$114 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 9/6. 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.
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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
7:15 am - 11:45 pmSJU-MSN
17h 30m1 stop
American Airlines Logo
5:00 am - 10:30 pmMSN-SJU
16h 30m1 stop
$315American Airlines
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Wed, May 14 - Sun, May 18
American Airlines Logo
1:30 pm - 11:45 pmSJU-MSN
11h 15m2 stops
American Airlines Logo
5:00 am - 10:30 pmMSN-SJU
16h 30m1 stop
$395American Airlines
Find Deal
Wed, May 14 - Sun, May 18
American Airlines Logo
3:50 pm - 11:45 pmSJU-MSN
8h 55m1 stop
American Airlines Logo
5:00 am - 10:30 pmMSN-SJU
16h 30m1 stop
$410American Airlines
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Wed, May 14 - Sun, May 18
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
$459United Airlines
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Tue, May 13 - Sun, May 18
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
$477American Airlines
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Wed, May 28 - Wed, Jun 4
American Airlines Logo
10:10 am - 11:45 pmMBJ-MSN
13h 35m1 stop
American Airlines Logo
7:17 am - 1:10 pmMSN-MBJ
5h 53m1 stop
$480American Airlines
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Fri, May 9 - Wed, Sep 3
American Airlines Logo
10:10 am - 11:45 pmMBJ-MSN
13h 35m1 stop
American Airlines Logo
6:43 pm - 9:35 amMSN-MBJ
14h 52m2 stops
$509American Airlines
Find Deal
Fri, May 9 - Wed, Sep 3
United Airlines Logo
7:45 am - 1:54 pmSJU-MSN
7h 09m1 stop
United Airlines Logo
3:55 pm - 11:54 pmMSN-SJU
6h 59m1 stop
$532United Airlines
Find Deal
Wed, May 28 - Wed, Jun 4
Delta Logo
7:00 am - 8:43 pmSJU-MSN
14h 43m2 stops
Delta Logo
6:00 am - 7:48 pmMSN-SJU
12h 48m2 stops
$561Delta
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Wed, May 28 - Wed, Jun 4
 Logo
12:07 pm - 4:19 pmMBJ-MSN
28h 12m3 stops
 Logo
6:08 pm - 9:14 amMSN-MBJ
15h 06m2 stops
Fri, May 9 - Wed, Sep 3

Good to know

Low season

February

High season

December

Cheapest flight

$114
Best time to beat the crowds with an average 6% 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 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 7920 reviews
8.2Boarding
7.9Comfort
8.5Crew
7.9Entertainment
7.3Food
Airline reviews

Delta flight was on time, seats were comfortable, and crew was nice.

8.0 ExcellentAnonymous, Apr 2025LAX - DEN
Read more Delta reviews

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

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 .

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Flight was delayed bc of mechanical issue. New plane had different configuration so some seats had to be switched. They called all passengers who needed new boarding cards. They did not call us so we thought our seats were the same and fine. When we boarded they informed us our receipts had changed and we are now all sitting separate and in the back row. Both my daughters had meltdowns and started to cry and once we got on the flight, we figured out how we could sit closer to each other, but this was very upsetting.

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Any sort of gluten free snack option would be nice

They lost my luggage and it didn’t get delivered until the next day.

Would have thought that they would gas up plane before everyone got on board

Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison

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