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Madison

$116+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
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 February 5, 2026.

This United Airlines deal was found by Cheapflights users on 2/1. 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 5/197:40 am
SJU
-
MSN
1 stop8h 20m
United Airlines
Wed 5/279:44 am
MSN
-
SJU
1 stop9h 50m
United Airlines
Deal found 2/1$281
This American Airlines deal was found by Cheapflights users on 2/2. 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 5/64:30 pm
SJU
-
MSN
1 stop8h 25m
American Airlines
Mon 5/118:24 pm
MSN
-
SJU
1 stop16h 55m
American Airlines
Deal found 2/2$326
This Priceline deal was found by Cheapflights users on 2/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/253:08 am
SJU
-
MSN
1 stop11h 13m
Frontier
Sun 3/295:46 pm
MSN
-
SJU
1 stop29h 12m
Frontier
Deal found 2/4$373
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/207:33 am
SJU
-
MSN
1 stop11h 31m
American Airlines
Sun 2/2210:54 am
MSN
-
SJU
1 stop8h 55m
American Airlines
Deal found 2/2$420
This American Airlines deal was found by Cheapflights users on 2/3. 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 5/216:00 am
SJU
-
MSN
1 stop17h 13m
American Airlines
Sun 5/247:02 am
MSN
-
SJU
1 stop14h 49m
American Airlines
Deal found 2/3$422
This American Airlines deal was found by Cheapflights users on 2/3. 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 7/2811:25 am
MSN
-
SJU
1 stop16h 07m
American Airlines
Deal found 2/3$432
This American Airlines deal was found by Cheapflights users on 2/4. 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 5/2111:55 am
MBJ
-
MSN
1 stop12h 03m
American Airlines
Wed 6/36:00 am
MSN
-
MBJ
1 stop7h 58m
American Airlines
Deal found 2/4$468
This American Airlines deal was found by Cheapflights users on 2/3. 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 5/104:37 pm
MBJ
-
MSN
2 stops18h 18m
American Airlines
Wed 5/137:45 am
MSN
-
MBJ
2 stops7h 52m
American Airlines
Deal found 2/3$470
This American Airlines deal was found by Cheapflights users on 2/4. 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 5/201:15 pm
MBJ
-
MSN
1 stop9h 00m
American Airlines
Wed 6/36:00 am
MSN
-
MBJ
1 stop7h 58m
American Airlines
Deal found 2/4$471
This Faresmojo deal was found by Cheapflights users on 2/2. 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.
Fri 3/273:30 pm
SJU
-
MSN
1 stop8h 28m
JetBlue
Sat 4/411:26 am
MSN
-
SJU
1 stop7h 52m
JetBlue
Deal found 2/2$476
This United Airlines deal was found by Cheapflights users on 2/3. 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 stops14h 52m
United Airlines
Sat 2/283:53 pm
MSN
-
SJU
2 stops12h 18m
United Airlines
Deal found 2/3$481
This United Airlines deal was found by Cheapflights users on 2/2. 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 5/212:40 pm
MBJ
-
MSN
2 stops24h 17m
United Airlines
Wed 6/36:30 am
MSN
-
MBJ
2 stops8h 40m
United Airlines
Deal found 2/2$483

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 February 5, 2026.

Round-trip from

$281
(United Airlines)

One-way from

$116
(Priceline)
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 February 5, 2026.
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

Tue 5/19

7:40 am-3:00 pm

1 stop8h 20m

Madison Truax Field

Wed 5/27

9:44 am-8:34 pm

1 stop9h 50m

$281

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 5/6

4:30 pm-11:55 pm

1 stop8h 25m

Madison Truax Field

Mon 5/11

8:24 pm-2:19 pm

1 stop16h 55m

$326

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 2/20

7:33 am-5:04 pm

1 stop11h 31m

Madison Truax Field

Sun 2/22

10:54 am-9:49 pm

1 stop8h 55m

$420

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 5/21

6:00 am-10:13 pm

1 stop17h 13m

Madison Truax Field

Sun 5/24

7:02 am-10:51 pm

1 stop14h 49m

$422

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

11:25 am-4:32 am

1 stop16h 07m

$432

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 5/21

11:55 am-11:58 pm

1 stop12h 03m

Madison Truax Field

Wed 6/3

6:00 am-1:58 pm

1 stop7h 58m

$468

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Sun 5/10

4:37 pm-10:55 am

2 stops18h 18m

Madison Truax Field

Wed 5/13

7:45 am-3:37 pm

2 stops7h 52m

$470

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 7/17

1:09 pm-10:35 pm

1 stop10h 26m

Madison Truax Field

Tue 7/28

11:11 am-8:07 pm

1 stop7h 56m

$476

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sat 3/28

3:30 pm-10:58 pm

1 stop8h 28m

Madison Truax Field

Sun 4/5

6:00 am-2:15 pm

1 stop7h 15m

$476

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Wed 5/20

12:56 pm-11:55 pm

2 stops10h 59m

Madison Truax Field

Wed 6/3

6:00 am-1:58 pm

1 stop7h 58m

$476

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 28 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 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 5, 2026.
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
8,146 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

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
8,146 reviews
Delta
7.9
Good
8,146 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

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 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 American Airlines fly from Caribbean Islands to Madison in about 8h 20m. The time it takes to get you to your destination can typically vary by up to 05m. 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 $140 on United Airlines. Other airlines that offer cheap prices include American Airlines from $184 and Delta from $259 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 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 Islands to Madison

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Top 2 airlines flying from Caribbean Islands to Madison

Discover the top 2 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 February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$550FlexibilityNo cancel feeOn-time71%
DeltaCheapest$449Average$495FlexibilityNo cancel feeOn-timeN/A

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