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Find cheap flights from Madison to Caribbean from $194

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 5/25. 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
Wed 5/29
Wed 6/5

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana2 stops$460
Montego Bay
Montego Bay2 stops$509
Santo Domingo
Santo Domingo2 stops$535
Oranjestad
Oranjestad1 stop$635
Nassau
Nassau1 stop$443
Simpson Bay
Simpson Bay1 stop$475
Providenciales
Providenciales2 stops$461
Bridgetown
Bridgetown2 stops$601
George Town
George Town1 stop$522
Aguadilla
Aguadilla2 stops$814
St. John's
St. John's2 stops$730

Good to know

Low season

September

High season

March

Cheapest flight

$194
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 17% increase in price.
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 to Caribbean from Madison 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 to Caribbean with an airline and back to Madison 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 to Caribbean from Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 21% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 4 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.
8.0
DeltaOverall score based on 10913 reviews
8.2boarding
7.9comfort
8.0entertainment
7.4food
8.6crew
Airline reviews

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

8.0 ExcellentCynthia, Apr 2024ATL - SJD
Read more about Delta reviews

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

Our original business class flight was cancelled so we not only downgraded but we were also spread out across the plane not sitting together in separate middle seats. My poor kids were scared and couldn’t see me on the flight and the crew wasn’t sensitive to the situation and what the airlines did to us. Very dissatisfied with United airlines.

Crew were fine, drinks and snacks were as well but we were delayed for around 2 hrs which made our entry into Mexico delayed as well with the influx of arrivals at the same time. Sort of wasted our first day of vacation. We left Pittsburgh at 630am and did not arrive in Mexico until late dinner time.

The ride was good but no food ot entertainment hence, it was just over an hour flight.

There was a group of school age passengers that were very loud and unruly with their chaperones were no where to be found.

Boarding was unorganized. They expected passengers to ask people to move their assigned seat they paid for in order to sit together. The seats even in comfort are smaller than other airlines and the flight attendants appeared not to be well prepared

The WiFi didn’t work and the seats are too close together. Very uncomfortable.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

So so. Terrible aircraft choice for that leg of the flight.

Too bad that first class seats do not recline significantly causing discomfort

I think the seats on some of their planes are uncomfortable. You can be ok on a short flight of two hours but no more than that. The delays, and also the refreshments on the plane were not enough.

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

Not sure why JAL partnered with American Airlines because their service is no where near similar. Flight attendants were not friendly and didn’t smile. Food was horrible…

this is starting to seem like an american airlines standard. delayed flights and fake apologies… getting tired of it

Terrible boarding , Business class seats are sub standard. As usual crew will miss your food too

Just get Economy Plus for international flights, so worth it the extra room, bigger seats…

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Madison to Caribbean

Recent round-trip flight deals

5/26Sun
1 stopAmerican Airlines
9h 05mMSN-SJU
5/31Fri
1 stopAmerican Airlines
15h 23mSJU-MSN
$331
5/26Sun
2 stopsAmerican Airlines
9h 30mMSN-SJU
5/31Fri
1 stopAmerican Airlines
15h 23mSJU-MSN
$333
6/26Wed
1 stopDelta
11h 08mMSN-SJU
7/5Fri
2 stopsDelta
15h 14mSJU-MSN
$334
6/26Wed
1 stopDelta
11h 08mMSN-SJU
7/4Thu
2 stopsDelta
13h 54mSJU-MSN
$367
5/12Sun
1 stopAmerican Airlines
9h 05mMSN-SJU
5/30Thu
1 stopAmerican Airlines
17h 18mSJU-MSN
$396
5/2Thu
2 stopsFrontier
23h 16mMSN-PUJ
5/9Thu
2 stopsFrontier
27h 14mPUJ-MSN
$460
5/27Mon
2 stopsUnited Airlines
21h 33mMSN-NAS
5/30Thu
2 stopsUnited Airlines
24h 43mNAS-MSN
$508
5/25Sat
3 stops
39h 42mMSN-SJU
5/28Tue
1 stop
8h 31mSJU-MSN
$525
6/5Wed
2 stopsUnited Airlines
28h 18mMSN-NAS
6/9Sun
2 stopsUnited Airlines
21h 50mNAS-MSN
$548
5/15Wed
3 stops
26h 01mMSN-MBJ
5/25Sat
2 stops
25h 57mMBJ-MSN
$1,324

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Recent one-way flight deals

5/25Sat
2 stops
15h 42mMSN-SJU
$194
5/25Sat
1 stopDelta
7h 11mMSN-SJU
$200
9/3Tue
2 stopsAmerican Airlines
18h 39mMSN-MBJ
$212
5/25Sat
1 stopAmerican Airlines
10h 56mMSN-SJU
$231
5/25Sat
3 stops
39h 42mMSN-SJU
$235
5/23Thu
1 stopAmerican Airlines
16h 00mMSN-SJU
$269
5/24Fri
1 stopAmerican Airlines
17h 34mMSN-SJU
$311
5/23Thu
2 stopsAmerican Airlines
21h 29mMSN-SJU
$338
5/24Fri
2 stopsAmerican Airlines
25h 49mMSN-SJU
$351
5/23Thu
3 stopsUnited Airlines
30h 25mMSN-SJU
$751

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Last minute flights from Madison to Caribbean

Last minute flight, train and bus deals

5/1Wed
multi-stop
14h 46mMSN-SDQ
5/10Fri
multi-stop
26h 43mSDQ-MSN
$444
5/1Wed
multi-stop
15h 33mMSN-SDQ
5/10Fri
multi-stop
26h 43mSDQ-MSN
$448
5/2Thu
multi-stopFrontier
23h 16mMSN-PUJ
5/9Thu
multi-stopFrontier
27h 14mPUJ-MSN
$460
5/2Thu
multi-stopAmerican Airlines
18h 54mMSN-PUJ
5/9Thu
multi-stopAmerican Airlines
7h 03mPUJ-MSN
$600
5/2Thu
multi-stopAmerican Airlines
18h 54mMSN-PUJ
5/9Thu
multi-stopAmerican Airlines
16h 58mPUJ-MSN
$605
5/3Fri
multi-stopAmerican Airlines
17h 35mMSN-SDQ
5/10Fri
multi-stopAmerican Airlines
18h 58mSDQ-MSN
$692
5/1Wed
multi-stopDelta
9h 46mMSN-SDQ
5/10Fri
multi-stopDelta
17h 24mSDQ-MSN
$695
4/29Mon
multi-stopDelta
6h 40mMSN-SDQ
5/2Thu
multi-stopDelta
8h 23mSDQ-MSN
$770
5/3Fri
multi-stopUnited Airlines
7h 00mMSN-SDQ
5/10Fri
multi-stopUnited Airlines
8h 58mSDQ-MSN
$780
5/3Fri
multi-stopUnited Airlines
13h 50mMSN-SDQ
5/10Fri
multi-stopUnited Airlines
8h 58mSDQ-MSN
$785

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