$133 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 9/8. 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 Cana1 stop$530
Santo Domingo
Santo Domingo2 stops$620
Montego Bay
Montego Bay1 stop$372
Oranjestad
Oranjestad1 stop$490
Nassau
Nassau1 stop$518
Simpson Bay
Simpson Bay2 stops$520
Providenciales
Providenciales1 stop$533
Port of Spain
Port of Spain2 stops$784
Bridgetown
Bridgetown2 stops$762
George Town
George Town1 stop$475
Aguadilla
Aguadilla2 stops$296
St. John's
St. John's2 stops$835
Punta Cana
Punta Cana1 stop$530
Santo Domingo
Santo Domingo2 stops$620
Montego Bay
Montego Bay1 stop$372
Oranjestad
Oranjestad1 stop$490
Nassau
Nassau1 stop$518
Simpson Bay
Simpson Bay2 stops$520
Providenciales
Providenciales1 stop$533
Port of Spain
Port of Spain2 stops$784
Bridgetown
Bridgetown2 stops$762
George Town
George Town1 stop$475
Aguadilla
Aguadilla2 stops$296
St. John's
St. John's2 stops$835

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

Sat, Oct 17 - Tue, Oct 27
United Airlines Logo
6:42 am - 8:38 pm
MSN
-
SJU
12h 56m
2 stops
United Airlines Logo
7:05 am - 5:02 pm
SJU
-
MSN
10h 57m
2 stops
$296United Airlines
Wed, Sep 9 - Sat, Sep 12
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:00 am - 9:40 am
SJU
-
MSN
9h 40m
2 stops
$301United Airlines
Sun, Sep 6 - Wed, Sep 16
Delta Logo
5:43 am - 4:38 pm
MSN
-
SJU
9h 55m
1 stop
Delta Logo
2:59 pm - 10:53 pm
SJU
-
MSN
8h 54m
1 stop
$323Delta
Sat, Aug 22 - Fri, Aug 28
American Airlines Logo
6:40 am - 9:55 pm
MSN
-
SJU
14h 15m
2 stops
American Airlines Logo
12:55 am - 9:26 am
SJU
-
MSN
9h 31m
1 stop
$326American Airlines
Wed, Aug 12 - Tue, Aug 18
Multiple Airlines Logo
10:27 am - 12:41 am
MSN
-
SJU
13h 14m
1 stop
Multiple Airlines Logo
5:37 pm - 9:47 am
SJU
-
MSN
17h 10m
1 stop
$355Multiple Airlines
Tue, Aug 25 - Fri, Aug 28
United Airlines Logo
6:30 am - 8:38 pm
MSN
-
SJU
13h 08m
2 stops
United Airlines Logo
7:00 am - 8:53 pm
SJU
-
MSN
14h 53m
2 stops
$356United Airlines
Sun, Sep 6 - Wed, Sep 16
Delta Logo
5:43 am - 4:38 pm
MSN
-
SJU
9h 55m
1 stop
Delta Logo
2:59 pm - 10:53 pm
SJU
-
MSN
8h 54m
1 stop
$362Delta
Sat, Aug 22 - Sat, Aug 29
United Airlines Logo
8:10 am - 8:38 pm
MSN
-
SJU
11h 28m
2 stops
United Airlines Logo
7:00 am - 6:56 pm
SJU
-
MSN
12h 56m
2 stops
$364United Airlines
Mon, Oct 19 - Wed, Oct 28
American Airlines Logo
8:25 pm - 1:45 pm
MSN
-
SJU
16h 20m
1 stop
American Airlines Logo
6:00 am - 10:19 pm
SJU
-
MSN
17h 19m
1 stop
$366American Airlines
Wed, Sep 16 - Mon, Sep 21
Multiple Airlines Logo
9:40 am - 2:35 pm
MSN
-
BGI
27h 55m
2 stops
Multiple Airlines Logo
4:50 pm - 6:24 pm
BGI
-
MSN
26h 34m
2 stops
$2,032Multiple Airlines
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 March, when tickets cost $163 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $418 and $356 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 3 weeks before departure, which saves you about 26% 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$133
Best time to beat the crowds with an average 14% drop 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.
7.8
DeltaOverall score based on 8453 reviews
7.2Food
7.8Comfort
7.8Entertainment
8.5Crew
8.1Boarding
Airline reviews

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

4.0 OkayLinda, Jun 2026
BNA - ATL
Read more Delta reviews

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

I needed internet for critical matters and it never worked.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

2 hours delay on my flight causing me to miss my connecting flight. Cause was for maintenance. I understand maintenance is important but maintenance should be done before boarding people!

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

Boarding was relatively fast and easy and the crew was attentive throughout.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports