$468 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 3/12. 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

Thu, Mar 12 - Sun, Mar 15
United Airlines Logo
6:30 am - 12:45 pm
MSN
-
GCM
6h 15m
1 stop
United Airlines Logo
1:50 pm - 10:32 pm
GCM
-
MSN
8h 42m
1 stop
$468United Airlines
Mon, Mar 23 - Mon, Mar 30
United Airlines Logo
6:30 am - 12:45 pm
MSN
-
GCM
6h 15m
1 stop
United Airlines Logo
1:50 pm - 9:57 am
GCM
-
MSN
20h 07m
1 stop
$485United 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
$500American 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
$502American Airlines
Wed, Mar 4 - Tue, Mar 10
American Airlines Logo
8:24 pm - 11:50 am
MSN
-
GCM
14h 26m
2 stops
American Airlines Logo
12:00 pm - 10:00 pm
GCM
-
MSN
10h 00m
2 stops
$508American Airlines
Mon, Mar 23 - Mon, Mar 30
American Airlines Logo
6:00 am - 7:15 pm
MSN
-
GCM
13h 15m
2 stops
American Airlines Logo
2:44 pm - 11:04 am
GCM
-
MSN
20h 20m
1 stop
$517American Airlines
Tue, Mar 24 - Sun, Mar 29
American Airlines Logo
6:30 am - 2:25 pm
MSN
-
GCM
7h 55m
1 stop
American Airlines Logo
4:38 pm - 10:39 am
GCM
-
MSN
18h 01m
1 stop
$520American Airlines
Thu, Mar 12 - Thu, Mar 19
United Airlines Logo
6:30 am - 12:45 pm
MSN
-
GCM
6h 15m
1 stop
United Airlines Logo
1:50 pm - 10:32 pm
GCM
-
MSN
8h 42m
1 stop
$525United Airlines
Thu, Mar 12 - Thu, Mar 19
United Airlines Logo
6:30 am - 12:45 pm
MSN
-
GCM
6h 15m
1 stop
United Airlines Logo
4:45 pm - 2:58 pm
GCM
-
MSN
22h 13m
2 stops
$530United Airlines
Wed, Mar 4 - Tue, Mar 10
Delta Logo
5:38 am - 12:29 pm
MSN
-
GCM
5h 51m
1 stop
Delta Logo
1:12 pm - 10:34 pm
GCM
-
MSN
9h 22m
1 stop
$543Delta
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.

Which airlines provide the cheapest flights from Madison to the Cayman Islands?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Madison to the Cayman Islands were found on United Airlines ($468) and American Airlines ($500).

Good to know

Low seasonMarch
Cheapest flight$468
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 18% 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 9308 reviews
8.1Crew
7.3Comfort
6.6Food
7.7Boarding
7.1Entertainment
Airline reviews

Entertainment kept turning itself off. Gave up on watching a movie.

8.0 ExcellentLeslie, Feb 2026
SFO - YYZ
Read more United Airlines reviews

Entertainment kept turning itself off. Gave up on watching a movie.

Both the WIFI and entertainment did not work for 2.5h

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.

Both of my flights arrived early and check in process was smooth

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

The flight was fine, once we got underway. It was more than hour delayed

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

Waited for oxygen tanks for 30 minutes after boarding was complete.

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

Information on your arrival and departure airports