 3/1

3:53 pm-6:11 am

2 stops12h 18m

$430

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 2/25

10:20 am-4:52 pm

1 stop8h 32m

Madison Truax Field

Sun 3/1

11:22 am-11:31 pm

1 stop10h 09m

$430

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 7/16

12:59 am-9:23 am

1 stop9h 24m

Madison Truax Field

Tue 7/28

7:02 am-10:51 pm

1 stop14h 49m

$443

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Mon 4/27

3:20 pm-11:28 pm

1 stop8h 08m

Madison Truax Field

Thu 6/4

7:00 am-1:31 pm

1 stop6h 31m

$471

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 7/16

2:35 pm-8:40 pm

1 stop7h 05m

Madison Truax Field

Tue 7/28

5:45 am-1:33 pm

1 stop6h 48m

$476

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

$520

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 4/16

11:43 am-9:25 pm

2 stops10h 42m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 37 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 June is currently the most expensive (average of $355). 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.

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 February 13, 2026.
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
8,191 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.1

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
8,191 reviews
Delta
7.9
Good
8,191 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.1

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
11,277 reviews
Delta
7.9
Good
8,191 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.1

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?

    American Airlines and United Airlines can get you from Caribbean to Madison in just under 8h 53m. Your travel time can differ by up to 16m. 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 United Airlines, which is currently one of the cheapest options available, starting at $140. American Airlines flights start at $184 while deals on Delta start at $259 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 June is currently the most expensive (average of $355). 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 February 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$550FlexibilityNo cancel feeOn-time71%
DeltaCheapest$449Average$495FlexibilityNo cancel feeOn-timeN/A

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