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$134+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Apr 30 — May 71
Wed 4/30
Wed 5/7
1 adult, Economy
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Cheap flight deals from Caribbean to Madison

Keep the following information in mind while searching for Caribbean to Madison flight deals. Data was last updated April 25, 2025.

Round-trip from

$298
(American Airlines)

One-way from

$134
(American Airlines)

Popular in

November

Cheapest in

August

Average price

$548
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. 8% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 25, 2025.

This American Airlines deal was found by Cheapflights users on 4/24. 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 5/146:10 amSJU - MSN
2 stops10h 43mAmerican Airlines
Sun 5/185:00 amMSN - SJU
1 stop16h 30mAmerican Airlines
Deal found 4/24$298
This Delta deal was found by Cheapflights users on 4/24. 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 4/253:34 pmSJU - MSN
1 stop7h 58mDelta
Tue 5/67:00 amMSN - SJU
2 stops12h 23mDelta
Deal found 4/24$369
This United Airlines deal was found by Cheapflights users on 4/24. 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 4/241:25 pmSJU - MSN
1 stop8h 25mUnited Airlines
Tue 5/63:55 pmMSN - SJU
1 stop6h 59mUnited Airlines
Deal found 4/24$459
This American Airlines deal was found by Cheapflights users on 4/25. 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 5/910:53 amMBJ - MSN
1 stop12h 01mAmerican Airlines
Wed 9/37:17 amMSN - MBJ
1 stop5h 53mAmerican Airlines
Deal found 4/25$480
This Mytrip deal was found by Cheapflights users on 4/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2812:54 amSJU - MSN
2 stops34h 07mMultiple Airlines
Sat 5/35:05 pmMSN - SJU
2 stops25h 35mMultiple Airlines
Deal found 4/24$681
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Mon 6/92:53 pmNAS - MSN
2 stops20h 18mUnited Airlines
Mon 6/162:35 pmMSN - NAS
2 stops22h 15mUnited Airlines
Deal found 4/25$694
This Mytrip deal was found by Cheapflights users on 4/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/912:07 pmMBJ - MSN
3 stops28h 12mMultiple Airlines
Wed 9/36:08 pmMSN - MBJ
2 stops15h 06mMultiple Airlines
Deal found 4/25$807

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 April 25, 2025.
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 5/14

6:10 am-3:53 pm

2 stops10h 43m

Madison Truax Field

Sun 5/18

5:00 am-10:30 pm

1 stop16h 30m

$298

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 5/13

1:05 am-12:12 pm

2 stops12h 07m

Madison Truax Field

Sun 5/18

2:27 pm-11:54 pm

1 stop8h 27m

$459

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

6:00 am-4:31 pm

2 stops9h 31m

$463

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Fri 5/9

10:53 am-10:54 pm

1 stop12h 01m

Madison Truax Field

Wed 9/3

7:17 am-1:10 pm

1 stop5h 53m

$480

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Mon 6/9

2:53 pm-10:11 am

2 stops20h 18m

Madison Truax Field

Mon 6/16

2:35 pm-1:50 pm

2 stops22h 15m

$694

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Fri 5/9

12:07 pm-4:19 pm

3 stops28h 12m

Madison Truax Field

Wed 9/3

6:08 pm-9:14 am

2 stops15h 06m

$807

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 7/29

6:04 am-12:02 am

2 stops18h 58m

$134

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 5/1

2:20 pm-8:21 pm

1 stop7h 01m

$185

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 8/1

3:56 pm-10:15 pm

1 stop7h 19m

$230

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 5/23

8:12 pm-4:19 pm

2 stops21h 07m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 13 results
1
2

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, 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 April 25, 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 April 25, 2025.
Delta
8.0
Very good
7,920 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

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
8,685 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

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
7,920 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

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 American Airlines, which is currently one of the cheapest options available, starting at $134. Delta flights start at $185 while deals on United Airlines start at $230 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 Simpson Bay Princess Juliana - 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

Browse thousands of different options on Cheapflights for your next trip

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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 April 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$308Average$559FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$341Average$616FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$369Average$578FlexibilityNo cancel feeOn-time71%

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