$167 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 12/23. 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

Tue, Mar 24 - Mon, Mar 30
United Airlines Logo
6:30 am - 12:45 pm
MSN
-
GCM
6h 15m1 stop
United Airlines Logo
1:50 pm - 10:40 pm
GCM
-
MSN
8h 50m1 stop
$376United Airlines
Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
4:47 pm - 11:35 am
MSN
-
GCM
17h 48m1 stop
American Airlines Logo
3:15 pm - 11:59 pm
GCM
-
MSN
9h 44m1 stop
$406American Airlines
Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
4:47 pm - 11:26 am
MSN
-
GCM
17h 39m2 stops
American Airlines Logo
3:15 pm - 11:59 pm
GCM
-
MSN
9h 44m1 stop
$411American Airlines
Sat, Jan 31 - Sun, Feb 8
American Airlines Logo
3:09 pm - 11:50 am
MSN
-
GCM
19h 41m2 stops
American Airlines Logo
3:45 pm - 10:55 am
GCM
-
MSN
20h 10m2 stops
$416American Airlines
Tue, Feb 3 - Sat, Feb 7
American Airlines Logo
5:22 pm - 2:35 pm
MSN
-
GCM
20h 13m1 stop
American Airlines Logo
4:25 pm - 5:11 pm
GCM
-
MSN
25h 46m1 stop
$421American Airlines
Sat, Jan 31 - Sun, Feb 8
American Airlines Logo
4:30 pm - 11:26 am
MSN
-
GCM
17h 56m1 stop
American Airlines Logo
3:45 pm - 10:55 am
GCM
-
MSN
20h 10m2 stops
$424American Airlines
Tue, Feb 24 - Sun, Mar 1
American Airlines Logo
6:00 am - 2:33 pm
MSN
-
GCM
7h 33m1 stop
American Airlines Logo
3:36 pm - 9:13 am
GCM
-
MSN
18h 37m1 stop
$434American Airlines
Tue, Feb 24 - Sun, Mar 1
American Airlines Logo
6:00 am - 8:15 pm
MSN
-
GCM
13h 15m2 stops
American Airlines Logo
3:36 pm - 9:13 am
GCM
-
MSN
18h 37m1 stop
$439American Airlines
Thu, Jan 29 - Sun, Feb 8
American Airlines Logo
4:30 pm - 12:05 pm
MSN
-
GCM
18h 35m2 stops
American Airlines Logo
3:45 pm - 10:43 am
GCM
-
MSN
19h 58m2 stops
$446American Airlines
Thu, Mar 12 - Thu, Mar 19
American Airlines Logo
6:00 am - 1:29 pm
MSN
-
GCM
7h 29m1 stop
American Airlines Logo
7:45 am - 10:42 pm
GCM
-
MSN
14h 57m2 stops
$451American 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.

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 ($376) and American Airlines ($411).

Find deals

Good to know

Low seasonMarch
Cheapest flight$167
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 17% 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 11050 reviews
6.9Entertainment
7.2Comfort
6.5Food
7.5Boarding
8.0Crew
Airline reviews

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

2.0 MediocreJohn, Dec 2025
GSO - ORD
Read more American Airlines reviews

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

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

Information on your arrival and departure airports

Madison (MSN)