What airlines fly to Caribbean?

American Airlines, Delta and Southwest 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.

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

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

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 July 2026.

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.

$148 Cheap Flights from Madison to Caribbean in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Madison to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:32 am - 10:29 pm

MSN

SJU

11h 57m

2 stops

2:59 pm - 10:41 pm

SJU

MSN

8h 42m

1 stop

$286Delta

Sun, Sep 6 - Wed, Sep 16

6:15 am - 11:50 pm

MSN

SJU

15h 35m

2 stops

5:15 pm - 10:55 pm

SJU

MSN

7h 40m

1 stop

$286Delta

Sun, Jan 17 - Fri, Jan 22

6:15 am - 11:50 pm

MSN

SJU

15h 35m

2 stops

3:20 pm - 10:55 pm

SJU

MSN

9h 35m

1 stop

$286Delta

Sun, Jan 17 - Thu, Jan 21

6:49 am - 2:44 pm

MSN

SJU

6h 55m

1 stop

7:05 am - 5:51 pm

SJU

MSN

11h 46m

2 stops

$304United Airlines

Mon, Oct 19 - Wed, Oct 28

6:49 am - 2:44 pm

MSN

SJU

6h 55m

1 stop

3:55 pm - 10:53 pm

SJU

MSN

7h 58m

1 stop

$304United Airlines

Mon, Oct 19 - Wed, Oct 28

6:30 am - 2:44 pm

MSN

SJU

7h 14m

1 stop

1:00 am - 9:40 am

SJU

MSN

9h 40m

2 stops

$308United Airlines

Tue, Sep 8 - Thu, Sep 10

12:20 pm - 9:39 pm

MSN

SJU

7h 19m

1 stop

6:00 am - 10:46 pm

SJU

MSN

18h 46m

1 stop

$346American Airlines

Sat, Jan 23 - Sat, Jan 30

6:16 am - 3:18 pm

MSN

SJU

7h 02m

1 stop

6:00 am - 10:46 pm

SJU

MSN

18h 46m

1 stop

$346American Airlines

Sun, Jan 24 - Sat, Jan 30

6:50 pm - 12:41 am

MSN

SJU

52h 51m

2 stops

5:37 pm - 9:47 am

SJU

MSN

17h 10m

1 stop

$467Multiple Airlines

Fri, Aug 14 - Fri, Aug 21

7:55 pm - 7:57 am

MSN

SJU

11h 02m

1 stop

12:13 pm - 7:15 pm

SJU

MSN

8h 02m

1 stop

$482Multiple Airlines

Sat, Aug 8 - Sat, Aug 15

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United Airlines flights from Madison to Caribbean

Our best United Airlines deals on Madison to Caribbean flight tickets

United Airlines

Oct 19

MSN6:49 amMadison Truax Field

6h 55m

1 stop

SJU2:44 pmSan Juan Luis Munoz Marin Intl

Oct 28

SJU7:05 amSan Juan Luis Munoz Marin Intl

11h 46m

2 stops

MSN5:51 pmMadison Truax Field

$304

United Airlines

Sep 8

MSN6:30 amMadison Truax Field

7h 14m

1 stop

SJU2:44 pmSan Juan Luis Munoz Marin Intl

Sep 10

SJU1:00 amSan Juan Luis Munoz Marin Intl

9h 40m

2 stops

MSN9:40 amMadison Truax Field

$308

United Airlines

Aug 23

MSN6:30 amMadison Truax Field

7h 14m

1 stop

SJU2:44 pmSan Juan Luis Munoz Marin Intl

Sep 1

SJU1:25 pmSan Juan Luis Munoz Marin Intl

7h 50m

1 stop

MSN8:15 pmMadison Truax Field

$311

Delta flights from Madison to Caribbean

Our best Delta deals on Madison to Caribbean flight tickets

Delta

Sep 6

MSN9:32 amMadison Truax Field

11h 57m

2 stops

SJU10:29 pmSan Juan Luis Munoz Marin Intl

Sep 16

SJU2:59 pmSan Juan Luis Munoz Marin Intl

8h 42m

1 stop

MSN10:41 pmMadison Truax Field

$286

Delta

Jan 17

MSN6:15 amMadison Truax Field

15h 35m

2 stops

SJU11:50 pmSan Juan Luis Munoz Marin Intl

Feb 9

SJU6:15 amSan Juan Luis Munoz Marin Intl

12h 22m

2 stops

MSN4:37 pmMadison Truax Field

$296

Delta

Jan 20

MSN6:15 amMadison Truax Field

15h 35m

2 stops

SJU11:50 pmSan Juan Luis Munoz Marin Intl

Feb 2

SJU7:00 amSan Juan Luis Munoz Marin Intl

15h 45m

2 stops

MSN8:45 pmMadison Truax Field

$391

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/6

9:32 am-10:29 pm

2 stops11h 57m

San Juan Luis Munoz Marin Intl

Wed 9/16

2:59 pm-10:41 pm

1 stop8h 42m

$286

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 1/17

6:15 am-11:50 pm

2 stops15h 35m

San Juan Luis Munoz Marin Intl

Fri 1/22

5:15 pm-10:55 pm

1 stop7h 40m

$286

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 1/17

6:15 am-11:50 pm

2 stops15h 35m

San Juan Luis Munoz Marin Intl

Thu 1/21

3:20 pm-10:55 pm

1 stop9h 35m

$286

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 10/19

6:49 am-2:44 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Wed 10/28

7:05 am-5:51 pm

2 stops11h 46m

$304

Quickest round-trip

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 10/19

6:49 am-2:44 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Wed 10/28

3:55 pm-10:53 pm

1 stop7h 58m

$304

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 9/8

6:30 am-2:44 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Thu 9/10

1:00 am-9:40 am

2 stops9h 40m

$308

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 1/23

12:20 pm-9:39 pm

1 stop7h 19m

San Juan Luis Munoz Marin Intl

Sat 1/30

6:00 am-10:46 pm

1 stop18h 46m

$346

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 1/24

6:16 am-3:18 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Sat 1/30

6:00 am-10:46 pm

1 stop18h 46m

$346

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Fri 8/14

6:50 pm-12:41 am

2 stops52h 51m

San Juan Luis Munoz Marin Intl

Fri 8/21

5:37 pm-9:47 am

1 stop17h 10m

$467

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 8/8

7:55 pm-7:57 am

1 stop11h 02m

San Juan Luis Munoz Marin Intl

Sat 8/15

12:13 pm-7:15 pm

1 stop8h 02m

$482

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, August 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 $422. If you don’t want to visit Caribbean in August, then you should wait until May to fly from Madison, when ticket prices are also cheap, with an average price of $499.

How far in advance should I book a flight from Madison 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 $517 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 $308 on momondo.

Can stopping save me money on Madison to Caribbean flights?

You could potentially save up to 14% 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

Fastest flight time	5h 47m
Direct flights	None

The fastest flight from Madison to Caribbean takes 5h 47m

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

Search flight deals

Frequently asked questions about flying from Madison to Caribbean

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 July 2026.
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
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 10,046 reviews	Search United Airlines flights
Delta	PriceFrom $246	Free Cancellation	Rating 7.8 8,482 reviews	Search Delta flights
American Airlines	PriceFrom $295	Free Cancellation	Rating 7.1 11,839 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.