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$132 Find Cheap Flights from Caribbean Islands 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 12/10. 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
0 bags

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Good to know

Low season

March

High season

May

Cheapest flight

$132
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from San Juan to Madison

FAQs for booking flights from Caribbean Islands to Madison

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

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

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

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands 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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Caribbean Islands to Madison?

Find which airlines fly direct from Caribbean Islands to Madison Truax Field Airport, which days they fly and book direct flights.

Nonstop departures

Caribbean Islands to Madison Truax Field

Monday

ANA, Aeromexico, Air Canada, +22 more

ANA, Aeromexico, +23 more

Tuesday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Wednesday

ANA, Aeromexico, Air Canada, +23 more

ANA, Aeromexico, +24 more

Thursday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Friday

ANA, Aeromexico, Air Canada, +22 more

ANA, Aeromexico, +23 more

Saturday

ANA, Aeromexico, Air Canada, +23 more

ANA, Aeromexico, +24 more

Sunday

ANA, Aeromexico, Air Canada, +23 more

ANA, Aeromexico, +24 more

See more direct flights

Nonstop returns

Madison Truax Field to Caribbean Islands

Monday

ANA, Aeromexico, Air Canada, +22 more

ANA, Aeromexico, +23 more

Tuesday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Wednesday

ANA, Aeromexico, Air Canada, +23 more

ANA, Aeromexico, +24 more

Thursday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Friday

ANA, Aeromexico, Air Canada, +22 more

ANA, Aeromexico, +23 more

Saturday

ANA, Aeromexico, Air Canada, +23 more

ANA, Aeromexico, +24 more

Sunday

ANA, Aeromexico, Air Canada, +23 more

ANA, Aeromexico, +24 more

See more direct flights
See more direct flights

Top 3 airlines serving from Caribbean Islands to Madison

Need help choosing which airline to fly with from Caribbean Islands 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.
8.0
DeltaOverall score based on 8771 reviews
8.5Crew
7.9Entertainment
8.2Boarding
7.3Food
7.9Comfort
Airline reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

8.0 ExcellentAndrew, Nov 2024MCO - LGA
Read more Delta reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

I love my flight attendant Faith, always smiles always helpful. She makes the flight experience wonderful thank you

My return flights were changed by the airline and my preferred seat selection with extra legroom was not transferred to the new flights

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

Very dissatisfied with the fact that I had upgraded to first class for the second part of my trip only to find out that the lounge was still not available to me, as well as not having any food or drink service on the flight due to weather, so I lost out more than what I paid for.

The crew was outstanding. And the food was surprisingly good. The chicken and the pasta dish were both delicious and I was supposed with a pizza twist near Landing. We hit a lot of turbulence and the crew was calm and kind. Loved the TV in screen. Tons of new releases.

It was a good flight. Nothing comes to mind about how it could have been better. It was a newer plane, seemed like a great upgrade from your older ones. Staff was very good as well.

boarding was uneventful. Snack was pathetic. A tiny fruit bar. Entertainment was limited to just select movies on your own tablet or phone. No live TV. I recently flew Jetblue and they had unlimited snacks and live satellite TV the entire flight. My seat was an exit seat, 20A. It was super uncomfortable. It felt cramped and the middle seat was taken up by a large woman who pushed into my shoulder and arm. Horrible flight.

They canceled our flight and left us stranded to figure it out

Cabin was pitch black, even during meal service. The reading lights for seat 2E/F did not work, and seat 2E did not recline.

The first flight was an hour and a half late leaving, thus missing my connection. The second flight Departure was two hours late Leaving.

Smooth boarding. I liked the pilots communicated potential turbulence upcoming.

Long wait before take off without an update for 20 minutes. Flight was good otherwise.

Plane still had screens for watching movies. Good selection too.

The plane’s radio wasn’t working. This delayed the plane for an hour and a half. Then we all broaded and taxied down the runway only to get called back because the radio was still not working. Had to get off the plane and then find another plane making the trip 4 hours delayed. Maybe a different plane should have been chosen sooner?!?!?!

