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Cheap flights from Caribbean to Madison from $133

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 4/22. 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.
Frontier Logo
12:07 pm - 11:34 am
SJU
-
MSN
24h 27m
1 stop
Frontier Logo
12:14 pm - 1:58 am
MSN
-
SJU
12h 44m
1 stop
$336Frontier
Do, Mrz 12 - So, Mrz 15
American Airlines Logo
12:59 am - 7:45 am
SJU
-
MSN
7h 46m
1 stop
American Airlines Logo
2:35 pm - 12:15 am
MSN
-
SJU
8h 40m
1 stop
$352American Airlines
Do, Mai 21 - Di, Mai 26
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
American Airlines Logo
11:35 am - 8:51 pm
MSN
-
SJU
8h 16m
1 stop
$378American Airlines
Do, Apr 9 - Mi, Apr 15
American Airlines Logo
12:59 am - 7:45 am
SJU
-
MSN
7h 46m
1 stop
American Airlines Logo
1:25 pm - 9:39 am
MSN
-
SJU
19h 14m
2 stops
$397American Airlines
Do, Mai 21 - Mo, Mai 25
American Airlines Logo
12:59 am - 7:45 am
SJU
-
MSN
7h 46m
1 stop
American Airlines Logo
6:00 am - 6:25 pm
MSN
-
SJU
11h 25m
2 stops
$421American Airlines
Do, Mai 21 - Di, Mai 26
American Airlines Logo
12:59 am - 7:45 am
SJU
-
MSN
7h 46m
1 stop
American Airlines Logo
2:35 pm - 12:15 am
MSN
-
SJU
8h 40m
1 stop
$456American Airlines
Do, Mai 21 - Mi, Mai 27
American Airlines Logo
4:38 pm - 12:03 pm
SJU
-
MSN
20h 25m
2 stops
American Airlines Logo
4:34 pm - 2:06 pm
MSN
-
SJU
20h 32m
2 stops
$469American Airlines
Fr, Jun 5 - Mo, Jun 8
JetBlue Logo
7:30 am - 4:25 pm
SJU
-
MSN
9h 55m
1 stop
JetBlue Logo
11:11 am - 7:53 pm
MSN
-
SJU
7h 42m
1 stop
$486JetBlue
Fr, Jun 5 - Mo, Jun 8
American Airlines Logo
1:31 pm - 11:28 pm
SJU
-
MSN
10h 57m
2 stops
American Airlines Logo
6:45 am - 6:10 pm
MSN
-
SJU
10h 25m
2 stops
$490American Airlines
Do, Apr 9 - Mi, Apr 15
United Airlines Logo
1:00 am - 10:09 am
SJU
-
MSN
10h 09m
1 stop
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
$491United Airlines
Do, Jun 4 - Di, Jun 9

Frontier flights from Caribbean to Madison

Our best Frontier deals on Caribbean to Madison flight tickets
Frontier
Mar 12
SJU12:07 pmSan Juan Luis Munoz Marin Intl
24h 27m
1 stop
MSN11:34 amMadison Truax Field
Mar 15
MSN12:14 pmMadison Truax Field
12h 44m
1 stop
SJU1:58 amSan Juan Luis Munoz Marin Intl
$336
Frontier
Mar 5
SJU3:58 amSan Juan Luis Munoz Marin Intl
9h 21m
1 stop
MSN11:19 amMadison Truax Field
Mar 9
MSN12:29 pmMadison Truax Field
12h 29m
1 stop
SJU1:58 amSan Juan Luis Munoz Marin Intl
$346
Frontier
Mar 22
SJU6:30 amSan Juan Luis Munoz Marin Intl
11h 32m
1 stop
MSN5:02 pmMadison Truax Field
Mar 26
MSN2:16 pmMadison Truax Field
7h 29m
1 stop
SJU10:45 pmSan Juan Luis Munoz Marin Intl
$890

American Airlines flights from Caribbean to Madison

Our best American Airlines deals on Caribbean to Madison flight tickets
American Airlines
May 21
SJU12:59 amSan Juan Luis Munoz Marin Intl
7h 46m
1 stop
MSN7:45 amMadison Truax Field
May 26
MSN2:35 pmMadison Truax Field
8h 40m
1 stop
SJU12:15 amSan Juan Luis Munoz Marin Intl
$352
American Airlines
Apr 9
SJU11:59 pmSan Juan Luis Munoz Marin Intl
12h 06m
1 stop
MSN11:05 amMadison Truax Field
Apr 15
MSN11:35 amMadison Truax Field
8h 16m
1 stop
SJU8:51 pmSan Juan Luis Munoz Marin Intl
$378
American Airlines
May 21
SJU12:59 amSan Juan Luis Munoz Marin Intl
7h 46m
1 stop
MSN7:45 amMadison Truax Field
May 25
MSN1:25 pmMadison Truax Field
19h 14m
2 stops
SJU9:39 amSan Juan Luis Munoz Marin Intl
$397

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 Februar 28, 2026.
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

Do 3/12

12:07 pm-11:34 am

1 stop24h 27m

Madison Truax Field

So 3/15

12:14 pm-1:58 am

1 stop12h 44m

$336

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Do 5/21

12:59 am-7:45 am

1 stop7h 46m

Madison Truax Field

Di 5/26

2:35 pm-12:15 am

1 stop8h 40m

$352

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Do 4/9

11:59 pm-11:05 am

1 stop12h 06m

Madison Truax Field

Mi 4/15

11:35 am-8:51 pm

1 stop8h 16m

$378

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Do 5/21

12:59 am-7:45 am

1 stop7h 46m

Madison Truax Field

Mo 5/25

1:25 pm-9:39 am

2 stops19h 14m

$397

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Do 5/21

12:59 am-7:45 am

1 stop7h 46m

Madison Truax Field

Di 5/26

6:00 am-6:25 pm

2 stops11h 25m

$421

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Do 5/21

12:59 am-7:45 am

1 stop7h 46m

Madison Truax Field

Mi 5/27

2:35 pm-12:15 am

1 stop8h 40m

$456

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fr 6/5

4:38 pm-12:03 pm

2 stops20h 25m

Madison Truax Field

Mo 6/8

4:34 pm-2:06 pm

2 stops20h 32m

$469

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fr 6/5

7:30 am-4:25 pm

1 stop9h 55m

Madison Truax Field

Mo 6/8

11:11 am-7:53 pm

1 stop7h 42m

$486

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Do 4/9

1:31 pm-11:28 pm

2 stops10h 57m

Madison Truax Field

Mi 4/15

6:45 am-6:10 pm

2 stops10h 25m

$490

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Do 6/4

1:00 am-10:09 am

1 stop10h 09m

Madison Truax Field

Di 6/9

6:30 am-2:44 pm

1 stop7h 14m

$491

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

Can stopping save me money on Caribbean to Madison flights?

You could potentially save up to 4% 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 37m

Direct flights

None
The fastest flight from Caribbean to Madison takes 7h 37m
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
7.1
11,367 reviews
Search American Airlines flights
DeltaPriceFrom $449Free CancellationRating
7.9
8,245 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
Fitchburg
Portage
Sun Prairie
Middleton
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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