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Madison

$210+ 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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$387
(American Airlines)

One-way from

$210
(American Airlines)
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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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 5/141:10 pmSJU - MSN
1 stop11h 35mAmerican Airlines
Sun 5/186:13 amMSN - SJU
1 stop13h 20mAmerican Airlines
Deal found 4/30$387
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/287:00 amSJU - MSN
2 stops14h 43mDelta
Wed 6/46:00 amMSN - SJU
2 stops12h 48mDelta
Deal found 4/30$405
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/203:40 pmMBJ - MSN
2 stops16h 21mAmerican Airlines
Sun 8/316:45 pmMSN - MBJ
2 stops14h 40mAmerican Airlines
Deal found 4/29$484
This eDestinos deal was found by Cheapflights users on 4/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/133:56 amSJU - MSN
1 stop13h 23mMultiple Airlines
Sun 5/187:56 pmMSN - SJU
2 stops22h 48mMultiple Airlines
Deal found 4/30$510
This United Airlines deal was found by Cheapflights users on 4/30. 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 5/271:05 amSJU - MSN
2 stops12h 08mUnited Airlines
Wed 6/42:35 pmMSN - SJU
1 stop8h 19mUnited Airlines
Deal found 4/30$562

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 May 1, 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

Wed 5/14

1:10 pm-11:45 pm

1 stop11h 35m

Madison Truax Field

Sun 5/18

6:13 am-8:33 pm

1 stop13h 20m

$387

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 5/28

7:00 am-8:43 pm

2 stops14h 43m

Madison Truax Field

Wed 6/4

11:04 am-7:48 pm

1 stop7h 44m

$405

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Tue 5/20

3:40 pm-8:01 am

2 stops16h 21m

Madison Truax Field

Sun 8/31

6:45 pm-9:25 am

2 stops14h 40m

$484

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 5/13

3:56 am-4:19 pm

1 stop13h 23m

Madison Truax Field

Sun 5/18

7:56 pm-7:44 pm

2 stops22h 48m

$510

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 5/27

1:05 am-12:13 pm

2 stops12h 08m

Madison Truax Field

Wed 6/4

2:35 pm-11:54 pm

1 stop8h 19m

$562

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sat 6/7

8:00 am-11:59 pm

1 stop16h 59m

$210

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Fri 5/30

12:07 pm-4:19 pm

2 stops28h 12m

$265

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 6/6

1:59 am-9:39 am

1 stop8h 40m

$267

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 5/8

4:12 pm-9:28 pm

2 stops29h 16m

$273

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 6/6

1:05 am-10:11 am

2 stops10h 06m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 11 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, 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 June is currently the most expensive (average of $423). 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 May 1, 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.

Rainfall in Madison by month

Plan your trip to Madison by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Madison ranges from 1.2 - 4.5 inches per month. June is typically the wettest month, when rainfall can reach 4.5 in. January is typically the driest time to visit Madison when rainfall is around 1.2 in.

Temperature in Madison by month

Plan your trip to Madison by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Madison, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

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 May 1, 2025.
Read reviews from past customers who have flown Delta, United Airlines and American Airlines from Caribbean Islands to Madison. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,826 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • 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 $210 on American Airlines. Other airlines that offer cheap prices include United Airlines from $273 and WestJet from $956 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, 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 June is currently the most expensive (average of $423). 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 Caribbean Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Portage
Middleton
Baraboo

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Alternative routes for Caribbean Islands to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$308Average$561FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$341Average$616FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$369Average$583FlexibilityNo cancel feeOn-time71%

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