$148 Find Cheap Flights from Madison to Caribbean Islands - Compare and Save

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 Islands departing on 10/27. 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.
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Cheap Flights from Madison to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$536
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$490
Nassau
Nassau1 stop$470
Simpson Bay
Simpson Bay2 stops$542
Providenciales
Providenciales2 stops$448
Port of Spain
Port of Spain2 stops$679
Bridgetown
Bridgetown2 stops$752
George Town
George Town1 stop$419
Aguadilla
Aguadilla2 stops$296
St. John's
St. John's2 stops$830
Punta Cana
Punta Cana1 stop$536
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$490
Nassau
Nassau1 stop$470
Simpson Bay
Simpson Bay2 stops$542
Providenciales
Providenciales2 stops$448
Port of Spain
Port of Spain2 stops$679
Bridgetown
Bridgetown2 stops$752
George Town
George Town1 stop$419
Aguadilla
Aguadilla2 stops$296
St. John's
St. John's2 stops$830

Book Cheap Madison to Caribbean Islands 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 Islands 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 Islands

Sun, Sep 6 - Wed, Sep 16
Delta Logo
9:32 am - 10:29 pm
MSN
-
SJU
11h 57m
2 stops
Delta Logo
2:59 pm - 10:41 pm
SJU
-
MSN
8h 42m
1 stop
$286Delta
Sun, Jan 17 - Fri, Jan 22
Delta Logo
6:15 am - 11:50 pm
MSN
-
SJU
15h 35m
2 stops
Delta Logo
5:15 pm - 10:55 pm
SJU
-
MSN
7h 40m
1 stop
$286Delta
Sun, Sep 6 - Wed, Sep 16
Delta Logo
5:43 am - 1:42 pm
MSN
-
SJU
6h 59m
1 stop
Delta Logo
2:59 pm - 10:41 pm
SJU
-
MSN
8h 42m
1 stop
$286Delta
Sun, Aug 23 - Tue, Sep 1
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:25 pm - 8:15 pm
SJU
-
MSN
7h 50m
1 stop
$311United Airlines
Tue, Sep 1 - Thu, Sep 10
United Airlines Logo
5:00 am - 8:38 pm
MSN
-
SJU
14h 38m
2 stops
United Airlines Logo
1:00 am - 9:40 am
SJU
-
MSN
9h 40m
2 stops
$311United Airlines
Sun, Aug 23 - Mon, Aug 31
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:00 am - 1:42 pm
SJU
-
MSN
13h 42m
2 stops
$316United Airlines
Mon, Oct 19 - Wed, Oct 28
American Airlines Logo
6:00 am - 10:57 pm
MSN
-
SJU
15h 57m
1 stop
American Airlines Logo
10:36 am - 8:07 pm
SJU
-
MSN
10h 31m
2 stops
$346American Airlines
Tue, Sep 1 - Fri, Sep 11
American Airlines Logo
6:30 am - 11:59 pm
MSN
-
SJU
16h 29m
1 stop
American Airlines Logo
2:58 pm - 12:17 am
SJU
-
MSN
10h 19m
2 stops
$346American Airlines
Sat, Aug 15 - Sat, Aug 22
Multiple Airlines Logo
7:55 pm - 7:57 am
MSN
-
SJU
11h 02m
1 stop
Multiple Airlines Logo
5:37 pm - 8:25 am
SJU
-
MSN
39h 48m
2 stops
$419Multiple Airlines
Sat, Aug 15 - Fri, Aug 21
Multiple Airlines Logo
7:55 pm - 7:57 am
MSN
-
SJU
11h 02m
1 stop
Multiple Airlines Logo
3:10 am - 7:15 pm
SJU
-
MSN
17h 05m
1 stop
$431Multiple Airlines
Booking Insights

KAYAK's insights & trends for Madison to Caribbean Islands flights

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

Can I save money by flying with a layover from Madison to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $460, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Caribbean Islands, 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 Islands is February, when tickets cost $591 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $760 and $745 respectively.

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

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 Islands, 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 Islands, you should book around 2 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 season

July

Cheapest flight

$148
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Madison to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Madison to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Madison to Caribbean Islands? 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 8490 reviews
7.8Comfort
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

Staff is friendly and helpful but flight was delayed by one hour from Detroit, making for tight window in Toronto to clear Canada Customs and pass through security screening in order to get to connecting flight on time.

6.0 GoodAnonymous, Jul 2026
DTW - YYZ
Read more Delta reviews

Staff is friendly and helpful but flight was delayed by one hour from Detroit, making for tight window in Toronto to clear Canada Customs and pass through security screening in order to get to connecting flight on time.

Delta staff was exceptionally helpful and considerate. However, the first two of three flight legs were delayed making connections tentative and stressful.

The Delta assistsed services were awesome for my aunt. So very helpful.

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.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

My flight was delayed so bad i missed u it so i just said never mind

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

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.

Horrible. No AC. No Air inside the plane. We had to deplane twice! It is late almost 5 hrs in total. I almost passed out and about to call 911. I asked the crew to be honest and open the door. The lady next to me was lay down in the floor due to heat and no air inside the plane. I got headaches, can’t wait the replacement flight about midnight Dallas time. I end it up rebook for next day flight and stay overnight using my own pocket in a hotel nearby due to headaches and can’t breath. I still have a headache this morning. Still not decided yes how to file this issue to AA and/or FAA.

They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.

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 Islands

Information on your arrival and departure airports