$412 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 3/25. 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

Wed, Mar 25 - Wed, Apr 1
United Airlines Logo
6:30 am - 12:45 pmMSN-GCM
6h 15m1 stop
United Airlines Logo
1:50 pm - 10:40 pmGCM-MSN
8h 50m1 stop
$412United Airlines
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Sat, Jan 31 - Wed, Feb 4
American Airlines Logo
4:30 pm - 11:50 amMSN-GCM
18h 20m2 stops
American Airlines Logo
8:50 am - 10:05 pmGCM-MSN
14h 15m2 stops
$417American Airlines
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Fri, Feb 6 - Fri, Feb 13
Delta Logo
5:38 am - 12:40 pmMSN-GCM
6h 02m1 stop
Delta Logo
3:55 pm - 10:38 pmGCM-MSN
7h 43m1 stop
$419Delta
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Sat, Jan 31 - Wed, Feb 4
American Airlines Logo
8:10 am - 11:26 amMSN-GCM
26h 16m1 stop
American Airlines Logo
3:30 pm - 10:05 pmGCM-MSN
7h 35m1 stop
$421American Airlines
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Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
4:47 pm - 11:50 amMSN-GCM
18h 03m2 stops
American Airlines Logo
3:15 pm - 11:59 pmGCM-MSN
9h 44m1 stop
$424American Airlines
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Sat, Feb 14 - Sat, Feb 21
Delta Logo
6:20 am - 2:31 pmMSN-GCM
7h 11m1 stop
Delta Logo
3:56 pm - 10:38 pmGCM-MSN
7h 42m1 stop
$426Delta
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Thu, Mar 12 - Thu, Mar 19
American Airlines Logo
5:17 pm - 10:45 amMSN-GCM
17h 28m2 stops
American Airlines Logo
2:15 pm - 10:14 amGCM-MSN
19h 59m1 stop
$432American Airlines
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Sat, Jan 31 - Sun, Feb 8
American Airlines Logo
3:09 pm - 11:50 amMSN-GCM
19h 41m2 stops
American Airlines Logo
3:45 pm - 10:55 amGCM-MSN
20h 10m2 stops
$451American Airlines
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Sat, Jan 31 - Sun, Feb 8
American Airlines Logo
4:30 pm - 11:26 amMSN-GCM
17h 56m1 stop
American Airlines Logo
3:45 pm - 10:43 amGCM-MSN
19h 58m2 stops
$459American Airlines
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Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
4:30 pm - 11:50 amMSN-GCM
18h 20m2 stops
American Airlines Logo
8:45 am - 10:50 pmGCM-MSN
15h 05m2 stops
$464American 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 $531.

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 ($412) and Delta ($419).

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Good to know

Low seasonOctober
Cheapest flight$412
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 9% 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 11043 reviews
7.2Comfort
8.0Crew
6.4Food
6.9Entertainment
7.5Boarding
Airline reviews

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

8.0 ExcellentWayne, Nov 2025MIA - BWI
Read more American Airlines reviews

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

I had a positive experience on American. I'm blind and traveling with a guide dog and the flight attendants were so kind, friendly, and helpful towards us. They checked in on us during the flight and they made us feel comfortable and welcomed. There was an hour delay before depature, but overall the flight was a smooth ride. I appreciate that there were no issues on this long flight back home.

We were told the flight was delayed 5 times, then it was moved to the next day.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

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

Information on your arrival and departure airports

Madison (MSN)