$128 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 2/13. 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
$346
Typical prices: $417-$517
United Airlines
Tue 2/24Sat 2/28
SJU - MSN • 2 stops
Cheapest one-way
$128
Typical prices: $185-$364
American Airlines
Fri 2/13
SJU - MSN • 1 stop
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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 02m
2 stops
United Airlines Logo
2:48 pm - 6:11 am
MSN
-
SJU
13h 23m
2 stops
$346United Airlines
Fri, Jul 17 - Tue, Jul 28
JetBlue Logo
7:30 am - 4:35 pm
SJU
-
MSN
10h 05m
1 stop
JetBlue Logo
5:45 am - 1:33 pm
MSN
-
SJU
6h 48m
1 stop
$356JetBlue
Fri, Feb 20 - Mon, Feb 23
American Airlines Logo
3:47 pm - 10:59 pm
NAS
-
MSN
8h 12m
1 stop
American Airlines Logo
8:09 am - 7:51 pm
MSN
-
NAS
10h 42m
2 stops
$408American Airlines
Fri, Feb 20 - Mon, Feb 23
American Airlines Logo
3:47 pm - 10:59 pm
NAS
-
MSN
8h 12m
1 stop
American Airlines Logo
5:17 pm - 12:57 pm
MSN
-
NAS
18h 40m
1 stop
$413American Airlines
Mon, Mar 9 - Mon, Mar 16
United Airlines Logo
2:35 pm - 11:38 am
NAS
-
MSN
22h 03m
2 stops
United Airlines Logo
6:05 am - 2:32 pm
MSN
-
NAS
7h 27m
1 stop
$457United Airlines
Thu, Feb 5 - Tue, Feb 10
United Airlines Logo
2:05 am - 2:10 pm
SJU
-
MSN
14h 05m
2 stops
United Airlines Logo
6:30 am - 9:26 pm
MSN
-
SJU
12h 56m
2 stops
$510United Airlines
Fri, Feb 20 - Mon, Feb 23
American Airlines Logo
12:48 pm - 11:26 pm
NAS
-
MSN
11h 38m
2 stops
American Airlines Logo
8:09 am - 7:51 pm
MSN
-
NAS
10h 42m
2 stops
$514American Airlines
Tue, May 19 - Wed, Jun 3
Delta Logo
12:55 pm - 10:35 pm
MBJ
-
MSN
9h 40m
1 stop
Delta Logo
5:45 am - 3:29 pm
MSN
-
MBJ
9h 44m
1 stop
$515Delta
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:57 pm
SJU
-
MSN
8h 27m
1 stop
United Airlines Logo
2:48 pm - 9:00 pm
MSN
-
SJU
28h 12m
1 stop
$539United Airlines
Tue, May 19 - Wed, Jun 3
American Airlines Logo
4:44 pm - 11:04 am
MBJ
-
MSN
18h 20m
2 stops
American Airlines Logo
6:30 pm - 11:42 am
MSN
-
MBJ
17h 12m
2 stops
$554American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$128
Best time to beat the crowds but there is an average 30% increase in price.
Most popular time to fly and prices are also 13% 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 8095 reviews
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
7.9Comfort
Airline reviews

I've flown several other airlines, and Delta is really on top on things.

10.0 ExcellentBob, Jan 2026
SCL - MIA
Read more Delta reviews

I've flown several other airlines, and Delta is really on top on things.

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Trip delayed for 2 hours because of rain. We boarded and have to get down the flight and reboard again.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

This flight captain and crew were amazing, started ahead of time of departure and reached 30 mins before arrival time. Amazing!

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

No enough space plus only allowing one laggage instead of two like other airlines.

It was good. But the gate team made me check my carry on when there was plenty of space for my luggage on the plane. Otherwise our trip was fine.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

The comfort of Business Class made this trip far more comfortable. I was indeed surprised when I asked one of the flight attendant to help me set up my "bed", she responded that "We don't make beds in Business Class any longer...only First Class" I believe her name was Giselle, but I'm not certain. She did instruct me how to adjust the seat, place the hooded cover and I clearly understood how to place the blanket and the cover. Additionally, the meal I was served (a beef dish) was almost inedible. The beef was tough and odd tasting. I didn't mention it as I was hoping to quickly settle down and try to get some sleep.

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