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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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/14. 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 12/303:35 pmNAS - MSN
1 stop7h 55mUnited Airlines
Sat 1/36:00 amMSN - NAS
1 stop6h 48mUnited Airlines
Deal found 12/14$463
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Fri 12/193:20 pmMBJ - MSN
2 stops24h 45mUnited Airlines
Sun 1/46:40 amMSN - MBJ
2 stops30h 20mUnited Airlines
Deal found 12/17$474
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/192:31 pmSJU - MSN
2 stops11h 28mAmerican Airlines
Sun 12/218:10 pmMSN - SJU
1 stop6h 50mAmerican Airlines
Deal found 12/17$499
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/251:27 pmMBJ - MSN
1 stop10h 30mUnited Airlines
Sun 1/45:26 pmMSN - MBJ
2 stops19h 34mUnited Airlines
Deal found 12/17$517
This Delta deal was found by Cheapflights users on 12/17. 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.
Fri 12/1912:35 pmMBJ - MSN
1 stop10h 51mDelta
Sun 1/46:31 amMSN - MBJ
1 stop7h 19mDelta
Deal found 12/17$551
This Delta deal was found by Cheapflights users on 12/15. 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 12/2512:30 pmMBJ - MSN
1 stop9h 06mDelta
Sat 12/275:40 amMSN - MBJ
1 stop14h 01mDelta
Deal found 12/15$620
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Fri 12/197:45 amSJU - MSN
2 stops11h 00mUnited Airlines
Sun 12/215:26 pmMSN - SJU
2 stops10h 45mUnited Airlines
Deal found 12/15$646
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/253:20 pmMBJ - MSN
2 stops23h 34mUnited Airlines
Sat 12/272:29 pmMSN - MBJ
2 stops22h 31mUnited Airlines
Deal found 12/15$720

Find 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 December 18, 2025.

Round-trip from

$325
(United Airlines)

One-way from

$118
(Delta)
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 December 18, 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

Thu 1/22

8:35 am-2:10 pm

1 stop7h 35m

Madison Truax Field

Mon 1/26

6:30 am-3:40 pm

1 stop7h 10m

$325

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Fri 1/30

4:25 pm-11:44 pm

1 stop8h 19m

Madison Truax Field

Fri 2/6

12:32 pm-3:03 pm

1 stop25h 31m

$410

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Tue 12/30

3:35 pm-10:30 pm

1 stop7h 55m

Madison Truax Field

Sat 1/3

6:00 am-1:48 pm

1 stop6h 48m

$463

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Tue 3/24

1:48 pm-2:58 pm

1 stop25h 10m

Madison Truax Field

Fri 5/8

6:30 am-3:10 pm

2 stops8h 40m

$493

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 1/29

3:40 pm-2:52 pm

2 stops25h 12m

Madison Truax Field

Mon 2/2

5:25 pm-4:00 pm

2 stops20h 35m

$1,621

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 1/29

2:55 pm-10:50 pm

2 stops32h 55m

Madison Truax Field

Mon 2/2

1:31 pm-7:17 pm

2 stops28h 46m

$3,272

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 2/6

3:20 pm-10:50 pm

2 stops9h 30m

$118

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 1/23

8:20 am-6:44 pm

2 stops12h 24m

$151

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Wed 2/18

4:05 pm-10:38 pm

1 stop7h 33m

$260

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 12/30

4:55 pm-5:28 pm

1 stop26h 33m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 21 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 $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 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 December 18, 2025.

It’s optimal to fly from Caribbean Islands to Madison in the evening. By choosing this option you can save up to 33% on the cost of your flight, compared to a flight in the afternoon.

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 18, 2025.
See what other customers who have flown with Delta 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.
Delta
7.9
Good
8,005 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

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
8,005 reviews
Delta
7.9
Good
8,005 reviews

Entertainment

7.9

Food

7.3

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

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 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 United Airlines and Air Canada fly from Caribbean Islands to Madison in about 7h 35m. The time it takes to get you to your destination can typically vary by up to 17h 37m. 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 $112 on Delta. Other airlines that offer cheap prices include American Airlines from $132 and United Airlines from $140 one-way.

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

    Most travelers choose Montego Bay Sangster Intl - Madison Truax Field, San Juan Luis Munoz Marin 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 $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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Top 3 airlines flying from Caribbean Islands to Madison

Discover the top 3 airlines 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$550FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$273Average$404FlexibilityNo cancel feeOn-time69%
DeltaCheapest$449Average$495FlexibilityNo cancel feeOn-timeN/A

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