$133 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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Everything you should know

Cheapest round-trip
$266
American Airlines
Wed 4/15Wed 4/22
SJU - MSN • 1 stop
Cheapest one-way
$133
Typical prices: $196-$351
American Airlines
Wed 4/15
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

Wed, Apr 15 - Wed, Apr 22
American Airlines Logo
3:19 pm - 11:28 pm
SJU
-
MSN
9h 09m
1 stop
American Airlines Logo
11:35 am - 8:51 pm
MSN
-
SJU
8h 16m
1 stop
$266American Airlines
Wed, Apr 15 - Wed, Apr 22
American Airlines Logo
7:25 am - 5:06 pm
SJU
-
MSN
10h 41m
2 stops
American Airlines Logo
8:00 am - 8:51 pm
MSN
-
SJU
11h 51m
2 stops
$329American Airlines
Wed, Feb 25 - Sun, Mar 1
United Airlines Logo
8:30 am - 2:57 pm
SJU
-
MSN
8h 27m
1 stop
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
$430United Airlines
Thu, Jul 2 - Sun, Jul 12
American Airlines Logo
12:59 am - 9:23 am
SJU
-
MSN
9h 24m
1 stop
American Airlines Logo
7:00 am - 12:17 am
MSN
-
SJU
16h 17m
1 stop
$442American Airlines
Thu, Jul 16 - Tue, Jul 28
American Airlines Logo
12:59 am - 9:23 am
SJU
-
MSN
9h 24m
1 stop
American Airlines Logo
7:02 am - 10:51 pm
MSN
-
SJU
14h 49m
1 stop
$443American Airlines
Thu, Mar 26 - Sun, Mar 29
Frontier Logo
6:30 am - 1:21 pm
SJU
-
MSN
7h 51m
1 stop
Frontier Logo
5:46 pm - 2:13 am
MSN
-
SJU
7h 27m
1 stop
$458Frontier
Mon, Apr 27 - Thu, Jun 4
American Airlines Logo
3:20 pm - 11:28 pm
MBJ
-
MSN
8h 08m
1 stop
American Airlines Logo
7:00 am - 1:31 pm
MSN
-
MBJ
6h 31m
1 stop
$471American Airlines
Thu, Jul 16 - Tue, Jul 28
JetBlue Logo
2:40 pm - 10:35 pm
SJU
-
MSN
8h 55m
1 stop
JetBlue Logo
5:45 am - 4:43 pm
MSN
-
SJU
9h 58m
1 stop
$476JetBlue
Thu, Mar 26 - Sun, Mar 29
Frontier Logo
6:30 am - 1:21 pm
SJU
-
MSN
7h 51m
1 stop
Frontier Logo
5:46 pm - 2:13 am
MSN
-
SJU
7h 27m
1 stop
$518Frontier
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:57 pm
SJU
-
MSN
8h 27m
1 stop
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
$520United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$133
Best time to beat the crowds but there is an average 32% 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.
7.9
DeltaOverall score based on 8193 reviews
7.9Comfort
8.1Boarding
7.2Food
7.8Entertainment
8.5Crew
Airline reviews

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

4.0 OkayDuane, Feb 2026
ATL - FLL
Read more Delta reviews

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The gate agent was most helpful in getting me on to fly standby. I greatly appreciate it.

bulkhead seat had very little legroom - even in bsiness class.

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

This is the first time I've been disappointed with Delta. I was called by Delta to see if I would volunteer to change flights since my original flight home was overbooked. I accepted. The modified booking only provided me a 35 minute layover - when you subtract the fact that boarding closes for a flight 15 minutes early, that gave me 20 minutes to run for one end of the airport to the other. I barely made it. On the 2.5 hour flight to Tampa, the crew repeatedly let us know over the intercom that they cannot serve drinks or snacks due to safety/turbulence. I would have accepted this reason if they did not CONTINUALLY SERVE DRINKS AND COOKED FOOD to First class. If safety is the excuse then the entire plane should be strapped in for safety. On top of this the air conditioning vents were not working correctly and the plane was uncomfortably warm. I love Delta and am a loyal Delta traveler, and I have never had an experience like this. I don't know if there's a disconnect between availability among third-party sites like KAYAK and the airlines or what, but when overbooking causes issues like this for travelers it should be reviewed and changes to the booking process should be made. I blame BOTH KAYAK and Delta for this terrible experience.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Smooth boarding, pleasant and professional lady checking us in. Crew service was excellent, again pleasant, but professional. Nice touch-down on landing! Thank you Delta. 💗

Originally, I was booked in economy. I paid several hundred additional dollars to upgrade to first class. Then I paid several more hundred dollars to change my flight to a slightly earlier flight. I asked if the changed flight would also seat me in first class, and I was told that it would. When I boarded the plane, however, I was seated in economy. So, I paid $500-600 more than I paid for my original ticket for an upgrade and a changed flight - received the changed flight (which was nice), but did not receive the upgrade. So, I was not completely satisfied.

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