$118 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 2/5. 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
$274
Overall average: $520
American Airlines
Thu 4/30Tue 5/5
SJU - MSN • 1 stop
Cheapest one-way
$118
Typical prices: $194-$382
American Airlines
Thu 2/5
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

Thu, Apr 30 - Tue, May 5
American Airlines Logo
5:40 am - 10:29 pm
SJU
-
MSN
17h 49m1 stop
American Airlines Logo
6:38 am - 12:10 am
MSN
-
SJU
16h 32m1 stop
$274American Airlines
Thu, Apr 30 - Tue, May 5
American Airlines Logo
5:40 am - 10:29 pm
SJU
-
MSN
17h 49m1 stop
American Airlines Logo
6:27 am - 7:55 pm
MSN
-
SJU
12h 28m2 stops
$307American Airlines
Wed, Jan 28 - Sat, Jan 31
United Airlines Logo
8:35 am - 2:10 pm
SJU
-
MSN
7h 35m1 stop
United Airlines Logo
12:32 pm - 12:36 am
MSN
-
SJU
10h 04m2 stops
$325United Airlines
Tue, Jan 27 - Sat, Jan 31
United Airlines Logo
2:05 am - 11:51 am
SJU
-
MSN
11h 46m2 stops
United Airlines Logo
12:32 pm - 12:36 am
MSN
-
SJU
10h 04m2 stops
$368United Airlines
Wed, Jan 21 - Mon, Jan 26
United Airlines Logo
2:05 am - 2:52 pm
SJU
-
MSN
14h 47m2 stops
United Airlines Logo
6:30 am - 9:26 pm
MSN
-
SJU
12h 56m2 stops
$411United Airlines
Thu, Apr 30 - Tue, May 5
United Airlines Logo
7:20 am - 7:19 pm
SJU
-
MSN
12h 59m2 stops
United Airlines Logo
8:23 am - 11:50 pm
MSN
-
SJU
14h 27m2 stops
$432United Airlines
Wed, Jan 28 - Sat, Jan 31
United Airlines Logo
8:35 am - 2:10 pm
SJU
-
MSN
7h 35m1 stop
United Airlines Logo
5:26 pm - 3:40 pm
MSN
-
SJU
20h 14m1 stop
$475United Airlines
Wed, Jan 28 - Sat, Jan 31
United Airlines Logo
8:35 am - 2:52 pm
SJU
-
MSN
8h 17m1 stop
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m1 stop
$515United Airlines
Wed, Dec 31 - Sun, Jan 4
United Airlines Logo
2:05 am - 11:48 am
SJU
-
MSN
11h 43m2 stops
United Airlines Logo
6:40 am - 3:40 pm
MSN
-
SJU
7h 00m1 stop
$575United Airlines
Sat, Mar 28 - Sat, Apr 4
American Airlines Logo
5:30 am - 2:30 pm
SJU
-
MSN
10h 00m1 stop
American Airlines Logo
6:45 am - 2:45 pm
MSN
-
SJU
7h 00m1 stop
$627American Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$118
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 3% 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 8018 reviews
8.5Crew
7.3Food
7.9Entertainment
7.9Comfort
8.1Boarding
Airline reviews

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

2.0 MediocreGina, Dec 2025
DTW - ELM
Read more Delta reviews

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

Flight was operated by Virgin Atlantic and it was up to their usual high standard. Minor grips about some issues, but they are really first world issues and as a whole, was an excellent flight.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Delta One upgrade it would have been great if my tray extended (it was jammed and wouldn’t pull out), seatbelt had too much slack & my little cabin door didn’t close properly

I paid for a business class ticket on Delta. It was sourced to Virgin Atlantic. They changed out the aircraft which had fewer upper class tickets. Even though I'd checked into the lounge, was receiving alerts via kayak about the delay and changes; no one informed me that the seat would be changed - until I attempted to board and was told that I would have an economy seat or they could search to put me on another airline. Even the flight crew were informed of this change (10 passengers were bumped out of Upper Class) around 2 pm (1400) time. Hours would have helped to consider alternatives instead of making a last minute change. There needs to be compensation from both Delta and Virgin given this change in service/experience.

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Every single flight that we got on was delayed by several hours or more. I honestly didn’t think we would get out of Atlanta because our flight was supposed to leave at 7:59 and it kept getting kicked back further and further. Delta stands for Don’t Ever Leave The Airport!

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

Did not understand a single word the attendant said on the pa system. I was glad it was not an emergency.

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

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