$364 Find Cheap Flights from Madison to the Cayman Islands

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to the Cayman Islands departing on 3/7. 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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Book Cheap Madison to the Cayman Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to the Cayman Islands 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 Madison to the Cayman Islands

Sat, Mar 7 - Tue, Mar 10
American Airlines Logo
8:22 pm - 1:13 pm
MSN
-
GCM
15h 51m
2 stops
American Airlines Logo
7:45 am - 9:39 pm
GCM
-
MSN
13h 54m
2 stops
$364American Airlines
Sat, Mar 7 - Tue, Mar 10
American Airlines Logo
8:22 pm - 1:44 pm
MSN
-
GCM
16h 22m
1 stop
American Airlines Logo
2:44 pm - 9:08 am
GCM
-
MSN
18h 24m
1 stop
$365American Airlines
Sun, Mar 1 - Sun, Mar 8
American Airlines Logo
8:24 pm - 2:14 pm
MSN
-
GCM
16h 50m
2 stops
American Airlines Logo
2:15 pm - 11:35 pm
GCM
-
MSN
9h 20m
1 stop
$435American Airlines
Sun, Mar 1 - Sun, Mar 8
American Airlines Logo
8:24 pm - 2:35 pm
MSN
-
GCM
17h 11m
1 stop
American Airlines Logo
12:00 pm - 11:35 pm
GCM
-
MSN
11h 35m
1 stop
$436American Airlines
Sat, Mar 7 - Sun, Mar 15
American Airlines Logo
8:22 pm - 1:13 pm
MSN
-
GCM
15h 51m
2 stops
American Airlines Logo
2:44 pm - 9:08 am
GCM
-
MSN
18h 24m
1 stop
$441American Airlines
Tue, Mar 3 - Wed, Mar 18
American Airlines Logo
5:00 am - 2:35 pm
MSN
-
GCM
8h 35m
1 stop
American Airlines Logo
2:44 pm - 11:22 pm
GCM
-
MSN
8h 38m
1 stop
$461American Airlines
Tue, Mar 3 - Wed, Mar 18
American Airlines Logo
7:15 am - 8:15 pm
MSN
-
GCM
12h 00m
2 stops
American Airlines Logo
12:05 pm - 11:35 pm
GCM
-
MSN
11h 30m
2 stops
$466American Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
8:24 pm - 11:09 am
MSN
-
GCM
14h 45m
2 stops
American Airlines Logo
3:50 pm - 11:05 am
GCM
-
MSN
19h 15m
1 stop
$490American Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
8:24 pm - 1:44 pm
MSN
-
GCM
17h 20m
1 stop
American Airlines Logo
3:50 pm - 11:05 am
GCM
-
MSN
19h 15m
1 stop
$492American Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
8:24 pm - 10:40 am
MSN
-
GCM
14h 16m
2 stops
American Airlines Logo
3:50 pm - 11:05 am
GCM
-
MSN
19h 15m
1 stop
$525American Airlines
Booking Insights

KAYAK's insights & trends for Madison to the Cayman Islands flights

Get data-powered insights and trends into flights from Madison to the Cayman Islands to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from Madison to the Cayman Islands take?

The duration of a flight to the Cayman Islands depends on your arrival airport. The shortest route to the Cayman Islands from Madison is to George Town, which takes 5h 51m.

Good to know

Cheapest flight$364
Most popular time to fly and prices are also 14% lower on average.
Flight from Madison to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Madison to the Cayman Islands?

    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 Madison to the Cayman Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to the Cayman Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison to the Cayman Islands 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 Madison to the Cayman Islands?

    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 from Madison to the Cayman Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to the Cayman Islands?

    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 from Madison to the Cayman Islands 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 Madison to the Cayman Islands

 
Need help choosing which airline to fly with from Madison to the Cayman Islands? 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.
7.4
United AirlinesOverall score based on 9245 reviews
7.3Comfort
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
Airline reviews

Same thing as flight from Pheonix to Newark. Uograded and Promised extra leg room and when I got to the seat it had none.

2.0 MediocrePiers, Feb 2026
EWR - DXB
Read more United Airlines reviews

Same thing as flight from Pheonix to Newark. Uograded and Promised extra leg room and when I got to the seat it had none.

I upgraded my seat and was promised it would be next to the emergency door for extra leg room and they said it was premium plus but it was at the back of the plane...same thing happened from Newark to Dubai

Everything except the food and entertainment. It was a great experience though

Bad food, bad service, cold cabin with no additional blankets when asked for (they told me they don’t provide additional blankets). I’m a frequent traveler and this is one of the worst companies I traveled with (by the way I thought that I booked my ticket with Lufthansa but I didn’t see that the flights were handled by United).

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

The attendant on board was amazing. She should be doing business/first international long haul.

Although our flight was delayed the overall boarding process was very smooth and the crew was accommodating.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

This was a horrible experience. I’ve experienced several delays at this point and still not home. I was supposed to be home by 8:30 last night and here I sit at 7 am on a plane STILL unable to go home because of American Airlines.

Lexus in first class was absolutely amazing! Beat flight attendant i’ve ever seen.

Generally good. Flight left on time and the seats are comfortable. Plenty of space in front if you in you choose a comfort plus seat, completely worth spending the extra money given the amount of hours the flight lasts. The food tastes good but I would say it’s a the amount is too little. The crew was friendly and efficient. There was a some turbulence at different points into the flight. American Airlines has good deals to NZ if you book with plenty of time before you plan on going.

the plane was so hot!! the air-conditioning was barely blowing. The flight was delayed, and we had to sit on the hot plane before take off for an extended amount of time, waiting on international passengers. Would not have been so bad if it was not so hot. They said it would get better after take off, but it did not.

They are always late and seats was also not having working charger

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

did not have enough meal for first class passengers so offer us snack

Arrived 40 min early which was great - sat in runway for 35 min so no gain. Then waited for luggage 45 min. They need to staff accordingly knowing its one of the busiest week in Phx

Broke my luggage and I can't get a resolution yet.

My flight got rerouted due to crew rest. I was sent to Dallas customer service was not very polite. Was given a $40 room voucher for Motel 6 and $12 to eat with. It delayed me by a day. Where if I would have just stuck with my original flight Arizona was delayed to Cleveland and I could have made it home. They put me on a 9:00 flight out of Dallas to Cleveland without my knowledge or consent. When originally I was told it would be 8:45 a.m. on February 1st. I told them I could not take the 9:00 flight because I did not have anybody to pick me up from the airport at that time. I'm extremely disappointed in how I was treated. And I will not fly American Airlines again.

Everything you need to know for your flight from Madison to the Cayman Islands

Information on your arrival and departure airports