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.

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

Delta, American Airlines, and United 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 February 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.

$133 Cheap Flights from Madison to Caribbean in 2026

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Find the cheapest flights from Madison to Caribbean

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:24 pm - 12:13 pm

MSN

MBJ

15h 49m

1 stop

2:23 pm - 7:45 am

MBJ

MSN

17h 22m

1 stop

$317American Airlines

Thu, May 14 - Thu, May 21

8:40 pm - 1:30 pm

MSN

MBJ

16h 50m

2 stops

12:52 pm - 8:55 am

MBJ

MSN

20h 03m

2 stops

$322United Airlines

Thu, May 14 - Fri, May 22

8:24 pm - 12:13 pm

MSN

MBJ

15h 49m

1 stop

4:37 pm - 10:55 am

MBJ

MSN

18h 18m

2 stops

$326American Airlines

Fri, Apr 10 - Fri, Apr 17

4:12 pm - 9:13 am

MSN

MBJ

17h 01m

2 stops

4:37 pm - 10:55 am

MBJ

MSN

18h 18m

2 stops

$327American Airlines

Wed, May 6 - Sat, May 9

6:30 am - 12:46 pm

MSN

MBJ

6h 16m

1 stop

4:12 pm - 10:07 am

MBJ

MSN

17h 55m

2 stops

$329United Airlines

Tue, Mar 24 - Tue, Mar 31

5:08 pm - 11:51 am

MSN

MBJ

18h 43m

2 stops

12:25 pm - 10:55 am

MBJ

MSN

22h 30m

1 stop

$332American Airlines

Wed, Apr 15 - Wed, Apr 22

3:29 pm - 10:53 am

MSN

SJU

18h 24m

2 stops

3:19 pm - 11:28 pm

SJU

MSN

9h 09m

1 stop

$333American Airlines

Tue, Apr 14 - Wed, Apr 15

6:00 am - 2:15 pm

MSN

SJU

7h 15m

1 stop

7:15 am - 9:15 pm

SJU

MSN

15h 00m

2 stops

$346Delta

Tue, Apr 7 - Wed, Apr 15

5:45 am - 11:48 am

MSN

NAS

5h 03m

1 stop

1:13 pm - 10:35 pm

NAS

MSN

10h 22m

1 stop

$556Delta

Mon, Aug 24 - Fri, Aug 28

5:30 am - 2:26 pm

MSN

SDQ

7h 56m

1 stop

2:37 pm - 10:34 pm

SDQ

MSN

8h 57m

1 stop

$730JetBlue

Sat, Mar 28 - Sat, Apr 4

Delta flights from Madison to Caribbean

Our best Delta deals on Madison to Caribbean flight tickets

Delta

Apr 7

MSN6:00 amMadison Truax Field

7h 15m

1 stop

SJU2:15 pmSan Juan Luis Munoz Marin Intl

Apr 15

SJU7:15 amSan Juan Luis Munoz Marin Intl

15h 00m

2 stops

MSN9:15 pmMadison Truax Field

$346

Delta

Mar 4

MSN5:38 amMadison Truax Field

8h 44m

1 stop

STT4:22 pmSaint Thomas Island Cyril E King

Mar 11

STT3:00 pmSaint Thomas Island Cyril E King

8h 34m

1 stop

MSN10:34 pmMadison Truax Field

$425

Delta

Apr 1

MSN7:00 amMadison Truax Field

12h 18m

2 stops

SJU8:18 pmSan Juan Luis Munoz Marin Intl

Apr 9

SJU6:15 amSan Juan Luis Munoz Marin Intl

12h 32m

2 stops

MSN5:47 pmMadison Truax Field

$426

United Airlines flights from Madison to Caribbean

Our best United Airlines deals on Madison to Caribbean flight tickets

United Airlines

May 14

MSN8:40 pmMadison Truax Field

16h 50m

2 stops

MBJ1:30 pmMontego Bay Sangster Intl

May 22

MBJ12:52 pmMontego Bay Sangster Intl

20h 03m

2 stops

MSN8:55 amMadison Truax Field

$322

United Airlines

Mar 24

MSN6:30 amMadison Truax Field

6h 16m

1 stop

MBJ12:46 pmMontego Bay Sangster Intl

Mar 31

MBJ4:12 pmMontego Bay Sangster Intl

17h 55m

2 stops

MSN10:07 amMadison Truax Field

$329

United Airlines

Apr 15

MSN10:05 amMadison Truax Field

9h 29m

1 stop

SJU8:34 pmSan Juan Luis Munoz Marin Intl

Apr 27

SJU1:00 amSan Juan Luis Munoz Marin Intl

10h 11m

2 stops

MSN10:11 amMadison Truax Field

$345

Fly from

Fly to

Route

Depart

Return

Price

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:24 pm-12:13 pm

1 stop15h 49m

Montego Bay Sangster Intl

Thu 5/21

2:23 pm-7:45 am

1 stop17h 22m

$317

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:40 pm-1:30 pm

2 stops16h 50m

Montego Bay Sangster Intl

Fri 5/22

12:52 pm-8:55 am

2 stops20h 03m

$322

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 4/10

8:24 pm-12:13 pm

1 stop15h 49m

Montego Bay Sangster Intl

Fri 4/17

4:37 pm-10:55 am

2 stops18h 18m

$326

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 5/6

4:12 pm-9:13 am

2 stops17h 01m

Montego Bay Sangster Intl

Sat 5/9

4:37 pm-10:55 am

2 stops18h 18m

$327

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 3/24

6:30 am-12:46 pm

1 stop6h 16m

Montego Bay Sangster Intl

Tue 3/31

4:12 pm-10:07 am

2 stops17h 55m

$329

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 4/15

5:08 pm-11:51 am

2 stops18h 43m

Montego Bay Sangster Intl

Wed 4/22

12:25 pm-10:55 am

1 stop22h 30m

$332

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 4/14

3:29 pm-10:53 am

2 stops18h 24m

San Juan Luis Munoz Marin Intl

Wed 4/15

3:19 pm-11:28 pm

1 stop9h 09m

$333

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 4/7

6:00 am-2:15 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Wed 4/15

7:15 am-9:15 pm

2 stops15h 00m

$346

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Mon 8/24

5:45 am-11:48 am

1 stop5h 03m

Nassau Intl

Fri 8/28

1:13 pm-10:35 pm

1 stop10h 22m

$556

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Sat 3/28

5:30 am-2:26 pm

1 stop7h 56m

Santo Domingo Las Americas

Sat 4/4

2:37 pm-10:34 pm

1 stop8h 57m

$730

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 October to fly from Madison, when ticket prices are also cheap, with an average price of $394.

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 $507 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 $403 on momondo.

Can stopping save me money on Madison to Caribbean flights?

You could potentially save up to 20% 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 03m
Direct flights	None

The fastest flight from Madison to Caribbean takes 5h 03m

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 February 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 $257	Free Cancellation	Rating 7.4 9,351 reviews	Search United Airlines flights
American Airlines	PriceFrom $268	Free Cancellation	Rating 7.2 11,357 reviews	Search American Airlines flights
Delta	PriceFrom $275	Free Cancellation	Rating 7.9 8,242 reviews	Search Delta 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.