$123 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 7/30. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Madison

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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, May 6 - Thu, Sep 10
United Airlines Logo
2:40 pm - 8:55 am
MBJ
-
MSN
18h 15m
2 stops
United Airlines Logo
8:30 pm - 1:30 pm
MSN
-
MBJ
41h 00m
2 stops
$312United Airlines
Fri, May 8 - Tue, Sep 8
American Airlines Logo
12:25 pm - 11:54 pm
MBJ
-
MSN
11h 29m
1 stop
American Airlines Logo
6:00 am - 1:58 pm
MSN
-
MBJ
7h 58m
1 stop
$316American Airlines
Thu, May 14 - Sat, Aug 29
Delta Logo
4:59 pm - 8:49 am
MBJ
-
MSN
15h 50m
2 stops
Delta Logo
7:00 am - 3:34 pm
MSN
-
MBJ
8h 34m
2 stops
$317Delta
Fri, May 8 - Tue, Sep 8
American Airlines Logo
10:17 am - 11:54 pm
MBJ
-
MSN
13h 37m
1 stop
American Airlines Logo
5:46 pm - 10:50 am
MSN
-
MBJ
17h 04m
2 stops
$321American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
1:25 pm - 11:28 pm
SJU
-
MSN
11h 03m
1 stop
American Airlines Logo
6:45 am - 6:10 pm
MSN
-
SJU
10h 25m
2 stops
$326American Airlines
Sun, May 17 - Wed, Sep 9
American Airlines Logo
4:37 pm - 10:55 am
MBJ
-
MSN
18h 18m
2 stops
American Airlines Logo
6:23 pm - 10:50 am
MSN
-
MBJ
16h 27m
2 stops
$331American Airlines
Fri, May 15 - Mon, May 18
American Airlines Logo
6:45 am - 10:32 pm
SJU
-
MSN
16h 47m
1 stop
American Airlines Logo
6:10 am - 10:05 pm
MSN
-
SJU
14h 55m
1 stop
$334American Airlines
Thu, May 7 - Tue, May 12
Delta Logo
6:15 am - 4:25 pm
SJU
-
MSN
11h 10m
1 stop
Delta Logo
5:43 am - 4:33 pm
MSN
-
SJU
9h 50m
1 stop
$408Delta
Sun, Jul 5 - Fri, Jul 17
Multiple Airlines Logo
8:00 am - 8:25 am
SJU
-
MSN
25h 25m
1 stop
Multiple Airlines Logo
6:50 pm - 5:36 pm
MSN
-
SJU
21h 46m
2 stops
$434Multiple Airlines
Sun, Jul 5 - Mon, Jul 13
Multiple Airlines Logo
8:00 am - 8:25 am
SJU
-
MSN
25h 25m
1 stop
Multiple Airlines Logo
6:50 pm - 4:34 pm
MSN
-
SJU
20h 44m
1 stop
$449Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$123
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 8% 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 8438 reviews
7.2Food
8.1Boarding
8.5Crew
7.9Comfort
7.8Entertainment
Airline reviews

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

4.0 OkayAnonymous, Apr 2026
MYR - ATL
Read more Delta reviews

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

On time departure and early arrival. Flight attendant very nice.

As we approached Denver, we encountered quite a bit of turbulence. I know this can sometimes be the case as I frequently fly this route but not on American. My gripe: Usually a pilot or co-pilot alerts passengers to the possibility of turbulance ahead of time. This did not occur nor did he communiucate during what was a pretty rough ride.

The staff was nice. I appreciated that I was able to take an earlier flight, even though it was last minute. The boarding process felt rather chaotic.

Overall a good experience, however Wifi was not working on the flight.

Airlines should be prohibited from using the seats they get away with.

My flight got delayed a total of five times. And the boarding gate changed four times. most of the time the platform was not up-to-date with the changes taking place. The most discouraging part of the entire trip by far.

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

American delayed the flight for a crew rest period. The delay occurred late in the evening - the earliest i can find is 10:20 pm. With a 6 am flight anyone on the flight would have already have been asleep (unless you are insane, a vampire or on drugs) and at least for me i was already on the way to the airport at 445 am the next morning when i discovered they delayed the flight until 9 am. Given the incoming flight was in the air at 6 pm the evening before this should have been figured out a lot more timely that was there only crew to use. Just frustrating given there is no consideration for customer experience anymore in flying.

Returned home with a blood clot from flight homes and the uncomfortable aircraft I was on.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Baraboo
Windsor
Evansville
Cambridge
Oxford

Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison