$180 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 4/14. 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, May 5 - Tue, May 12
United Airlines Logo
3:56 pm - 12:30 pm
MSN
-
GCM
20h 34m
2 stops
United Airlines Logo
1:35 pm - 8:56 am
GCM
-
MSN
19h 21m
2 stops
$384United Airlines
Tue, May 5 - Tue, May 12
American Airlines Logo
4:51 pm - 11:31 am
MSN
-
GCM
18h 40m
1 stop
American Airlines Logo
12:35 pm - 10:56 pm
GCM
-
MSN
10h 21m
1 stop
$387American Airlines
Sun, Sep 13 - Thu, Sep 17
American Airlines Logo
8:18 pm - 11:10 am
MSN
-
GCM
14h 52m
2 stops
American Airlines Logo
1:20 pm - 9:02 am
GCM
-
MSN
19h 42m
2 stops
$472American Airlines
Sun, Sep 13 - Thu, Sep 17
American Airlines Logo
7:15 am - 11:10 am
MSN
-
GCM
27h 55m
1 stop
American Airlines Logo
12:35 pm - 12:21 am
GCM
-
MSN
11h 46m
1 stop
$477American Airlines
Mon, May 4 - Thu, May 7
United Airlines Logo
8:55 pm - 12:30 pm
MSN
-
GCM
15h 35m
2 stops
United Airlines Logo
1:35 pm - 10:54 pm
GCM
-
MSN
33h 19m
2 stops
$510United Airlines
Wed, Apr 8 - Wed, Apr 15
United Airlines Logo
6:00 am - 12:45 pm
MSN
-
GCM
6h 45m
1 stop
United Airlines Logo
1:50 pm - 9:21 pm
GCM
-
MSN
7h 31m
1 stop
$523United Airlines
Wed, Apr 8 - Wed, Apr 15
United Airlines Logo
5:00 am - 12:45 pm
MSN
-
GCM
7h 45m
1 stop
United Airlines Logo
12:55 pm - 8:56 am
GCM
-
MSN
20h 01m
2 stops
$528United Airlines
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
5:08 pm - 11:31 am
MSN
-
GCM
18h 23m
1 stop
American Airlines Logo
4:03 pm - 11:56 pm
GCM
-
MSN
7h 53m
1 stop
$531American Airlines
Wed, Apr 8 - Wed, Apr 15
American Airlines Logo
8:24 pm - 1:10 pm
MSN
-
GCM
16h 46m
2 stops
American Airlines Logo
2:05 pm - 8:45 am
GCM
-
MSN
18h 40m
2 stops
$533American Airlines
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
5:08 pm - 1:10 pm
MSN
-
GCM
20h 02m
2 stops
American Airlines Logo
2:10 pm - 9:48 am
GCM
-
MSN
19h 38m
2 stops
$578American 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 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 ($384) and American Airlines ($472).

Good to know

Low seasonApril
Cheapest flight$180
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 15% 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 9460 reviews
7.1Entertainment
7.7Boarding
7.3Comfort
8.1Crew
6.6Food
Airline reviews

I will never fly ANA again. They lost one of my large pieces of checked luggage, the heaviest one with the most valuable items in it, and they said they will not send me an email unless they can't find it, even though the paper they gave me to track the status of my lost luggage requires a code from an email they are supposed to send me so I can do baggage tracing. They claim to be an international airline, but they also insist on calling a Japanese telephone number to confirm where to send the lost baggage if they find it. It is impossible to find an actual contact email address for customer support on their website, and their AI chatbot is unhelpful, directing you to a webpage that says it is for contact information but does not have any actual email addresses or phone numbers listed on it. My seat in economy did not recline at all, even though I was not sitting in an exit row nor the very back row. I had to sit in the fully upright position for over ten hours of international travel. Awful experience overall.

2.0 MediocreJenny, Mar 2026
BWI - SFO
Read more United Airlines reviews

I will never fly ANA again. They lost one of my large pieces of checked luggage, the heaviest one with the most valuable items in it, and they said they will not send me an email unless they can't find it, even though the paper they gave me to track the status of my lost luggage requires a code from an email they are supposed to send me so I can do baggage tracing. They claim to be an international airline, but they also insist on calling a Japanese telephone number to confirm where to send the lost baggage if they find it. It is impossible to find an actual contact email address for customer support on their website, and their AI chatbot is unhelpful, directing you to a webpage that says it is for contact information but does not have any actual email addresses or phone numbers listed on it. My seat in economy did not recline at all, even though I was not sitting in an exit row nor the very back row. I had to sit in the fully upright position for over ten hours of international travel. Awful experience overall.

No seat back entertainment. And app had a hard time getting entertainment loaded.

ticket agent lady wás very helpful , she arranged wheel chair for my elderly mother

Didn't make the flight because the first leg of my flight was canceled and the next leg was already booked.

My flight was canceled a few hours before boarding. I was rebooked on Copa airlines and missed an important meeting .

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Business class seats felt very cramped compared to other airlines.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

OK, we were delayed and had to de plane and reboard.

I would have liked a pillow. The vegetarian wrap and oaten cake was good.

I would have liked vegetarian and gluten free options for evening dinner time flight. I would have like a pillow on the international overnight flight . The veg wrap and oaten desert on the international flight was good

The experience at checkin for my American Airlines flight from Sacramento to LAX was very good including the assistance I received in getting my bags checked in and boarding passes printed. Was pleasantly surprised the my bags were checked through all the way to my destination at Clark International Airport in Angeles, Philippines.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Great experience. Good dinner and service. FA's were very nice and attentive.

It was great. Smooth flight, comfortable, left on time and landed on time.

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

Information on your arrival and departure airports