$128 Find Cheap Flights from Madison to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Caribbean departing on 3/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Madison to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$415
Santo Domingo
Santo Domingo1 stop$700
Montego Bay
Montego Bay1 stop$429
Oranjestad
Oranjestad1 stop$539
Nassau
Nassau1 stop$404
Simpson Bay
Simpson Bay2 stops$610
Providenciales
Providenciales2 stops$368
Bridgetown
Bridgetown2 stops$652
George Town
George Town1 stop$359
St. John's
St. John's2 stops$784
Aguadilla
Aguadilla2 stops$558
Punta Cana
Punta Cana2 stops$415
Santo Domingo
Santo Domingo1 stop$700
Montego Bay
Montego Bay1 stop$429
Oranjestad
Oranjestad1 stop$539
Nassau
Nassau1 stop$404
Simpson Bay
Simpson Bay2 stops$610
Providenciales
Providenciales2 stops$368
Bridgetown
Bridgetown2 stops$652
George Town
George Town1 stop$359
St. John's
St. John's2 stops$784
Aguadilla
Aguadilla2 stops$558

Book Cheap Madison to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Caribbean

mar., mar. 3 - mar., mar. 10
American Airlines Logo
7:15 am - 9:34 pm
MSN
-
SJU
12h 19m
2 stops
American Airlines Logo
1:30 am - 10:39 am
SJU
-
MSN
10h 09m
1 stop
$256American Airlines
mar., mar. 3 - mié., mar. 11
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m
1 stop
United Airlines Logo
3:52 pm - 10:42 pm
SJU
-
MSN
7h 50m
1 stop
$286United Airlines
mar., may. 5 - lun., may. 11
United Airlines Logo
9:55 am - 9:24 pm
MSN
-
SJU
10h 29m
2 stops
United Airlines Logo
1:00 am - 10:12 am
SJU
-
MSN
10h 12m
2 stops
$288United Airlines
mar., mar. 3 - mié., mar. 11
United Airlines Logo
8:15 am - 10:22 pm
MSN
-
SJU
12h 07m
2 stops
United Airlines Logo
3:52 pm - 10:42 pm
SJU
-
MSN
7h 50m
1 stop
$306United Airlines
lun., abr. 20 - mar., abr. 21
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
American Airlines Logo
6:00 am - 12:35 pm
SJU
-
MSN
7h 35m
1 stop
$314American Airlines
mié., abr. 15 - jue., abr. 30
United Airlines Logo
10:05 am - 8:34 pm
MSN
-
SJU
9h 29m
1 stop
United Airlines Logo
7:40 am - 3:00 pm
SJU
-
MSN
8h 20m
1 stop
$317United Airlines
mar., feb. 24 - mié., mar. 4
Delta Logo
7:00 am - 9:12 pm
MSN
-
SJU
12h 12m
2 stops
Delta Logo
4:30 pm - 10:48 pm
SJU
-
MSN
8h 18m
1 stop
$338Delta
mié., mar. 4 - mar., mar. 10
Delta Logo
5:38 am - 12:29 pm
MSN
-
GCM
5h 51m
1 stop
Delta Logo
1:12 pm - 10:34 pm
GCM
-
MSN
9h 22m
1 stop
$359Delta
mar., feb. 24 - jue., mar. 5
Air Canada Logo
12:57 pm - 2:45 pm
MSN
-
BGI
23h 48m
2 stops
Air Canada Logo
4:10 pm - 5:09 pm
BGI
-
MSN
26h 59m
2 stops
$1,492Air Canada
lun., mar. 2 - jue., mar. 5
Air Canada Logo
5:44 pm - 2:35 pm
MSN
-
BGI
18h 51m
2 stops
Air Canada Logo
4:10 pm - 2:58 pm
BGI
-
MSN
24h 48m
2 stops
$2,050Air Canada
Booking Insights

KAYAK's insights & trends for Madison to Caribbean flights

Get data-powered insights and trends into flights from Madison to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Madison to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Madison to Caribbean is September, when tickets cost $310 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $640 and $621 respectively.

