Cheap flights from Madison (MSN) to Caribbean

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How to find the cheapest flight from
Madison (MSN) to Caribbean

All the information you need to plan the best MSN to SJU flight in 2021: compare Madison to Caribbean flight prices with the expected peak season, weather and rainfall in Caribbean.
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.

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

To save up to 11% on this flight, we recommend booking at least 53 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 $503 1-2 weeks out and tickets from $503 for flights departing within the next 72 hours.

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

August is one of the best times of the year to fly to Caribbean from Madison. Prices for August average $484 per person but you can even find prices for as low as $202. The most expensive prices can be found in the month of May. Opting for a August flight can save you 29% on your journey compared to booking in August

Cheap flights from Madison to Caribbean in December, January 2022

The best prices found for MSN to Caribbean flights for December, January
24 Jan - 7 Feb
$348pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field
24 Jan - 7 Feb
$352pp
MSN
Madison Truax Field
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field
25 Jan - 30 Jan
$357pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field

Madison Truax Field to Caribbean 2022 flight deals

Cheap flights to Caribbean from Madison found for this year
10 Dec - 12 Dec
$470pp
MSN
Madison Truax Field
Frontier
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Frontier
 
1 STOP
MSN
Madison Truax Field
10 Dec - 12 Dec
$517pp
MSN
Madison Truax Field
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
   
2 STOPS
MSN
Madison Truax Field
10 Dec - 12 Dec
$525pp
MSN
Madison Truax Field
Multiple Airlines
 
1 STOP
SJU
San Juan Luis Munoz Marin Intl
SJU
San Juan Luis Munoz Marin Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field

Last minute flights from Madison to Caribbean

Late deals on round-trip flights to Caribbean from Madison, departing today and this week
16 Dec - 21 Dec
$553pp
MSN
Madison Truax Field
United Airlines
 
1 STOP
AUA
Oranjestad Reina Beatrix
AUA
Oranjestad Reina Beatrix
United Airlines
 
1 STOP
MSN
Madison Truax Field
16 Dec - 21 Dec
$570pp
MSN
Madison Truax Field
United Airlines
 
1 STOP
AUA
Oranjestad Reina Beatrix
AUA
Oranjestad Reina Beatrix
United Airlines
   
2 STOPS
MSN
Madison Truax Field
16 Dec - 21 Dec
$571pp
MSN
Madison Truax Field
United Airlines
   
2 STOPS
AUA
Oranjestad Reina Beatrix
AUA
Oranjestad Reina Beatrix
United Airlines
 
1 STOP
MSN
Madison Truax Field

One-way flights to Caribbean from Madison

The cheapest one-way flights from Madison to Caribbean
2:05 pm - 7:40 am
Frontier
2 Stops
39h 35m
MSN - SJU
Frontier
$302
Kiwi.com
2:30 am - 7:54 pm
United Airlines
1 Stop
15h 24m
MSN - SJU
United Airlines
$319
United
2:25 pm - 8:09 am
Multiple Airlines
3 Stops
39h 44m
MSN - SJU
Multiple Airlines
$335
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Madison</span> to <span class="emphasized">Caribbean</span> flights.

Flight FAQs

From Madison to Caribbean

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 $400 on Cheapflights?

Yes, there are multiple flights from Madison to Caribbean for under $400. The cheapest flight booked recently is on Multiple Airlines for just $327, but on average you can expect to pay $370.

Are there last-minute flights available from Madison to Caribbean for under $600?

There are currently 20+ open flights from Madison to Caribbean within the next 7 days for less than $600.

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

For one-way options, check prices for Frontier. According to our data, you can fly for as low as $128. Users have also found prices from $267 and $277 on American Airlines and United Airlines, 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 - Saint Thomas Island Cyril E King and Madison Truax Field - Punta Cana.

What are the cheapest flights from Madison to Caribbean?

While on average a flight from Madison to Caribbean is generally $295, our data shows the cheapest flight currently is $136. When looking at the most popular route, (Madison Truax Field - San Juan Luis Munoz Marin Intl), you can expect to pay $348 for that flight.

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

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

Destination points for flights from Madison to Caribbean

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

Destination information for Caribbean

Things to know before you go - useful duration and weather info for your trip from Madison to Caribbean.
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Airports servicing Madison

Top 4 airlines flying from Madison Truax Field 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.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$146 $335 No cancel fee 62%
United Airlines
$241 $662 No cancel fee 69%
American Airlines
$259 $770 No cancel fee 71%
Delta
$262 $752 No cancel fee N/A
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