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Cheap flights from Caribbean to Madison 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 Caribbean to Madison departing on 2/6. 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 Caribbean to Madison

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
7:07 am - 5:11 pm
SJU
-
MSN
12h 04m1 stop
American Airlines Logo
7:25 am - 8:50 pm
MSN
-
SJU
11h 25m2 stops
$235American Airlines
jue., ene. 22 - jue., ene. 29
American Airlines Logo
6:30 am - 4:20 pm
SJU
-
MSN
11h 50m1 stop
American Airlines Logo
7:00 am - 10:26 pm
MSN
-
SJU
13h 26m1 stop
$268American Airlines
jue., ene. 22 - jue., ene. 29
American Airlines Logo
5:40 am - 10:29 pm
SJU
-
MSN
17h 49m1 stop
American Airlines Logo
6:38 am - 12:10 am
MSN
-
SJU
16h 32m1 stop
$273American Airlines
mié., abr. 29 - mar., may. 5
American Airlines Logo
7:00 am - 4:20 pm
SJU
-
MSN
11h 20m1 stop
American Airlines Logo
10:45 am - 11:27 pm
MSN
-
SJU
10h 42m2 stops
$298American Airlines
mié., feb. 11 - mié., feb. 18
United Airlines Logo
8:35 am - 2:10 pm
SJU
-
MSN
7h 35m1 stop
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m1 stop
$325United Airlines
jue., ene. 22 - lun., ene. 26
United Airlines Logo
2:05 am - 2:10 pm
SJU
-
MSN
14h 05m2 stops
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m1 stop
$368United Airlines
mié., ene. 21 - lun., ene. 26
Air Canada Logo
3:40 pm - 4:50 pm
SXM
-
MSN
27h 10m2 stops
Air Canada Logo
12:32 pm - 4:00 pm
MSN
-
SXM
25h 28m2 stops
$1,430Air Canada
jue., ene. 29 - lun., feb. 2
Air Canada Logo
3:40 pm - 2:52 pm
SXM
-
MSN
25h 12m2 stops
Air Canada Logo
12:32 pm - 4:00 pm
MSN
-
SXM
25h 28m2 stops
$1,463Air Canada
jue., ene. 29 - lun., feb. 2
WestJet Logo
2:55 pm - 8:54 pm
MBJ
-
MSN
30h 59m2 stops
WestJet Logo
6:20 pm - 7:17 pm
MSN
-
MBJ
23h 57m2 stops
$3,271WestJet
jue., ene. 29 - lun., feb. 2
WestJet Logo
2:55 pm - 5:36 pm
MBJ
-
MSN
27h 41m2 stops
WestJet Logo
11:00 am - 7:17 pm
MSN
-
MBJ
31h 17m2 stops
$3,273WestJet
jue., ene. 29 - lun., feb. 2

American Airlines flights from Caribbean to Madison

Our best American Airlines deals on Caribbean to Madison flight tickets
American Airlines
Jan 22
SJU7:07 amSan Juan Luis Munoz Marin Intl
12h 04m
1 stop
MSN5:11 pmMadison Truax Field
Jan 29
MSN7:25 amMadison Truax Field
11h 25m
2 stops
SJU8:50 pmSan Juan Luis Munoz Marin Intl
$235
Find similar
American Airlines
Jan 22
SJU6:30 amSan Juan Luis Munoz Marin Intl
11h 50m
1 stop
MSN4:20 pmMadison Truax Field
Jan 29
MSN7:00 amMadison Truax Field
13h 26m
1 stop
SJU10:26 pmSan Juan Luis Munoz Marin Intl
$268
Find similar
American Airlines
Apr 29
SJU5:40 amSan Juan Luis Munoz Marin Intl
17h 49m
1 stop
MSN10:29 pmMadison Truax Field
May 5
MSN6:38 amMadison Truax Field
16h 32m
1 stop
SJU12:10 amSan Juan Luis Munoz Marin Intl
$273
Find similar

United Airlines flights from Caribbean to Madison

Our best United Airlines deals on Caribbean to Madison flight tickets
United Airlines
Jan 22
SJU8:35 amSan Juan Luis Munoz Marin Intl
7h 35m
1 stop
MSN2:10 pmMadison Truax Field
Jan 26
MSN6:30 amMadison Truax Field
7h 10m
1 stop
SJU3:40 pmSan Juan Luis Munoz Marin Intl
$325
Find similar
United Airlines
Jan 21
SJU2:05 amSan Juan Luis Munoz Marin Intl
14h 05m
2 stops
MSN2:10 pmMadison Truax Field
Jan 26
MSN6:30 amMadison Truax Field
7h 10m
1 stop
SJU3:40 pmSan Juan Luis Munoz Marin Intl
$368
Find similar
United Airlines
Dec 25
NAS1:05 pmNassau Intl
8h 58m
2 stops
MSN9:03 pmMadison Truax Field
Jan 3
MSN5:26 pmMadison Truax Field
19h 07m
2 stops
NAS1:33 pmNassau Intl
$410
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean to Madison 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 Caribbean to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

