$123 Find Cheap Flights from Caribbean to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Madison departing on 5/15. 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 Caribbean to Madison

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Madison 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 Caribbean to Madison

jue., may. 7 - mar., may. 12
United Airlines Logo
3:56 pm - 10:54 pm
SJU
-
MSN
7h 58m
1 stop
United Airlines Logo
9:55 am - 8:34 pm
MSN
-
SJU
9h 39m
1 stop
$308United Airlines
vie., may. 8 - mar., sep. 8
American Airlines Logo
12:25 pm - 11:54 pm
MBJ
-
MSN
11h 29m
1 stop
American Airlines Logo
6:00 am - 1:58 pm
MSN
-
MBJ
7h 58m
1 stop
$316American Airlines
jue., may. 7 - dom., may. 10
JetBlue Logo
2:48 pm - 10:44 pm
SJU
-
MSN
8h 56m
1 stop
JetBlue Logo
5:43 am - 4:33 pm
MSN
-
SJU
9h 50m
1 stop
$316JetBlue
vie., may. 1 - jue., sep. 3
American Airlines Logo
12:25 pm - 11:55 pm
MBJ
-
MSN
11h 30m
1 stop
American Airlines Logo
4:21 pm - 9:25 am
MSN
-
MBJ
17h 04m
2 stops
$321American Airlines
jue., may. 7 - mar., may. 12
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
American Airlines Logo
6:45 am - 6:10 pm
MSN
-
SJU
10h 25m
2 stops
$326American Airlines
mié., abr. 22 - mié., abr. 29
United Airlines Logo
7:40 am - 1:51 pm
SJU
-
MSN
7h 11m
1 stop
United Airlines Logo
8:30 am - 9:24 pm
MSN
-
SJU
11h 54m
2 stops
$328United Airlines
dom., may. 17 - mié., sep. 9
American Airlines Logo
4:37 pm - 10:55 am
MBJ
-
MSN
18h 18m
2 stops
American Airlines Logo
6:23 pm - 10:50 am
MSN
-
MBJ
16h 27m
2 stops
$331American Airlines
sáb., may. 2 - sáb., may. 9
United Airlines Logo
4:12 pm - 8:56 am
MBJ
-
MSN
16h 44m
2 stops
United Airlines Logo
4:02 pm - 1:30 pm
MSN
-
MBJ
21h 28m
2 stops
$346United Airlines
vie., jun. 5 - lun., jun. 8
American Airlines Logo
6:20 am - 9:20 pm
SJU
-
MSN
16h 00m
1 stop
American Airlines Logo
6:01 am - 11:01 pm
MSN
-
SJU
16h 00m
1 stop
$366American Airlines
jue., ago. 20 - lun., ago. 31
Multiple Airlines Logo
5:15 pm - 8:25 am
SJU
-
MSN
16h 10m
2 stops
Multiple Airlines Logo
6:50 pm - 4:34 pm
MSN
-
SJU
20h 44m
1 stop
$399Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$123
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from San Juan to Madison

FAQs for booking flights from Caribbean to Madison

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

    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 Caribbean to Madison.

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

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

    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 to Madison with an airline and back to Caribbean with another airline.

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

    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 to Madison from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Caribbean to Madison

 
Need help choosing which airline to fly with from Caribbean to Madison? 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 8388 reviews
7.2Food
7.9Comfort
7.8Entertainment
8.5Crew
8.1Boarding
Airline reviews

Okay considering we had weather delays which the Pilot notified us of immediately!

8.0 ExcellentPaul A, Apr 2026
ORD - ATL
Read more Delta reviews

Okay considering we had weather delays which the Pilot notified us of immediately!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

Buying ticket from kayak instant booking was a huge mistake, never to be repeated again! The Kayak didn’t book the tickets directly, it handed it off to a third party Underpricer, that booked a code shared American Airlines flight operated by Cathay Pacific!! When managing the booking American Airlines would recognize the itinerary but wouldn’t let me do anything stating, the flight is operated by Cathay Pacific so go to their website. Cathay Pacific would recognize the itinerary, neither by reservation ID or ticket number…asking to reach out to the third party Underpricer….calling Underpricer resulted in no help like seat requests, mileage number or upgrade request, 15hr layover accommodation voucher guidance…so net in net avoid booking through three layers of intermediaries

I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight

A chaotic and uncomfortable experience from start to finish. The boarding process was a disaster; despite group numbers, it was a free-for-all that the staff failed to manage (especially after group 5). Once on board, the "entertainment" was non-existent. There are no seatback screens, and the mobile app selection is incredibly thin. The hardware is severely dated. My seat had zero cushioning left—it felt like sitting on a hard board for the entire flight—and the legroom was cramped. To make matters worse, the bathroom was repulsive, with toilet paper, soiled paper towels and liquid/pee all over the floor. When I did interact with the crew, they provided the absolute bare minimum and made me feel like an inconvenience for asking for anything. Avoid this flight if you can.

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

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