What airlines fly to Caribbean Islands?

American Airlines, Delta and United Airlines are the top three most popular airlines that fly to Caribbean Islands 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 Islands. Keep in mind that there are 7 different airlines that fly to Caribbean Islands 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 Islands?

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

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

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

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

The number of operators available for flights from Madison Truax Field Airport to Caribbean Islands is 3 as of April 2026.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Caribbean Islands.

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

The necessary travel and health documents for your Caribbean Islands 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.

$152 Cheap Flights from Madison to Caribbean Islands in 2026

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Find the cheapest flights from Madison to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:45 am - 4:35 pm

MSN

SJU

9h 50m

1 stop

7:00 am - 8:40 pm

SJU

MSN

14h 40m

2 stops

$317Delta

Sun, Sep 6 - Wed, Sep 16

8:25 pm - 1:45 pm

MSN

SJU

16h 20m

1 stop

8:30 am - 6:56 pm

SJU

MSN

11h 26m

2 stops

$326American Airlines

Mon, Oct 19 - Wed, Oct 28

12:40 pm - 12:15 am

MSN

SJU

10h 35m

2 stops

6:30 am - 6:49 pm

SJU

MSN

13h 19m

2 stops

$329American Airlines

Sun, Sep 6 - Wed, Sep 16

5:52 pm - 11:47 am

MSN

MBJ

17h 55m

2 stops

5:17 pm - 12:34 pm

MBJ

MSN

19h 17m

2 stops

$357American Airlines

Tue, Jul 14 - Tue, Jul 28

6:45 am - 8:55 pm

MSN

SJU

13h 10m

1 stop

12:44 am - 10:38 am

SJU

MSN

10h 54m

1 stop

$366American Airlines

Sat, May 16 - Fri, May 22

10:27 am - 12:23 am

MSN

SJU

12h 56m

1 stop

8:00 am - 8:25 am

SJU

MSN

25h 25m

1 stop

$368Multiple Airlines

Sat, Aug 22 - Sun, Aug 30

6:02 am - 11:01 pm

MSN

SJU

15h 59m

1 stop

12:59 am - 7:49 am

SJU

MSN

7h 50m

1 stop

$371American Airlines

Wed, May 27 - Mon, Jun 1

6:30 am - 3:10 pm

MSN

MBJ

8h 40m

2 stops

4:33 pm - 2:57 pm

MBJ

MSN

22h 24m

2 stops

$583United Airlines

Wed, May 27 - Sat, May 30

6:00 am - 3:20 pm

MSN

AUA

8h 20m

1 stop

3:10 pm - 8:06 am

AUA

MSN

17h 56m

2 stops

$666United Airlines

Tue, May 19 - Tue, May 26

1:31 pm - 2:12 pm

MSN

UVF

23h 41m

2 stops

3:28 pm - 12:54 pm

UVF

MSN

22h 26m

2 stops

$727Delta

Mon, Aug 3 - Thu, Aug 13

Delta flights from Madison to Caribbean Islands

Our best Delta deals on Madison to Caribbean Islands flight tickets

Delta

Sep 6

MSN5:45 amMadison Truax Field

9h 50m

1 stop

SJU4:35 pmSan Juan Luis Munoz Marin Intl

Sep 16

SJU7:00 amSan Juan Luis Munoz Marin Intl

14h 40m

2 stops

MSN8:40 pmMadison Truax Field

$317

Delta

May 3

MSN5:30 amMadison Truax Field

9h 53m

1 stop

SJU4:23 pmSan Juan Luis Munoz Marin Intl

May 7

SJU6:15 amSan Juan Luis Munoz Marin Intl

11h 10m

1 stop

MSN4:25 pmMadison Truax Field

$326

Delta

Apr 24

MSN6:22 pmMadison Truax Field

17h 11m

1 stop

MBJ11:33 amMontego Bay Sangster Intl

May 15

MBJ1:18 pmMontego Bay Sangster Intl

9h 26m

1 stop

MSN10:44 pmMadison Truax Field

$429

United Airlines flights from Madison to Caribbean Islands

Our best United Airlines deals on Madison to Caribbean Islands flight tickets

United Airlines

May 5

MSN9:55 amMadison Truax Field

9h 39m

1 stop

SJU8:34 pmSan Juan Luis Munoz Marin Intl

May 9

SJU7:40 amSan Juan Luis Munoz Marin Intl

8h 22m

1 stop

MSN3:02 pmMadison Truax Field

$416

United Airlines

Sep 26

MSN6:45 amMadison Truax Field

6h 59m

1 stop

SJU2:44 pmSan Juan Luis Munoz Marin Intl

Sep 30

SJU3:56 pmSan Juan Luis Munoz Marin Intl

7h 54m

1 stop

MSN10:50 pmMadison Truax Field

$432

United Airlines

Apr 23

MSN5:00 amMadison Truax Field

10h 10m

2 stops

MBJ3:10 pmMontego Bay Sangster Intl

Apr 25

MBJ1:52 pmMontego Bay Sangster Intl

9h 01m

1 stop

MSN10:53 pmMadison Truax Field

$496

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/6

5:45 am-4:35 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Wed 9/16

7:00 am-8:40 pm

2 stops14h 40m

$317

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 10/19

8:25 pm-1:45 pm

1 stop16h 20m

San Juan Luis Munoz Marin Intl

Wed 10/28

8:30 am-6:56 pm

