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

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

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.

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 April 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.

$152 Cheap Flights from Madison to Caribbean in 2026

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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.

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

5:45 am - 3:00 pm

MSN

STT

8h 15m

1 stop

4:10 pm - 10:35 pm

STT

MSN

7h 25m

1 stop

$487Delta

Sat, Aug 22 - Sat, Aug 29

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

Delta flights from Madison to Caribbean

Our best Delta deals on Madison to Caribbean 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

American Airlines flights from Madison to Caribbean

Our best American Airlines deals on Madison to Caribbean flight tickets

American Airlines

Oct 19

MSN8:25 pmMadison Truax Field

16h 20m

1 stop

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Oct 28

SJU8:35 amSan Juan Luis Munoz Marin Intl

11h 21m

2 stops

MSN6:56 pmMadison Truax Field

$326

American Airlines

Sep 6

MSN12:40 pmMadison Truax Field

10h 35m

2 stops

SJU12:15 amSan Juan Luis Munoz Marin Intl

Sep 16

SJU6:30 amSan Juan Luis Munoz Marin Intl

13h 19m

2 stops

MSN6:49 pmMadison Truax Field

$329

American Airlines

Jul 14

MSN5:52 pmMadison Truax Field

17h 55m

2 stops

MBJ11:47 amMontego Bay Sangster Intl

Jul 28

MBJ5:17 pmMontego Bay Sangster Intl

19h 17m

2 stops

MSN12:34 pmMadison Truax Field

$357

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

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

Quickest round-trip

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Sat 8/22

5:45 am-3:00 pm

1 stop8h 15m

Saint Thomas Island Cyril E King

Sat 8/29

4:10 pm-10:35 pm

1 stop7h 25m

$487

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

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 $313.

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 $505 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	6h 50m
Direct flights	None

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

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 April 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 8,430 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?

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.