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 50% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 7 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?

United Airlines, American Airlines, and Delta 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 August 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.

$146 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.

5:00 am - 2:44 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

8h 44m1 stop Chicago O'Hare Intl

1:00 am - 10:14 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 14m1 stop Newark

$296United Airlines

Tue, Sep 15 - Mon, Sep 21

6:30 am - 8:38 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 08m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

1:00 am - 10:14 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 14m1 stop Newark

$296United Airlines

Tue, Sep 15 - Mon, Sep 21

1:45 pm - 10:29 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

7h 44m1 stop Atlanta Hartsfield-Jackson

2:59 pm - 10:41 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

8h 42m1 stop Atlanta Hartsfield-Jackson

$296Delta

Sun, Sep 6 - Wed, Sep 16

5:43 am - 1:42 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

6h 59m1 stop Atlanta Hartsfield-Jackson

2:59 pm - 10:41 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

8h 42m1 stop Atlanta Hartsfield-Jackson

$296Delta

Sun, Sep 6 - Wed, Sep 16

6:30 am - 8:38 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 08m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

1:00 am - 12:03 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

12h 03m2 stops Newark Chicago O'Hare Intl

$296United Airlines

Sun, Sep 6 - Tue, Sep 15

10:27 am - 12:56 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 29m1 stop Tampa

6:35 am - 9:53 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

28h 18m2 stops Fort Lauderdale Tampa

$311Multiple Airlines

Wed, Sep 2 - Tue, Sep 8

10:27 am - 12:56 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 29m1 stop Tampa

5:37 pm - 9:53 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

17h 16m1 stop Tampa

$321Multiple Airlines

Wed, Sep 2 - Tue, Sep 8

5:50 am - 4:49 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

9h 59m1 stop Atlanta Hartsfield-Jackson

12:56 pm - 10:41 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 45m1 stop Atlanta Hartsfield-Jackson

$321Delta

Fri, Sep 11 - Fri, Sep 18

12:38 pm - 12:15 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

10h 37m2 stops Washington, D.C. Reagan-National Charlotte Douglas

11:51 am - 10:10 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

11h 19m2 stops Miami Chicago O'Hare Intl

$346American Airlines

Sun, Sep 6 - Wed, Sep 16

1:24 pm - 9:42 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

19h 18m2 stops Charlotte Douglas Miami

8:30 am - 4:53 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 23m1 stop Philadelphia

$346American Airlines

Sat, Oct 31 - Fri, Nov 6

Cheap last minute flights

Enter your travel dates to find the best prices.

10:27 am - 12:41 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 14m1 stop Tampa

3:10 am - 5:25 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

15h 15m1 stop Orlando

$425Multiple Airlines

Sat, Aug 15 - Tue, Aug 18

10:27 am - 12:41 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 14m1 stop Tampa

6:35 am - 9:47 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

28h 12m2 stops Fort Lauderdale Tampa

$427Multiple Airlines

Sat, Aug 15 - Tue, Aug 25

10:27 am - 12:41 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 14m1 stop Tampa

6:35 am - 9:47 amSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

28h 12m2 stops Fort Lauderdale Tampa

$430Multiple Airlines

Sat, Aug 15 - Fri, Aug 21

6:30 am - 6:33 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

11h 03m2 stops Charlotte Douglas Miami

1:38 pm - 11:09 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 31m2 stops Miami Charlotte Douglas

$568American Airlines

Mon, Aug 17 - Sat, Aug 22

2:45 pm - 11:15 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

7h 30m1 stop Chicago O'Hare Intl

7:03 am - 5:17 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

11h 14m1 stop Philadelphia

$568American Airlines

Mon, Aug 17 - Sat, Aug 22

6:30 am - 8:38 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

13h 08m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

3:56 pm - 10:41 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

7h 45m1 stop Chicago O'Hare Intl

$658United Airlines

Sat, Aug 15 - Tue, Aug 25

5:00 am - 2:44 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

8h 44m1 stop Chicago O'Hare Intl

3:56 pm - 10:41 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

7h 45m1 stop Chicago O'Hare Intl

$658United Airlines

Mon, Aug 17 - Tue, Aug 25

6:30 am - 2:44 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

7h 14m1 stop Chicago O'Hare Intl

1:00 am - 1:42 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

13h 42m2 stops Newark Chicago O'Hare Intl

$670United Airlines

Sat, Aug 15 - Tue, Aug 18

1:55 pm - 12:15 amMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

9h 20m1 stop Charlotte Douglas

1:38 pm - 11:09 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 31m2 stops Miami Charlotte Douglas

