$222 Find Cheap Flights from Madison to the Cayman Islands

This is the cheapest one-way 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 11/5. 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

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Flight Deals

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

Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
4:47 pm - 11:35 amMSN-GCM
17h 48m1 stop
American Airlines Logo
3:45 pm - 9:26 pmGCM-MSN
6h 41m1 stop
$548American Airlines
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Thu, Mar 12 - Thu, Mar 19
American Airlines Logo
7:20 am - 1:20 pmMSN-GCM
6h 00m1 stop
American Airlines Logo
3:15 pm - 10:35 amGCM-MSN
19h 20m2 stops
$553American Airlines
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Thu, Mar 12 - Thu, Mar 19
American Airlines Logo
6:33 am - 11:56 amMSN-GCM
5h 23m1 stop
American Airlines Logo
1:00 pm - 10:45 amGCM-MSN
21h 45m1 stop
$554American Airlines
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Thu, Jan 29 - Sun, Feb 8
American Airlines Logo
5:23 pm - 11:49 amMSN-GCM
17h 26m2 stops
American Airlines Logo
3:40 pm - 10:43 amGCM-MSN
20h 03m2 stops
$558American Airlines
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Wed, Nov 5 - Fri, Nov 7
American Airlines Logo
3:37 pm - 2:14 pmMSN-GCM
21h 37m1 stop
American Airlines Logo
3:10 pm - 11:30 pmGCM-MSN
9h 20m1 stop
$559American Airlines
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Thu, Jan 29 - Sun, Feb 8
American Airlines Logo
1:16 pm - 2:35 pmMSN-GCM
24h 19m1 stop
American Airlines Logo
8:45 am - 10:59 pmGCM-MSN
15h 14m2 stops
$564American Airlines
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Sat, Jan 31 - Sun, Feb 8
American Airlines Logo
8:10 am - 11:49 amMSN-GCM
26h 39m1 stop
American Airlines Logo
3:40 pm - 10:55 amGCM-MSN
20h 15m2 stops
$568American Airlines
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Thu, Jan 29 - Sun, Feb 8
United Airlines Logo
6:30 am - 1:45 pmMSN-GCM
6h 15m1 stop
United Airlines Logo
2:50 pm - 9:05 pmGCM-MSN
7h 15m1 stop
$658United Airlines
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Sat, Jan 31 - Sun, Feb 8
United Airlines Logo
12:38 pm - 1:45 pmMSN-GCM
24h 07m1 stop
United Airlines Logo
2:50 pm - 9:05 pmGCM-MSN
7h 15m1 stop
$665United Airlines
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Fri, Jan 9 - Sat, Jan 17
Multiple Airlines Logo
12:12 pm - 1:40 pmMSN-GCM
24h 28m3 stops
Multiple Airlines Logo
5:25 pm - 5:40 pmGCM-MSN
25h 15m2 stops
$779Multiple Airlines
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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 fly non-stop between Madison and Cayman Islands?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Madison to the Cayman Islands.

There is just one airline that flies from Madison to the Cayman Islands direct and that is American Airlines. The best round-trip deal found from American Airlines for the route is to George Town (GCM) and costs $537.

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 American Airlines ($548) and United Airlines ($658).

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Good to know

Low seasonOctober
Cheapest flight$222
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 5% 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.

  • What is the cheapest time of day to fly to the Cayman Islands?

    The cheapest time of day to fly to the Cayman Islands is generally in the evening, when round-trip flights cost $580 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $637.

Reviews of the top airline 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.
7.2
American AirlinesOverall score based on 11042 reviews
6.9Entertainment
7.5Boarding
6.4Food
8.0Crew
7.2Comfort
Airline reviews

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

8.0 ExcellentMaryann, Oct 2025SFO - CLT
Read more American Airlines reviews

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Flight attendants on this flight were very attentive and friendly

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Food should be better quality. Video screens have poor resolution and the library of movies is poor. The other airlines are much better.

the trip to madrid was uncomfortable with my legs touching the seat in front of me

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

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

Information on your arrival and departure airports

Madison (MSN)

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