$133 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 4/15. 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
$266
American Airlines
Wed 4/15Wed 4/22
SJU - MSN • 1 stop
Cheapest one-way
$133
Typical prices: $196-$351
American Airlines
Wed 4/15
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

Wed, Apr 15 - Wed, Apr 22
American Airlines Logo
3:19 pm - 11:28 pm
SJU
-
MSN
9h 09m
1 stop
American Airlines Logo
11:35 am - 8:51 pm
MSN
-
SJU
8h 16m
1 stop
$266American Airlines
Wed, Apr 29 - Fri, May 8
American Airlines Logo
3:19 pm - 11:28 pm
SJU
-
MSN
9h 09m
1 stop
American Airlines Logo
8:24 pm - 2:19 pm
MSN
-
SJU
16h 55m
1 stop
$329American Airlines
Wed, Apr 29 - Fri, May 8
American Airlines Logo
7:25 am - 5:06 pm
SJU
-
MSN
10h 41m
2 stops
American Airlines Logo
6:01 am - 6:10 pm
MSN
-
SJU
11h 09m
2 stops
$418American 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
7:02 am - 10:51 pm
MSN
-
SJU
14h 49m
1 stop
$443American Airlines
Thu, Mar 26 - Sun, Mar 29
Frontier Logo
6:30 am - 1:21 pm
SJU
-
MSN
7h 51m
1 stop
Frontier Logo
5:46 pm - 2:13 am
MSN
-
SJU
7h 27m
1 stop
$458Frontier
Mon, Apr 27 - Thu, Jun 4
American Airlines Logo
3:20 pm - 11:28 pm
MBJ
-
MSN
8h 08m
1 stop
American Airlines Logo
7:00 am - 1:31 pm
MSN
-
MBJ
6h 31m
1 stop
$471American Airlines
Thu, Jul 16 - Tue, Jul 28
JetBlue Logo
2:35 pm - 8:40 pm
SJU
-
MSN
7h 05m
1 stop
JetBlue Logo
5:45 am - 1:33 pm
MSN
-
SJU
6h 48m
1 stop
$476JetBlue
Mon, Apr 27 - Thu, Jun 4
American Airlines Logo
3:20 pm - 11:28 pm
MBJ
-
MSN
8h 08m
1 stop
American Airlines Logo
5:52 pm - 11:19 am
MSN
-
MBJ
17h 27m
2 stops
$476American Airlines
Thu, Mar 26 - Sun, Mar 29
Frontier Logo
6:30 am - 1:21 pm
SJU
-
MSN
7h 51m
1 stop
Frontier Logo
5:46 pm - 2:13 am
MSN
-
SJU
7h 27m
1 stop
$518Frontier
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 2:57 pm
SJU
-
MSN
14h 52m
2 stops
United Airlines Logo
5:44 pm - 6:11 am
MSN
-
SJU
10h 27m
2 stops
$520United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$133
Best time to beat the crowds but there is an average 32% increase in price.
Most popular time to fly and prices are also 7% 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 8203 reviews
7.9Comfort
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
Airline reviews

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

2.0 MediocreMansoor, Feb 2026
DTW - RIC
Read more Delta reviews

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Awful - both legs. The check in was awful, getting on the plane required walking down a spiral staircase (dangerous), then taking a bus about 5 miles out from the terminal. The seat was broken (I was in business), there was no internet during the flight (both legs). The aircraft was very old. I saw rust in some place, tape holding things up in the bathroom. This was an unacceptable experience for such a long haul flight.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The gate agent was most helpful in getting me on to fly standby. I greatly appreciate it.

bulkhead seat had very little legroom - even in bsiness class.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

The flight was fine, once we got underway. It was more than hour delayed

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

Waited for oxygen tanks for 30 minutes after boarding was complete.

The seats are too uncomfortable for anyone over 5ft 8in. I'm 5'10" with a back and hip issue and I was in pai for the full duration of the flight.

The gates should be ready when we land. Waiting on the runway for a hour is ridiculous.

The flight was on time/early, attentive crew, and everything overall went smoothly. Disappointed that WIFI was not working for the flight.

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