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$206 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 5/20. 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
Fri 6/14
Fri 6/21

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In the last 7 days travelers have searched 42,393,389 times on KAYAK, and here is why:

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Good to know

Low season

March

High season

May

Cheapest flight

$206
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 0% 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.

See more FAQs

Prefer to fly non-stop from Caribbean to Madison?

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

Nonstop departures

Caribbean to Madison Truax Field

Monday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Tuesday

ANA, Aeromexico, Air Canada, +19 more

ANA, Aeromexico, +20 more

Wednesday

ANA, Aeromexico, Air Canada, +22 more

ANA, Aeromexico, +23 more

Thursday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Friday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Saturday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Sunday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

See more direct flights

Nonstop returns

Madison Truax Field to Caribbean

Monday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Tuesday

ANA, Aeromexico, Air Canada, +19 more

ANA, Aeromexico, +20 more

Wednesday

ANA, Aeromexico, Air Canada, +22 more

ANA, Aeromexico, +23 more

Thursday

ANA, Aeromexico, Air Canada, +20 more

ANA, Aeromexico, +21 more

Friday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Saturday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

Sunday

ANA, Aeromexico, Air Canada, +21 more

ANA, Aeromexico, +22 more

See more direct flights
See more direct flights

Top 3 airlines serving 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.
8.0
DeltaOverall score based on 10691 reviews
8.2Boarding
8.0Entertainment
7.9Comfort
8.6Crew
7.4Food
Airline reviews

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

4.0 OkayReginald, May 2024MCI - LGA
Read more about Delta reviews

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

The boarding was horrible. You couldn’t hear the announcements at all. Probably because there is so much in the area for businesses. They need a louder PA system. Other than that it was a good Delta experience.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

We enjoyed that we boarded and took off on time. We didn’t like that our connection flight was a twenty minute walk through the airport with only one hour in between flights.

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

We ended up with seats in the very back. So they did not recline. Have no idea why, we reserved and checked in very early. The isles were very narrow and the seats had very little leg room. But they did give us water, and a snack.

Boarding was terrible. My wife uses a wheel chair and she was in an incredibly hot closed metal cargo box for close to 20 minutes before getting on board

Check in etc was very good. As for on the plane, it was like flying in a freezer. It was so cold, i have flown for years and never been so cold on a plane. Staff on board said its always cold when flying which is a load of rubbish. They wouldnt put any heating on and now i have the flu because of this .

I’ve had a couple flights this week on United that were delayed by an hour or more

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

It was okay, no wifi or entertainment real disappointment. Staff onboard not very friendly.

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

It started with multiple delays, cancellations, re booking, 5 hour lay over and finally on a plane from Chicago to Pittsburgh. Gates, times, etc were changed multiply times. Once on the plane, staff was fine, but built in tv did not work and could not even turn it off. Light at eye level the entire trip, so sleeping was near impossible. No snacks or drinks given.

Tray table was filthy when I sat down. I needed to have someone come clean it because there was food and stains on it WiFi didn’t work after paying for in-flight WiFi. Food was terrible and was not filling at all Chicken was rubbery Flight attendant had an attitude, interrupted me and wasn’t able to answer basic questions about the food selection such as “does the chicken have red sauce in it”. If your flight attendants are not going to know what is in the meals so we can make an educated decision based on dietary restrictions, they shouldn’t be on the plane. My 1.5 year old niece was sleeping and dropped her binkie. I went on the ground under the chairs looking for it. It was at that time that she came up to me as I’m CLEARLY on all 4s with a flashlight and said “I need to get by”. I said one moment please I’m getting something from under the seat (while my head was literally under the seat). Her reply was “no you need to move now” and proceeded to almost push me out of the way. I looked up and all I saw was her toes under my eyes. When I looked in front of me, her private parts were inches away from my face. I then made a comment “you couldn’t waited 2 seconds?” and her response was, “no I need to use the bathroom”. I understand that and would never want to be the reason someone couldn’t get to the bathroom but I was under the seat. She could’ve gone around the other way instead of harassing me, basically placing her private parts on my head and borderline pushing me out of the way. You don’t pay that much for this deplorable experience. This was by far the worst experience I have ever had on American. I will be absolutely thinking twice and thrice about flying American Airlines again. I would rather pay more to fly delta because at least I know their WiFi will work and their flight attendants won’t have a shitty attitude for no reason, nor will they act the way this woman did. Unacceptable.

Liked - nothing. Disliked - delayed 35+ min sitting on the plane. Caused me to miss my connection in Charlotte. American Airlines is the worst US Air Carrier company with atrocious customer service.

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

I like the boarding process, it was fast. The seat doesn’t have a TV for a long flight and food wasn’t served, just snacks.

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Book cheap flights from Caribbean to Madison

Recent round-trip flight deals

6/12Wed
2 stopsFrontier
29h 07mSJU-MSN
6/19Wed
2 stopsFrontier
21h 45mMSN-SJU
$319
8/27Tue
1 stopAmerican Airlines
15h 19mSJU-MSN
9/7Sat
2 stopsAmerican Airlines
15h 33mMSN-SJU
$331
8/27Tue
2 stopsAmerican Airlines
9h 59mSJU-MSN
9/7Sat
2 stopsAmerican Airlines
15h 33mMSN-SJU
$333
8/24Sat
1 stopDelta
10h 48mSJU-MSN
8/28Wed
1 stopDelta
9h 18mMSN-SJU
$367
9/20Fri
1 stopDelta
10h 12mNAS-MSN
9/24Tue
1 stopDelta
6h 23mMSN-NAS
$443
9/4Wed
2 stopsUnited Airlines
21h 22mMBJ-MSN
9/7Sat
2 stopsUnited Airlines
19h 40mMSN-MBJ
$448
9/4Wed
2 stopsUnited Airlines
22h 59mMBJ-MSN
9/7Sat
2 stopsUnited Airlines
19h 40mMSN-MBJ
$498
7/4Thu
2 stops
27h 34mMBJ-MSN
8/31Sat
3 stops
24h 05mMSN-MBJ
$1,314
5/29Wed
2 stopsAir Canada
27h 28mMBJ-MSN
9/8Sun
2 stopsAir Canada
27h 25mMSN-MBJ
$1,394
6/13Thu
3 stops
28h 40mMBJ-MSN
6/20Thu
3 stops
27h 20mMSN-MBJ
$1,508

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Recent one-way flight deals

5/20Mon
2 stops
32h 00mSJU-MSN
$206
5/21Tue
2 stops
21h 03mSJU-MSN
$210
5/24Fri
2 stops
21h 10mSJU-MSN
$211
11/9Sat
2 stopsAmerican Airlines
18h 34mSJU-MSN
$231
11/9Sat
1 stopAmerican Airlines
8h 37mSJU-MSN
$232
6/13Thu
1 stopAmerican Airlines
11h 55mMBJ-MSN
$261
6/12Wed
2 stopsAmerican Airlines
17h 19mMBJ-MSN
$271
6/9Sun
1 stopUnited Airlines
7h 36mMBJ-MSN
$288
5/22Wed
1 stopUnited Airlines
10h 23mMBJ-MSN
$316
5/22Wed
2 stopsUnited Airlines
19h 30mMBJ-MSN
$320

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Flights to Madison

Destination:

Madison (MSN)United States

Return flight deals:

Madison - Caribbean

Cabin classes:

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