$163 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 11/7. 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

Wed, Aug 26 - Mon, Aug 31
Delta Logo
2:59 pm - 10:38 pm
SJU
-
MSN
8h 39m
1 stop
Delta Logo
5:43 am - 4:38 pm
MSN
-
SJU
9h 55m
1 stop
$256Delta
Sat, Dec 5 - Sat, Dec 12
United Airlines Logo
3:20 pm - 12:12 am
MBJ
-
MSN
33h 52m
2 stops
United Airlines Logo
2:25 pm - 1:46 pm
MSN
-
MBJ
22h 21m
1 stop
$323United Airlines
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
5:04 pm - 11:49 pm
MBJ
-
MSN
7h 45m
1 stop
American Airlines Logo
3:55 pm - 10:12 am
MSN
-
MBJ
17h 17m
1 stop
$326American Airlines
Wed, Aug 26 - Mon, Aug 31
American Airlines Logo
10:33 am - 11:09 pm
SJU
-
MSN
13h 36m
2 stops
American Airlines Logo
5:00 am - 11:15 pm
MSN
-
SJU
17h 15m
1 stop
$326American Airlines
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
7:00 am - 11:29 pm
SJU
-
MSN
17h 29m
1 stop
American Airlines Logo
6:30 am - 9:55 pm
MSN
-
SJU
14h 25m
2 stops
$366American Airlines
Fri, Sep 25 - Tue, Sep 29
United Airlines Logo
1:00 am - 1:37 pm
SJU
-
MSN
13h 37m
2 stops
United Airlines Logo
6:49 am - 2:44 pm
MSN
-
SJU
6h 55m
1 stop
$381United Airlines
Thu, Jul 16 - Mon, Aug 3
JetBlue Logo
2:42 pm - 10:38 pm
SJU
-
MSN
8h 56m
1 stop
JetBlue Logo
5:43 am - 4:38 pm
MSN
-
SJU
9h 55m
1 stop
$391JetBlue
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
10:33 am - 11:09 pm
SJU
-
MSN
13h 36m
2 stops
American Airlines Logo
7:47 am - 9:55 pm
MSN
-
SJU
13h 08m
2 stops
$409American Airlines
Sun, Jul 26 - Sun, Aug 2
JetBlue Logo
7:30 am - 3:51 pm
SJU
-
MSN
9h 21m
1 stop
JetBlue Logo
5:48 am - 4:39 pm
MSN
-
SJU
9h 51m
1 stop
$416JetBlue
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
7:00 am - 9:41 pm
SJU
-
MSN
15h 41m
1 stop
American Airlines Logo
7:00 am - 10:59 pm
MSN
-
SJU
14h 59m
1 stop
$449American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$163
Best time to beat the crowds but there is an average 40% increase in price.
Most popular time to fly and prices are also 7% 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 airline 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.
7.1
American AirlinesOverall score based on 11640 reviews
7.9Crew
7.2Comfort
6.4Food
6.9Entertainment
7.5Boarding
Airline reviews

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

4.0 OkayAnonymous, Jun 2026
DEN - ORD
Read more American Airlines reviews

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight back to Dallas was delayed, which has happened to me several times with American Airlines. There was no announcement, no update sent out, no compensation offered for the inconvenience.

It wa sort of on time; the cab was left with some trash

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

Very hard to beat a British Airways international flight…the crews are always so amazing! One flight attendant that really stood out was Emma…she was very personable and accommodating with any request we had!!

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

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