$213 Find Cheap Flights from Madison to the Cayman Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Price, demand and travel trends for Madison to the Cayman Islands flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Madison to the Cayman Islands right now?

The cheapest fare from Madison to the Cayman Islands in the last week was $516 round-trip, to George Town Owen Roberts Intl (GCM).

Which airport in the Cayman Islands is the cheapest to fly to from Madison?

All flights from Madison to the Cayman Islands arrive at George Town Owen Roberts Intl (GCM). On average, round-trip fares are around $570.

What’s the cheapest day to fly from Madison to the Cayman Islands?

Thursday tends to be the cheapest day to fly from Madison to the Cayman Islands, while Saturday is the most expensive. Fares run about 36% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Madison to the Cayman Islands?

Data from the past 12 months shows it's cheapest to fly to the Cayman Islands during the evening, but the difference compared with the morning, the most expensive time to fly, is minimal, just 3%.

Key details for Madison to the Cayman Islands flights

Cheapest flight

$213
The most popular month to fly with an average 99% increase in travelers.
One-way flight from Madison to George Town

Your Madison to the Cayman Islands flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Madison to the Cayman Islands?

    Fares from Madison to the Cayman Islands are around their usual level right now. A round-trip under $487 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch price changes.

  • How much should I budget for a flight from Madison to the Cayman Islands?

    Over the past 12 months, round-trip fares from Madison to the Cayman Islands have ranged from $487 to $755.

  • What airlines fly nonstop from Madison to the Cayman Islands?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Madison to the Cayman Islands. One-stop options include:

    • Delta
    • United Airlines
    • American Airlines

  • Which cabin classes are available on flights from Madison to the Cayman Islands?

    On flights from Madison to the Cayman Islands you can only book Economy Class.

Your guide to booking Madison to the Cayman Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for April when flights are typically cheapest and avoid July when prices are at their highest.
  • Flying on Thursday is usually the cheapest. Flights on Saturday cost about 36% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in George Town, which is the most popular destination in the Cayman Islands. From there, it's easy to continue on to other popular destinations such as West Bay, East End and North Side.

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 10362 reviews
8.1Crew
7.3Comfort
7.7Boarding
6.7Food
7.1Entertainment
Airline reviews

A couple flight attendants in business class had bad attitudes and provided poor service. They did provide drinks or refill drinks. They talked to certain passengers for long periods of time and ignored others.

4.0 OkayDavid, Oct 2026
Read more United Airlines reviews

A couple flight attendants in business class had bad attitudes and provided poor service. They did provide drinks or refill drinks. They talked to certain passengers for long periods of time and ignored others.

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

Fantastic experience once again flying with United! There was great communication from the cockpit and one of the flight attendants went out of her way to get my two little kids some special treats which elevated our travel experience coming home.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

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.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

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

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.

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