$175 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 4/14. 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
$326
Overall average: $528
United Airlines
Tue 2/24Sat 2/28
SJU - MSN • 2 stops
Cheapest one-way
$175
Typical prices: $185-$390
Multiple Airlines
Tue 4/14
SJU - MSN • 1 stop
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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

Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 2:07 pm
SJU
-
MSN
14h 02m2 stops
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m2 stops
$326United Airlines
Wed, Mar 11 - Sat, Mar 21
American Airlines Logo
1:30 am - 10:36 am
SJU
-
MSN
10h 06m1 stop
American Airlines Logo
8:22 pm - 4:24 am
MSN
-
SJU
7h 02m1 stop
$366American Airlines
Sat, Mar 28 - Sat, Apr 4
United Airlines Logo
7:30 am - 2:57 pm
SJU
-
MSN
8h 27m1 stop
United Airlines Logo
12:13 pm - 8:34 pm
MSN
-
SJU
7h 21m1 stop
$441United Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:07 pm
SJU
-
MSN
7h 37m1 stop
United Airlines Logo
2:48 pm - 9:00 pm
MSN
-
SJU
28h 12m1 stop
$476United Airlines
Tue, Apr 14 - Fri, May 29
United Airlines Logo
4:12 pm - 9:16 pm
MBJ
-
MSN
29h 04m2 stops
United Airlines Logo
5:30 pm - 12:49 pm
MSN
-
MBJ
19h 19m1 stop
$511United Airlines
Tue, Apr 14 - Fri, May 29
American Airlines Logo
2:19 pm - 11:01 pm
MBJ
-
MSN
8h 42m1 stop
American Airlines Logo
6:00 am - 1:58 pm
MSN
-
MBJ
7h 58m1 stop
$513American Airlines
Sat, Mar 28 - Sat, Apr 4
United Airlines Logo
7:30 am - 2:57 pm
SJU
-
MSN
8h 27m1 stop
United Airlines Logo
12:13 pm - 11:50 pm
MSN
-
SJU
10h 37m2 stops
$516United Airlines
Thu, Mar 12 - Sat, Mar 21
American Airlines Logo
6:00 am - 3:52 pm
SJU
-
MSN
10h 52m2 stops
American Airlines Logo
8:22 pm - 4:24 am
MSN
-
SJU
7h 02m1 stop
$533American Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:07 pm
SJU
-
MSN
7h 37m1 stop
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m1 stop
$581United Airlines
Fri, Feb 6 - Mon, Feb 9
WestJet Logo
2:55 pm - 8:54 pm
MBJ
-
MSN
30h 59m2 stops
WestJet Logo
5:54 pm - 7:17 pm
MSN
-
MBJ
24h 23m2 stops
$3,276WestJet
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$175
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 5% 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 8038 reviews
7.8Entertainment
7.9Comfort
7.2Food
8.1Boarding
8.5Crew
Airline reviews

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

8.0 ExcellentG, Jan 2026
FLL - ATL
Read more Delta reviews

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

Lower WiFi prices; allow us to see our flight on a map; more variety of drink choices.

I was originally scheduled on AA 1763. When I landed in Miami, I went to the counter for flight AA 2115 to try to move my flight to this one. I was in a first class seat on AA 1763. While they moved to me this flight, I was told that there were no other 1st class seats available and they assigned me into coach. However, when I was getting off the plane I noticed that one of the pilots who was also in line to go jump seat - somehow miraculously got a 1st class seat on this flight. It is actually infuriating that I had a paid 1st class seat yet somehow they would move an AA employee ahead of that. At a bare minimum, they should have compensated me for the fare difference and I really think paying customers should ALWAYs get the premiere seats.

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

Seats were much more cramped then on the 737. Narrower and rows closer together. Flight was absolutely packed and the plugs under the seats didn't work. Was forced to check my bag even though previous flight had no issue with it.

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

The flight was on time and arrived early. The crew were friendly and helpful.

We had a 2 hour delay that impacted our comanions further travel. I have a feeling AA knows there is a problem at the Cabo airport and does not account for that.

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