$125 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 4/23. 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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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

Thu, May 14 - Mon, May 18
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
$287American Airlines
Fri, Apr 24 - Sat, May 16
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
$311American Airlines
Sat, Jul 4 - Sat, Jul 18
United Airlines Logo
4:33 pm - 10:59 pm
MBJ
-
MSN
30h 26m
2 stops
United Airlines Logo
8:10 am - 1:30 pm
MSN
-
MBJ
29h 20m
2 stops
$312United Airlines
Thu, May 7 - Tue, Sep 1
American Airlines Logo
4:37 pm - 10:55 am
MBJ
-
MSN
18h 18m
2 stops
American Airlines Logo
4:21 pm - 9:25 am
MSN
-
MBJ
17h 04m
2 stops
$321American Airlines
Thu, May 7 - Tue, Sep 1
American Airlines Logo
12:25 pm - 10:55 am
MBJ
-
MSN
22h 30m
1 stop
American Airlines Logo
6:46 am - 2:20 pm
MSN
-
MBJ
7h 34m
1 stop
$323American Airlines
Sat, May 23 - Sat, Jun 6
United Airlines Logo
4:12 pm - 8:55 am
MBJ
-
MSN
16h 43m
2 stops
United Airlines Logo
6:30 am - 12:50 pm
MSN
-
MBJ
6h 20m
1 stop
$336United Airlines
Fri, Apr 24 - Sat, May 16
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
American Airlines Logo
9:18 am - 8:55 pm
MSN
-
SJU
10h 37m
2 stops
$339American Airlines
Thu, May 28 - Sun, Aug 30
Delta Logo
4:59 pm - 8:49 am
MBJ
-
MSN
15h 50m
2 stops
Delta Logo
5:50 pm - 1:04 pm
MSN
-
MBJ
19h 14m
2 stops
$363Delta
Thu, May 14 - Mon, May 18
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
American Airlines Logo
6:45 am - 9:24 pm
MSN
-
SJU
13h 39m
2 stops
$370American Airlines
Thu, Apr 16 - Mon, Apr 20
United Airlines Logo
1:00 am - 10:11 am
SJU
-
MSN
10h 11m
2 stops
United Airlines Logo
10:05 am - 8:34 pm
MSN
-
SJU
9h 29m
1 stop
$401United Airlines
Useful Info

Good to know

Low seasonAugust
Cheapest flight$125
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 16% increase in price.
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 8291 reviews
8.1Boarding
7.9Comfort
7.8Entertainment
7.2Food
8.5Crew
Airline reviews

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

2.0 MediocreSusan, Mar 2026
JAX - ATL
Read more Delta reviews

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

Movie selections were very limited. Meals were not f So good.

Older airplane with worn out seats. No entertainment system at all. Connecting to Wi-Fi was problematic and hit and miss.

AA is flying sub par aging 787's to Tokyo. I fly other 787's long haul and these are at the bottom. Seats don't work well, tray tables don't work well and were dirty. The flight was great, the plane was not.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Our flight was delayed 3 times and this is why I am giving such low reviews. Everything else was okay but being in the airport at 4:30pm for my initial flight at 7pm to not leave until after 9:30pm is insane,

Flights were constantly delayed. CRW took 50 minutes to get bags

Flight has been delayed every time I've ever taken it. Seats uncomfortable. Children behind me yelling the entire flight. Some of this is out of their control but overall just consistently not a great experience.

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Where do I start!! I was delayed with my flight from Dallas to Tampa. On the way back from Tampa to Dallas the flight was delayed over 4 hours+. I was put on another flight that was also delayed but not as long. Traveling on American Airlines is becoming exhausing.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

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