jue. 1/22

7:07 am-5:11 pm

1 stop12h 04m

Madison Truax Field

jue. 1/29

7:25 am-8:50 pm

2 stops11h 25m

$235

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

jue. 1/22

6:30 am-4:20 pm

1 stop11h 50m

Madison Truax Field

jue. 1/29

7:00 am-10:26 pm

1 stop13h 26m

$268

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

mié. 4/29

5:40 am-10:29 pm

1 stop17h 49m

Madison Truax Field

mar. 5/5

6:38 am-12:10 am

1 stop16h 32m

$273

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

mié. 2/11

7:00 am-4:20 pm

1 stop11h 20m

Madison Truax Field

mié. 2/18

10:45 am-11:27 pm

2 stops10h 42m

$298

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

jue. 1/22

8:35 am-2:10 pm

1 stop7h 35m

Madison Truax Field

lun. 1/26

6:30 am-3:40 pm

1 stop7h 10m

$325

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

mié. 1/21

2:05 am-2:10 pm

2 stops14h 05m

Madison Truax Field

lun. 1/26

6:30 am-3:40 pm

1 stop7h 10m

$368

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

jue. 1/29

3:40 pm-4:50 pm

2 stops27h 10m

Madison Truax Field

lun. 2/2

12:32 pm-4:00 pm

2 stops25h 28m

$1,430

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

jue. 1/29

3:40 pm-2:52 pm

2 stops25h 12m

Madison Truax Field

lun. 2/2

12:32 pm-4:00 pm

2 stops25h 28m

$1,463

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

jue. 1/29

2:55 pm-8:54 pm

2 stops30h 59m

Madison Truax Field

lun. 2/2

6:20 pm-7:17 pm

2 stops23h 57m

$3,271

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

jue. 1/29

2:55 pm-5:36 pm

2 stops27h 41m

Madison Truax Field

lun. 2/2

11:00 am-7:17 pm

2 stops31h 17m

$3,273

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 Madison from

How to get the cheapest flight ticket from Caribbean to Madison

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 Madison?

The month of September is, on average, the cheapest month to fly to Madison from Caribbean, with most prices found around $285. If you’re not able to fly to Madison in September, then October is your next best option. Flight prices from Caribbean to Madison during October average around $296.

What is the cheapest day to depart on your flight to Madison?

The cheapest day to depart from Caribbean to Madison is on a Tuesday when prices can be found for as low as $452. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Saturday is $617.

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

According to our data, the cheapest time of day to fly to Madison is in the morning. momondo users have found flights departing from Caribbean to Madison in the morning for as low as $477. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Madison is in the afternoon when prices are around $604.

Can stopping save me money on Caribbean to Madison flights?

You could potentially save up to 36% on your flight if you consider stops on a Caribbean to Madison flight.

Cheap Caribbean to Madison flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Caribbean to Madison

Fastest flight time

7h 25m

Direct flights

None
The fastest flight from Caribbean to Madison takes 7h 25m
There are no direct flights from Caribbean to Madison. There are no popular flight routes from Caribbean to Madison.
Search flight deals

  • When did momondo last update prices for flights from Caribbean to Madison Truax Field Airport?

    Prices for flights from Caribbean to Madison Truax Field Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Caribbean to Madison Truax Field Airport?

  • How old do you have to be to fly from Caribbean to Madison Truax Field Airport?

    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 Caribbean to Madison Truax Field Airport.

  • What documentation or ID do you need to fly to Madison Truax Field Airport?

    The travel and health documents required for your trip to Madison Truax Field Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Madison Truax Field Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Caribbean to Madison

Compare and see reviews for airlines that fly from Caribbean to Madison with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $265Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
DeltaPriceFrom $449Free CancellationRating
7.9
8,007 reviews
Search Delta flights

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Wisconsin Dells
Baraboo
Middleton
Portage
Fitchburg
Sun Prairie
Windsor
Cambridge
Oxford
Evansville

Why use momondo?

Why should I use momondo to find a flight deal from Caribbean to Madison?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Caribbean to Madison for you.

Can I find flights from Caribbean to Madison with flexible booking policies on momondo?

All flight searches from Caribbean to Madison on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Caribbean to Madison?

Once all potential Caribbean to Madison 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 Caribbean to Madison right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Madison from Caribbean. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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