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Cheap flights from Madison to Caribbean Islands from $147

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 12/9. 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

Enter your travel dates to find the best prices.
Delta Logo
11:00 am - 11:44 pmMSN-SJU
10h 44m2 stops
Delta Logo
7:30 am - 4:19 pmSJU-MSN
10h 49m1 stop
$235Delta
Find Deal
mar., ene. 20 - mié., ene. 28
United Airlines Logo
8:15 am - 12:36 amMSN-SJU
14h 21m2 stops
United Airlines Logo
7:35 am - 1:52 pmSJU-MSN
7h 17m1 stop
$257United Airlines
Find Deal
mar., mar. 3 - mié., mar. 11
United Airlines Logo
8:15 am - 10:22 pmMSN-SJU
12h 07m2 stops
United Airlines Logo
8:30 am - 4:45 pmSJU-MSN
10h 15m2 stops
$264United Airlines
Find Deal
mar., dic. 9 - mar., dic. 16
American Airlines Logo
5:45 am - 10:09 pmMSN-SJU
14h 24m2 stops
American Airlines Logo
11:00 am - 9:56 pmSJU-MSN
12h 56m2 stops
$268American Airlines
Find Deal
mar., dic. 9 - mar., dic. 16
Delta Logo
10:54 am - 11:58 pmMSN-SJU
11h 04m2 stops
Delta Logo
6:15 am - 4:19 pmSJU-MSN
12h 04m1 stop
$278Delta
Find Deal
mar., feb. 24 - mié., mar. 4
American Airlines Logo
3:59 pm - 5:52 pmMSN-SJU
23h 53m2 stops
American Airlines Logo
8:20 am - 9:55 pmSJU-MSN
15h 35m2 stops
$295American Airlines
Find Deal
mar., dic. 2 - vie., dic. 5
American Airlines Logo
11:29 am - 9:39 pmMSN-SJU
8h 10m1 stop
American Airlines Logo
7:00 am - 4:20 pmSJU-MSN
11h 20m1 stop
$298American Airlines
Find Deal
jue., ene. 29 - mar., feb. 3
American Airlines Logo
11:23 am - 11:59 pmMSN-SJU
10h 36m2 stops
American Airlines Logo
6:00 am - 3:27 pmSJU-MSN
11h 27m2 stops
$301American Airlines
Find Deal
sáb., ene. 31 - jue., feb. 5
Delta Logo
11:44 am - 11:20 pmMSN-SJU
9h 36m1 stop
Delta Logo
7:00 am - 4:21 pmSJU-MSN
11h 21m1 stop
$317Delta
Find Deal
dom., dic. 7 - mié., dic. 10
Air Canada Logo
12:57 pm - 3:00 pmMSN-AUA
24h 03m2 stops
Air Canada Logo
3:05 pm - 3:02 pmAUA-MSN
24h 57m2 stops
$3,679Air Canada
Find Deal
mar., feb. 24 - mar., mar. 10

United Airlines flights from Madison to Caribbean Islands

Our best United Airlines deals on Madison to Caribbean Islands flight tickets
United Airlines
Mar 3
MSN8:15 amMadison Truax Field
14h 21m
2 stops
SJU12:36 amSan Juan Luis Munoz Marin Intl
Mar 11
SJU7:35 amSan Juan Luis Munoz Marin Intl
7h 17m
1 stop
MSN1:52 pmMadison Truax Field
$257
Find similar
United Airlines
Dec 9
MSN8:15 amMadison Truax Field
12h 07m
2 stops
SJU10:22 pmSan Juan Luis Munoz Marin Intl
Dec 16
SJU2:10 pmSan Juan Luis Munoz Marin Intl
10h 35m
1 stop
MSN10:45 pmMadison Truax Field
$264
Find similar
United Airlines
Mar 3
MSN6:30 amMadison Truax Field
7h 10m
1 stop
SJU3:40 pmSan Juan Luis Munoz Marin Intl
Mar 10
SJU1:05 amSan Juan Luis Munoz Marin Intl
14h 57m
2 stops
MSN3:02 pmMadison Truax Field
$319
Find similar

American Airlines flights from Madison to Caribbean Islands

Our best American Airlines deals on Madison to Caribbean Islands flight tickets
American Airlines
Dec 9
MSN10:25 amMadison Truax Field
11h 27m
1 stop
SJU11:52 pmSan Juan Luis Munoz Marin Intl
Dec 16
SJU6:00 amSan Juan Luis Munoz Marin Intl
10h 55m
2 stops
MSN2:55 pmMadison Truax Field
$268
Find similar
American Airlines
Dec 2
MSN3:59 pmMadison Truax Field
23h 53m
2 stops
SJU5:52 pmSan Juan Luis Munoz Marin Intl
Dec 5
SJU8:20 amSan Juan Luis Munoz Marin Intl
15h 35m
2 stops
MSN9:55 pmMadison Truax Field
$295
Find similar
American Airlines
Jan 29
MSN11:29 amMadison Truax Field
8h 10m
1 stop
SJU9:39 pmSan Juan Luis Munoz Marin Intl
Feb 3
SJU7:00 amSan Juan Luis Munoz Marin Intl
11h 20m
1 stop
MSN4:20 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 noviembre 5, 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

mar. 1/20

11:00 am-11:44 pm

2 stops10h 44m

San Juan Luis Munoz Marin Intl

mié. 1/28

7:30 am-4:19 pm

1 stop10h 49m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 3/3

8:15 am-12:36 am

2 stops14h 21m

San Juan Luis Munoz Marin Intl

mié. 3/11

7:35 am-1:52 pm

1 stop7h 17m

$257

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 12/9

8:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

mar. 12/16

8:30 am-4:45 pm

2 stops10h 15m

$264

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 12/9

5:45 am-10:09 pm

2 stops14h 24m

San Juan Luis Munoz Marin Intl

mar. 12/16

11:00 am-9:56 pm

2 stops12h 56m

$268

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 2/24

10:54 am-11:58 pm

2 stops11h 04m

San Juan Luis Munoz Marin Intl

mié. 3/4

6:15 am-4:19 pm

1 stop12h 04m

$278

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 12/2

3:59 pm-5:52 pm

2 stops23h 53m

San Juan Luis Munoz Marin Intl

vie. 12/5

8:20 am-9:55 pm

2 stops15h 35m

$295

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

jue. 1/29

11:29 am-9:39 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

mar. 2/3

7:00 am-4:20 pm

1 stop11h 20m

$298

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

sáb. 1/31

11:23 am-11:59 pm

2 stops10h 36m

San Juan Luis Munoz Marin Intl

jue. 2/5

6:00 am-3:27 pm

2 stops11h 27m

$301

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dom. 12/7

11:44 am-11:20 pm

1 stop9h 36m

San Juan Luis Munoz Marin Intl

mié. 12/10

7:00 am-4:21 pm

1 stop11h 21m

$317

MadisonOranjestad

MSN - AUA

MSNAUA

Madison Truax Field

mar. 2/24

12:57 pm-3:00 pm

2 stops24h 03m

Oranjestad Reina Beatrix

mar. 3/10

3:05 pm-3:02 pm

2 stops24h 57m

$3,679

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 $409.

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 $504 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 $225Free CancellationRating
7.9
8,004 reviews
Search Delta flights
United AirlinesPriceFrom $260Free CancellationRating
7.4
9,002 reviews
Search United Airlines flights
American AirlinesPriceFrom $269Free CancellationRating
7.2
11,042 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.

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1 adult
vie. 12/5
vie. 12/12
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