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 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 September 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.

$145 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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11:11 am - 11:50 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

10h 39m1 stop Atlanta Hartsfield-Jackson

3:15 pm - 8:45 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

7h 30m1 stop Detroit Metropolitan Wayne County

$356Delta

Mon, Jan 18 - Thu, Jan 21

9:26 am - 11:50 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

12h 24m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

3:20 pm - 10:55 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

9h 35m1 stop Minneapolis St Paul

$356Delta

Tue, Jan 26 - Thu, Jan 28

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

7h 00m1 stop Chicago O'Hare Intl

2:05 am - 2:05 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

14h 00m2 stops Newark Chicago O'Hare Intl

$356United Airlines

Tue, Jan 19 - Thu, Jan 21

5:00 am - 2:40 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

8h 40m1 stop Chicago O'Hare Intl

1:00 pm - 11:07 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

12h 07m2 stops Newark Chicago O'Hare Intl

$356United Airlines

Mon, Oct 26 - Mon, Nov 2

11:11 am - 11:50 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

10h 39m1 stop Atlanta Hartsfield-Jackson

7:30 am - 4:34 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

11h 04m1 stop Atlanta Hartsfield-Jackson

$356Delta

Sun, Jan 24 - Fri, Jan 29

6:00 am - 3:40 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

7h 40m1 stop Chicago O'Hare Intl

8:25 am - 2:59 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

8h 34m1 stop Chicago O'Hare Intl

$356United Airlines

Tue, Jan 26 - Wed, Feb 3

10:30 am - 9:18 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

21h 48m1 stop Orlando

8:45 am - 9:58 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

26h 13m2 stops Fort Lauderdale Tampa

$360Multiple Airlines

Tue, Oct 13 - Tue, Oct 20

12:15 pm - 1:52 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

12h 37m1 stop Orlando

7:15 am - 9:58 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

27h 43m2 stops Fort Lauderdale Tampa

$362Multiple Airlines

Tue, Sep 29 - Fri, Oct 2

9:04 pm - 3:14 pmMSN Madison Truax Field-STT Saint Thomas Island Cyril E King

16h 10m1 stop Chicago O'Hare Intl

4:55 pm - 11:00 amSTT Saint Thomas Island Cyril E King-MSN Madison Truax Field

20h 05m2 stops Miami Chicago O'Hare Intl

$381American Airlines

Wed, Jan 6 - Wed, Jan 13

7:07 pm - 4:05 pmMSN Madison Truax Field-STT Saint Thomas Island Cyril E King

18h 58m2 stops Chicago O'Hare Intl Miami

4:55 pm - 11:00 amSTT Saint Thomas Island Cyril E King-MSN Madison Truax Field

20h 05m2 stops Miami Chicago O'Hare Intl

$381American Airlines

Wed, Jan 6 - Wed, Jan 13

Cheap last minute flights

Enter your travel dates to find the best prices.

5:50 am - 1:53 pmMSN Madison Truax Field-NAS Nassau Intl

7h 03m1 stop Atlanta Hartsfield-Jackson

3:18 pm - 10:41 pmNAS Nassau Intl-MSN Madison Truax Field

8h 23m1 stop Atlanta Hartsfield-Jackson

$776Delta

Mon, Sep 21 - Wed, Sep 30

6:00 am - 5:55 pmMSN Madison Truax Field-NAS Nassau Intl

10h 55m2 stops Philadelphia Miami

10:32 am - 7:46 pmNAS Nassau Intl-MSN Madison Truax Field

10h 14m2 stops Miami New York LaGuardia

$779American Airlines

Mon, Sep 21 - Wed, Sep 30

5:51 pm - 11:21 amMSN Madison Truax Field-NAS Nassau Intl

16h 30m2 stops Dallas/Fort Worth Miami

2:39 pm - 8:50 pmNAS Nassau Intl-MSN Madison Truax Field

7h 11m1 stop Charlotte Douglas

$779American Airlines

Mon, Sep 21 - Wed, Sep 30

4:05 pm - 12:40 pmMSN Madison Truax Field-PUJ Punta Cana

19h 35m2 stops Chicago O'Hare Intl Washington, D.C. Reagan-National

2:20 pm - 9:54 amPUJ Punta Cana-MSN Madison Truax Field

20h 34m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

$921United Airlines

Sat, Sep 19 - Sat, Sep 26

6:30 am - 3:00 pmMSN Madison Truax Field-PUJ Punta Cana

7h 30m1 stop Chicago O'Hare Intl

1:50 pm - 10:35 pmPUJ Punta Cana-MSN Madison Truax Field

9h 45m1 stop Chicago O'Hare Intl

$1,016United Airlines

Sat, Sep 19 - Sat, Sep 26

5:49 pm - 2:00 pmMSN Madison Truax Field-AUA Oranjestad Reina Beatrix

19h 11m2 stops Chicago O'Hare Intl Newark

4:30 pm - 9:00 pmAUA Oranjestad Reina Beatrix-MSN Madison Truax Field

29h 30m2 stops Newark Chicago O'Hare Intl

$1,077United Airlines

Wed, Sep 23 - Wed, Sep 30

5:49 pm - 12:40 pmMSN Madison Truax Field-PUJ Punta Cana

17h 51m2 stops Chicago O'Hare Intl Washington, D.C. Reagan-National

1:50 pm - 9:00 pmPUJ Punta Cana-MSN Madison Truax Field

8h 10m1 stop Chicago O'Hare Intl

$1,151United Airlines

Sat, Sep 19 - Sat, Sep 26

10:57 am - 2:00 pmMSN Madison Truax Field-AUA Oranjestad Reina Beatrix

26h 03m1 stop Newark

4:30 pm - 1:37 pmAUA Oranjestad Reina Beatrix-MSN Madison Truax Field

22h 07m2 stops Newark Chicago O'Hare Intl

$1,217United Airlines

Wed, Sep 23 - Wed, Sep 30

8:15 am - 5:55 pmMSN Madison Truax Field-NAS Nassau Intl

8h 40m3 stops Charlotte Douglas Tampa Miami

12:01 pm - 8:50 pmNAS Nassau Intl-MSN Madison Truax Field

9h 49m2 stops Miami Charlotte Douglas

$2,186American Airlines

Mon, Sep 21 - Wed, Sep 30

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United Airlines flights from Madison to Caribbean

