$176 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 2/6. 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
$169
Typical prices: $185-$364
Multiple Airlines
Fri 2/6
SJU - MSN • 1 stop
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean Islands to Madison

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

Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 2:57 pm
SJU
-
MSN
14h 52m
2 stops
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
$346United Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:07 pm
SJU
-
MSN
7h 37m
1 stop
United Airlines Logo
2:48 pm - 6:11 am
MSN
-
SJU
13h 23m
2 stops
$389United Airlines
Fri, Feb 20 - Mon, Feb 23
United Airlines Logo
3:35 pm - 10:14 am
NAS
-
MSN
19h 39m
1 stop
United Airlines Logo
8:15 am - 3:22 pm
MSN
-
NAS
6h 07m
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, Feb 11 - Sun, Feb 15
American Airlines Logo
6:05 am - 12:46 pm
SJU
-
MSN
8h 41m
1 stop
American Airlines Logo
6:14 am - 11:31 pm
MSN
-
SJU
15h 17m
1 stop
$420American 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, Feb 10 - Sun, Feb 15
United Airlines Logo
2:05 am - 11:51 am
SJU
-
MSN
11h 46m
2 stops
United Airlines Logo
8:15 am - 10:22 pm
MSN
-
SJU
12h 07m
2 stops
$455United Airlines
Wed, May 27 - Tue, Jun 9
Delta Logo
4:55 pm - 8:46 am
MBJ
-
MSN
15h 51m
2 stops
Delta Logo
5:45 am - 3:25 pm
MSN
-
MBJ
9h 40m
1 stop
$498Delta
Thu, May 7 - Mon, May 11
Delta Logo
3:20 pm - 8:46 am
SXM
-
MSN
18h 26m
2 stops
Delta Logo
5:45 am - 1:59 pm
MSN
-
SXM
7h 14m
1 stop
$705Delta
Thu, May 7 - Mon, May 11
Delta Logo
3:20 pm - 10:35 pm
SXM
-
MSN
8h 15m
1 stop
Delta Logo
5:45 am - 1:59 pm
MSN
-
SXM
7h 14m
1 stop
$869Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$169
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 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.

Reviews of the top airline flying 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.
7.9
DeltaOverall score based on 8123 reviews
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
7.9Comfort
Airline reviews

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.

10.0 ExcellentZebrina, Jan 2026
LGA - CAE
Read more Delta reviews

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!

Flight from MEX to ATL had to divert to Tampa. When we got off the plane, there were non directions on what to do. Nearly 30 minutes just standing around. Finally told to go through security with no boarding passes, and turned away. Then told to to go back. Took forever to leave Tampa for ATL. Missed my connection to Harrisburg.

This long-haul international flight was the most comfortable among any of the same kind of flight operated by an American-headquartered airline - second to none!

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