$422 Find Cheap Flights from Madison to the Cayman Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

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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 5 days
Sort by: Cheapest
George Town
6h 05m2 stops
from $422per person
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?

In the past 5 days, the cheapest round-trip tickets from Madison to the Cayman Islands were found on United Airlines ($527) and Delta ($579).

Good to know

Cheapest flight

$422
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 10214 reviews
7.7Boarding
7.1Entertainment
7.3Comfort
8.1Crew
6.7Food
Airline reviews

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

2.0 MediocreKristel, Sep 2026
Read more United Airlines reviews

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Delayed too much. 1.5 hrs in the airport and another 1 hr in the runway. Got too late in the night. There was no proper food available.

awesome team work seen since on board till off plane in my destination. thanks you so much.

Job well done, being treated for good and helping a lot . thanks you so much till will meet against.

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.

More options for your flight from Madison to the Cayman Islands

Complete your trip to the Cayman Islands with a hotel stay or car rental