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$162+ Cheap flights from Madison (MSN) to Caribbean

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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Madison to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Caribbean (0CB). 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 November 21, 2024.

Find flight deals from Madison to Caribbean

Cheapest flights from Madison to Caribbean
Explore the most affordable flight options available from Madison to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This Mytrip deal was found by Cheapflights users on 11/20. 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.
Sat 12/76:05 pmMSN - PUJ
2 stops19h 43mMultiple Airlines
Fri 12/134:43 pmPUJ - MSN
3 stops26h 42mMultiple Airlines
Deal found 11/20$519
This American Airlines deal was found by Cheapflights users on 11/20. 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 12/74:19 pmMSN - PUJ
1 stop17h 21mAmerican Airlines
Fri 12/131:10 pmPUJ - MSN
1 stop11h 53mAmerican Airlines
Deal found 11/20$553
This American Airlines deal was found by Cheapflights users on 11/21. 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 12/52:51 pmMSN - STT
2 stops18h 53mAmerican Airlines
Thu 12/124:30 pmSTT - MSN
1 stop9h 26mAmerican Airlines
Deal found 11/21$603
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/146:30 amMSN - MBJ
1 stop7h 08mDelta
Wed 12/182:12 pmMBJ - MSN
1 stop8h 54mDelta
Deal found 11/20$660
This United Airlines deal was found by Cheapflights users on 11/21. 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 12/107:00 amMSN - PUJ
2 stops8h 35mUnited Airlines
Sat 12/143:15 pmPUJ - MSN
2 stops27h 28mUnited Airlines
Deal found 11/21$663
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Sun 12/86:30 pmMSN - GCM
2 stops17h 10mAmerican Airlines
Wed 12/113:30 pmGCM - MSN
2 stops19h 51mAmerican Airlines
Deal found 11/20$685
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Sun 12/17:40 pmMSN - SJU
1 stop15h 54mAmerican Airlines
Thu 12/58:15 amSJU - MSN
1 stop17h 41mAmerican Airlines
Deal found 11/20$693
This American Airlines deal was found by Cheapflights users on 11/21. 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 12/74:19 pmMSN - AUA
1 stop17h 56mAmerican Airlines
Tue 12/175:45 pmAUA - MSN
2 stops19h 21mAmerican Airlines
Deal found 11/21$701
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/145:51 amMSN - MBJ
1 stop6h 19mAmerican Airlines
Wed 12/182:00 pmMBJ - MSN
2 stops10h 56mAmerican Airlines
Deal found 11/19$710
This United deal was found by Cheapflights users on 11/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2312:15 pmMSN - GCM
2 stops27h 10mUnited Airlines
Sat 12/286:00 pmGCM - MSN
2 stops28h 13mUnited Airlines
Deal found 11/21$712
This United Airlines deal was found by Cheapflights users on 11/21. 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 12/37:00 amMSN - SJU
1 stop11h 55mUnited Airlines
Fri 12/62:05 amSJU - MSN
2 stops14h 44mUnited Airlines
Deal found 11/21$721
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Tue 12/176:00 amMSN - MBJ
1 stop7h 29mUnited Airlines
Tue 12/242:48 pmMBJ - MSN
1 stop8h 42mUnited Airlines
Deal found 11/19$772

Find flights from Madison to Caribbean within your budget

Customize your flight search to find flights from Madison to Caribbean 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 2,612,795 searches. Data last updated November 21, 2024.

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Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/28

11:14 am-11:45 pm

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Fri 1/31

4:25 pm-10:39 pm

1 stop8h 14m

$274

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/21

11:43 am-11:58 pm

1 stop10h 15m

San Juan Luis Munoz Marin Intl

Thu 1/23

4:40 pm-11:55 pm

1 stop9h 15m

$275

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 1/27

6:30 am-10:22 pm

2 stops13h 52m

San Juan Luis Munoz Marin Intl

Mon 2/3

2:05 am-11:54 am

2 stops11h 49m

$336

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Mon 1/6

6:35 am-5:15 pm

1 stop8h 40m

Punta Cana

Thu 1/9

3:30 pm-10:39 pm

1 stop9h 09m

$483

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sat 1/18

3:30 pm-11:40 am

2 stops18h 10m

Punta Cana

Wed 1/22

5:05 pm-11:13 am

2 stops20h 08m

$488

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Sun 2/2

4:16 pm-11:50 am

1 stop17h 34m

Saint Thomas Island Cyril E King

Sat 2/8

6:31 pm-11:00 am

2 stops18h 29m

$508

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sat 12/7

6:05 pm-3:48 pm

2 stops19h 43m

Punta Cana

Fri 12/13

4:43 pm-5:25 pm

3 stops26h 42m

$519

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Fri 1/24

6:00 am-1:48 pm

1 stop6h 48m

Nassau Intl

Mon 1/27

3:57 pm-9:03 pm

1 stop6h 06m

$528

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 1/11

6:00 am-2:37 pm

1 stop7h 37m

Montego Bay Sangster Intl

Sat 1/18

2:48 pm-9:20 pm

1 stop7h 32m

$529

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 2/19

11:17 am-8:52 pm

1 stop8h 35m

Montego Bay Sangster Intl

Fri 2/28

8:00 am-4:28 pm

1 stop9h 28m

$539

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 40 results
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Best time to book a flight from Madison to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Madison 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 Madison to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean (average of $254). Flying from Madison to Caribbean in March is currently the most expensive (average of $335). 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 MSN to CB?

Find hourly flight availability from Madison to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Caribbean as you normally would.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated November 21, 2024.
Delta
8.0
Very good
8,755 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,755 reviews
Delta
8.0
Very good
8,755 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

LATAM Airlines
7.5
Good
1,932 reviews
Delta
8.0
Very good
8,755 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
9,172 reviews
Delta
8.0
Very good
8,755 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,755 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air Canada
7.0
Good
8,246 reviews
Delta
8.0
Very good
8,755 reviews

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Madison to Caribbean. 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 from for flights from Madison to Caribbean?

    Most people fly from Madison Truax Field (MSN) if they book a flight from Madison to Caribbean. Madison Truax Field is conveniently located just 5.4 mi from Madison’s city center.

  • What are the cheapest airlines to fly from Madison to Caribbean one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $162. Users have also found prices from $252 and $253 on United Airlines and Delta, respectively.

  • What are the most popular routes from Madison to Caribbean?

    The most popular flight routes from Madison to Caribbean are Madison Truax Field - San Juan Luis Munoz Marin Intl, Madison Truax Field - Punta Cana and Madison Truax Field - Montego Bay Sangster Intl.

  • Can I find deals for flights from Madison to Caribbean that include hotel bookings?

    Yes. In addition to deals on Madison to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Caribbean.

  • Can I find deals for business class flights from Madison to Caribbean?

    Yes. Cheapflights offers flight deals from Madison to Caribbean 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 Madison to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean (average of $254). Flying from Madison to Caribbean in March is currently the most expensive (average of $335). 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

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Top 4 airlines flying from Madison to Caribbean

Discover the top 4 airlines that operate flights from Madison to Caribbean. 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$234Average$275FlexibilityNo cancel feeOn-time62%
DeltaCheapest$284Average$660FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$339Average$639FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$358Average$639FlexibilityNo cancel feeOn-time69%
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