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$138+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from Caribbean to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean (0CB) to Madison (MSN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Round-trip from

$500
(American Airlines)

One-way from

$138
(Delta)

Popular in

November

Cheapest in

February

Average price

$582
From Caribbean to Madison Truax Field
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One-way flight from Caribbean to Madison Truax Field
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Highest demand for flights based on searches. 12% potential increase in price ($79 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in January 2025
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Find 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 January 30, 2025.

This American Airlines deal was found by Cheapflights users on 1/30. 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 2/267:45 amSJU - MSN
2 stops11h 30mAmerican Airlines
Wed 3/511:45 amMSN - SJU
2 stops10h 10mAmerican Airlines
Deal found 1/30$500
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Fri 3/72:55 pmNAS - MSN
2 stops22h 09mUnited Airlines
Thu 3/132:19 pmMSN - NAS
2 stops22h 29mUnited Airlines
Deal found 1/30$506
This Delta deal was found by Cheapflights users on 1/30. 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 2/264:10 pmSJU - MSN
1 stop8h 32mDelta
Wed 3/56:35 amMSN - SJU
1 stop7h 52mDelta
Deal found 1/30$515
This United Airlines deal was found by Cheapflights users on 1/30. 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 2/252:05 amSJU - MSN
2 stops13h 39mUnited Airlines
Wed 3/58:34 amMSN - SJU
2 stops14h 02mUnited Airlines
Deal found 1/30$532
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Fri 3/73:55 pmNAS - MSN
1 stop8h 20mAmerican Airlines
Thu 3/135:30 amMSN - NAS
1 stop6h 54mAmerican Airlines
Deal found 1/30$540
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Thu 2/132:48 pmMBJ - MSN
1 stop7h 23mUnited Airlines
Thu 2/203:42 pmMSN - MBJ
2 stops45h 18mUnited Airlines
Deal found 1/30$658
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Thu 2/1311:55 amMBJ - MSN
1 stop12h 10mAmerican Airlines
Thu 2/204:13 pmMSN - MBJ
1 stop23h 06mAmerican Airlines
Deal found 1/30$718

Find flights from Caribbean to Madison within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 2/26

7:45 am-5:15 pm

2 stops11h 30m

Madison Truax Field

Wed 3/5

11:45 am-11:55 pm

2 stops10h 10m

$500

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Fri 3/7

2:55 pm-12:04 pm

2 stops22h 09m

Madison Truax Field

Thu 3/13

2:19 pm-1:48 pm

2 stops22h 29m

$506

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 2/26

4:10 pm-10:42 pm

1 stop8h 32m

Madison Truax Field

Wed 3/5

6:35 am-4:27 pm

1 stop7h 52m

$515

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 2/25

2:05 am-1:44 pm

2 stops13h 39m

Madison Truax Field

Wed 3/5

8:34 am-12:36 am

2 stops14h 02m

$532

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Fri 3/7

3:55 pm-11:15 pm

1 stop8h 20m

Madison Truax Field

Thu 3/13

5:30 am-1:24 pm

1 stop6h 54m

$540

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 2/13

2:48 pm-9:11 pm

1 stop7h 23m

Madison Truax Field

Thu 2/20

3:42 pm-2:00 pm

2 stops45h 18m

$658

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 2/13

11:55 am-11:05 pm

1 stop12h 10m

Madison Truax Field

Thu 2/20

4:13 pm-4:19 pm

1 stop23h 06m

$718

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 4/9

6:15 am-4:36 pm

1 stop11h 21m

$138

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 4/8

1:05 am-12:17 pm

2 stops12h 12m

$183

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Tue 4/29

3:05 pm-9:01 am

2 stops17h 56m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 13 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.

Travel insights for flights from Caribbean to Madison

Get recent, data-driven insights about flights from Caribbean to Madison including ideal travel times, pricing trends, and more.

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

Currently, January is the cheapest month in which you can book a flight from Caribbean to Madison (average of $338). Flying from Caribbean 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 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 January 30, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean 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 January 30, 2025.
Delta
8.0
Very good
8,450 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

8.0

Food

7.3

Entertainment

7.9

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
8,450 reviews
Delta
8.0
Very good
8,450 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

8.0

Food

7.3

Entertainment

7.9

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
8,906 reviews
Delta
8.0
Very good
8,450 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

8.0

Food

7.3

Entertainment

7.9

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
8,450 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

8.0

Food

7.3

Entertainment

7.9

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 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.

  • 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 $138. United Airlines flights start at $183 while deals on American Airlines start at $293 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 Nassau Intl - Madison Truax Field or Montego Bay Sangster 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, January is the cheapest month in which you can book a flight from Caribbean to Madison (average of $338). Flying from Caribbean 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?

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

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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 3 airlines flying from Caribbean to Madison

Discover the top 3 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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$334Average$515FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$341Average$616FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$348Average$553FlexibilityNo cancel feeOn-time71%
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