What airlines fly to Caribbean Islands?

American Airlines, Delta and Southwest are the top three most popular airlines that fly to Caribbean Islands 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 Islands. Keep in mind that there are 6 different airlines that fly to Caribbean Islands 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 Islands?

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

When did momondo last update prices for flights from Madison Truax Field Airport to Caribbean Islands?

Prices for flights from Madison Truax Field Airport to Caribbean Islands are updated daily.

How many operators does momondo search for flights from Madison Truax Field Airport to Caribbean Islands?

The number of operators available for flights from Madison Truax Field Airport to Caribbean Islands is 3 as of June 2026.

How old do you have to be to fly from Madison Truax Field Airport to Caribbean Islands?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The necessary travel and health documents for your Caribbean Islands 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 Islands in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Madison to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:30 am - 2:44 pm

MSN

SJU

7h 14m

1 stop

1:00 am - 1:42 pm

SJU

MSN

13h 42m

2 stops

$293United Airlines

Sun, Sep 6 - Tue, Sep 15

9:32 am - 10:29 pm

MSN

SJU

11h 57m

2 stops

12:56 pm - 10:38 pm

SJU

MSN

10h 42m

1 stop

$296Delta

Tue, Aug 25 - Mon, Aug 31

5:00 am - 10:54 pm

MSN

SJU

16h 54m

1 stop

7:00 am - 11:29 pm

SJU

MSN

17h 29m

1 stop

$326American Airlines

Sat, Aug 22 - Tue, Aug 25

6:30 am - 8:38 pm

MSN

SJU

13h 08m

2 stops

1:00 am - 9:40 am

SJU

MSN

9h 40m

2 stops

$331United Airlines

Thu, Sep 10 - Sat, Sep 12

4:59 pm - 11:25 am

MSN

MBJ

18h 26m

2 stops

5:14 pm - 12:13 pm

MBJ

MSN

18h 59m

2 stops

$357American Airlines

Tue, Jul 21 - Tue, Jul 28

3:55 pm - 10:12 am

MSN

MBJ

17h 17m

1 stop

2:30 pm - 9:19 am

MBJ

MSN

19h 49m

1 stop

$358American Airlines

Fri, Dec 4 - Thu, Dec 10

3:55 pm - 10:12 am

MSN

MBJ

17h 17m

1 stop

11:13 am - 9:56 pm

MBJ

MSN

11h 43m

2 stops

$362American Airlines

Fri, Dec 4 - Thu, Dec 10

1:45 pm - 10:29 pm

MSN

SJU

7h 44m

1 stop

2:26 pm - 10:39 pm

SJU

MSN

9h 13m

1 stop

$383Delta

Sun, Sep 6 - Wed, Sep 16

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

$1,835Air Canada

Sun, Nov 8 - Thu, Nov 12

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Delta flights from Madison to Caribbean Islands

