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

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 48% 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 November 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.

$213 Cheap Flights from Madison to Caribbean in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Madison to Caribbean

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One-way

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Cheap round-trip flights

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6:15 am - 8:20 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 05m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

6:15 am - 7:05 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

13h 50m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul

$416Delta

Sun, Apr 18 - Tue, Apr 27

11:26 am - 11:58 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

10h 32m1 stop Atlanta Hartsfield-Jackson

7:45 am - 4:32 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 47m1 stop Atlanta Hartsfield-Jackson

$416Delta

Tue, Jan 19 - Wed, Jan 27

8:15 am - 9:24 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

11h 09m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

8:05 am - 4:46 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 41m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

$416United Airlines

Sun, Jan 31 - Tue, Feb 9

6:06 am - 3:40 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

7h 34m1 stop Chicago O'Hare Intl

7:40 am - 7:48 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

14h 08m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

$416United Airlines

Sun, Jan 31 - Tue, Feb 9

5:45 am - 1:25 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

6h 40m1 stop Atlanta Hartsfield-Jackson

1:00 pm - 10:34 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 34m1 stop Atlanta Hartsfield-Jackson

$416Delta

Wed, Apr 21 - Tue, Apr 27

8:15 am - 10:22 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

12h 07m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

2:52 pm - 9:38 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

8h 46m1 stop Newark

$416United Airlines

Wed, Feb 3 - Tue, Feb 9

6:01 am - 9:28 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 27m2 stops Washington, D.C. Reagan-National Charlotte Douglas

1:20 am - 5:07 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

17h 47m1 stop Dallas/Fort Worth

$426American Airlines

Tue, Feb 23 - Fri, Feb 26

10:25 am - 11:39 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

11h 14m1 stop Chicago O'Hare Intl

3:41 pm - 12:14 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 33m1 stop Chicago O'Hare Intl

$426American Airlines

Sun, Jan 10 - Thu, Jan 14

10:38 am - 2:43 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

26h 05m2 stops Tampa Atlanta Hartsfield-Jackson

10:53 pm - 5:20 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

20h 27m1 stop Orlando

$460Multiple Airlines

Sat, Feb 6 - Wed, Feb 17

10:38 am - 12:29 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

11h 51m1 stop Tampa

3:16 am - 9:58 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

32h 42m2 stops Philadelphia Tampa

$480Multiple Airlines

Wed, Jan 20 - Mon, Jan 25

Cheap last minute flights

Enter your travel dates to find the best prices.

