$185 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 4/7. 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.
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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.

Recent round-trip flight deals from Caribbean Islands to Madison

KAYAK's recommended round-trip deals from the most popular airlines that fly from Caribbean Islands to Madison.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
American Airlines Logo
5:30 am - 10:44 pmSJU-MSN
18h 14m1 stop
American Airlines Logo
11:23 am - 5:00 amMSN-SJU
16h 37m1 stop
$491American Airlines
Find Deal
Wed, Apr 16 - Sun, Apr 20
American Airlines Logo
12:05 pm - 11:14 pmSJU-MSN
12h 09m2 stops
American Airlines Logo
7:21 am - 2:45 pmMSN-SJU
6h 24m1 stop
$545American Airlines
Find Deal
Sun, Aug 10 - Sun, Aug 31
American Airlines Logo
6:03 am - 4:50 pmSJU-MSN
11h 47m2 stops
American Airlines Logo
7:16 am - 11:55 pmMSN-SJU
15h 39m1 stop
$555American Airlines
Find Deal
Wed, Jul 16 - Sun, Jul 20
American Airlines Logo
2:50 pm - 8:01 amSJU-MSN
18h 11m1 stop
American Airlines Logo
6:13 am - 8:33 pmMSN-SJU
13h 20m1 stop
$570American Airlines
Find Deal
Thu, May 8 - Sun, May 11
American Airlines Logo
12:59 am - 10:46 amSJU-MSN
10h 47m1 stop
American Airlines Logo
7:16 am - 11:55 pmMSN-SJU
15h 39m1 stop
$605American Airlines
Find Deal
Fri, Jul 4 - Fri, Jul 11
American Airlines Logo
3:50 pm - 11:14 pmSJU-MSN
8h 24m2 stops
American Airlines Logo
6:52 am - 11:00 pmMSN-SJU
15h 08m1 stop
$617American Airlines
Find Deal
Sun, Aug 10 - Sun, Aug 31
American Airlines Logo
12:05 pm - 11:14 pmSJU-MSN
12h 09m2 stops
American Airlines Logo
6:42 am - 8:15 pmMSN-SJU
12h 33m2 stops
$637American Airlines
Find Deal
Sun, Aug 10 - Sun, Aug 31
American Airlines Logo
12:59 am - 10:46 amSJU-MSN
10h 47m1 stop
American Airlines Logo
11:26 am - 11:55 pmMSN-SJU
11h 29m2 stops
$645American Airlines
Find Deal
Fri, Jul 4 - Fri, Jul 11
United Airlines Logo
1:05 am - 10:13 amSJU-MSN
10h 08m2 stops
United Airlines Logo
5:26 pm - 9:24 pmMSN-SJU
26h 58m2 stops
$750United Airlines
Find Deal
Fri, Jul 4 - Fri, Jul 11
United Airlines Logo
1:05 am - 1:52 pmSJU-MSN
13h 47m2 stops
United Airlines Logo
6:30 am - 2:44 pmMSN-SJU
7h 14m1 stop
$754United Airlines
Find Deal
Tue, Apr 15 - Sun, Apr 20

Good to know

Low season

February

High season

December

Cheapest flight

$185
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 1% increase in price.
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

Top airlines 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.
8.0
DeltaOverall score based on 7897 reviews
8.2Boarding
7.9Entertainment
7.3Food
7.9Comfort
8.5Crew
Airline reviews

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

10.0 ExcellentSunderesh, Mar 2025AUS - BOS
Read more Delta reviews

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

I love the free WiFi!! Crew was nice. Bathroom was decent. First time flying delta in a long time and I enjoyed it. Will definitely look into booking with Delta more but I think Delta is a little more expensive than the other airlines.

third trip overseas with delta recently where the TV did not work- not acceptable for a 8 hour flight! your food really has declined crew great and I am loyal to delta

Boarding in Amsterdam is always chaotic. KLM/ Delta has not streamlined or made it efficient as it was boarding in Detroit . The food was mediocre The crew was unfriendly and more focused on getting things done quickly rather than service with a smile .

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Wonderful crew and early arrival to our destination. It was so nice to have free wifi access and movies too. Thank you!

Very friendly and efficient and smooth boarding. We were even way early arriving at my destination. Thank you.

The flight was late and we missed this connecting flight. American Airlines refused to put us anywhere for the night for their snafu. We had to find our own accommodations in Miami, and it was expensive for a crappy hotel.

The trip was very smooth and they provided great customer service

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Wonderful as usual except for other guests that were unruly and not kept in check by the Crew.

The flight was initially delayed, then cancelled. American Airlines says the cancellation was weather related, though the actual weather was not bad in both Washington and Providence and between. There were very few cancellations that day. In fact, AA2120 from Washington, DC to Boston flew with a minor delay at about the same time. So, the weather somehow affected only this particular flight AA5230. The next available flight was the following morning. The American Airlines refused to reimburse accommodation (hotel at DCA)

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

One bottle of water and a package of cookies for comfort plus. We had to literally beg a flight attendant for an extra bottle of water later in the flight due to feeling dehydrated.

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison

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