$118 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 5/1. 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
$325
Overall average: $528
United Airlines
Tue 2/24Sat 2/28
SJU - MSN • 2 stops
Cheapest one-way
$118
Typical prices: $190-$286
United Airlines
Fri 5/1
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

Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 2:07 pm
SJU
-
MSN
14h 02m2 stops
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m2 stops
$325United Airlines
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 11:53 am
SJU
-
MSN
11h 48m2 stops
United Airlines Logo
2:48 pm - 6:11 am
MSN
-
SJU
13h 23m2 stops
$368United Airlines
Tue, Jan 13 - Sat, Jan 17
Multiple Airlines Logo
3:47 pm - 9:08 am
SJU
-
MSN
19h 21m1 stop
Multiple Airlines Logo
6:16 pm - 12:32 pm
MSN
-
SJU
16h 16m2 stops
$382Multiple Airlines
Tue, Jan 13 - Sat, Jan 17
United Airlines Logo
7:45 am - 4:44 pm
SJU
-
MSN
10h 59m2 stops
United Airlines Logo
12:32 pm - 12:36 am
MSN
-
SJU
10h 04m2 stops
$399United Airlines
Tue, Jan 20 - Fri, Jan 30
United Airlines Logo
8:35 am - 4:44 pm
SJU
-
MSN
10h 09m1 stop
United Airlines Logo
3:48 pm - 6:11 am
MSN
-
SJU
12h 23m2 stops
$417United Airlines
Tue, Jan 20 - Fri, Jan 30
American Airlines Logo
6:00 am - 6:44 pm
SJU
-
MSN
14h 44m1 stop
American Airlines Logo
11:29 am - 9:39 pm
MSN
-
SJU
8h 10m1 stop
$420American Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:07 pm
SJU
-
MSN
7h 37m1 stop
United Airlines Logo
3:53 pm - 9:00 pm
MSN
-
SJU
27h 07m1 stop
$475United Airlines
Tue, Jan 20 - Fri, Jan 30
United Airlines Logo
7:45 am - 4:44 pm
SJU
-
MSN
10h 59m2 stops
United Airlines Logo
3:48 pm - 6:11 am
MSN
-
SJU
12h 23m2 stops
$485United Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:57 pm
SJU
-
MSN
8h 27m1 stop
United Airlines Logo
8:15 am - 9:00 pm
MSN
-
SJU
10h 45m1 stop
$615United Airlines
Fri, Mar 27 - Sat, Apr 4
American Airlines Logo
1:30 am - 10:36 am
SJU
-
MSN
10h 06m1 stop
American Airlines Logo
6:44 am - 5:11 pm
MSN
-
SJU
9h 27m1 stop
$625American Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$118
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 3% 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 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 8013 reviews
7.2Food
7.8Entertainment
8.1Boarding
8.5Crew
7.9Comfort
Airline reviews

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

6.0 GoodDorothy, Dec 2025
DTW - DCA
Read more Delta reviews

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

I went to washroom twice and once there was no toilet seat cover and the other no toilet paper at all. I don't think it was ever replenished or checked before we boarded as it was very early on in the flight.

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Original flight was canceled and rescheduled for the next day. Cancelation notice was sent in the middle of the night (only saw it in the morning), leaving no room to find other options. No offers to reimburse for the extra expenses or compensations. My flight to Rio on 12/12 was also delayed for 16 hours. This seems to be the new normal for AA.

Better service. No food options, but we did get drinks and a cookie.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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