$271 Find Cheap Flights from Madison to the Cayman Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals
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.

How long does a flight from Madison to the Cayman Islands take?

The duration of a flight to the Cayman Islands depends on your arrival airport. The shortest route to the Cayman Islands from Madison is to George Town, which takes 5h 56m.

Good to know

Cheapest flight

$271
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 10105 reviews
7.1Entertainment
6.7Food
7.3Comfort
7.7Boarding
8.1Crew
Airline reviews

The flight was excellent. Their was no service as we boarded, the flight attendants spent about 30 minutes just taking and not really caring that the cabin was about 80 degrees and did not offered any beverage to first class passengers or any passenger. The flight from DEN to ONT is not long but not under an hour, we received one drink and bag of chips if you were lucky. I was in first class…. I did leave my hat on the plane and it only took less than five minutes for a United rep to locate and bring it to me.

10.0 ExcellentFred, Aug 2026
Read more United Airlines reviews

The flight was excellent. Their was no service as we boarded, the flight attendants spent about 30 minutes just taking and not really caring that the cabin was about 80 degrees and did not offered any beverage to first class passengers or any passenger. The flight from DEN to ONT is not long but not under an hour, we received one drink and bag of chips if you were lucky. I was in first class…. I did leave my hat on the plane and it only took less than five minutes for a United rep to locate and bring it to me.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Very Poor. Significant delays getting to Chicago and then very poor communication on delays in Chicago to Cleveland. We could have rented a car and driven there faster than the delays ended up being.

A little more friendliness from that crew of the day.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

Flight left more than 5 hours late. American's policy did not allow flight to be fueled or bags to be loaded due to intermittent lightning. We were on the plane for hours before having to deplane. They then changed the departure time to an earlier than expected time. We re-boarded and had to wait another 1.5 hours on the plane before it finally took off. Flight crew did not serve any food or drinks while airborne.

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

Boarding was relatively fast and easy and the crew was attentive throughout.

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

Information on your arrival and departure airports