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Cheap flights from Caribbean to Madison from $203

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 12/5. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Caribbean to Madison

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:00 am - 9:15 pm
SJU
-
MSN
15h 15m
2 stops
Delta Logo
6:00 am - 1:16 pm
MSN
-
SJU
6h 16m
1 stop
$256Delta
Thu, Sep 17 - Mon, Sep 21
American Airlines Logo
3:47 pm - 11:09 pm
SJU
-
MSN
8h 22m
1 stop
American Airlines Logo
6:00 am - 10:24 pm
MSN
-
SJU
15h 24m
1 stop
$336American Airlines
Thu, Aug 20 - Thu, Sep 3
Multiple Airlines Logo
6:31 pm - 4:00 pm
SJU
-
MSN
22h 29m
1 stop
Multiple Airlines Logo
4:40 pm - 1:50 am
MSN
-
SJU
8h 10m
1 stop
$341Multiple Airlines
Mon, Sep 14 - Tue, Sep 22
Delta Logo
7:30 am - 4:18 pm
SJU
-
MSN
9h 48m
1 stop
Delta Logo
6:00 am - 1:16 pm
MSN
-
SJU
6h 16m
1 stop
$357Delta
Thu, Sep 17 - Mon, Sep 21
American Airlines Logo
10:16 am - 7:46 pm
SJU
-
MSN
10h 30m
2 stops
American Airlines Logo
8:05 pm - 2:50 pm
MSN
-
SJU
17h 45m
2 stops
$366American Airlines
Mon, Sep 14 - Tue, Sep 22
American Airlines Logo
6:00 am - 3:33 pm
SJU
-
MSN
10h 33m
2 stops
American Airlines Logo
6:30 am - 11:59 pm
MSN
-
SJU
16h 29m
1 stop
$376American Airlines
Thu, Aug 20 - Thu, Sep 3
United Airlines Logo
3:56 pm - 10:35 pm
SJU
-
MSN
7h 39m
1 stop
United Airlines Logo
5:00 am - 2:44 pm
MSN
-
SJU
8h 44m
1 stop
$381United Airlines
Wed, Sep 30 - Sat, Oct 3
American Airlines Logo
7:00 am - 9:41 pm
SJU
-
MSN
15h 41m
1 stop
American Airlines Logo
7:00 am - 10:59 pm
MSN
-
SJU
14h 59m
1 stop
$406American Airlines
Wed, Jul 8 - Tue, Jul 14
British Airways Logo
4:45 pm - 12:06 pm
SXM
-
MSN
20h 21m
2 stops
British Airways Logo
5:00 am - 3:44 pm
MSN
-
SXM
9h 44m
2 stops
$922British Airways
Sat, Jul 4 - Wed, Jul 8
United Airlines Logo
12:52 pm - 8:39 am
MBJ
-
MSN
19h 47m
2 stops
United Airlines Logo
5:00 am - 3:10 pm
MSN
-
MBJ
10h 10m
3 stops
$2,721United Airlines
Fri, Jul 3 - Mon, Aug 17

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Delta flights from Caribbean to Madison

Our best Delta deals on Caribbean to Madison flight tickets
Delta
Sep 17
SJU7:00 amSan Juan Luis Munoz Marin Intl
15h 15m
2 stops
MSN9:15 pmMadison Truax Field
Sep 21
MSN6:00 amMadison Truax Field
6h 16m
1 stop
SJU1:16 pmSan Juan Luis Munoz Marin Intl
$256
Delta
Sep 17
SJU7:30 amSan Juan Luis Munoz Marin Intl
9h 48m
1 stop
MSN4:18 pmMadison Truax Field
Sep 21
MSN6:00 amMadison Truax Field
6h 16m
1 stop
SJU1:16 pmSan Juan Luis Munoz Marin Intl
$357
Delta
Jul 4
SXM3:40 pmSimpson Bay Princess Juliana
23h 39m
1 stop
MSN2:19 pmMadison Truax Field
Jul 8
MSN5:48 amMadison Truax Field
7h 07m
1 stop
SXM1:55 pmSimpson Bay Princess Juliana
$1,416

American Airlines flights from Caribbean to Madison

Our best American Airlines deals on Caribbean to Madison flight tickets
American Airlines
Aug 20
SJU3:47 pmSan Juan Luis Munoz Marin Intl
8h 22m
1 stop
MSN11:09 pmMadison Truax Field
Sep 3
MSN6:00 amMadison Truax Field
15h 24m
1 stop
SJU10:24 pmSan Juan Luis Munoz Marin Intl
$336
American Airlines
Sep 14
SJU10:16 amSan Juan Luis Munoz Marin Intl
10h 30m
2 stops
MSN7:46 pmMadison Truax Field
Sep 22
MSN8:05 pmMadison Truax Field
17h 45m
2 stops
SJU2:50 pmSan Juan Luis Munoz Marin Intl
$366
American Airlines
Aug 20
SJU6:00 amSan Juan Luis Munoz Marin Intl
10h 33m
2 stops
MSN3:33 pmMadison Truax Field
Sep 3
MSN6:30 amMadison Truax Field
16h 29m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
$376

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 June 19, 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

Cheapest round-trip

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 9/17

7:00 am-9:15 pm

2 stops15h 15m

Madison Truax Field

Mon 9/21

6:00 am-1:16 pm

1 stop6h 16m

$256

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 8/20

3:47 pm-11:09 pm

1 stop8h 22m

Madison Truax Field

Thu 9/3

6:00 am-10:24 pm

1 stop15h 24m

$336

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Mon 9/14

6:31 pm-4:00 pm

1 stop22h 29m

Madison Truax Field

Tue 9/22

4:40 pm-1:50 am

1 stop8h 10m

$341
Quickest round-trip

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 9/17

7:30 am-4:18 pm

1 stop9h 48m

Madison Truax Field

Mon 9/21

6:00 am-1:16 pm

1 stop6h 16m

$357

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Mon 9/14

10:16 am-7:46 pm

2 stops10h 30m

Madison Truax Field

Tue 9/22

8:05 pm-2:50 pm

2 stops17h 45m

$366

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 8/20

6:00 am-3:33 pm

2 stops10h 33m

Madison Truax Field

Thu 9/3

6:30 am-11:59 pm

1 stop16h 29m

$376

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 9/30

3:56 pm-10:35 pm

1 stop7h 39m

Madison Truax Field

Sat 10/3

5:00 am-2:44 pm

1 stop8h 44m

$381

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 7/8

7:00 am-9:41 pm

1 stop15h 41m

Madison Truax Field

Tue 7/14

7:00 am-10:59 pm

1 stop14h 59m

$406

Simpson BayMadison

SXM - MSN

SXMMSN

Simpson Bay Princess Juliana

Sat 7/4

4:45 pm-12:06 pm

2 stops20h 21m

Madison Truax Field

Wed 7/8

5:00 am-3:44 pm

2 stops9h 44m

$922

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Fri 7/3

12:52 pm-8:39 am

2 stops19h 47m

Madison Truax Field

Mon 8/17

5:00 am-3:10 pm

3 stops10h 10m

$2,721

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 $108. 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 $240.

Can stopping save me money on Caribbean to Madison flights?

You could potentially save up to 24% 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 39m

Direct flights

None
The fastest flight from Caribbean to Madison takes 7h 39m
There are no direct flights from Caribbean to Madison. There are no popular flight routes from Caribbean to Madison.
Search flight deals

Frequently asked questions about flying from Caribbean to Madison

  • 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
11,703 reviews
Search American Airlines flights

Traveling to a place near Madison?

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

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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