2 stops11h 26m

$326

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/6

12:40 pm-12:15 am

2 stops10h 35m

San Juan Luis Munoz Marin Intl

Wed 9/16

6:30 am-6:49 pm

2 stops13h 19m

$329

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 7/14

5:52 pm-11:47 am

2 stops17h 55m

Montego Bay Sangster Intl

Tue 7/28

5:17 pm-12:34 pm

2 stops19h 17m

$357

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 5/16

6:45 am-8:55 pm

1 stop13h 10m

San Juan Luis Munoz Marin Intl

Fri 5/22

12:44 am-10:38 am

1 stop10h 54m

$366

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 8/22

10:27 am-12:23 am

1 stop12h 56m

San Juan Luis Munoz Marin Intl

Sun 8/30

8:00 am-8:25 am

1 stop25h 25m

$368

Quickest round-trip

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 5/27

6:02 am-11:01 pm

1 stop15h 59m

San Juan Luis Munoz Marin Intl

Mon 6/1

12:59 am-7:49 am

1 stop7h 50m

$371

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 5/27

6:30 am-3:10 pm

2 stops8h 40m

Montego Bay Sangster Intl

Sat 5/30

4:33 pm-2:57 pm

2 stops22h 24m

$583

MadisonOranjestad

MSN - AUA

MSNAUA

Madison Truax Field

Tue 5/19

6:00 am-3:20 pm

1 stop8h 20m

Oranjestad Reina Beatrix

Tue 5/26

3:10 pm-8:06 am

2 stops17h 56m

$666

MadisonCastries

MSN - UVF

MSNUVF

Madison Truax Field

Mon 8/3

1:31 pm-2:12 pm

2 stops23h 41m

Castries Hewanorra

Thu 8/13

3:28 pm-12:54 pm

2 stops22h 26m

$727

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 Islands

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 Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Madison, with most prices found around $310. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Madison averaging around $313.

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

You are more likely to see cheaper flights to Caribbean Islands from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $505 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Madison for as low as $252 on momondo.

Can stopping save me money on Madison to Caribbean Islands flights?

You could potentially save up to 10% on your flight if you consider stops on a Madison to Caribbean Islands flight.

Cheap Madison to Caribbean Islands flight deals and tips

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

Fastest flight time	6h 50m
Direct flights	None

The fastest flight from Madison to Caribbean Islands takes 6h 50m

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

Search flight deals

Frequently asked questions about flying from Madison to Caribbean Islands

When did momondo last update prices for flights from Madison Truax Field Airport to Caribbean Islands?
Prices for flights from Madison Truax Field Airport to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Madison Truax Field Airport to Caribbean Islands?
The number of operators available for flights from Madison Truax Field Airport to Caribbean Islands is 3 as of April 2026.
How old do you have to be to fly from Madison Truax Field Airport to Caribbean Islands?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The necessary travel and health documents for your Caribbean Islands 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.
What is the most popular plane model from Madison to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Madison to Caribbean Islands is Boeing 737-800, representing 15.19% of all bookings. The subsequent popular models are Embraer 175 at 10.00%, Airbus A319 at 9.36%, and Airbus A320-100/200 at 9.09%.

Best airlines flying from Madison to Caribbean Islands

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $225	Free Cancellation	Rating 7.9 8,430 reviews	Search Delta flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 9,625 reviews	Search United Airlines flights
American Airlines	PriceFrom $268	Free Cancellation	Rating 7.1 11,647 reviews	Search American Airlines flights

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Madison to Caribbean Islands. momondo saves you time and could save you money on your trip.

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

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

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

Once all potential Madison to Caribbean Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Price alerts on flights to Caribbean Islands from Madison are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.