How far in advance should I book a flight from Madison to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Madison to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Madison to Caribbean, you should book around 2 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$128
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Madison to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Madison to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Madison to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Madison to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Madison to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Madison to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Madison to Caribbean

 
Need help choosing which airline to fly with from Madison to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8169 reviews
7.9Comfort
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
Airline reviews

The flight was great as well as the airline staff

10.0 ExcellentPatty, Feb 2026
TPA - ATL
Read more Delta reviews

The flight was great as well as the airline staff

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

They double booked seats, the gate staff changed my ticket as I was boarding she went over to the computer and changed it without telling me. She messed up an entire three row section for me and others. Other travelers were outraged but the gate staff were so rude, so condescending saying it wasn't their problem to solve. I would rate this a zero if I could. Will not fly Delta again I'll stick with United and American.

It was nt delta. It was aeromexo. Service was awful. They served a very small drink and NO snack for a 3hr and 35min flight. Then for the first 30 min of the flight is was talk and talk over head interruption the movie/ show i picked to watch.

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

Terrible. Our first time back on United for 10 years, the seats in Polaris class are small and uncomfortable. They have squished too many people in to get more $$$. The staff are not friendly and not wanting to accommodate. I asked for two salads rather than a main meal and was advised no we wont do that. Then asked what I would like for breakfast and given something else anyway. I will not be flying United International anytime soon.

Same thing as flight from Pheonix to Newark. Uograded and Promised extra leg room and when I got to the seat it had none.

I upgraded my seat and was promised it would be next to the emergency door for extra leg room and they said it was premium plus but it was at the back of the plane...same thing happened from Newark to Dubai

Everything except the food and entertainment. It was a great experience though

Bad food, bad service, cold cabin with no additional blankets when asked for (they told me they don’t provide additional blankets). I’m a frequent traveler and this is one of the worst companies I traveled with (by the way I thought that I booked my ticket with Lufthansa but I didn’t see that the flights were handled by United).

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

The attendant on board was amazing. She should be doing business/first international long haul.

Although our flight was delayed the overall boarding process was very smooth and the crew was accommodating.

This was a horrible experience. I’ve experienced several delays at this point and still not home. I was supposed to be home by 8:30 last night and here I sit at 7 am on a plane STILL unable to go home because of American Airlines.

Lexus in first class was absolutely amazing! Beat flight attendant i’ve ever seen.

Generally good. Flight left on time and the seats are comfortable. Plenty of space in front if you in you choose a comfort plus seat, completely worth spending the extra money given the amount of hours the flight lasts. The food tastes good but I would say it’s a the amount is too little. The crew was friendly and efficient. There was a some turbulence at different points into the flight. American Airlines has good deals to NZ if you book with plenty of time before you plan on going.

the plane was so hot!! the air-conditioning was barely blowing. The flight was delayed, and we had to sit on the hot plane before take off for an extended amount of time, waiting on international passengers. Would not have been so bad if it was not so hot. They said it would get better after take off, but it did not.

They are always late and seats was also not having working charger

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

did not have enough meal for first class passengers so offer us snack

Arrived 40 min early which was great - sat in runway for 35 min so no gain. Then waited for luggage 45 min. They need to staff accordingly knowing its one of the busiest week in Phx

Broke my luggage and I can't get a resolution yet.

My flight got rerouted due to crew rest. I was sent to Dallas customer service was not very polite. Was given a $40 room voucher for Motel 6 and $12 to eat with. It delayed me by a day. Where if I would have just stuck with my original flight Arizona was delayed to Cleveland and I could have made it home. They put me on a 9:00 flight out of Dallas to Cleveland without my knowledge or consent. When originally I was told it would be 8:45 a.m. on February 1st. I told them I could not take the 9:00 flight because I did not have anybody to pick me up from the airport at that time. I'm extremely disappointed in how I was treated. And I will not fly American Airlines again.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports