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

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

What airlines fly to Caribbean Islands?

American Airlines, Delta and United Airlines 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.

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 March 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.

$123 Cheap Flights from Madison to Caribbean Islands in 2026

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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.

5:30 am - 1:19 pm

MSN

MBJ

7h 49m

2 stops

4:37 pm - 10:55 am

MBJ

MSN

18h 18m

2 stops

$317American Airlines

Tue, Apr 14 - Sat, Apr 18

8:24 pm - 12:13 pm

MSN

MBJ

15h 49m

1 stop

1:15 pm - 8:45 am

MBJ

MSN

19h 30m

1 stop

$318American Airlines

Tue, Apr 14 - Sat, Apr 18

8:24 pm - 12:13 pm

MSN

MBJ

15h 49m

1 stop

12:47 pm - 10:38 am

MBJ

MSN

21h 51m

1 stop

$319American Airlines

Thu, May 14 - Thu, May 21

8:24 pm - 11:24 am

MSN

MBJ

15h 00m

2 stops

2:23 pm - 7:45 am

MBJ

MSN

17h 22m

1 stop

$322American Airlines

Thu, May 14 - Thu, May 21

8:24 pm - 1:25 pm

MSN

MBJ

17h 01m

2 stops

12:47 pm - 10:38 am

MBJ

MSN

21h 51m

1 stop

$323American Airlines

Thu, May 14 - Thu, May 21

10:05 am - 8:34 pm

MSN

SJU

9h 29m

1 stop

1:00 am - 10:11 am

SJU

MSN

10h 11m

2 stops

$345United Airlines

Wed, Apr 15 - Mon, Apr 27

5:30 am - 4:23 pm

MSN

SJU

9h 53m

1 stop

7:30 am - 5:34 pm

SJU

MSN

11h 04m

2 stops

$348Delta

Sun, May 3 - Sat, May 9

6:50 pm - 11:05 pm

MSN

SJU

27h 15m

1 stop

5:56 pm - 9:47 am

SJU

MSN

16h 51m

2 stops

$349Multiple Airlines

Mon, Aug 10 - Fri, Aug 21

6:30 am - 9:24 pm

MSN

SJU

13h 54m

2 stops

1:00 am - 11:38 am

SJU

MSN

11h 38m

2 stops

$356United Airlines

Sat, May 16 - Fri, May 22

5:45 am - 11:48 am

MSN

NAS

5h 03m

1 stop

1:13 pm - 10:35 pm

NAS

MSN

10h 22m

1 stop

$556Delta

Mon, Aug 24 - Fri, Aug 28

United Airlines flights from Madison to Caribbean Islands

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

United Airlines

Apr 15

MSN10:05 amMadison Truax Field

9h 29m

1 stop

SJU8:34 pmSan Juan Luis Munoz Marin Intl

Apr 27

SJU1:00 amSan Juan Luis Munoz Marin Intl

10h 11m

2 stops

MSN10:11 amMadison Truax Field

$345

United Airlines

May 14

MSN8:55 pmMadison Truax Field

16h 35m

2 stops

MBJ1:30 pmMontego Bay Sangster Intl

May 21

MBJ2:40 pmMontego Bay Sangster Intl

18h 15m

2 stops

MSN8:55 amMadison Truax Field

$347

United Airlines

May 16

MSN6:30 amMadison Truax Field

13h 54m

2 stops

SJU9:24 pmSan Juan Luis Munoz Marin Intl

May 22

SJU1:00 amSan Juan Luis Munoz Marin Intl

11h 38m

2 stops

MSN11:38 amMadison Truax Field

$356

Frontier flights from Madison to Caribbean Islands

Our best Frontier deals on Madison to Caribbean Islands flight tickets

Frontier

Mar 6

MSN12:04 pmMadison Truax Field

12h 54m

1 stop

SJU2:58 amSan Juan Luis Munoz Marin Intl

Mar 14

SJU3:08 amSan Juan Luis Munoz Marin Intl

9h 21m

1 stop

MSN11:29 amMadison Truax Field

$361

Frontier

Mar 6

MSN12:04 pmMadison Truax Field

12h 54m

1 stop

SJU2:58 amSan Juan Luis Munoz Marin Intl

Mar 14

SJU3:08 amSan Juan Luis Munoz Marin Intl

9h 21m

1 stop

MSN11:29 amMadison Truax Field

$376

Frontier

Mar 9

MSN12:29 pmMadison Truax Field

12h 29m

1 stop

SJU1:58 amSan Juan Luis Munoz Marin Intl

Mar 15

SJU3:08 amSan Juan Luis Munoz Marin Intl

9h 26m

1 stop

MSN11:34 amMadison Truax Field

$386

Fly from

Fly to

Route

Depart

Return

Price

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 4/14

5:30 am-1:19 pm

2 stops7h 49m

Montego Bay Sangster Intl

Sat 4/18

4:37 pm-10:55 am

2 stops18h 18m

$317

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 4/14

8:24 pm-12:13 pm

1 stop15h 49m

Montego Bay Sangster Intl

Sat 4/18

1:15 pm-8:45 am

1 stop19h 30m

$318

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:24 pm-12:13 pm

1 stop15h 49m

Montego Bay Sangster Intl

Thu 5/21

12:47 pm-10:38 am

1 stop21h 51m

$319

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:24 pm-11:24 am

2 stops15h 00m

Montego Bay Sangster Intl

Thu 5/21

2:23 pm-7:45 am

1 stop17h 22m

$322

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 5/14

8:24 pm-1:25 pm

2 stops17h 01m

Montego Bay Sangster Intl

Thu 5/21

12:47 pm-10:38 am

1 stop21h 51m

$323

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 4/15

10:05 am-8:34 pm

1 stop9h 29m

San Juan Luis Munoz Marin Intl

Mon 4/27

1:00 am-10:11 am

2 stops10h 11m

$345

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 5/3

5:30 am-4:23 pm

1 stop9h 53m

San Juan Luis Munoz Marin Intl

Sat 5/9

7:30 am-5:34 pm

2 stops11h 04m

$348

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 8/10

6:50 pm-11:05 pm

1 stop27h 15m

San Juan Luis Munoz Marin Intl

Fri 8/21

5:56 pm-9:47 am

2 stops16h 51m

$349

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 5/16

6:30 am-9:24 pm

2 stops13h 54m

San Juan Luis Munoz Marin Intl

Fri 5/22

1:00 am-11:38 am

2 stops11h 38m

$356

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Mon 8/24

5:45 am-11:48 am

1 stop5h 03m

Nassau Intl

Fri 8/28

1:13 pm-10:35 pm

1 stop10h 22m

$556

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 September is, on average, the cheapest month to fly to Caribbean Islands from Madison, with most prices found around $310. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Madison averaging around $407.

How far in advance should I book a flight 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 $506 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 $403 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 41m
Direct flights	None

The fastest flight from Madison to Caribbean Islands takes 5h 41m

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

Search flight deals

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 March 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 Boeing 737-800, representing 18.18% of all bookings. The subsequent popular models are Airbus A319 at 10.95%, Embraer 175 at 10.39%, and Airbus A320-100/200 at 10.11%.

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 $257	Free Cancellation	Rating 7.4 9,377 reviews	Search United Airlines flights
American Airlines	PriceFrom $268	Free Cancellation	Rating 7.1 11,375 reviews	Search American Airlines flights
Delta	PriceFrom $275	Free Cancellation	Rating 7.9 8,242 reviews	Search Delta 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.