$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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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

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
$250American Airlines
Thu, Apr 23 - Mon, Apr 27
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
American Airlines Logo
6:00 am - 6:10 pm
MSN
-
SJU
11h 10m
2 stops
$255American Airlines
Fri, Apr 24 - Sat, May 16
American Airlines Logo
11:38 am - 11:55 pm
SJU
-
MSN
13h 17m
1 stop
American Airlines Logo
1:05 pm - 10:05 pm
MSN
-
SJU
8h 00m
1 stop
$300American Airlines
Fri, May 1 - Fri, May 8
United Airlines Logo
2:40 pm - 8:56 am
MBJ
-
MSN
18h 16m
2 stops
United Airlines Logo
8:55 pm - 1:30 pm
MSN
-
MBJ
16h 35m
2 stops
$312United Airlines
Fri, May 15 - Mon, May 18
American Airlines Logo
2:29 pm - 11:54 pm
MBJ
-
MSN
9h 25m
1 stop
American Airlines Logo
6:45 am - 1:25 pm
MSN
-
MBJ
6h 40m
1 stop
$316American Airlines
Thu, Apr 23 - Mon, Apr 27
American Airlines Logo
1:31 pm - 11:28 pm
SJU
-
MSN
10h 57m
2 stops
American Airlines Logo
6:00 am - 6:10 pm
MSN
-
SJU
11h 10m
2 stops
$317American Airlines
Sat, May 16 - Tue, May 19
American Airlines Logo
10:13 am - 7:54 pm
MBJ
-
MSN
9h 41m
2 stops
American Airlines Logo
6:45 am - 3:37 pm
MSN
-
MBJ
8h 52m
2 stops
$321American Airlines
Sat, May 23 - Sat, Jun 6
United Airlines Logo
1:52 pm - 8:49 pm
MBJ
-
MSN
6h 57m
1 stop
United Airlines Logo
5:00 am - 3:10 pm
MSN
-
MBJ
10h 10m
2 stops
$331United 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
8:05 am - 8:55 pm
MSN
-
SJU
11h 50m
2 stops
$351American Airlines
Fri, Apr 24 - Sat, May 16
American Airlines Logo
1:31 pm - 11:55 pm
SJU
-
MSN
11h 24m
2 stops
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
$357American 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 8292 reviews
7.8Entertainment
7.9Comfort
8.1Boarding
8.5Crew
7.2Food
Airline reviews

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

4.0 OkayAnonymous, Mar 2026
CAE - ATL
Read more Delta reviews

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

No pilots so we were two hours late taking off and then no gate agents when we arrived in Salt Lake.

Crew was rude, almost 6 hour flight after horrific customs re entry line and near flight miss (unable to bug airport food) without food offerings.

Not good. One of my luggage is missing. And until now they can’t find it

Horrible experience upon landing. Probably more due to DCA utter incompetence than AA.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

My 9:50AM flight was delayed to 3:40PM "due to incoming aircraft delay". No aircraft is "delayed" that long. Found out once we did board (after several changes in times) that the aircraft had a maintenance issue and we had to wait for another aircraft. Just tell us that. The aircraft we did get was old and the seats need to be updated. I have been traveling for several weeks with AA and you should refresh your entertainment content as frequent flyers have gone through most of your new content. I have Celiac and a shellfish allergy and continue to have struggles with meals on business and first class flights. Please keep this in mind. Sorry - was a long travel day yesterday and a bit cranky this morning with my experience comments. Still an AA fan.

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

We changed our flight because of weather. Unfortunately we were on hold for over an hour, but since we were 5 people who all booked individually, we felt more comfortable doing it with an agent. It all worked out in the end.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

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