$688American Airlines

Sun, Aug 16 - Fri, Aug 21

5:43 am - 4:38 pmMSN Madison Truax Field-SJU San Juan Luis Munoz Marin Intl

9h 55m1 stop Atlanta Hartsfield-Jackson

7:00 am - 4:20 pmSJU San Juan Luis Munoz Marin Intl-MSN Madison Truax Field

10h 20m1 stop Atlanta Hartsfield-Jackson

$723Delta

Mon, Aug 17 - Fri, Aug 21

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

Delta flights from Madison to Caribbean Islands

Our best Delta deals on Madison to Caribbean Islands flight tickets

Delta

Sep 6

MSN5:43 amMadison Truax Field

6h 59m

1 stop

SJU1:42 pmSan Juan Luis Munoz Marin Intl

Sep 16

SJU2:59 pmSan Juan Luis Munoz Marin Intl

8h 42m

1 stop

MSN10:41 pmMadison Truax Field

$296

Delta

Jan 10

MSN6:15 amMadison Truax Field

7h 55m

1 stop

SJU4:10 pmSan Juan Luis Munoz Marin Intl

Jan 14

SJU3:20 pmSan Juan Luis Munoz Marin Intl

9h 35m

1 stop

MSN10:55 pmMadison Truax Field

$391

Delta

Sep 30

MSN5:50 amMadison Truax Field

6h 55m

1 stop

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Oct 5

SJU2:59 pmSan Juan Luis Munoz Marin Intl

8h 42m

1 stop

MSN10:41 pmMadison Truax Field

$416

United Airlines flights from Madison to Caribbean Islands

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

United Airlines

Sep 15

MSN8:05 amMadison Truax Field

11h 33m

2 stops

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Sep 21

SJU1:00 amSan Juan Luis Munoz Marin Intl

13h 42m

2 stops

MSN1:42 pmMadison Truax Field

$313

United Airlines

Oct 17

MSN5:00 amMadison Truax Field

8h 44m

1 stop

SJU2:44 pmSan Juan Luis Munoz Marin Intl

Oct 27

SJU7:25 amSan Juan Luis Munoz Marin Intl

7h 38m

1 stop

MSN2:03 pmMadison Truax Field

$341

United Airlines

Oct 17

MSN12:39 pmMadison Truax Field

10h 11m

2 stops

SJU11:50 pmSan Juan Luis Munoz Marin Intl

Oct 27

SJU6:40 amSan Juan Luis Munoz Marin Intl

12h 15m

2 stops

MSN5:55 pmMadison Truax Field

$353

momondo Fare Finder

Use the filters below to find and compare flights from Madison to Caribbean Islands that are best for you.

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

Tue 9/15

5:00 am-2:44 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Mon 9/21

1:00 am-10:14 am

1 stop10h 14m

$296

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Tue 9/15

6:30 am-8:38 pm

2 stops13h 08m

San Juan Luis Munoz Marin Intl

Mon 9/21

1:00 am-10:14 am

1 stop10h 14m

$296

MadisonSan Juan

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

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

2:59 pm-10:41 pm

1 stop8h 42m

$296

Quickest round-trip

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Sun 9/6

5:43 am-1:42 pm

1 stop6h 59m

San Juan Luis Munoz Marin Intl

Wed 9/16

2:59 pm-10:41 pm

1 stop8h 42m

$296

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Sun 9/6

6:30 am-8:38 pm

2 stops13h 08m

San Juan Luis Munoz Marin Intl

Tue 9/15

1:00 am-12:03 pm

2 stops12h 03m

$296

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Wed 9/2

10:27 am-12:56 am

1 stop13h 29m

San Juan Luis Munoz Marin Intl

Tue 9/8

6:35 am-9:53 am

2 stops28h 18m

$311

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Wed 9/2

10:27 am-12:56 am

1 stop13h 29m

San Juan Luis Munoz Marin Intl

Tue 9/8

5:37 pm-9:53 am

1 stop17h 16m

$321

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Fri 9/11

5:50 am-4:49 pm

1 stop9h 59m

San Juan Luis Munoz Marin Intl

Fri 9/18

12:56 pm-10:41 pm

1 stop10h 45m

$321

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Sun 9/6

12:38 pm-12:15 am

2 stops10h 37m

San Juan Luis Munoz Marin Intl

Wed 9/16

11:51 am-10:10 pm

2 stops11h 19m

$346

MadisonSan Juan

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

MSNSJU

Madison Truax Field

Sat 10/31

1:24 pm-9:42 am

2 stops19h 18m

San Juan Luis Munoz Marin Intl

Fri 11/6

8:30 am-4:53 pm

1 stop10h 23m

$346

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 May is, on average, the cheapest month to fly to Caribbean Islands from Madison, with most prices found around $581. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Madison averaging around $608.

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 $517 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 $308 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 08m
Direct flights	None

The fastest flight from Madison to Caribbean Islands takes 5h 08m

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 August 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 16.97% of all bookings. The subsequent popular models are Embraer 175 at 10.88%, Boeing 737-900 at 10.12%, and Embraer 170 at 7.89%.

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
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 10,111 reviews	Search United Airlines flights
Delta	PriceFrom $246	Free Cancellation	Rating 7.8 8,505 reviews	Search Delta flights
American Airlines	PriceFrom $295	Free Cancellation	Rating 7.1 11,913 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.