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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 2/9. 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.
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m1 stop
United Airlines Logo
2:05 am - 11:51 am
SJU
-
MSN
11h 46m2 stops
$235United Airlines
mar., ene. 27 - vie., ene. 30
United Airlines Logo
8:15 am - 10:22 pm
MSN
-
SJU
12h 07m2 stops
United Airlines Logo
1:05 am - 11:58 am
SJU
-
MSN
11h 53m2 stops
$257United Airlines
mar., mar. 3 - mar., mar. 10
American Airlines Logo
7:00 am - 10:26 pm
MSN
-
SJU
13h 26m1 stop
American Airlines Logo
6:00 am - 12:46 pm
SJU
-
MSN
8h 46m1 stop
$268American Airlines
jue., ene. 29 - jue., feb. 5
American Airlines Logo
3:33 pm - 4:00 am
MSN
-
SJU
11h 27m1 stop
American Airlines Logo
11:45 am - 10:51 pm
SJU
-
MSN
12h 06m2 stops
$290American Airlines
mar., abr. 28 - mié., abr. 29
American Airlines Logo
4:30 pm - 12:27 pm
MSN
-
SJU
17h 57m2 stops
American Airlines Logo
5:51 pm - 10:57 pm
SJU
-
MSN
7h 06m1 stop
$295American Airlines
mar., feb. 10 - mié., feb. 18
Delta Logo
6:20 am - 4:09 pm
MSN
-
PUJ
7h 49m1 stop
Delta Logo
4:32 pm - 2:04 pm
PUJ
-
MSN
22h 32m2 stops
$408Delta
mar., mar. 3 - mié., mar. 11
Delta Logo
6:20 am - 4:09 pm
MSN
-
PUJ
7h 49m1 stop
Delta Logo
1:45 pm - 10:58 pm
PUJ
-
MSN
10h 13m1 stop
$474Delta
lun., mar. 2 - lun., mar. 9
Multiple Airlines Logo
6:36 pm - 2:31 pm
MSN
-
STT
17h 55m1 stop
Multiple Airlines Logo
3:36 pm - 5:56 pm
STT
-
MSN
28h 20m1 stop
$511Multiple Airlines
mié., feb. 18 - mar., feb. 24
Multiple Airlines Logo
6:36 pm - 2:31 pm
MSN
-
STT
17h 55m1 stop
Multiple Airlines Logo
5:40 pm - 5:56 pm
STT
-
MSN
26h 16m2 stops
$540Multiple Airlines
mié., feb. 18 - mar., feb. 24
Copa Airlines Logo
8:15 am - 11:32 am
MSN
-
SDQ
25h 17m2 stops
Copa Airlines Logo
7:05 pm - 7:07 pm
SDQ
-
MSN
26h 02m2 stops
$699Copa Airlines
jue., ene. 15 - lun., ene. 19

Delta flights from Madison to Caribbean Islands

Our best Delta deals on Madison to Caribbean Islands flight tickets
Delta
Jan 20
MSN11:31 amMadison Truax Field
10h 14m
2 stops
SJU11:45 pmSan Juan Luis Munoz Marin Intl
Jan 28
SJU7:00 amSan Juan Luis Munoz Marin Intl
12h 11m
2 stops
MSN5:11 pmMadison Truax Field
$245
Find similar
Delta
Jan 18
MSN1:20 pmMadison Truax Field
8h 25m
1 stop
SJU11:45 pmSan Juan Luis Munoz Marin Intl
Jan 28
SJU7:00 amSan Juan Luis Munoz Marin Intl
12h 11m
2 stops
MSN5:11 pmMadison Truax Field
$288
Find similar
Delta
Jan 18
MSN1:20 pmMadison Truax Field
8h 25m
1 stop
SJU11:45 pmSan Juan Luis Munoz Marin Intl
Jan 23
SJU4:30 pmSan Juan Luis Munoz Marin Intl
8h 20m
1 stop
MSN10:50 pmMadison Truax Field
$331
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 22
MSN7:25 amMadison Truax Field
11h 25m
2 stops
SJU8:50 pmSan Juan Luis Munoz Marin Intl
Jan 27
SJU1:24 pmSan Juan Luis Munoz Marin Intl
11h 35m
2 stops
MSN10:59 pmMadison Truax Field
$268
Find similar
American Airlines
Feb 10
MSN7:00 amMadison Truax Field
13h 26m
1 stop
SJU10:26 pmSan Juan Luis Munoz Marin Intl
Feb 18
SJU7:00 amSan Juan Luis Munoz Marin Intl
10h 30m
2 stops
MSN3:30 pmMadison Truax Field
$295
Find similar
American Airlines
Jan 31
MSN8:00 amMadison Truax Field
10h 50m
2 stops
SJU8:50 pmSan Juan Luis Munoz Marin Intl
Feb 5
SJU6:00 amSan Juan Luis Munoz Marin Intl
11h 27m
2 stops
MSN3:27 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 diciembre 11, 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. 1/27

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

vie. 1/30

2:05 am-11:51 am

2 stops11h 46m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 3/3

8:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

mar. 3/10

1:05 am-11:58 am

2 stops11h 53m

$257

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

jue. 1/29

7:00 am-10:26 pm

1 stop13h 26m

San Juan Luis Munoz Marin Intl

jue. 2/5

6:00 am-12:46 pm

1 stop8h 46m

$268

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 4/28

3:33 pm-4:00 am

1 stop11h 27m

San Juan Luis Munoz Marin Intl

mié. 4/29

11:45 am-10:51 pm

2 stops12h 06m

$290

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 2/10

4:30 pm-12:27 pm

2 stops17h 57m

San Juan Luis Munoz Marin Intl

mié. 2/18

5:51 pm-10:57 pm

1 stop7h 06m

$295

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

mar. 3/3

6:20 am-4:09 pm

1 stop7h 49m

Punta Cana

mié. 3/11

4:32 pm-2:04 pm

2 stops22h 32m

$408

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

lun. 3/2

6:20 am-4:09 pm

1 stop7h 49m

Punta Cana

lun. 3/9

1:45 pm-10:58 pm

1 stop10h 13m

$474

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

mié. 2/18

6:36 pm-2:31 pm

1 stop17h 55m

Saint Thomas Island Cyril E King

mar. 2/24

3:36 pm-5:56 pm

1 stop28h 20m

$511

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

mié. 2/18

6:36 pm-2:31 pm

1 stop17h 55m

Saint Thomas Island Cyril E King

mar. 2/24

5:40 pm-5:56 pm

2 stops26h 16m

$540

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

jue. 1/15

8:15 am-11:32 am

2 stops25h 17m

Santo Domingo Las Americas

lun. 1/19

7:05 pm-7:07 pm

2 stops26h 02m

$699

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 October is another great option to travel to Caribbean Islands, with average flight prices from Madison averaging around $407.

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 $502 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 $375 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 51m

Direct flights

None
The fastest flight from Madison to Caribbean Islands takes 5h 51m
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
8,008 reviews
Search Delta flights
United AirlinesPriceFrom $257Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
American AirlinesPriceFrom $269Free CancellationRating
7.2
11,050 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.

An easier way to manage your Caribbean Islands trip

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