7:00 pm - 12:48 pmMSN Madison Truax Field-MBJ Montego Bay Sangster Intl

16h 48m2 stops Chicago O'Hare Intl Newark

5:21 pm - 10:00 amMBJ Montego Bay Sangster Intl-MSN Madison Truax Field

17h 39m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

$562United Airlines

Fri, Nov 6 - Sat, Nov 14

6:38 pm - 12:02 pmMSN Madison Truax Field-MBJ Montego Bay Sangster Intl

16h 24m1 stop Charlotte Douglas

6:09 pm - 10:46 amMBJ Montego Bay Sangster Intl-MSN Madison Truax Field

17h 37m2 stops Miami Chicago O'Hare Intl

$571American Airlines

Fri, Nov 6 - Sat, Nov 14

8:41 pm - 1:38 pmMSN Madison Truax Field-STT Saint Thomas Island Cyril E King

14h 57m2 stops Chicago O'Hare Intl Charlotte Douglas

1:07 pm - 10:27 pmSTT Saint Thomas Island Cyril E King-MSN Madison Truax Field

11h 20m2 stops Miami Washington, D.C. Reagan-National

$575American Airlines

Thu, Nov 5 - Thu, Nov 12

6:38 pm - 12:16 pmMSN Madison Truax Field-STT Saint Thomas Island Cyril E King

15h 38m2 stops Charlotte Douglas Miami

4:33 pm - 11:59 pmSTT Saint Thomas Island Cyril E King-MSN Madison Truax Field

9h 26m1 stop Charlotte Douglas

$575American Airlines

Thu, Nov 5 - Thu, Nov 12

5:00 am - 2:31 pmMSN Madison Truax Field-STT Saint Thomas Island Cyril E King

7h 31m1 stop Chicago O'Hare Intl

3:00 pm - 9:05 pmSTT Saint Thomas Island Cyril E King-MSN Madison Truax Field

8h 05m1 stop Chicago O'Hare Intl

$674United Airlines

Sat, Nov 7 - Sun, Nov 22

5:00 am - 2:31 pmMSN Madison Truax Field-STT Saint Thomas Island Cyril E King

7h 31m1 stop Chicago O'Hare Intl

3:00 pm - 11:07 pmSTT Saint Thomas Island Cyril E King-MSN Madison Truax Field

10h 07m1 stop Chicago O'Hare Intl

$674United Airlines

Sun, Nov 8 - Sat, Nov 21

5:00 am - 2:31 pmMSN Madison Truax Field-STT Saint Thomas Island Cyril E King

7h 31m1 stop Chicago O'Hare Intl

3:00 pm - 11:07 pmSTT Saint Thomas Island Cyril E King-MSN Madison Truax Field

10h 07m1 stop Chicago O'Hare Intl

$674United Airlines

Sat, Nov 7 - Sat, Nov 21

5:51 am - 2:37 pmMSN Madison Truax Field-STT Saint Thomas Island Cyril E King

6h 46m1 stop Atlanta Hartsfield-Jackson

3:53 pm - 10:50 pmSTT Saint Thomas Island Cyril E King-MSN Madison Truax Field

8h 57m1 stop Atlanta Hartsfield-Jackson

$679Delta

Tue, Nov 3 - Wed, Nov 11

5:51 am - 2:37 pmMSN Madison Truax Field-STT Saint Thomas Island Cyril E King

6h 46m1 stop Atlanta Hartsfield-Jackson

3:53 pm - 10:50 pmSTT Saint Thomas Island Cyril E King-MSN Madison Truax Field

8h 57m1 stop Atlanta Hartsfield-Jackson

$704Delta

Tue, Nov 3 - Wed, Nov 11

5:51 am - 2:37 pmMSN Madison Truax Field-STT Saint Thomas Island Cyril E King

6h 46m1 stop Atlanta Hartsfield-Jackson

3:53 pm - 10:50 pmSTT Saint Thomas Island Cyril E King-MSN Madison Truax Field

8h 57m1 stop Atlanta Hartsfield-Jackson

$842Delta

Tue, Nov 3 - Wed, Nov 11

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Delta flights from Madison to Caribbean

