Cheap flights from Madison (MSN) to Caribbean

MSN — SJU
Nov 28 — Dec 51

How far in advance should I book a flight from Madison to Caribbean?

To save up to 16% on this flight, we recommend booking at least 24 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Madison to Caribbean from $678 1-2 weeks out and tickets from $794 for flights departing within the next 72 hours.

What is the cheapest month to fly from Madison to Caribbean?

February is one of the best times of the year to fly to Caribbean from Madison. Prices for February average $703 per person but you can even find prices for as low as $380. The most expensive prices can be found in the month of June. Opting for a February flight can save you 25% on your journey compared to booking in June

When is the cheapest time to fly from Madison to Caribbean (MSN - CB)?

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.

Cheap flights from Madison to Caribbean in November, December 2022

The best prices found for MSN to Caribbean flights for November, December
Dec 1 - Dec 4
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

1 stop

13h 03m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

1 stop

10h 16m
$345

Multiple Airlines

Pick Dates

Deal found 11/22

Dec 15 - Dec 24
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

1 stop

13h 01m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

1 stop

15h 17m
$373

Frontier

Pick Dates

Deal found 11/20

Nov 27 - Dec 5
MSN

Madison Truax Field

PUJ

Punta Cana

1 stop

23h 35m
PUJ

Punta Cana

MSN

Madison Truax Field

2 stops

35h 07m
$393

Multiple Airlines

Pick Dates

Deal found 11/20

Madison to Caribbean 2022 flight deals

Cheap flights to Caribbean from Madison found for this year
Dec 1 - Dec 4
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

1 stop

13h 03m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

1 stop

10h 16m
$345

Multiple Airlines

Pick Dates

Deal found 11/22

Dec 15 - Dec 24
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

1 stop

13h 01m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

1 stop

15h 17m
$373

Frontier

Pick Dates

Deal found 11/20

Nov 27 - Dec 5
MSN

Madison Truax Field

PUJ

Punta Cana

1 stop

23h 35m
PUJ

Punta Cana

MSN

Madison Truax Field

2 stops

35h 07m
$393

Multiple Airlines

Pick Dates

Deal found 11/20

Cheap Frontier flights from Madison to Caribbean

Feb 13 - Feb 21
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

1 stop

16h 28m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

1 stop

8h 22m
$303

Frontier

Pick Dates

Deal found 11/22

Feb 8 - Feb 21
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

1 stop

16h 28m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

1 stop

8h 22m
$326

Frontier

Pick Dates

Deal found 11/22

Feb 13 - Feb 23
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

1 stop

16h 28m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

1 stop

8h 06m
$347

Frontier

Pick Dates

Deal found 11/22

Cheap United Airlines flights from Madison to Caribbean

Jan 18 - Jan 25
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

2 stops

19h 19m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

2 stops

20h 50m
$349

United Airlines

Pick Dates

Deal found 11/23

Jan 18 - Jan 25
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

2 stops

19h 19m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

1 stop

20h 30m
$359

United Airlines

Pick Dates

Deal found 11/23

Jan 19 - Mar 7
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

1 stop

15h 15m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

2 stops

18h 42m
$369

United Airlines

Pick Dates

Deal found 11/21

Last minute flights from Madison to Caribbean

Late deals on return flights to Caribbean from Madison, departing today and this week
Dec 1 - Dec 4
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

1 stop

13h 03m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

1 stop

10h 16m
$345

Multiple Airlines

Pick Dates

Deal found 11/22

Nov 28 - Dec 8
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

2 stops

46h 22m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

1 stop

8h 33m
$430

Multiple Airlines

Pick Dates

Deal found 11/22

Dec 1 - Dec 4
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

1 stop

13h 03m
SJU

San Juan Luis Munoz Marin Intl

MSN

Madison Truax Field

2 stops

25h 08m
$455

Multiple Airlines

Pick Dates

Deal found 11/22

One-way flights to Caribbean from Madison

The cheapest one-way flights from Madison to Caribbean
Jan 19
MSN

Madison Truax Field

SJU

San Juan Luis Munoz Marin Intl

2 stops

14h 32m
$225

United Airlines

Pick Dates

Deal found 11/22

Feb 14
MSN

Madison Truax Field

AUA

Oranjestad Reina Beatrix

3 stops

42h 12m
$283

Multiple Airlines

Pick Dates

Deal found 11/22

Feb 28
MSN

Madison Truax Field

AUA

Oranjestad Reina Beatrix

3 stops

35h 46m
$297

Multiple Airlines

Pick Dates

Deal found 11/21

Related info for your journey

Useful info, stats and facts about Madison to Caribbean flights.

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.

Which airlines flying from Madison Truax Field to Caribbean have flexible cancellations due to COVID-19?

Some of our airline partners flying from Madison Truax Field to Caribbean have new flexible policies in place due to COVID-19. American Airlines, Delta, and United Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like American Airlines with this kind of flexibility.

Can I find flights from Madison to Caribbean for under $300 on Cheapflights?

Yes, there are multiple flights from Madison to Caribbean for under $300. The cheapest flight booked recently is on Multiple Airlines for just $258, but on average you can expect to pay $334.

Are there last-minute flights available from Madison to Caribbean for under $400?

There are currently 20+ open flights from Madison to Caribbean within the next 7 days for less than $400.

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

For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $225. Users have also found prices from $300 and $333 on American Airlines and Frontier, 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 - Montego Bay Sangster Intl and Madison Truax Field - Oranjestad Reina Beatrix.

What are the most popular airlines that fly from Madison to Caribbean?

Consider American Airlines, Alaska Airlines or Delta when booking your flight. These represent the most popular airlines when flying from Madison to Caribbean.

What are the cheapest flights from Madison to Caribbean?

While on average a flight from Madison to Caribbean is generally $943, our data shows the cheapest flight currently is $263. When looking at the most popular route, (Madison Truax Field - San Juan Luis Munoz Marin Intl), you can expect to pay $269 for that flight.

Destination points for flights from Madison to Caribbean

Select to see more specific information for flights from Madison to all places in Caribbean

Top 4 airlines flying from Madison to Caribbean

The chart below displays the airlines Cheapflights users traveling from Madison to Caribbean choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
United AirlinesCheapest$291Average$724FlexibilityNo cancel feeOn-time69%COVID-19 safety
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American AirlinesCheapest$405Average$728FlexibilityNo cancel feeOn-time71%COVID-19 safety
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DeltaCheapest$469Average$817FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
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Alaska AirlinesCheapest$815Average$815FlexibilityNo cancel feeOn-time75%COVID-19 safety
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