$152 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 8/31. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$535
Santo Domingo
Santo Domingo2 stops$620
Montego Bay
Montego Bay1 stop$480
Oranjestad
Oranjestad1 stop$666
Nassau
Nassau1 stop$611
Simpson Bay
Simpson Bay2 stops$575
Providenciales
Providenciales2 stops$593
Port of Spain
Port of Spain2 stops$774
George Town
George Town1 stop$579
Aguadilla
Aguadilla2 stops$718
St. John's
St. John's2 stops$756
Punta Cana
Punta Cana2 stops$535
Santo Domingo
Santo Domingo2 stops$620
Montego Bay
Montego Bay1 stop$480
Oranjestad
Oranjestad1 stop$666
Nassau
Nassau1 stop$611
Simpson Bay
Simpson Bay2 stops$575
Providenciales
Providenciales2 stops$593
Port of Spain
Port of Spain2 stops$774
George Town
George Town1 stop$579
Aguadilla
Aguadilla2 stops$718
St. John's
St. John's2 stops$756

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

Sun, Sep 6 - Wed, Sep 16
Delta Logo
5:45 am - 4:35 pm
MSN
-
SJU
9h 50m
1 stop
Delta Logo
7:00 am - 8:40 pm
SJU
-
MSN
14h 40m
2 stops
$317Delta
Sun, Sep 6 - Wed, Sep 16
American Airlines Logo
9:10 am - 12:15 am
MSN
-
SJU
14h 05m
1 stop
American Airlines Logo
3:55 pm - 12:21 am
SJU
-
MSN
9h 26m
1 stop
$326American Airlines
Sat, May 16 - Fri, May 22
American Airlines Logo
9:18 am - 8:55 pm
MSN
-
SJU
10h 37m
2 stops
American Airlines Logo
12:44 am - 10:38 am
SJU
-
MSN
10h 54m
1 stop
$366American Airlines
Sat, Aug 22 - Sun, Aug 30
Multiple Airlines Logo
10:27 am - 12:23 am
MSN
-
SJU
12h 56m
1 stop
Multiple Airlines Logo
8:00 am - 8:25 am
SJU
-
MSN
25h 25m
1 stop
$368Multiple Airlines
Sat, Sep 26 - Wed, Sep 30
United Airlines Logo
6:45 am - 8:38 pm
MSN
-
SJU
12h 53m
2 stops
United Airlines Logo
3:56 pm - 10:50 pm
SJU
-
MSN
7h 54m
1 stop
$371United Airlines
Sat, Aug 22 - Sun, Aug 30
Multiple Airlines Logo
10:27 am - 4:34 pm
MSN
-
SJU
29h 07m
2 stops
Multiple Airlines Logo
8:00 am - 8:25 am
SJU
-
MSN
25h 25m
1 stop
$402Multiple Airlines
Sat, Sep 12 - Sat, Sep 19
American Airlines Logo
7:15 am - 2:45 pm
MSN
-
SJU
6h 30m
1 stop
American Airlines Logo
3:55 pm - 12:21 am
SJU
-
MSN
9h 26m
1 stop
$406American Airlines
Tue, Jun 2 - Tue, Jun 30
American Airlines Logo
6:02 am - 11:01 pm
MSN
-
SJU
15h 59m
1 stop
American Airlines Logo
10:29 am - 7:52 pm
SJU
-
MSN
10h 23m
2 stops
$408American Airlines
Tue, May 5 - Fri, May 8
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:00 am - 11:37 am
SJU
-
MSN
11h 37m
2 stops
$416United Airlines
Sat, Aug 22 - Sat, Aug 29
Delta Logo
5:45 am - 3:00 pm
MSN
-
STT
8h 15m
1 stop
Delta Logo
4:10 pm - 10:35 pm
STT
-
MSN
7h 25m
1 stop
$487Delta
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 April and March, when the average cost of round-trip tickets is $676 and $658 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 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$152
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Madison to Montego Bay

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 8434 reviews
7.8Entertainment
7.2Food
7.9Comfort
8.5Crew
8.1Boarding
Airline reviews

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

10.0 ExcellentDavid, Apr 2026
DTW - SFO
Read more Delta reviews

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

Didn't like sitting on the waiting pad for 30 minutes right after departing the gate. If you're going to do that, just don't board so people can still get up and walk around in the terminal. My luggage was damaged by the baggage handlers.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

My bags were misplaced!!! Im in a foreign country with no bags

The entertainment options on the seat back video boards were nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

The crew was very kind, but no in-flight entertainment monitors and a 2 hour and 30 minute delay was extremely frustrating.

Everything was delayed and the staff sent me to the wrong gate, causing me to miss one of my flights. I arrived at my destination 6 hours later than I was supposed to.

Got home at 3am after deboarding the plane. No compensation offered by American

Delayed flight. Missed connection, AA put us on a later connecting flight. The connection flight was delayed 4 times and we had to deplane. Didnt get home until 3am, when I was supposed to be home at 8:30p. Zero compensation offered from American. I would not fly them again.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

It was really a terrific experience both going and returning on AA. Staff and crew were professional.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports