What is the cheapest airline that flies from Madison Truax Field to Caribbean?

United Airlines, American Airlines, and Frontier are the most popular carriers operating from Madison Truax Field to Caribbean

What airlines fly to Caribbean?

American Airlines, Delta and United Airlines are the top three most popular airlines that fly to Caribbean from Madison according to our data. American Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 7 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Madison Truax Field Airport to Caribbean?

Prices for flights from Madison Truax Field Airport to Caribbean are updated daily.

How many operators does momondo search for flights from Madison Truax Field Airport to Caribbean?

The number of operators available for flights from Madison Truax Field Airport to Caribbean is 3 as of November 2025.

How old do you have to be to fly from Madison Truax Field Airport to Caribbean?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Madison Truax Field Airport to Caribbean.

What documentation or ID do you need to fly to Caribbean?

The necessary travel and health documents for your Caribbean trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$147 Cheap Flights from Madison to Caribbean in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

11:00 am - 11:44 pmMSN-SJU

10h 44m2 stops

7:30 am - 4:19 pmSJU-MSN

10h 49m1 stop

$235Delta

Find Deal

mar., ene. 20 - mié., ene. 28

8:15 am - 9:26 pmMSN-SJU

11h 11m2 stops

7:35 am - 1:52 pmSJU-MSN

7h 17m1 stop

$257United Airlines

Find Deal

mar., mar. 3 - mié., mar. 11

8:15 am - 10:22 pmMSN-SJU

12h 07m2 stops

2:05 am - 11:44 amSJU-MSN

11h 39m2 stops

$264United Airlines

Find Deal

mar., dic. 9 - lun., dic. 15

5:45 am - 10:09 pmMSN-SJU

14h 24m2 stops

11:00 am - 9:56 pmSJU-MSN

12h 56m2 stops

$268American Airlines

Find Deal

mar., dic. 9 - mar., dic. 16

11:20 am - 11:49 pmMSN-SJU

10h 29m1 stop

6:15 am - 4:19 pmSJU-MSN

12h 04m1 stop

$278Delta

Find Deal

mar., feb. 24 - mié., mar. 4

5:01 pm - 12:35 pmMSN-SJU

18h 34m2 stops

3:45 pm - 10:18 amSJU-MSN

19h 33m2 stops

$295American Airlines

Find Deal

mar., mar. 10 - mié., mar. 11

11:29 am - 9:39 pmMSN-SJU

8h 10m1 stop

7:00 am - 4:20 pmSJU-MSN

11h 20m1 stop

$298American Airlines

Find Deal

jue., ene. 29 - mar., feb. 3

11:23 am - 11:59 pmMSN-SJU

10h 36m2 stops

6:00 am - 4:52 pmSJU-MSN

12h 52m2 stops

$301American Airlines

Find Deal

sáb., ene. 31 - jue., feb. 5

12:38 pm - 2:35 pmMSN-BGI

23h 57m2 stops

4:10 pm - 2:52 pmBGI-MSN

24h 42m2 stops

$3,425Air Canada

Find Deal

dom., ene. 25 - sáb., feb. 7

12:38 pm - 2:35 pmMSN-BGI

23h 57m2 stops

4:10 pm - 2:52 pmBGI-MSN

24h 42m2 stops

$3,580Air Canada

Find Deal

dom., ene. 25 - sáb., feb. 7

American Airlines flights from Madison to Caribbean

Our best American Airlines deals on Madison to Caribbean flight tickets

American Airlines

Dec 9

MSN5:45 amMadison Truax Field

14h 24m

2 stops

SJU10:09 pmSan Juan Luis Munoz Marin Intl

Dec 16

SJU11:00 amSan Juan Luis Munoz Marin Intl

12h 56m

2 stops

MSN9:56 pmMadison Truax Field

$268

Find similar

American Airlines

Mar 10

MSN5:01 pmMadison Truax Field

18h 34m

2 stops

SJU12:35 pmSan Juan Luis Munoz Marin Intl

Mar 11

SJU3:45 pmSan Juan Luis Munoz Marin Intl

19h 33m

2 stops

MSN10:18 amMadison Truax Field

$295

Find similar

American Airlines

Jan 29

MSN11:29 amMadison Truax Field

8h 10m

1 stop

SJU9:39 pmSan Juan Luis Munoz Marin Intl

Feb 3

SJU7:00 amSan Juan Luis Munoz Marin Intl

11h 20m

1 stop

MSN4:20 pmMadison Truax Field

$298

Find similar

United Airlines flights from Madison to Caribbean

Our best United Airlines deals on Madison to Caribbean flight tickets

United Airlines

Mar 3

MSN8:15 amMadison Truax Field

11h 11m

2 stops

SJU9:26 pmSan Juan Luis Munoz Marin Intl

Mar 11

SJU7:35 amSan Juan Luis Munoz Marin Intl

7h 17m

1 stop

MSN1:52 pmMadison Truax Field

$257

Find similar

United Airlines

Dec 9

MSN8:15 amMadison Truax Field

12h 07m

2 stops

SJU10:22 pmSan Juan Luis Munoz Marin Intl

Dec 15

SJU2:05 amSan Juan Luis Munoz Marin Intl

11h 39m

2 stops

MSN11:44 amMadison Truax Field

$264

Find similar

United Airlines

Mar 3

MSN6:30 amMadison Truax Field

7h 10m

1 stop

SJU3:40 pmSan Juan Luis Munoz Marin Intl

Mar 10

SJU1:05 amSan Juan Luis Munoz Marin Intl

14h 57m

2 stops

MSN3:02 pmMadison Truax Field

$319

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 1/20

11:00 am-11:44 pm

2 stops10h 44m

San Juan Luis Munoz Marin Intl

mié. 1/28

7:30 am-4:19 pm

1 stop10h 49m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 3/3

8:15 am-9:26 pm

2 stops11h 11m

San Juan Luis Munoz Marin Intl

mié. 3/11

7:35 am-1:52 pm

1 stop7h 17m

$257

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 12/9

8:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

lun. 12/15

2:05 am-11:44 am

2 stops11h 39m

$264

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 12/9

5:45 am-10:09 pm

2 stops14h 24m

San Juan Luis Munoz Marin Intl

mar. 12/16

11:00 am-9:56 pm

2 stops12h 56m

$268

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 2/24

11:20 am-11:49 pm

1 stop10h 29m

San Juan Luis Munoz Marin Intl

mié. 3/4

6:15 am-4:19 pm

1 stop12h 04m

$278

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 3/10

5:01 pm-12:35 pm

2 stops18h 34m

San Juan Luis Munoz Marin Intl

mié. 3/11

3:45 pm-10:18 am

2 stops19h 33m

$295

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

jue. 1/29

11:29 am-9:39 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

mar. 2/3

7:00 am-4:20 pm

1 stop11h 20m

$298

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

sáb. 1/31

11:23 am-11:59 pm

2 stops10h 36m

San Juan Luis Munoz Marin Intl

jue. 2/5

6:00 am-4:52 pm

2 stops12h 52m

$301

MadisonBridgetown

MSN - BGI

MSNBGI

Madison Truax Field

dom. 1/25

12:38 pm-2:35 pm

2 stops23h 57m

Bridgetown Grantley Adams Intl

sáb. 2/7

4:10 pm-2:52 pm

2 stops24h 42m

$3,425

MadisonBridgetown

MSN - BGI

MSNBGI

Madison Truax Field

dom. 1/25

12:38 pm-2:35 pm

2 stops23h 57m

Bridgetown Grantley Adams Intl

sáb. 2/7

4:10 pm-2:52 pm

2 stops24h 42m

$3,580

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Madison to Caribbean

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Caribbean?

In general, September is the cheapest month to fly from Madison to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $310. If you don’t want to visit Caribbean in September, then you should wait until January to fly from Madison, when ticket prices are also cheap, with an average price of $409.

What is the cheapest day to depart on your flight to Caribbean?

The cheapest day to depart from Madison to Caribbean is on a Monday when prices can be found for as low as $494. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $609. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

What is the cheapest time of day to depart on your flight to Caribbean?

In the afternoon is the cheapest time of day to fly from Madison to Caribbean when you can find flight prices for as low as $370. Flying to Caribbean in the afternoon is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $701.

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

You are more likely to see cheaper flights to Caribbean from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $504 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Madison for as low as $365 on momondo.

Can stopping save me money on Madison to Caribbean flights?

You could potentially save up to 13% on your flight if you consider stops on a Madison to Caribbean flight.

Cheap Madison to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Caribbean

Direct flights	None

There are no direct flights from Madison to Caribbean. There are no popular flight routes from Madison to Caribbean.

Search flight deals

When did momondo last update prices for flights from Madison Truax Field Airport to Caribbean?
Prices for flights from Madison Truax Field Airport to Caribbean are updated daily.
How many operators does momondo search for flights from Madison Truax Field Airport to Caribbean?
The number of operators available for flights from Madison Truax Field Airport to Caribbean is 3 as of November 2025.
How old do you have to be to fly from Madison Truax Field Airport to Caribbean?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Madison Truax Field Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The necessary travel and health documents for your Caribbean trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Madison to Caribbean

Compare and see reviews for airlines that fly from Madison to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $225	Free Cancellation	Rating 7.9 8,001 reviews	Search Delta flights
United Airlines	PriceFrom $260	Free Cancellation	Rating 7.4 9,007 reviews	Search United Airlines flights
American Airlines	PriceFrom $269	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Caribbean?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Madison to Caribbean for you.

Can I find flights from Madison to Caribbean with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Madison to Caribbean flights to just show those with flexible booking policies.

How can momondo help me find flights from Madison to Caribbean?

momondo helps you find the best flight between Madison and Caribbean by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Madison to Caribbean right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Madison to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.