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Cheap flights from Madison to Caribbean Islands from $108

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 1/28. 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

American Airlines Logo
5:08 pm - 11:11 amMSN-SJU
17h 03m2 stops
American Airlines Logo
4:45 pm - 9:59 amSJU-MSN
18h 14m2 stops
$215American Airlines
Find Deal
Sat, Sep 6 - Sat, Sep 13
United Airlines Logo
6:30 am - 3:40 pmMSN-SJU
7h 10m1 stop
United Airlines Logo
8:10 am - 2:54 pmSJU-MSN
8h 44m1 stop
$225United Airlines
Find Deal
Sun, Nov 9 - Wed, Nov 19
United Airlines Logo
6:30 am - 2:44 pmMSN-SJU
7h 14m1 stop
United Airlines Logo
3:56 pm - 10:28 pmSJU-MSN
7h 32m1 stop
$244United Airlines
Find Deal
Fri, Oct 3 - Tue, Oct 7
American Airlines Logo
6:20 am - 6:15 pmMSN-SJU
10h 55m2 stops
American Airlines Logo
3:00 pm - 11:36 pmSJU-MSN
9h 36m1 stop
$245American Airlines
Find Deal
Mon, Sep 29 - Tue, Oct 7
American Airlines Logo
8:10 am - 11:37 pmMSN-SJU
14h 27m2 stops
American Airlines Logo
3:00 pm - 11:36 pmSJU-MSN
9h 36m1 stop
$255American Airlines
Find Deal
Mon, Sep 29 - Tue, Oct 7
Delta Logo
1:20 pm - 10:00 pmMSN-SJU
7h 40m1 stop
Delta Logo
7:00 am - 4:09 pmSJU-MSN
10h 09m2 stops
$345Delta
Find Deal
Sat, Sep 20 - Wed, Sep 24
Delta Logo
1:20 pm - 10:00 pmMSN-SJU
7h 40m1 stop
Delta Logo
7:30 am - 4:18 pmSJU-MSN
9h 48m1 stop
$445Delta
Find Deal
Sat, Sep 20 - Wed, Sep 24
Air Canada Logo
3:58 pm - 11:10 amMSN-MBJ
19h 12m2 stops
Air Canada Logo
12:10 pm - 8:43 pmMBJ-MSN
32h 33m2 stops
$1,100Air Canada
Find Deal
Wed, Sep 3 - Mon, Sep 15
LATAM Airlines Logo
5:15 pm - 3:15 pmMSN-PUJ
21h 00m2 stops
LATAM Airlines Logo
2:45 am - 10:30 pmPUJ-MSN
21h 45m2 stops
$2,512LATAM Airlines
Find Deal
Wed, Oct 29 - Mon, Nov 3
LATAM Airlines Logo
5:15 pm - 3:15 pmMSN-PUJ
21h 00m2 stops
LATAM Airlines Logo
2:45 am - 10:30 pmPUJ-MSN
21h 45m2 stops
$2,517LATAM Airlines
Find Deal
Wed, Oct 29 - Mon, Nov 3

American Airlines flights from Madison to Caribbean Islands

Our best American Airlines deals on Madison to Caribbean Islands flight tickets
American Airlines
Sep 6
MSN5:08 pmMadison Truax Field
17h 03m
2 stops
SJU11:11 amSan Juan Luis Munoz Marin Intl
Sep 13
SJU4:45 pmSan Juan Luis Munoz Marin Intl
18h 14m
2 stops
MSN9:59 amMadison Truax Field
$215
Find similar
American Airlines
Sep 29
MSN6:20 amMadison Truax Field
10h 55m
2 stops
SJU6:15 pmSan Juan Luis Munoz Marin Intl
Oct 7
SJU3:00 pmSan Juan Luis Munoz Marin Intl
9h 36m
1 stop
MSN11:36 pmMadison Truax Field
$245
Find similar
American Airlines
Sep 29
MSN8:10 amMadison Truax Field
14h 27m
2 stops
SJU11:37 pmSan Juan Luis Munoz Marin Intl
Oct 7
SJU3:00 pmSan Juan Luis Munoz Marin Intl
9h 36m
1 stop
MSN11:36 pmMadison Truax Field
$255
Find similar

