$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 4/24. 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 7 - Sun, May 10
JetBlue Logo
7:30 am - 4:25 pm
SJU
-
MSN
9h 55m
1 stop
JetBlue Logo
5:43 am - 1:38 pm
MSN
-
SJU
6h 55m
1 stop
$286JetBlue
Wed, May 20 - Sat, Sep 5
American Airlines Logo
2:29 pm - 11:54 pm
MBJ
-
MSN
9h 25m
1 stop
American Airlines Logo
8:26 pm - 12:31 pm
MSN
-
MBJ
16h 05m
1 stop
$316American Airlines
Wed, May 20 - Sat, Sep 5
American Airlines Logo
12:56 pm - 7:49 am
MBJ
-
MSN
18h 53m
2 stops
American Airlines Logo
6:45 pm - 12:20 pm
MSN
-
MBJ
17h 35m
2 stops
$321American Airlines
Mon, Jun 1 - Tue, Jun 16
JetBlue Logo
2:48 pm - 10:44 pm
SJU
-
MSN
8h 56m
1 stop
JetBlue Logo
5:48 am - 1:31 pm
MSN
-
SJU
6h 43m
1 stop
$321JetBlue
Wed, May 6 - Sat, May 16
American Airlines Logo
4:30 pm - 12:04 am
SJU
-
MSN
8h 34m
1 stop
American Airlines Logo
11:35 am - 8:55 pm
MSN
-
SJU
8h 20m
1 stop
$334American Airlines
Thu, May 7 - Tue, May 12
United Airlines Logo
3:56 pm - 10:54 pm
SJU
-
MSN
7h 58m
1 stop
United Airlines Logo
8:10 am - 9:24 pm
MSN
-
SJU
12h 14m
2 stops
$349United Airlines
Mon, Jun 1 - Thu, Jun 11
JetBlue Logo
7:30 am - 4:25 pm
SJU
-
MSN
9h 55m
1 stop
JetBlue Logo
5:48 am - 1:31 pm
MSN
-
SJU
6h 43m
1 stop
$356JetBlue
Fri, May 1 - Wed, May 6
Delta Logo
2:45 pm - 10:27 pm
SJU
-
MSN
8h 42m
1 stop
Delta Logo
6:00 am - 8:26 pm
MSN
-
SJU
13h 26m
2 stops
$358Delta
Wed, May 6 - Sat, May 16
American Airlines Logo
1:31 pm - 12:04 am
SJU
-
MSN
11h 33m
2 stops
American Airlines Logo
9:18 am - 8:55 pm
MSN
-
SJU
10h 37m
2 stops
$375American Airlines
Wed, May 13 - Thu, Sep 3
United Airlines Logo
2:40 pm - 3:00 pm
MBJ
-
MSN
24h 20m
2 stops
United Airlines Logo
8:30 pm - 1:30 pm
MSN
-
MBJ
41h 00m
2 stops
$382United Airlines
Useful Info

Good to know

Low seasonAugust
Cheapest flight$113
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 8368 reviews
7.2Food
7.8Entertainment
7.9Comfort
8.5Crew
8.1Boarding
Airline reviews

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

10.0 ExcellentAnonymous, Apr 2026
MIA - DTW
Read more Delta reviews

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Our recent international travel was from Newark, NJ to Grenada via Atlanta. During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta as it did not wait for arriving passengers. Consequently, we were delayed by 24 hours before the next available flight was provided. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for me as a resident of New Jersey.

This was my first flight with Delta, the overall experience was good. I would definitely consider them more with my future flights.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

I have never been assaulted they way I was today in Charlotte - shame on American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Delayed 24 hours. Should have called it much earlier They provided quality accommodations, food vouchers etc. FINALLY The issues started at 8 AM and they cancelled the flight at 11:30 PM, with no plans for a new flight.

Better snacks but flight and crew were amazing on this flight

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

It was the most un-special flight experience in my life.

Plane was super cold. No entertainment unless you were with mileage program Getting off the plane was super slow

Flight was on-time, boarding was flawless and the crew was friendly.

The staff are very, very professional. It's what flying should feel like.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

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