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Madison

$113+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$405
(United Airlines)

One-way from

$113
(American Airlines)

Popular in

November

Cheapest in

August

Average price

$694
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. 9% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 18, 2025.

This United Airlines deal was found by Cheapflights users on 6/18. 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 10/302:36 pmMBJ - MSN
1 stop8h 09mUnited Airlines
Mon 12/16:30 amMSN - MBJ
1 stop6h 16mUnited Airlines
Deal found 6/18$405
This American Airlines deal was found by Cheapflights users on 6/18. 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 10/304:25 pmMBJ - MSN
2 stops17h 35mAmerican Airlines
Mon 12/18:00 amMSN - MBJ
1 stop5h 48mAmerican Airlines
Deal found 6/18$409
This American Airlines deal was found by Cheapflights users on 6/16. 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 8/71:36 pmSJU - MSN
2 stops11h 23mAmerican Airlines
Mon 8/186:19 amMSN - SJU
1 stop15h 30mAmerican Airlines
Deal found 6/16$425
This United Airlines deal was found by Cheapflights users on 6/17. 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 8/15:00 pmNAS - MSN
2 stops30h 30mUnited Airlines
Fri 8/84:00 pmMSN - NAS
2 stops20h 50mUnited Airlines
Deal found 6/17$490
This United Airlines deal was found by Cheapflights users on 6/17. 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 6/201:05 amSJU - MSN
2 stops10h 06mUnited Airlines
Mon 6/236:30 amMSN - SJU
1 stop7h 14mUnited Airlines
Deal found 6/17$532
This American Airlines deal was found by Cheapflights users on 6/17. 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 8/111:05 amNAS - MSN
1 stop13h 45mAmerican Airlines
Fri 8/86:19 amMSN - NAS
1 stop7h 01mAmerican Airlines
Deal found 6/17$550
This Delta deal was found by Cheapflights users on 6/17. 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.
Sat 7/192:36 pmSJU - MSN
2 stops9h 51mDelta
Fri 7/256:45 amMSN - SJU
2 stops12h 54mDelta
Deal found 6/17$904

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 June 18, 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

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 10/30

12:25 pm-10:45 pm

1 stop10h 20m

Madison Truax Field

Mon 12/1

6:30 am-1:46 pm

1 stop6h 16m

$405

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 10/30

4:25 pm-10:00 am

2 stops17h 35m

Madison Truax Field

Mon 12/1

8:00 am-2:48 pm

1 stop5h 48m

$409

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 8/7

1:36 pm-11:59 pm

2 stops11h 23m

Madison Truax Field

Mon 8/18

6:19 am-10:49 pm

1 stop15h 30m

$425

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Fri 8/1

5:00 pm-10:30 pm

2 stops30h 30m

Madison Truax Field

Fri 8/8

4:00 pm-1:50 pm

2 stops20h 50m

$490

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Fri 8/1

11:05 am-11:50 pm

1 stop13h 45m

Madison Truax Field

Fri 8/8

6:19 am-2:20 pm

1 stop7h 01m

$550

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 8/6

1:05 am-10:13 am

2 stops10h 08m

Madison Truax Field

Mon 8/18

4:00 pm-11:54 pm

1 stop6h 54m

$587

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sat 7/19

2:36 pm-11:27 pm

2 stops9h 51m

Madison Truax Field

Fri 7/25

6:45 am-8:39 pm

2 stops12h 54m

$904

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sat 10/4

7:05 pm-10:31 am

2 stops16h 26m

$113

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 10/3

1:05 am-9:55 am

2 stops9h 50m

$158

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 6/24

1:02 pm-5:45 pm

3 stops29h 43m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

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 March is currently the most expensive (average of $422). 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 June 18, 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 June 18, 2025.
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,809 reviews
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 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 Nassau 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 March is currently the most expensive (average of $422). 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
Fitchburg

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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 airline flying from Caribbean to Madison

Discover the top airline 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$369Average$578FlexibilityNo cancel feeOn-time71%

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