United Airlines flights from Madison to Caribbean Islands

Our best United Airlines deals on Madison to Caribbean Islands flight tickets
United Airlines
Nov 9
MSN6:30 amMadison Truax Field
7h 10m
1 stop
SJU3:40 pmSan Juan Luis Munoz Marin Intl
Nov 19
SJU8:10 amSan Juan Luis Munoz Marin Intl
8h 44m
1 stop
MSN2:54 pmMadison Truax Field
$225
Find similar
United Airlines
Oct 3
MSN6:30 amMadison Truax Field
7h 14m
1 stop
SJU2:44 pmSan Juan Luis Munoz Marin Intl
Oct 7
SJU3:56 pmSan Juan Luis Munoz Marin Intl
7h 32m
1 stop
MSN10:28 pmMadison Truax Field
$244
Find similar
United Airlines
Oct 3
MSN6:30 amMadison Truax Field
7h 14m
1 stop
SJU2:44 pmSan Juan Luis Munoz Marin Intl
Oct 6
SJU1:05 amSan Juan Luis Munoz Marin Intl
11h 40m
2 stops
MSN11:45 amMadison Truax Field
$344
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 August 2, 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

Sat 9/6

5:08 pm-11:11 am

2 stops17h 03m

San Juan Luis Munoz Marin Intl

Sat 9/13

4:45 pm-9:59 am

2 stops18h 14m

$215

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 11/9

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Wed 11/19

8:10 am-2:54 pm

1 stop8h 44m

$225

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Fri 10/3

6:30 am-2:44 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Tue 10/7

3:56 pm-10:28 pm

1 stop7h 32m

$244

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 9/29

6:20 am-6:15 pm

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Tue 10/7

3:00 pm-11:36 pm

1 stop9h 36m

$245

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 9/29

8:10 am-11:37 pm

2 stops14h 27m

San Juan Luis Munoz Marin Intl

Tue 10/7

3:00 pm-11:36 pm

1 stop9h 36m

$255

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 9/20

1:20 pm-10:00 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 9/24

7:00 am-4:09 pm

2 stops10h 09m

$345

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 9/20

1:20 pm-10:00 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 9/24

7:30 am-4:18 pm

1 stop9h 48m

$445

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Wed 9/3

3:58 pm-11:10 am

2 stops19h 12m

Montego Bay Sangster Intl

Mon 9/15

12:10 pm-8:43 pm

2 stops32h 33m

$1,100

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Wed 10/29

5:15 pm-3:15 pm

2 stops21h 00m

Punta Cana

Mon 11/3

2:45 am-10:30 pm

2 stops21h 45m

$2,512

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Wed 10/29

5:15 pm-3:15 pm

2 stops21h 00m

Punta Cana

Mon 11/3

2:45 am-10:30 pm

2 stops21h 45m

$2,517

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 $353. The month of November is another great option to travel to Caribbean Islands, with average flight prices from Madison averaging around $418.

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 $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 $356 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

Best Price Found

$108

Fastest flight time

5h 24m

Direct flights

None

Airports in Caribbean Islands

8 airports
The best one-way flight to Caribbean Islands from Madison in the past 72 hours is $108. The best round-trip flight deal from Madison to Caribbean Islands found on momondo in the last 72 hours is $215.
The fastest flight from Madison to Caribbean Islands takes 5h 24m
There are no direct flights from Madison to Caribbean Islands. Popular non-direct routes for this connection are Madison Truax Field Airport - Punta Cana Airport, Madison Truax Field Airport - San Juan Luis Munoz Marin Intl Airport and Madison Truax Field Airport - Montego Bay Sangster Intl Airport.
There are 8 airports near Caribbean Islands: George Town Owen Roberts Intl (GCM), Santo Domingo Las Americas (SDQ), Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), Oranjestad Reina Beatrix (AUA), San Juan Luis Munoz Marin Intl (SJU)
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  • 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 $264Free CancellationRating
8.0
7,983 reviews
Search Delta flights
American AirlinesPriceFrom $269Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $331Free CancellationRating
7.4
8,904 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.

An easier way to manage your Caribbean Islands trip

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