Our best United Airlines deals on Madison to Caribbean flight tickets

United Airlines

Jan 19

MSN6:00 amMadison Truax Field

6h 48m

1 stop

MBJ1:48 pmMontego Bay Sangster Intl

Jan 26

MBJ2:54 pmMontego Bay Sangster Intl

9h 16m

1 stop

MSN11:10 pmMadison Truax Field

$383

United Airlines

Jan 6

MSN8:22 amMadison Truax Field

14h 14m

2 stops

SJU12:36 amSan Juan Luis Munoz Marin Intl

Jan 13

SJU8:25 amSan Juan Luis Munoz Marin Intl

7h 40m

1 stop

MSN2:05 pmMadison Truax Field

$384

United Airlines

Jan 16

MSN12:30 pmMadison Truax Field

10h 06m

2 stops

SJU12:36 amSan Juan Luis Munoz Marin Intl

Jan 22

SJU8:05 amSan Juan Luis Munoz Marin Intl

10h 53m

2 stops

MSN4:58 pmMadison Truax Field

$401

Delta flights from Madison to Caribbean

Our best Delta deals on Madison to Caribbean flight tickets

Delta

Jan 26

MSN11:11 amMadison Truax Field

10h 39m

1 stop

SJU11:50 pmSan Juan Luis Munoz Marin Intl

Feb 3

SJU7:30 amSan Juan Luis Munoz Marin Intl

11h 04m

1 stop

MSN4:34 pmMadison Truax Field

$356

Delta

Jan 26

MSN9:26 amMadison Truax Field

12h 24m

2 stops

SJU11:50 pmSan Juan Luis Munoz Marin Intl

Jan 30

SJU6:15 amSan Juan Luis Munoz Marin Intl

7h 20m

1 stop

MSN11:35 amMadison Truax Field

$371

Delta

Jan 28

MSN6:15 amMadison Truax Field

15h 35m

2 stops

SJU11:50 pmSan Juan Luis Munoz Marin Intl

Feb 3

SJU7:30 amSan Juan Luis Munoz Marin Intl

11h 04m

1 stop

MSN4:34 pmMadison Truax Field

$431

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

Mon 1/18

11:11 am-11:50 pm

1 stop10h 39m

San Juan Luis Munoz Marin Intl

Thu 1/21

3:15 pm-8:45 pm

1 stop7h 30m

$356

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Tue 1/26

9:26 am-11:50 pm

2 stops12h 24m

San Juan Luis Munoz Marin Intl

Thu 1/28

3:20 pm-10:55 pm

1 stop9h 35m

$356

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Tue 1/19

6:40 am-3:40 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Thu 1/21

2:05 am-2:05 pm

2 stops14h 00m

$356

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Mon 10/26

5:00 am-2:40 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Mon 11/2

1:00 pm-11:07 pm

2 stops12h 07m

$356

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Sun 1/24

11:11 am-11:50 pm

1 stop10h 39m

San Juan Luis Munoz Marin Intl

Fri 1/29

7:30 am-4:34 pm

1 stop11h 04m

$356

Quickest round-trip

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Tue 1/26

6:00 am-3:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 2/3

8:25 am-2:59 pm

1 stop8h 34m

$356

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Tue 10/13

10:30 am-9:18 am

1 stop21h 48m

San Juan Luis Munoz Marin Intl

Tue 10/20

8:45 am-9:58 am

2 stops26h 13m

$360

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Tue 9/29

12:15 pm-1:52 am

1 stop12h 37m

San Juan Luis Munoz Marin Intl

Fri 10/2

7:15 am-9:58 am

2 stops27h 43m

$362

MadisonSaint Thomas Island

MSN Madison Truax Field - STT Saint Thomas Island Cyril E King

MSNSTT

Madison Truax Field

Wed 1/6

9:04 pm-3:14 pm

1 stop16h 10m

Saint Thomas Island Cyril E King

Wed 1/13

4:55 pm-11:00 am

2 stops20h 05m

$381

MadisonSaint Thomas Island

MSN Madison Truax Field - STT Saint Thomas Island Cyril E King

MSNSTT

Madison Truax Field

Wed 1/6

7:07 pm-4:05 pm

2 stops18h 58m

Saint Thomas Island Cyril E King

Wed 1/13

4:55 pm-11:00 am

2 stops20h 05m

$381

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 $497.

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 $527 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 $308 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	$145
Fastest flight time	5h 43m
Direct flights	None

The best one-way flight to Caribbean from Madison in the past 72 hours is $145. The best round-trip flight deal from Madison to Caribbean found on momondo in the last 72 hours is $356.

The fastest flight from Madison to Caribbean takes 5h 43m

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 September 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 $226	Free Cancellation	Rating 7.4 10,214 reviews	Search United Airlines flights
Delta	PriceFrom $246	Free Cancellation	Rating 7.8 8,581 reviews	Search Delta flights
American Airlines	PriceFrom $295	Free Cancellation	Rating 7.1 12,075 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.