Our best Delta deals on Madison to Caribbean Islands flight tickets

Delta

Aug 25

MSN9:32 amMadison Truax Field

11h 57m

2 stops

SJU10:29 pmSan Juan Luis Munoz Marin Intl

Aug 31

SJU12:56 pmSan Juan Luis Munoz Marin Intl

10h 42m

1 stop

MSN10:38 pmMadison Truax Field

$296

Delta

Sep 6

MSN1:45 pmMadison Truax Field

7h 44m

1 stop

SJU10:29 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

$383

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

United Airlines flights from Madison to Caribbean Islands

Our best United Airlines deals on Madison to Caribbean Islands flight tickets

United Airlines

Sep 6

MSN6:30 amMadison Truax Field

7h 14m

1 stop

SJU2:44 pmSan Juan Luis Munoz Marin Intl

Sep 15

SJU1:00 amSan Juan Luis Munoz Marin Intl

13h 42m

2 stops

MSN1:42 pmMadison Truax Field

$293

United Airlines

Sep 10

MSN6:30 amMadison Truax Field

13h 08m

2 stops

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Sep 12

SJU1:00 amSan Juan Luis Munoz Marin Intl

9h 40m

2 stops

MSN9:40 amMadison Truax Field

$331

United Airlines

Aug 29

MSN6:30 amMadison Truax Field

13h 08m

2 stops

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Sep 1

SJU1:00 amSan Juan Luis Munoz Marin Intl

13h 42m

2 stops

MSN1:42 pmMadison Truax Field

$381

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/6

6:30 am-2:44 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Tue 9/15

1:00 am-1:42 pm

2 stops13h 42m

$293

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 8/25

9:32 am-10:29 pm

2 stops11h 57m

San Juan Luis Munoz Marin Intl

Mon 8/31

12:56 pm-10:38 pm

1 stop10h 42m

$296

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 8/22

5:00 am-10:54 pm

1 stop16h 54m

San Juan Luis Munoz Marin Intl

Tue 8/25

7:00 am-11:29 pm

1 stop17h 29m

$326

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Thu 9/10

6:30 am-8:38 pm

2 stops13h 08m

San Juan Luis Munoz Marin Intl

Sat 9/12

1:00 am-9:40 am

2 stops9h 40m

$331

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 7/21

4:59 pm-11:25 am

2 stops18h 26m

Montego Bay Sangster Intl

Tue 7/28

5:14 pm-12:13 pm

2 stops18h 59m

$357

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

3:55 pm-10:12 am

1 stop17h 17m

Montego Bay Sangster Intl

Thu 12/10

2:30 pm-9:19 am

1 stop19h 49m

$358

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Fri 12/4

3:55 pm-10:12 am

1 stop17h 17m

Montego Bay Sangster Intl

Thu 12/10

11:13 am-9:56 pm

2 stops11h 43m

$362

Quickest round-trip

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/6

1:45 pm-10:29 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Wed 9/16

2:26 pm-10:39 pm

1 stop9h 13m

$383

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

$1,835

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 Islands

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 Islands?

The month of February is, on average, the cheapest month to fly to Caribbean Islands from Madison, with most prices found around $213. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Madison averaging around $350.

How far in advance should I book a flight from Madison to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $519 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Madison for as low as $252 on momondo.

Can stopping save me money on Madison to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Madison to Caribbean Islands.

Cheap Madison to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Caribbean Islands

Fastest flight time	5h 05m
Direct flights	None

The fastest flight from Madison to Caribbean Islands takes 5h 05m

There are no direct flights from Madison to Caribbean Islands. There are no popular flight routes from Madison to Caribbean Islands.

Search flight deals

Frequently asked questions about flying from Madison to Caribbean Islands

When did momondo last update prices for flights from Madison Truax Field Airport to Caribbean Islands?
Prices for flights from Madison Truax Field Airport to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Madison Truax Field Airport to Caribbean Islands?
The number of operators available for flights from Madison Truax Field Airport to Caribbean Islands is 3 as of June 2026.
How old do you have to be to fly from Madison Truax Field Airport to Caribbean Islands?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The necessary travel and health documents for your Caribbean Islands 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.
What is the most popular plane model from Madison to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Madison to Caribbean Islands is Embraer 175 (Enhanced Winglets), representing 13.34% of all bookings. The subsequent popular models are Boeing 737-800 at 10.75%, Canadair (Bombardier) Regional Jet 900 at 9.49%, and Embraer 175 at 8.65%.

Best airlines flying from Madison to Caribbean Islands

Compare and see reviews for airlines that fly from Madison to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $225	Free Cancellation	Rating 7.9 8,394 reviews	Search Delta flights
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 9,796 reviews	Search United Airlines flights
American Airlines	PriceFrom $268	Free Cancellation	Rating 7.1 11,640 reviews	Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Madison to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Madison to Caribbean Islands with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Madison to Caribbean Islands flights to just show those with flexible booking policies.

How can momondo help me find flights from Madison to Caribbean Islands?

Once all potential Madison to Caribbean Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Madison to Caribbean Islands right now. Can momondo alert me if prices change?

Price alerts on flights to Caribbean Islands from Madison are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.