$115 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 4/22. 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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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

Fri, May 22 - Mon, Aug 31
American Airlines Logo
12:31 pm - 11:59 pm
MBJ
-
MSN
11h 28m
1 stop
American Airlines Logo
8:26 pm - 12:31 pm
MSN
-
MBJ
16h 05m
1 stop
$296American Airlines
Fri, May 22 - Mon, Aug 31
American Airlines Logo
12:31 pm - 11:19 pm
MBJ
-
MSN
10h 48m
2 stops
American Airlines Logo
8:26 pm - 1:30 pm
MSN
-
MBJ
17h 04m
2 stops
$301American Airlines
Mon, May 18 - Sat, Sep 5
American Airlines Logo
1:15 pm - 8:45 am
MBJ
-
MSN
19h 30m
1 stop
American Airlines Logo
8:26 pm - 12:31 pm
MSN
-
MBJ
16h 05m
1 stop
$302American Airlines
Mon, May 25 - Sun, Aug 30
American Airlines Logo
5:17 pm - 12:37 pm
MBJ
-
MSN
19h 20m
2 stops
American Airlines Logo
6:46 am - 9:25 am
MSN
-
MBJ
26h 39m
2 stops
$306American Airlines
Sun, May 24 - Mon, Aug 31
American Airlines Logo
5:17 pm - 1:05 pm
MBJ
-
MSN
19h 48m
2 stops
American Airlines Logo
8:26 pm - 12:31 pm
MSN
-
MBJ
16h 05m
1 stop
$311American Airlines
Thu, May 28 - Mon, Aug 31
Delta Logo
1:18 pm - 8:49 am
MBJ
-
MSN
19h 31m
2 stops
Delta Logo
5:50 pm - 1:04 pm
MSN
-
MBJ
19h 14m
2 stops
$322Delta
Sat, Jun 6 - Sat, Jun 20
Multiple Airlines Logo
5:56 pm - 8:25 am
SJU
-
MSN
39h 29m
2 stops
Multiple Airlines Logo
9:54 am - 1:30 pm
MSN
-
SJU
26h 36m
1 stop
$386Multiple Airlines
Fri, Jun 12 - Sat, Jun 20
Multiple Airlines Logo
6:10 am - 9:14 am
SJU
-
MSN
28h 04m
1 stop
Multiple Airlines Logo
9:54 am - 1:30 pm
MSN
-
SJU
26h 36m
1 stop
$391Multiple Airlines
Sun, Apr 19 - Sun, Apr 26
United Airlines Logo
2:53 pm - 9:21 pm
NAS
-
MSN
31h 28m
2 stops
United Airlines Logo
8:35 pm - 2:57 pm
MSN
-
NAS
17h 22m
1 stop
$672United Airlines
Sun, Apr 19 - Sun, Apr 26
United Airlines Logo
3:59 pm - 11:49 pm
NAS
-
MSN
8h 50m
1 stop
United Airlines Logo
8:30 am - 2:57 pm
MSN
-
NAS
5h 27m
1 stop
$1,248United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$115
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 2% 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 8258 reviews
7.8Entertainment
7.9Comfort
8.5Crew
7.2Food
8.1Boarding
Airline reviews

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

10.0 ExcellentGary, Mar 2026
LGA - DTW
Read more Delta reviews

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

My seatback screen didn’t work so that sucked because that’s what I was going to do on the plane.

Left a few minutes early. Got in 15 minutes early. Very attentive service on board. Very organized boarding.

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

Snow delayed boarding several times, which I understand happens. Issue I had was that after we did board, pilot told us we were going to roll out to be de-iced, then on our way. We were de-iced once, taxied to the tarmac and then stopped. Sat for another 30 minutes or so, the another de-icing. Then we rolled out to a parking spot, only to sit for another hour due to a traffic stop in DCA, which I'm confident they knew would happen before we boarded. Pilot gave no updates other than we had to hold, attendants did speak to the crew, but when asked, said the pilot would be updating us. We on the ground in the plane waiting for over 2 hours. They did communicate that bathrooms would be open, but no other news until we left. Would have been better to be up front about status.

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

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