$128 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 4/14. 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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Everything you should know

Cheapest round-trip
$346
Overall average: $528
United Airlines
Tue 2/24Sat 2/28
SJU - MSN • 2 stops
Cheapest one-way
$128
Typical prices: $185-$390
United Airlines
Tue 4/14
SJU - MSN • 2 stops
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Flight Deals
Useful Info
Flight Deals

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

Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 2:07 pm
SJU
-
MSN
14h 02m
2 stops
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
$346United Airlines
Wed, Jul 29 - Tue, Aug 18
American Airlines Logo
6:00 am - 10:13 pm
SJU
-
MSN
17h 13m
1 stop
American Airlines Logo
6:00 am - 11:41 pm
MSN
-
SJU
16h 41m
1 stop
$368American Airlines
Thu, Feb 26 - Tue, Mar 3
United Airlines Logo
2:05 am - 2:57 pm
SJU
-
MSN
14h 52m
2 stops
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m
1 stop
$389United Airlines
Fri, Feb 20 - Mon, Feb 23
United Airlines Logo
3:35 pm - 4:44 pm
NAS
-
MSN
26h 09m
1 stop
United Airlines Logo
6:30 am - 3:22 pm
MSN
-
NAS
7h 52m
1 stop
$395United Airlines
Fri, Feb 20 - Mon, Feb 23
American Airlines Logo
3:47 pm - 10:59 pm
NAS
-
MSN
8h 12m
1 stop
American Airlines Logo
8:09 am - 7:51 pm
MSN
-
NAS
10h 42m
2 stops
$408American Airlines
Wed, Jul 29 - Tue, Aug 18
American Airlines Logo
3:40 pm - 11:58 pm
SJU
-
MSN
9h 18m
1 stop
American Airlines Logo
7:16 am - 6:15 pm
MSN
-
SJU
9h 59m
2 stops
$415American Airlines
Thu, Jul 16 - Tue, Jul 28
American Airlines Logo
12:59 am - 9:23 am
SJU
-
MSN
9h 24m
1 stop
American Airlines Logo
11:25 am - 4:32 am
MSN
-
SJU
16h 07m
1 stop
$427American Airlines
Thu, Jul 16 - Tue, Jul 28
American Airlines Logo
12:59 am - 9:23 am
SJU
-
MSN
9h 24m
1 stop
American Airlines Logo
11:25 am - 4:32 am
MSN
-
SJU
16h 07m
1 stop
$432American Airlines
Fri, Feb 20 - Mon, Feb 23
American Airlines Logo
11:58 am - 8:56 pm
NAS
-
MSN
9h 58m
2 stops
American Airlines Logo
8:09 am - 7:51 pm
MSN
-
NAS
10h 42m
2 stops
$448American Airlines
Tue, May 19 - Wed, Jun 3
Delta Logo
4:55 pm - 8:46 am
MBJ
-
MSN
15h 51m
2 stops
Delta Logo
5:45 am - 3:29 pm
MSN
-
MBJ
9h 44m
1 stop
$479Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$128
Best time to beat the crowds but there is an average 30% increase in price.
Most popular time to fly and prices are also 13% 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 8125 reviews
7.8Entertainment
8.1Boarding
7.2Food
7.9Comfort
8.5Crew
Airline reviews

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

10.0 ExcellentDr. Simon, Jan 2026
LAX - JFK
Read more Delta reviews

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Very convenient considering that is a non-stop flight, but the Aeromexico still has old model planes, so the entertainment was very poor and the space for carry-on luggage was very limited.

Flight taking off must have been behind, because there was no pre-departure drink for first class like normal. Also, person in front of mine’s seat got stuck in the as far back as it normally goes position for the whole flight even during landing, flight attendant unable to fix it. Gate was not empty when we arrived, but that is MSP’s fault since was overdue for push back, not Delta’s, so had to sit on tarmac for a while and international flight so then still had to go through customs. Flight crew was excellent throughout though!

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

Crew was clearly not loving their jobs at any point of the entire trip. Flight back from Mexico, I asked if they had food for sale for the 2.5+hr flight and they did not have any. The business class trip to Mexico also had noted that the catering company forgot to load food. The last leg of trip back had a similarly unhappy crew, a broken toilet, and my seat was broken (reclining would not lock which made landing a crossfit like event). This was a bad week for AA.

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

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