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

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 52% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 6 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 June 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.

$128 Cheap Flights from Madison to Caribbean in 2026

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

6:49 am - 8:38 pm

MSN

SJU

12h 49m

2 stops

3:56 pm - 10:35 pm

SJU

MSN

7h 39m

1 stop

$279United Airlines

Tue, Oct 20 - Fri, Oct 23

6:30 am - 2:44 pm

MSN

SJU

7h 14m

1 stop

1:00 am - 1:37 pm

SJU

MSN

13h 37m

2 stops

$317United Airlines

Sun, Sep 20 - Wed, Sep 23

6:01 am - 4:57 pm

MSN

SJU

9h 56m

2 stops

6:00 am - 3:24 pm

SJU

MSN

10h 24m

2 stops

$326American Airlines

Sat, Aug 22 - Tue, Aug 25

6:53 pm - 11:42 am

MSN

MBJ

16h 49m

2 stops

5:16 pm - 12:26 pm

MBJ

MSN

19h 10m

2 stops

$357American Airlines

Sat, Sep 5 - Sat, Sep 12

5:43 am - 4:38 pm

MSN

SJU

9h 55m

1 stop

2:26 pm - 10:39 pm

SJU

MSN

9h 13m

1 stop

$378Delta

Sun, Sep 6 - Wed, Sep 16

5:52 am - 4:46 pm

MSN

SJU

9h 54m

1 stop

2:42 pm - 10:38 pm

SJU

MSN

8h 56m

1 stop

$381JetBlue

Mon, Jun 29 - Fri, Jul 10

5:43 am - 4:38 pm

MSN

SJU

9h 55m

1 stop

2:26 pm - 10:39 pm

SJU

MSN

9h 13m

1 stop

$388Delta

Sun, Sep 6 - Wed, Sep 16

5:52 am - 1:16 pm

MSN

SDQ

6h 24m

1 stop

2:41 pm - 10:43 pm

SDQ

MSN

9h 02m

1 stop

$736JetBlue

Sun, Jun 28 - Mon, Jul 6

3:09 pm - 2:35 pm

MSN

BGI

21h 26m

2 stops

4:10 pm - 9:39 pm

BGI

MSN

31h 29m

2 stops

$1,818Air Canada

Sun, Nov 8 - Thu, Nov 12

3:09 pm - 2:35 pm

MSN

BGI

21h 26m

2 stops

4:10 pm - 9:39 pm

BGI

MSN

31h 29m

2 stops

$1,890Air Canada

Sun, Nov 8 - Thu, Nov 12

United Airlines flights from Madison to Caribbean

Our best United Airlines deals on Madison to Caribbean flight tickets

United Airlines

Oct 20

MSN6:49 amMadison Truax Field

12h 49m

2 stops

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Oct 23

SJU3:56 pmSan Juan Luis Munoz Marin Intl

7h 39m

1 stop

MSN10:35 pmMadison Truax Field

$279

United Airlines

Sep 20

MSN6:30 amMadison Truax Field

7h 14m

1 stop

SJU2:44 pmSan Juan Luis Munoz Marin Intl

Sep 23

SJU1:00 amSan Juan Luis Munoz Marin Intl

13h 37m

2 stops

MSN1:37 pmMadison Truax Field

$317

United Airlines

Sep 22

MSN6:30 amMadison Truax Field

13h 08m

2 stops

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Sep 26

SJU3:56 pmSan Juan Luis Munoz Marin Intl

7h 39m

1 stop

MSN10:35 pmMadison Truax Field

$371

Delta flights from Madison to Caribbean

Our best Delta deals on Madison to Caribbean flight tickets

Delta

Sep 6

MSN5:43 amMadison Truax Field

9h 55m

1 stop

SJU4:38 pmSan Juan Luis Munoz Marin Intl

Sep 16

SJU2:26 pmSan Juan Luis Munoz Marin Intl

9h 13m

1 stop

MSN10:39 pmMadison Truax Field

$378

Delta

Sep 6

MSN5:43 amMadison Truax Field

9h 55m

1 stop

SJU4:38 pmSan Juan Luis Munoz Marin Intl

Sep 16

SJU2:26 pmSan Juan Luis Munoz Marin Intl

9h 13m

1 stop

MSN10:39 pmMadison Truax Field

$388

Delta

Sep 25

MSN11:33 amMadison Truax Field

9h 27m

1 stop

SJU10:00 pmSan Juan Luis Munoz Marin Intl

Oct 3

SJU12:58 pmSan Juan Luis Munoz Marin Intl

10h 41m

1 stop

MSN10:39 pmMadison Truax Field

$428

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 10/20

6:49 am-8:38 pm

2 stops12h 49m

San Juan Luis Munoz Marin Intl

Fri 10/23

3:56 pm-10:35 pm

1 stop7h 39m

$279

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/20

6:30 am-2:44 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Wed 9/23

1:00 am-1:37 pm

2 stops13h 37m

$317

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 8/22

6:01 am-4:57 pm

2 stops9h 56m

San Juan Luis Munoz Marin Intl

Tue 8/25

6:00 am-3:24 pm

2 stops10h 24m

$326

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sat 9/5

6:53 pm-11:42 am

2 stops16h 49m

Montego Bay Sangster Intl

Sat 9/12

5:16 pm-12:26 pm

2 stops19h 10m

$357

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/6

5:43 am-4:38 pm

1 stop9h 55m

San Juan Luis Munoz Marin Intl

Wed 9/16

2:26 pm-10:39 pm

1 stop9h 13m

$378

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 6/29

5:52 am-4:46 pm

1 stop9h 54m

San Juan Luis Munoz Marin Intl

Fri 7/10

2:42 pm-10:38 pm

1 stop8h 56m

$381

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/6

5:43 am-4:38 pm

1 stop9h 55m

San Juan Luis Munoz Marin Intl

Wed 9/16

2:26 pm-10:39 pm

1 stop9h 13m

$388

Quickest round-trip

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Sun 6/28

5:52 am-1:16 pm

1 stop6h 24m

Santo Domingo Las Americas

Mon 7/6

2:41 pm-10:43 pm

1 stop9h 02m

$736

MadisonBridgetown

MSN - BGI

MSNBGI

Madison Truax Field

Sun 11/8

3:09 pm-2:35 pm

2 stops21h 26m

Bridgetown Grantley Adams Intl

Thu 11/12

4:10 pm-9:39 pm

2 stops31h 29m

$1,818

MadisonBridgetown

MSN - BGI

MSNBGI

Madison Truax Field

Sun 11/8

3:09 pm-2:35 pm

2 stops21h 26m

Bridgetown Grantley Adams Intl

Thu 11/12

4:10 pm-9:39 pm

2 stops31h 29m

$1,890

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, March 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 $163. If you don’t want to visit Caribbean in March, then you should wait until February to fly from Madison, when ticket prices are also cheap, with an average price of $213.

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 $511 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 $252 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 June 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
Delta	PriceFrom $225	Free Cancellation	Rating 7.9 8,396 reviews	Search Delta flights
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 9,777 reviews	Search United Airlines flights
American Airlines	PriceFrom $268	Free Cancellation	Rating 7.1 11,649 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.