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Madison

$272+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$424
(American Airlines)

One-way from

$272
(United 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 February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 11/13:50 pmSJU - MSN
1 stop6h 47mAmerican Airlines
Sat 11/81:22 pmMSN - SJU
2 stops10h 48mAmerican Airlines
Deal found 2/20$340
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 4/32:13 pmSJU - MSN
2 stops9h 47mDelta
Mon 4/76:10 amMSN - SJU
1 stop7h 53mDelta
Deal found 2/19$430
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 4/21:05 amSJU - MSN
2 stops12h 12mUnited Airlines
Mon 4/76:30 amMSN - SJU
1 stop7h 14mUnited Airlines
Deal found 2/19$485
This United Airlines deal was found by Cheapflights users on 2/20. 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 3/73:57 pmNAS - MSN
1 stop7h 33mUnited Airlines
Tue 3/115:15 pmMSN - NAS
1 stop20h 40mUnited Airlines
Deal found 2/20$584
This SmartFares deal was found by Cheapflights users on 2/19. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/34:30 amSJU - MSN
2 stops29h 44mMultiple Airlines
Mon 4/74:10 pmMSN - SJU
3 stops33h 13mMultiple Airlines
Deal found 2/19$587
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Thu 3/202:12 pmSJU - MSN
1 stop28h 27mFrontier
Sat 3/227:08 pmMSN - SJU
1 stop12h 27mFrontier
Deal found 2/19$810
This Mytrip deal was found by Cheapflights users on 2/20. 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 3/76:30 amNAS - MSN
3 stops34h 46mMultiple Airlines
Tue 3/1111:40 amMSN - NAS
2 stops22h 20mMultiple Airlines
Deal found 2/20$1,065

Find flights from Caribbean Islands to Madison within your budget

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 20, 2025.

Fly from

Caribbean Islands

Fly to

Madison

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 4/3

6:05 am-5:10 pm

1 stop12h 05m

Madison Truax Field

Mon 4/7

5:35 am-12:09 am

1 stop17h 34m

$424

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 4/3

2:13 pm-11:00 pm

2 stops9h 47m

Madison Truax Field

Mon 4/7

6:10 am-3:03 pm

1 stop7h 53m

$430

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 4/2

1:05 am-12:17 pm

2 stops12h 12m

Madison Truax Field

Mon 4/7

6:30 am-2:44 pm

1 stop7h 14m

$485

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Fri 3/7

3:57 pm-10:30 pm

1 stop7h 33m

Madison Truax Field

Tue 3/11

5:15 pm-2:55 pm

1 stop20h 40m

$584

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 4/3

4:30 am-9:14 am

2 stops29h 44m

Madison Truax Field

Mon 4/7

4:10 pm-2:23 am

3 stops33h 13m

$587

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 3/20

2:12 pm-5:39 pm

1 stop28h 27m

Madison Truax Field

Sat 3/22

7:08 pm-8:35 am

1 stop12h 27m

$810

NassauMadison

NAS - MSN

NASMSN

Nassau Intl

Fri 3/7

6:30 am-4:16 pm

3 stops34h 46m

Madison Truax Field

Tue 3/11

11:40 am-11:00 am

2 stops22h 20m

$1,065

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Wed 3/12

1:48 pm-10:19 am

1 stop20h 31m

$272

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Wed 3/12

7:00 am-8:22 pm

2 stops13h 22m

$274

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Wed 3/12

3:05 pm-5:36 pm

3 stops26h 31m

$483

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Caribbean Islands to Madison

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

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 February 20, 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 February 20, 2025.
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

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
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

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
8,220 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

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

Frontier
6.0
Okay
3,355 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

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 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$308Average$557FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$341Average$592FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$348Average$554FlexibilityNo cancel feeOn-time71%
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