$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 4/15. 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 14 - Mon, May 18
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
$306American Airlines
Fri, May 8 - Sun, May 31
United Airlines Logo
2:40 pm - 3:02 pm
MBJ
-
MSN
24h 22m
2 stops
United Airlines Logo
8:10 am - 3:10 pm
MSN
-
MBJ
31h 00m
2 stops
$310United Airlines
Wed, May 20 - Tue, Sep 8
American Airlines Logo
10:17 am - 11:54 pm
MBJ
-
MSN
13h 37m
1 stop
American Airlines Logo
6:00 am - 1:58 pm
MSN
-
MBJ
7h 58m
1 stop
$316American Airlines
Wed, May 20 - Tue, Sep 8
American Airlines Logo
2:29 pm - 11:54 pm
MBJ
-
MSN
9h 25m
1 stop
American Airlines Logo
4:20 pm - 10:50 am
MSN
-
MBJ
18h 30m
2 stops
$321American Airlines
Thu, May 7 - Tue, May 12
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
$338American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
American Airlines Logo
11:33 am - 8:51 pm
MSN
-
SJU
8h 18m
1 stop
$356American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
11:38 am - 10:11 pm
SJU
-
MSN
11h 33m
2 stops
American Airlines Logo
6:45 am - 8:51 pm
MSN
-
SJU
13h 06m
1 stop
$378American 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
Fri, May 1 - Thu, Sep 3
United Airlines Logo
4:12 pm - 7:07 pm
MBJ
-
MSN
26h 55m
2 stops
United Airlines Logo
8:30 pm - 1:30 pm
MSN
-
MBJ
41h 00m
2 stops
$389United Airlines
Fri, May 1 - Sat, May 9
American Airlines Logo
3:21 pm - 11:28 pm
NAS
-
MSN
9h 07m
1 stop
American Airlines Logo
5:08 pm - 1:32 pm
MSN
-
NAS
19h 24m
1 stop
$395American 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 8359 reviews
8.1Boarding
7.8Entertainment
7.9Comfort
7.2Food
8.5Crew
Airline reviews

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.

8.0 ExcellentLorna, Mar 2026
LAX - LIH
Read more Delta reviews

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

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Wonderful crew, great movie selection and good food. I prefer Airbus to Boeing, much more comfortable

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

Award tickets are some of the best... seats lack entertainment options.

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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