$113 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 10/4. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Madison

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights 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

Sat, Oct 18 - Tue, Oct 21
American Airlines Logo
3:50 pm - 11:51 pmSJU-MSN
9h 01m1 stop
American Airlines Logo
6:00 am - 2:08 pmMSN-SJU
7h 08m1 stop
$265American Airlines
Find Deal
Sat, Oct 18 - Tue, Oct 21
Delta Logo
2:15 pm - 9:54 pmSJU-MSN
8h 39m1 stop
Delta Logo
5:45 am - 4:18 pmMSN-SJU
9h 33m1 stop
$302Delta
Find Deal
Sat, Oct 18 - Tue, Oct 21
United Airlines Logo
3:56 pm - 10:28 pmSJU-MSN
7h 32m1 stop
United Airlines Logo
6:30 am - 2:44 pmMSN-SJU
7h 14m1 stop
$315United Airlines
Find Deal
Sat, Oct 18 - Tue, Oct 21
American Airlines Logo
3:55 pm - 10:18 amSJU-MSN
19h 23m2 stops
American Airlines Logo
6:00 am - 1:45 pmMSN-SJU
6h 45m1 stop
$370American Airlines
Find Deal
Fri, Oct 17 - Tue, Oct 21
United Airlines Logo
1:05 am - 9:55 amSJU-MSN
9h 50m2 stops
United Airlines Logo
6:30 am - 2:44 pmMSN-SJU
7h 14m1 stop
$385United Airlines
Find Deal
Thu, Oct 30 - Mon, Dec 1
United Airlines Logo
12:25 pm - 10:45 pmMBJ-MSN
10h 20m1 stop
United Airlines Logo
6:30 am - 1:46 pmMSN-MBJ
6h 16m1 stop
$404United Airlines
Find Deal
Thu, Oct 30 - Mon, Dec 1
American Airlines Logo
4:25 pm - 10:00 amMBJ-MSN
17h 35m2 stops
American Airlines Logo
6:26 am - 2:48 pmMSN-MBJ
7h 22m1 stop
$409American Airlines
Find Deal
Thu, Aug 7 - Mon, Aug 18
American Airlines Logo
3:50 pm - 11:59 pmSJU-MSN
9h 09m1 stop
American Airlines Logo
6:19 am - 10:49 pmMSN-SJU
15h 30m1 stop
$425American Airlines
Find Deal
Wed, Dec 24 - Fri, Jan 2
American Airlines Logo
6:40 am - 3:08 pmSJU-MSN
10h 28m1 stop
American Airlines Logo
6:29 pm - 11:45 amMSN-SJU
15h 16m1 stop
$430American Airlines
Find Deal
Wed, Dec 24 - Fri, Jan 2
Delta Logo
1:05 pm - 8:39 pmSJU-MSN
9h 34m2 stops
Delta Logo
7:00 am - 3:40 pmMSN-SJU
6h 40m1 stop
$450Delta
Find Deal
Useful Info

Good to know

Low seasonFebruary
High seasonDecember
Cheapest flight$113
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 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 airline 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.
7.2
American AirlinesOverall score based on 10000 reviews
6.5Food
6.9Entertainment
7.5Boarding
8.0Crew
7.2Comfort
Airline reviews

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

4.0 OkayAnonymous, Jun 2025BNA - DFW
Read more American Airlines reviews

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

This flight never occurred because AA couldn’t get their act together.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

A cookie and a soda, packed like sardines, will never be a positive experience. Also, boarded a 5:30 flight at 7:45pm

Am still mad at American airlines. You should know it's us travel nurses who are your customers and you treat us like nonsense it's not ok. American airlines took my money, no refund for whatsoever. A trip that was of 466 and I paid 466 and 833 then they chose for me where to sit and refund my seat choices and gave me expensive seats for 79 USD. Kayak doesn't help at all after booking you are on your own. Skyscanner is better

Flight was good & early meaning the gate was changed. With gate change there were no wheelchairs & the gate attendant left without making sure wheelchairs were coming to the changed gate. I had to go to another attendant at another desk to get this done.

This was a horrible experience. For a first class experience, my chair was held together by 3M tape - and I have a photo. The crew weren’t very attentive, somewhat dismissive and forgot my drink and snack, the chair reclined about 3 inches on a 6-hour cross country flight. I was also not informed that there was no lounge available in Newark airport because of renovations, so all around this was one of the worst experiences and I would actively avoid both American and Alaska Air going forward.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.