$158 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 7/18. 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$588
Santo Domingo
Santo Domingo1 stop$650
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad1 stop$661
Nassau
Nassau2 stops$576
Simpson Bay
Simpson Bay2 stops$620
Providenciales
Providenciales1 stop$523
Port of Spain
Port of Spain2 stops$774
Bridgetown
Bridgetown1 stop$757
George Town
George Town1 stop$499
Aguadilla
Aguadilla2 stops$528
St. John's
St. John's2 stops$780
Punta Cana
Punta Cana1 stop$588
Santo Domingo
Santo Domingo1 stop$650
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad1 stop$661
Nassau
Nassau2 stops$576
Simpson Bay
Simpson Bay2 stops$620
Providenciales
Providenciales1 stop$523
Port of Spain
Port of Spain2 stops$774
Bridgetown
Bridgetown1 stop$757
George Town
George Town1 stop$499
Aguadilla
Aguadilla2 stops$528
St. John's
St. John's2 stops$780

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

Tue, Oct 20 - Fri, Oct 23
United Airlines Logo
6:49 am - 8:38 pm
MSN
-
SJU
12h 49m
2 stops
United Airlines Logo
3:56 pm - 10:35 pm
SJU
-
MSN
7h 39m
1 stop
$279United Airlines
Sun, Sep 20 - Wed, Sep 23
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:00 am - 1:37 pm
SJU
-
MSN
13h 37m
2 stops
$317United Airlines
Sat, Aug 22 - Tue, Aug 25
American Airlines Logo
6:01 am - 4:57 pm
MSN
-
SJU
9h 56m
2 stops
American Airlines Logo
6:00 am - 3:24 pm
SJU
-
MSN
10h 24m
2 stops
$326American Airlines
Fri, Sep 25 - Fri, Oct 2
United Airlines Logo
6:49 am - 2:44 pm
MSN
-
SJU
6h 55m
1 stop
United Airlines Logo
1:00 am - 11:53 am
SJU
-
MSN
11h 53m
2 stops
$348United Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
6:53 pm - 11:42 am
MSN
-
MBJ
16h 49m
2 stops
American Airlines Logo
5:16 pm - 12:26 pm
MBJ
-
MSN
19h 10m
2 stops
$357American Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
9:57 am - 1:12 pm
MSN
-
MBJ
27h 15m
1 stop
American Airlines Logo
5:16 pm - 12:10 pm
MBJ
-
MSN
18h 54m
2 stops
$362American Airlines
Sun, Sep 6 - Wed, Sep 16
Delta Logo
5:43 am - 4:38 pm
MSN
-
SJU
9h 55m
1 stop
Delta Logo
2:26 pm - 10:39 pm
SJU
-
MSN
9h 13m
1 stop
$378Delta
Mon, Jun 29 - Fri, Jul 10
JetBlue Logo
5:52 am - 4:46 pm
MSN
-
SJU
9h 54m
1 stop
JetBlue Logo
2:42 pm - 10:38 pm
SJU
-
MSN
8h 56m
1 stop
$381JetBlue
Sat, Sep 5 - Sat, Sep 12
Delta Logo
5:43 am - 1:01 pm
MSN
-
MBJ
7h 18m
1 stop
Delta Logo
1:25 pm - 10:35 pm
MBJ
-
MSN
9h 10m
1 stop
$495Delta
Sun, Jun 28 - Mon, Jul 6
JetBlue Logo
5:52 am - 1:16 pm
MSN
-
SDQ
6h 24m
1 stop
JetBlue Logo
2:41 pm - 10:43 pm
SDQ
-
MSN
9h 02m
1 stop
$736JetBlue
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 August, when the average cost of round-trip tickets is $418 and $373 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 21% 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$158
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 7% 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.
7.8
DeltaOverall score based on 8395 reviews
7.2Food
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
Airline reviews

Connection flights should be spaced out farther because too close I missed my connection.

8.0 ExcellentAnonymous, Jun 2026
PHL - ATL
Read more Delta reviews

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

The crew were efficient. The pilots seemed professional. It was a bit chilly in our seats. The sheet provided weren’t very helpful.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

I flew from Santa Fe to Denver to catch a flight to London and the transfer of my luggage on arrival at Denver to the London flight worked perfectly. The crew on the ground and on board for the London flight were so friendly and efficient.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

Boarded early, left early, arrived 40 mins early! A win win for me!

New plane was lovely. Crew customer service is always lax but expected. Kraft on time and arrived safely.

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

It was a short flight so I was expecting too much

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

The flight took off an hour late which made the connection concerning

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

The flight from LA to Chicago was smooth and service was very good overall.

The flight from Dallas to Tokyo was not on Japan Airlines. It was on American Airlines. Very disappointed that we did not fly on Japan Airlines. Will not be using you liars again. I’ll just book direct from the airline next time. Wish you could make this right and has us fly on Japan Air when heading back home to the US.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

They made nearly everyone check their bag because the overhead bins are way too small. Extremely inconvenient

Delayed delayed. Poor professionalism. Our seats changed and we pay for them

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

Movies on my phone are great. It would be nice to have a gluten free snack option.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports