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 52% 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?

American Airlines, United Airlines, and Delta 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 September 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.

$118 Cheap Flights from Madison to Caribbean in 2025

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Find the cheapest flights from Madison to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

11:43 am - 11:40 pmMSN-SJU

9h 57m1 stop

9:25 am - 7:02 pmSJU-MSN

11h 37m2 stops

$235American Airlines

Find Deal

Sat, Jan 31 - Thu, Feb 5

2:56 pm - 6:11 amMSN-SJU

13h 15m2 stops

8:35 am - 2:10 pmSJU-MSN

7h 35m1 stop

$255United Airlines

Find Deal

Sat, Jan 31 - Thu, Feb 5

10:38 am - 12:05 amMSN-SJU

11h 27m2 stops

9:25 am - 6:42 pmSJU-MSN

11h 17m2 stops

$275American Airlines

Find Deal

Sat, Jan 31 - Thu, Feb 5

4:19 pm - 11:45 amMSN-SJU

17h 26m1 stop

4:45 pm - 9:26 pmSJU-MSN

6h 41m1 stop

$295American Airlines

Find Deal

Sat, Feb 28 - Wed, Mar 4

11:43 am - 12:05 amMSN-SJU

10h 22m2 stops

2:45 pm - 11:42 pmSJU-MSN

10h 57m2 stops

$315American Airlines

Find Deal

Tue, Jan 20 - Wed, Jan 28

8:15 am - 10:22 pmMSN-SJU

12h 07m2 stops

8:35 am - 2:52 pmSJU-MSN

8h 17m1 stop

$325United Airlines

Find Deal

Tue, Jan 20 - Wed, Jan 28

5:30 am - 1:49 pmMSN-NAS

7h 19m1 stop

2:30 pm - 10:29 pmNAS-MSN

8h 59m2 stops

$469Delta

Find Deal

Sat, Oct 18 - Sat, Oct 25

7:00 am - 6:24 pmMSN-SDQ

10h 24m2 stops

7:49 pm - 11:25 amSDQ-MSN

16h 36m2 stops

$519Delta

Find Deal

Tue, Oct 7 - Tue, Oct 14

12:38 pm - 6:05 pmMSN-MBJ

28h 27m2 stops

2:40 pm - 2:52 pmMBJ-MSN

25h 12m2 stops

$962Air Canada

Find Deal

Tue, Jan 27 - Tue, Feb 3

2:55 pm - 3:35 pmMSN-STT

22h 40m2 stops

4:31 pm - 5:40 pmSTT-MSN

27h 09m3 stops

$1,233Sun Country Air

Find Deal

Fri, Dec 26 - Sat, Jan 10

United Airlines flights from Madison to Caribbean

Our best United Airlines deals on Madison to Caribbean flight tickets

United Airlines

Jan 31

MSN2:56 pmMadison Truax Field

13h 15m

2 stops

SJU6:11 amSan Juan Luis Munoz Marin Intl

Feb 5

SJU8:35 amSan Juan Luis Munoz Marin Intl

7h 35m

1 stop

MSN2:10 pmMadison Truax Field

$255

Find similar

United Airlines

Jan 20

MSN8:15 amMadison Truax Field

12h 07m

2 stops

SJU10:22 pmSan Juan Luis Munoz Marin Intl

Jan 28

SJU8:35 amSan Juan Luis Munoz Marin Intl

8h 17m

1 stop

MSN2:52 pmMadison Truax Field

$325

Find similar

United Airlines

Jan 20

MSN6:30 amMadison Truax Field

7h 10m

1 stop

SJU3:40 pmSan Juan Luis Munoz Marin Intl

Jan 28

SJU8:35 amSan Juan Luis Munoz Marin Intl

8h 17m

1 stop

MSN2:52 pmMadison Truax Field

$365

Find similar

American Airlines flights from Madison to Caribbean

Our best American Airlines deals on Madison to Caribbean flight tickets

American Airlines

Jan 31

MSN11:43 amMadison Truax Field

9h 57m

1 stop

SJU11:40 pmSan Juan Luis Munoz Marin Intl

Feb 5

SJU9:25 amSan Juan Luis Munoz Marin Intl

11h 37m

2 stops

MSN7:02 pmMadison Truax Field

$235

Find similar

American Airlines

Jan 31

MSN10:38 amMadison Truax Field

11h 27m

2 stops

SJU12:05 amSan Juan Luis Munoz Marin Intl

Feb 5

SJU9:25 amSan Juan Luis Munoz Marin Intl

11h 17m

2 stops

MSN6:42 pmMadison Truax Field

$275

Find similar

American Airlines

Feb 28

MSN4:19 pmMadison Truax Field

17h 26m

1 stop

SJU11:45 amSan Juan Luis Munoz Marin Intl

Mar 4

SJU4:45 pmSan Juan Luis Munoz Marin Intl

6h 41m

1 stop

MSN9:26 pmMadison Truax Field

$295

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 1/31

11:43 am-11:40 pm

1 stop9h 57m

San Juan Luis Munoz Marin Intl

Thu 2/5

9:25 am-7:02 pm

2 stops11h 37m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 1/31

2:56 pm-6:11 am

2 stops13h 15m

San Juan Luis Munoz Marin Intl

Thu 2/5

8:35 am-2:10 pm

1 stop7h 35m

$255

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 1/31

10:38 am-12:05 am

2 stops11h 27m

San Juan Luis Munoz Marin Intl

Thu 2/5

9:25 am-6:42 pm

2 stops11h 17m

$275

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 2/28

4:19 pm-11:45 am

1 stop17h 26m

San Juan Luis Munoz Marin Intl

Wed 3/4

4:45 pm-9:26 pm

1 stop6h 41m

$295

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

11:43 am-12:05 am

2 stops10h 22m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:45 pm-11:42 pm

2 stops10h 57m

$315

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

8:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

Wed 1/28

8:35 am-2:52 pm

1 stop8h 17m

$325

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Sat 10/18

5:30 am-1:49 pm

1 stop7h 19m

Nassau Intl

Sat 10/25

2:30 pm-10:29 pm

2 stops8h 59m

$469

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Tue 10/7

7:00 am-6:24 pm

2 stops10h 24m

Santo Domingo Las Americas

Tue 10/14

7:49 pm-11:25 am

2 stops16h 36m

$519

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 1/27

12:38 pm-6:05 pm

2 stops28h 27m

Montego Bay Sangster Intl

Tue 2/3

2:40 pm-2:52 pm

2 stops25h 12m

$962

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Fri 12/26

2:55 pm-3:35 pm

2 stops22h 40m

Saint Thomas Island Cyril E King

Sat 1/10

4:31 pm-5:40 pm

3 stops27h 09m

$1,233

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 $353. If you don’t want to visit Caribbean in September, then you should wait until November to fly from Madison, when ticket prices are also cheap, with an average price of $418.

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 $521 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 $335 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 September 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 $254	Free Cancellation	Rating 7.9 7,965 reviews	Search Delta flights
American Airlines	PriceFrom $270	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $293	Free Cancellation	Rating 7.4 8,943 reviews	Search United 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.