Our best Delta deals on Madison to Caribbean flight tickets

Delta

Dec 7

MSN5:30 amMadison Truax Field

10h 08m

1 stop

SJU5:38 pmSan Juan Luis Munoz Marin Intl

Dec 15

SJU7:00 amSan Juan Luis Munoz Marin Intl

16h 24m

2 stops

MSN9:24 pmMadison Truax Field

$418

Delta

Apr 17

MSN9:26 amMadison Truax Field

9h 54m

2 stops

SJU8:20 pmSan Juan Luis Munoz Marin Intl

Apr 27

SJU6:15 amSan Juan Luis Munoz Marin Intl

13h 50m

2 stops

MSN7:05 pmMadison Truax Field

$421

Delta

Jan 31

MSN7:00 amMadison Truax Field

11h 56m

2 stops

SJU8:56 pmSan Juan Luis Munoz Marin Intl

Feb 9

SJU7:45 amSan Juan Luis Munoz Marin Intl

11h 56m

2 stops

MSN5:41 pmMadison Truax Field

$436

United Airlines flights from Madison to Caribbean

Our best United Airlines deals on Madison to Caribbean flight tickets

United Airlines

Jan 31

MSN6:25 amMadison Truax Field

7h 15m

1 stop

SJU3:40 pmSan Juan Luis Munoz Marin Intl

Feb 9

SJU2:52 pmSan Juan Luis Munoz Marin Intl

8h 46m

1 stop

MSN9:38 pmMadison Truax Field

$416

United Airlines

Dec 2

MSN8:15 amMadison Truax Field

12h 07m

2 stops

SJU10:22 pmSan Juan Luis Munoz Marin Intl

Dec 8

SJU8:25 amSan Juan Luis Munoz Marin Intl

8h 25m

1 stop

MSN2:50 pmMadison Truax Field

$430

United Airlines

Jan 19

MSN10:45 amMadison Truax Field

9h 37m

2 stops

SJU10:22 pmSan Juan Luis Munoz Marin Intl

Jan 26

SJU8:05 amSan Juan Luis Munoz Marin Intl

11h 26m

2 stops

MSN5:31 pmMadison Truax Field

$432

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonSan Juan

MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl

MSNSJU

Madison Truax Field

Sun 4/18

6:15 am-8:20 pm

2 stops13h 05m

San Juan Luis Munoz Marin Intl

Tue 4/27

6:15 am-7:05 pm

2 stops13h 50m

$416

MadisonSan Juan

MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl

MSNSJU

Madison Truax Field

Tue 1/19

11:26 am-11:58 pm

1 stop10h 32m

San Juan Luis Munoz Marin Intl

Wed 1/27

7:45 am-4:32 pm

1 stop10h 47m

$416

MadisonSan Juan

MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl

MSNSJU

Madison Truax Field

Sun 1/31

8:15 am-9:24 pm

2 stops11h 09m

San Juan Luis Munoz Marin Intl

Tue 2/9

8:05 am-4:46 pm

2 stops10h 41m

$416

MadisonSan Juan

MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl

MSNSJU

Madison Truax Field

Sun 1/31

6:06 am-3:40 pm

1 stop7h 34m

San Juan Luis Munoz Marin Intl

Tue 2/9

7:40 am-7:48 pm

2 stops14h 08m

$416

Quickest round-trip

MadisonSan Juan

MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl

MSNSJU

Madison Truax Field

Wed 4/21

5:45 am-1:25 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Tue 4/27

1:00 pm-10:34 pm

1 stop10h 34m

$416

MadisonSan Juan

MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl

MSNSJU

Madison Truax Field

Wed 2/3

8:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

Tue 2/9

2:52 pm-9:38 pm

1 stop8h 46m

$416

MadisonSan Juan

MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl

MSNSJU

Madison Truax Field

Tue 2/23

6:01 am-9:28 pm

2 stops13h 27m

San Juan Luis Munoz Marin Intl

Fri 2/26

1:20 am-5:07 pm

1 stop17h 47m

$426

MadisonSan Juan

MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl

MSNSJU

Madison Truax Field

Sun 1/10

10:25 am-11:39 pm

1 stop11h 14m

San Juan Luis Munoz Marin Intl

Thu 1/14

3:41 pm-12:14 am

1 stop10h 33m

$426

MadisonSan Juan

MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl

MSNSJU

Madison Truax Field

Sat 2/6

10:38 am-2:43 pm

2 stops26h 05m

San Juan Luis Munoz Marin Intl

Wed 2/17

10:53 pm-5:20 pm

1 stop20h 27m

$460

MadisonSan Juan

MSN Madison Truax Field - SJU San Juan Luis Munoz Marin Intl

MSNSJU

Madison Truax Field

Wed 1/20

10:38 am-12:29 am

1 stop11h 51m

San Juan Luis Munoz Marin Intl

Mon 1/25

3:16 am-9:58 am

2 stops32h 42m

$480

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, August 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 $496. If you don’t want to visit Caribbean in August, then you should wait until May to fly from Madison, when ticket prices are also cheap, with an average price of $506.

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 $565 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 $406 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

Best Price Found	$213
Fastest flight time	6h 00m
Direct flights	None

The best one-way flight to Caribbean from Madison in the past 72 hours is $213. The best round-trip flight deal from Madison to Caribbean found on momondo in the last 72 hours is $416.

The fastest flight from Madison to Caribbean takes 6h 00m

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 November 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 $235	Free Cancellation	Rating 7.3 10,459 reviews	Search United Airlines flights
Delta	PriceFrom $266	Free Cancellation	Rating 7.8 8,696 reviews	Search Delta flights
American Airlines	PriceFrom $309	Free Cancellation	Rating 7.0 12,229 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.