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Cheap flights from Caribbean to Madison from $123

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 7/30. 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.
United Airlines Logo
2:40 pm - 8:55 am
MBJ
-
MSN
18h 15m
2 stops
United Airlines Logo
8:30 pm - 1:30 pm
MSN
-
MBJ
41h 00m
2 stops
$312United Airlines
Wed, May 6 - Thu, Sep 10
American Airlines Logo
12:25 pm - 11:54 pm
MBJ
-
MSN
11h 29m
1 stop
American Airlines Logo
6:00 am - 1:58 pm
MSN
-
MBJ
7h 58m
1 stop
$316American Airlines
Fri, May 8 - Tue, Sep 8
Delta Logo
4:59 pm - 8:49 am
MBJ
-
MSN
15h 50m
2 stops
Delta Logo
7:00 am - 3:34 pm
MSN
-
MBJ
8h 34m
2 stops
$317Delta
Thu, May 14 - Sat, Aug 29
American Airlines Logo
10:17 am - 11:54 pm
MBJ
-
MSN
13h 37m
1 stop
American Airlines Logo
5:46 pm - 10:50 am
MSN
-
MBJ
17h 04m
2 stops
$321American Airlines
Fri, May 8 - Tue, Sep 8
American Airlines Logo
7:00 am - 11:59 pm
SJU
-
MSN
17h 59m
1 stop
American Airlines Logo
6:01 am - 11:01 pm
MSN
-
SJU
16h 00m
1 stop
$326American Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
6:45 am - 10:32 pm
SJU
-
MSN
16h 47m
1 stop
American Airlines Logo
6:10 am - 10:05 pm
MSN
-
SJU
14h 55m
1 stop
$334American Airlines
Fri, May 15 - Mon, May 18
American Airlines Logo
7:00 am - 11:59 pm
SJU
-
MSN
17h 59m
1 stop
American Airlines Logo
6:01 am - 6:25 pm
MSN
-
SJU
11h 24m
2 stops
$366American Airlines
Fri, Jun 5 - Mon, Jun 8
Delta Logo
6:15 am - 4:25 pm
SJU
-
MSN
11h 10m
1 stop
Delta Logo
5:43 am - 4:33 pm
MSN
-
SJU
9h 50m
1 stop
$408Delta
Thu, May 7 - Tue, May 12
Multiple Airlines Logo
8:00 am - 8:25 am
SJU
-
MSN
25h 25m
1 stop
Multiple Airlines Logo
6:50 pm - 5:36 pm
MSN
-
SJU
21h 46m
2 stops
$434Multiple Airlines
Sun, Jul 5 - Fri, Jul 17
Multiple Airlines Logo
8:00 am - 8:25 am
SJU
-
MSN
25h 25m
1 stop
Multiple Airlines Logo
6:50 pm - 4:34 pm
MSN
-
SJU
20h 44m
1 stop
$449Multiple Airlines
Sun, Jul 5 - Mon, Jul 13

United Airlines flights from Caribbean to Madison

Our best United Airlines deals on Caribbean to Madison flight tickets
United Airlines
May 6
MBJ2:40 pmMontego Bay Sangster Intl
18h 15m
2 stops
MSN8:55 amMadison Truax Field
Sep 10
MSN8:30 pmMadison Truax Field
41h 00m
2 stops
MBJ1:30 pmMontego Bay Sangster Intl
$312
United Airlines
May 1
MBJ2:40 pmMontego Bay Sangster Intl
28h 27m
2 stops
MSN7:07 pmMadison Truax Field
Sep 3
MSN8:30 pmMadison Truax Field
41h 00m
2 stops
MBJ1:30 pmMontego Bay Sangster Intl
$367
United Airlines
May 1
MBJ2:40 pmMontego Bay Sangster Intl
18h 16m
2 stops
MSN8:56 amMadison Truax Field
Sep 3
MSN8:30 pmMadison Truax Field
41h 00m
2 stops
MBJ1:30 pmMontego Bay Sangster Intl
$408

American Airlines flights from Caribbean to Madison

Our best American Airlines deals on Caribbean to Madison flight tickets
American Airlines
May 8
MBJ12:25 pmMontego Bay Sangster Intl
11h 29m
1 stop
MSN11:54 pmMadison Truax Field
Sep 8
MSN6:00 amMadison Truax Field
7h 58m
1 stop
MBJ1:58 pmMontego Bay Sangster Intl
$316
American Airlines
May 8
MBJ10:17 amMontego Bay Sangster Intl
13h 37m
1 stop
MSN11:54 pmMadison Truax Field
Sep 8
MSN5:46 pmMadison Truax Field
17h 04m
2 stops
MBJ10:50 amMontego Bay Sangster Intl
$321
American Airlines
Jun 5
SJU7:00 amSan Juan Luis Munoz Marin Intl
17h 59m
1 stop
MSN11:59 pmMadison Truax Field
Jun 8
MSN6:01 amMadison Truax Field
16h 00m
1 stop
SJU11:01 pmSan Juan Luis Munoz Marin Intl
$326

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 April 22, 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

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Wed 5/6

2:40 pm-8:55 am

2 stops18h 15m

Madison Truax Field

Thu 9/10

8:30 pm-1:30 pm

2 stops41h 00m

$312
Quickest round-trip

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Fri 5/8

12:25 pm-11:54 pm

1 stop11h 29m

Madison Truax Field

Tue 9/8

6:00 am-1:58 pm

1 stop7h 58m

$316

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Thu 5/14

4:59 pm-8:49 am

2 stops15h 50m

Madison Truax Field

Sat 8/29

7:00 am-3:34 pm

2 stops8h 34m

$317

Montego BayMadison

MBJ - MSN

MBJMSN

Montego Bay Sangster Intl

Fri 5/8

10:17 am-11:54 pm

1 stop13h 37m

Madison Truax Field

Tue 9/8

5:46 pm-10:50 am

2 stops17h 04m

$321

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 6/5

7:00 am-11:59 pm

1 stop17h 59m

Madison Truax Field

Mon 6/8

6:01 am-11:01 pm

1 stop16h 00m

$326

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 5/15

6:45 am-10:32 pm

1 stop16h 47m

Madison Truax Field

Mon 5/18

6:10 am-10:05 pm

1 stop14h 55m

$334

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 6/5

7:00 am-11:59 pm

1 stop17h 59m

Madison Truax Field

Mon 6/8

6:01 am-6:25 pm

2 stops11h 24m

$366

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 5/7

6:15 am-4:25 pm

1 stop11h 10m

Madison Truax Field

Tue 5/12

5:43 am-4:33 pm

1 stop9h 50m

$408

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sun 7/5

8:00 am-8:25 am

1 stop25h 25m

Madison Truax Field

Fri 7/17

6:50 pm-5:36 pm

2 stops21h 46m

$434

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sun 7/5

8:00 am-8:25 am

1 stop25h 25m

Madison Truax Field

Mon 7/13

6:50 pm-4:34 pm

1 stop20h 44m

$449

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 30% 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 58m

Direct flights

None
The fastest flight from Caribbean to Madison takes 7h 58m
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
11,647 reviews
Search American Airlines flights
DeltaPriceFrom $449Free CancellationRating
7.9
8,430 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
Sun Prairie
Middleton
Fitchburg
Portage
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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