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Cheap flights from Caribbean Islands 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 Islands 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 Islands 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
Thu, Jan 22 - Thu, Jan 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
Thu, Jan 22 - Thu, Jan 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
Wed, Apr 29 - Tue, 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
Wed, Feb 11 - Wed, 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
Thu, Jan 22 - Mon, Jan 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
Wed, Jan 21 - Mon, Jan 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
Thu, Jan 29 - Mon, 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
Thu, Jan 29 - Mon, 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
Thu, Jan 29 - Mon, 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
Thu, Jan 29 - Mon, Feb 2

American Airlines flights from Caribbean Islands to Madison

Our best American Airlines deals on Caribbean Islands 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 Islands to Madison

Our best United Airlines deals on Caribbean Islands 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 Islands 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 December 11, 2025.
Use the filters below to find and compare flights from Caribbean Islands 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

Thu 1/22

7:07 am-5:11 pm

1 stop12h 04m

Madison Truax Field

Thu 1/29

7:25 am-8:50 pm

2 stops11h 25m

$235

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 1/22

6:30 am-4:20 pm

1 stop11h 50m

Madison Truax Field

Thu 1/29

7:00 am-10:26 pm

1 stop13h 26m

$268

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 4/29

5:40 am-10:29 pm

1 stop17h 49m

Madison Truax Field

Tue 5/5

6:38 am-12:10 am

1 stop16h 32m

$273

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 2/11

7:00 am-4:20 pm

1 stop11h 20m

Madison Truax Field

Wed 2/18

10:45 am-11:27 pm

2 stops10h 42m

$298

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 1/22

8:35 am-2:10 pm

1 stop7h 35m

Madison Truax Field

Mon 1/26

6:30 am-3:40 pm

1 stop7h 10m

$325

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 1/21

2:05 am-2:10 pm

2 stops14h 05m

Madison Truax Field

Mon 1/26

6:30 am-3:40 pm

1 stop7h 10m

$368

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 1/29

3:40 pm-4:50 pm

2 stops27h 10m

Madison Truax Field

Mon 2/2

12:32 pm-4:00 pm

2 stops25h 28m

$1,430

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Thu 1/29

3:40 pm-2:52 pm

2 stops25h 12m

Madison Truax Field

Mon 2/2

12:32 pm-4:00 pm

2 stops25h 28m

$1,463

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 1/29

2:55 pm-8:54 pm

2 stops30h 59m

Madison Truax Field

Mon 2/2

6:20 pm-7:17 pm

2 stops23h 57m

$3,271

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 1/29

2:55 pm-5:36 pm

2 stops27h 41m

Madison Truax Field

Mon 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 Islands 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 Islands, 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 Islands 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 Islands 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 Islands 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 Islands to Madison flights?

No. A direct flight is the cheapest option for a flight between Caribbean Islands to Madison.

Cheap Caribbean Islands to Madison flight deals and tips

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

Fastest flight time

7h 25m

Direct flights

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

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

    Prices for flights from Caribbean Islands to Madison Truax Field Airport are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Caribbean Islands to Madison Truax Field Airport.

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

    The travel and health documents you'll need for your trip to Madison Truax Field Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Madison Truax Field Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Caribbean Islands to Madison?

Best airlines flying from Caribbean Islands to Madison

Compare and see reviews for airlines that fly from Caribbean Islands 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
8,008 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 Islands to Madison?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Caribbean Islands to Madison. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo enables you to select and highlight flights to Madison from Caribbean Islands with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Caribbean Islands to Madison.

I’m not ready to book a flight from Caribbean Islands to Madison right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Madison, momondo offers a useful price alert feature which will track prices for flights to Madison from Caribbean Islands and alert you when they change.

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