$552 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 11/1. 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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Cheap Flights from Madison to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town2 stops$552
George Town
George Town2 stops$552

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, Nov 1 - Sat, Nov 8
American Airlines Logo
7:40 am - 7:20 pmMSN-GCM
11h 40m2 stops
American Airlines Logo
1:25 pm - 11:51 pmGCM-MSN
11h 26m2 stops
$552American Airlines
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Thu, Jan 29 - Sun, Feb 8
American Airlines Logo
6:00 am - 7:51 pmMSN-GCM
12h 51m2 stops
American Airlines Logo
4:15 pm - 10:47 amGCM-MSN
19h 32m2 stops
$557American Airlines
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Sat, Nov 1 - Sat, Nov 8
American Airlines Logo
12:35 pm - 3:20 pmMSN-GCM
26h 45m1 stop
American Airlines Logo
4:10 pm - 11:51 pmGCM-MSN
8h 41m1 stop
$558American Airlines
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Thu, Jan 29 - Sun, Feb 8
American Airlines Logo
10:38 am - 12:56 pmMSN-GCM
25h 18m1 stop
American Airlines Logo
4:15 pm - 10:18 amGCM-MSN
19h 03m2 stops
$563American Airlines
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Sat, Jan 31 - Sun, Feb 8
American Airlines Logo
4:17 pm - 12:00 pmMSN-GCM
18h 43m1 stop
American Airlines Logo
4:15 pm - 10:47 amGCM-MSN
19h 32m2 stops
$568American Airlines
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Thu, Jan 29 - Sun, Feb 8
United Airlines Logo
7:00 am - 1:45 pmMSN-GCM
5h 45m1 stop
United Airlines Logo
2:50 pm - 1:48 pmGCM-MSN
23h 58m1 stop
$664United Airlines
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Sat, Jan 31 - Sun, Feb 8
United Airlines Logo
5:30 pm - 1:45 pmMSN-GCM
19h 15m1 stop
United Airlines Logo
2:50 pm - 3:25 pmGCM-MSN
25h 35m1 stop
$671United 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 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 ($552) and United Airlines ($664).

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Good to know

Low seasonJuly
Cheapest flight$552
Best time to beat the crowds with an average 18% 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 10000 reviews
6.5Food
8.0Crew
7.2Comfort
7.5Boarding
6.9Entertainment
Airline reviews

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

6.0 GoodMitchell, Aug 2025CMH - ORD
Read more American Airlines reviews

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

Great flight. No issues at all. I still think boarding could be more efficient but otherwise, a good experience.

Pretty good. The food was just mediocre, the boarding and crew were good.

The comfort of the seats was great, the crew eased my child’s anxieties and the fact that I had full cans of my beverage choice was great.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

Sat on the ground in Cincinnati for 50 minutes before deplaning

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

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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