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Cheap flights from Madison to Caribbean Islands from $118

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Caribbean Islands departing on 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Madison to Caribbean Islands

Cheap round-trip flights

Delta Logo
9:38 am - 11:10 pmMSN-SJU
11h 32m2 stops
Delta Logo
7:00 am - 4:23 pmSJU-MSN
11h 23m1 stop
$235Delta
Find Deal
Tue, Dec 9 - Tue, Dec 16
United Airlines Logo
8:15 am - 10:22 pmMSN-SJU
12h 07m2 stops
United Airlines Logo
2:05 am - 11:44 amSJU-MSN
11h 39m2 stops
$267United Airlines
Find Deal
Tue, Dec 9 - Mon, Dec 15
American Airlines Logo
11:43 am - 11:40 pmMSN-SJU
9h 57m1 stop
American Airlines Logo
7:20 am - 4:53 pmSJU-MSN
11h 33m1 stop
$268American Airlines
Find Deal
Tue, Jan 20 - Wed, Jan 28
Delta Logo
5:28 am - 2:14 pmMSN-SJU
6h 46m1 stop
Delta Logo
3:20 pm - 8:30 pmSJU-MSN
7h 10m1 stop
$278Delta
Find Deal
Wed, Dec 10 - Wed, Dec 17
American Airlines Logo
11:43 am - 11:40 pmMSN-SJU
9h 57m1 stop
American Airlines Logo
4:40 pm - 11:42 pmSJU-MSN
9h 02m1 stop
$295American Airlines
Find Deal
Sun, Jan 11 - Wed, Jan 21
American Airlines Logo
4:17 pm - 11:45 amMSN-SJU
17h 28m1 stop
American Airlines Logo
7:20 am - 4:53 pmSJU-MSN
11h 33m1 stop
$298American Airlines
Find Deal
Sat, Jan 31 - Thu, Feb 5
American Airlines Logo
4:19 pm - 11:45 amMSN-SJU
17h 26m1 stop
American Airlines Logo
7:20 am - 5:30 pmSJU-MSN
12h 10m1 stop
$301American Airlines
Find Deal
Sat, Feb 21 - Wed, Feb 25
United Airlines Logo
6:30 am - 3:40 pmMSN-SJU
7h 10m1 stop
United Airlines Logo
2:05 am - 11:44 amSJU-MSN
11h 39m2 stops
$311United Airlines
Find Deal
Tue, Dec 9 - Mon, Dec 15
LATAM Airlines Logo
1:20 pm - 3:15 pmMSN-PUJ
23h 55m2 stops
LATAM Airlines Logo
2:45 am - 10:38 pmPUJ-MSN
21h 53m2 stops
$2,710LATAM Airlines
Find Deal
Sat, Feb 14 - Fri, Feb 20
LATAM Airlines Logo
5:17 pm - 3:15 pmMSN-PUJ
19h 58m2 stops
LATAM Airlines Logo
2:45 am - 10:38 pmPUJ-MSN
21h 53m2 stops
$2,868LATAM Airlines
Find Deal
Wed, Jan 14 - Fri, Jan 16

United Airlines flights from Madison to Caribbean Islands

Our best United Airlines deals on Madison to Caribbean Islands flight tickets
United Airlines
Dec 9
MSN8:15 amMadison Truax Field
12h 07m
2 stops
SJU10:22 pmSan Juan Luis Munoz Marin Intl
Dec 15
SJU2:05 amSan Juan Luis Munoz Marin Intl
11h 39m
2 stops
MSN11:44 amMadison Truax Field
$267
Find similar
United Airlines
Dec 9
MSN6:30 amMadison Truax Field
7h 10m
1 stop
SJU3:40 pmSan Juan Luis Munoz Marin Intl
Dec 15
SJU2:05 amSan Juan Luis Munoz Marin Intl
11h 39m
2 stops
MSN11:44 amMadison Truax Field
$311
Find similar
United Airlines
Jan 20
MSN8:15 amMadison Truax Field
12h 07m
2 stops
SJU10:22 pmSan Juan Luis Munoz Marin Intl
Jan 27
SJU2:05 amSan Juan Luis Munoz Marin Intl
14h 47m
2 stops
MSN2:52 pmMadison Truax Field
$325
Find similar

American Airlines flights from Madison to Caribbean Islands

Our best American Airlines deals on Madison to Caribbean Islands flight tickets
American Airlines
Jan 20
MSN11:43 amMadison Truax Field
9h 57m
1 stop
SJU11:40 pmSan Juan Luis Munoz Marin Intl
Jan 28
SJU7:20 amSan Juan Luis Munoz Marin Intl
11h 33m
1 stop
MSN4:53 pmMadison Truax Field
$268
Find similar
American Airlines
Jan 11
MSN11:43 amMadison Truax Field
9h 57m
1 stop
SJU11:40 pmSan Juan Luis Munoz Marin Intl
Jan 21
SJU4:40 pmSan Juan Luis Munoz Marin Intl
9h 02m
1 stop
MSN11:42 pmMadison Truax Field
$295
Find similar
American Airlines
Jan 31
MSN4:17 pmMadison Truax Field
17h 28m
1 stop
SJU11:45 amSan Juan Luis Munoz Marin Intl
Feb 5
SJU7:20 amSan Juan Luis Munoz Marin Intl
11h 33m
1 stop
MSN4:53 pmMadison Truax Field
$298
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 19, 2025.
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

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 12/9

9:38 am-11:10 pm

2 stops11h 32m

San Juan Luis Munoz Marin Intl

Tue 12/16

7:00 am-4:23 pm

1 stop11h 23m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 12/9

8:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

Mon 12/15

2:05 am-11:44 am

2 stops11h 39m

$267

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

11:43 am-11:40 pm

1 stop9h 57m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:20 am-4:53 pm

1 stop11h 33m

$268

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 12/10

5:28 am-2:14 pm

1 stop6h 46m

San Juan Luis Munoz Marin Intl

Wed 12/17

3:20 pm-8:30 pm

1 stop7h 10m

$278

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 1/11

11:43 am-11:40 pm

1 stop9h 57m

San Juan Luis Munoz Marin Intl

Wed 1/21

4:40 pm-11:42 pm

1 stop9h 02m

$295

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 1/31

4:17 pm-11:45 am

1 stop17h 28m

San Juan Luis Munoz Marin Intl

Thu 2/5

7:20 am-4:53 pm

1 stop11h 33m

$298

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 2/21

4:19 pm-11:45 am

1 stop17h 26m

San Juan Luis Munoz Marin Intl

Wed 2/25

7:20 am-5:30 pm

1 stop12h 10m

$301

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 12/9

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Mon 12/15

2:05 am-11:44 am

2 stops11h 39m

$311

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sat 2/14

1:20 pm-3:15 pm

2 stops23h 55m

Punta Cana

Fri 2/20

2:45 am-10:38 pm

2 stops21h 53m

$2,710

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Wed 1/14

5:17 pm-3:15 pm

2 stops19h 58m

Punta Cana

Fri 1/16

2:45 am-10:38 pm

2 stops21h 53m

$2,868

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

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

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 January is another great option to travel to Caribbean Islands, with average flight prices from Madison averaging around $433.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Madison to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $494. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $609. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Madison to Caribbean Islands in the afternoon for as low as $370. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $701. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 $503 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 $365 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

Direct flights

None
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?

  • 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?

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
DeltaPriceFrom $254Free CancellationRating
7.9
7,964 reviews
Search Delta flights
American AirlinesPriceFrom $279Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $293Free CancellationRating
7.4
8,926 reviews
Search United 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.

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