Great thanks - a whole row to myself. Good food but film selection not great.

The departing flight from Newark to Charlotte was fine. It was the returning flight from Charlotte to Newark that was awful. We had scheduled an 8:35pm return flight time. We got delayed TEN times all the way to 5am in the morning! We were told over 4 different excuses as to why the flight kept getting delayed. First it was the flight crew needed to rest, then it was something technical with the plane, then it was something with air traffic control, and finally it was because they couldn’t find a captain and had to wait until the morning so the captain could get some rest. It was terrible sleeping overnight in the airport. They offered a $12 meal voucher. That was it! And the only place open in the middle of the night was Dunkin’ Donuts who didn’t even accept the voucher. They should have cancelled the flight much earlier on in the evening instead of just stringing us along hour by hour with more delays. Not professional and unacceptable. There was no refund for inconvenience. I probably will not be flying American Airlines again.

This leg they tried and did well with what they had to work from.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight was as good as it gets when flying. On time departure and arrival plus no lost luggage.

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Packed commercial flight was as comfortable as can be expected

My seat was very worn. Otherwise I had an excellent flight

I'm not a valued flyer so I'm always in the last group to board...that sucks, always

My flight back my reservations were list because they said I didn't pay my pet fee when I had a receipt

Book cheap flights from Caribbean Islands to Madison

Recent round-trip flight deals

12/4Wed
1 stop
14h 15mSJU-MSN
12/9Mon
3 stops
32h 05mMSN-SJU
$351
12/23Mon
2 stopsAmerican Airlines
11h 11mSJU-MSN
1/12Sun
1 stopAmerican Airlines
12h 28mMSN-SJU
$364
12/4Wed
2 stopsAmerican Airlines
13h 38mSJU-MSN
12/8Sun
1 stopAmerican Airlines
7h 10mMSN-SJU
$401
12/6Fri
1 stopAmerican Airlines
17h 41mSJU-MSN
12/10Tue
1 stopAmerican Airlines
7h 10mMSN-SJU
$404
12/17Tue
1 stopDelta
7h 13mSJU-MSN
12/24Tue
1 stopDelta
7h 16mMSN-SJU
$409
12/23Mon
1 stopDelta
9h 14mSJU-MSN
1/12Sun
1 stopDelta
10h 31mMSN-SJU
$433
12/4Wed
3 stops
28h 40mSJU-MSN
12/9Mon
3 stops
32h 05mMSN-SJU
$437
12/20Fri
1 stopUnited Airlines
7h 38mSJU-MSN
12/31Tue
2 stopsUnited Airlines
21h 53mMSN-SJU
$456
12/4Wed
1 stopAmerican Airlines
15h 48mSJU-MSN
12/8Sun
1 stopAmerican Airlines
7h 10mMSN-SJU
$476
12/22Sun
1 stopUnited Airlines
8h 42mMBJ-MSN
1/19Sun
1 stopUnited Airlines
7h 37mMSN-MBJ
$509

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Recent one-way flight deals

12/10Tue
1 stopUnited Airlines
8h 14mSJU-MSN
$132
12/13Fri
1 stopAmerican Airlines
17h 41mSJU-MSN
$133
12/9Mon
2 stopsUnited Airlines
12h 01mSJU-MSN
$177
12/13Fri
2 stops
22h 12mSJU-MSN
$178
12/12Thu
3 stops
31h 40mSJU-MSN
$190
12/12Thu
3 stops
31h 40mSJU-MSN
$191
12/13Fri
3 stops
30h 28mSJU-MSN
$201
12/13Fri
2 stopsAmerican Airlines
9h 16mSJU-MSN
$232
3/25Tue
2 stopsDelta
14h 51mSJU-MSN
$257
3/24Mon
2 stopsSun Country Air
43h 29mSJU-MSN
$416

Search by stops

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Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison