Find cheap flights from Madison to Grand Cayman - Compare and Save

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1 adult, Economy, 0 bags

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Price, demand and travel trends for Madison to Grand Cayman flights

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

How do fares from Madison to Grand Cayman vary by day of the week?

On average, Thursday is the cheapest day to fly from Madison to Grand Cayman and Saturday is the most expensive. Looking at the past 12 months of KAYAK data, it's 85% more expensive to fly on a Saturday compared to Thursday.

What's the best time of day to fly from Madison to Grand Cayman?

It's cheapest to fly to Grand Cayman in the evening, but the difference compared with the morning, the most expensive time to fly, is just 3%.

Key details for Madison to Grand Cayman flights

The most popular month to fly with an average 100% increase in travelers.

Your Madison to Grand Cayman flight questions, answered

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

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

    Over the past 12 months, round-trip fares from Madison to Grand Cayman have typically cost between $487 and $783.

  • What are the main airports serving Grand Cayman?

    Flights to Grand Cayman all arrive at George Town Owen Roberts Intl (GCM).

  • Which airlines fly nonstop from Madison to Grand Cayman?

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

    • Delta
    • United Airlines
    • American Airlines

  • Which cabin classes are available from Madison to Grand Cayman?

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

  • What are some popular landmarks around Grand Cayman?

    Grand Cayman is home to many popular sights. KAYAK travelers' favorites include:

    • Seven Mile Beach
    • Rum Point
    • Grand Cayman Blow Holes
    • 1919 Peace Memorial

Your guide to booking Madison to Grand Cayman flights

Get tips on when to book, when to fly and what to know before your trip.
  • Flexible with your dates? Fly in April to save some money. It's typically the cheapest month on this route, while flights in July will cost you the most.
  • Fly out on a Thursday to get the cheapest fares. Avoid Saturday flights, which are about 85% more expensive.
  • Start your trip in George Town, the most popular destination in Grand Cayman. From there, it's easy to continue on to other popular spots such as West Bay, East End and North Side.

Reviews of the top airlines flying from Madison to Grand Cayman

 
Need help choosing which airline to fly with from Madison to Grand Cayman? 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.
7.3
United AirlinesOverall score based on 10486 reviews
7.3Comfort
7.1Entertainment
8.1Crew
7.7Boarding
6.7Food
Airline reviews

We left nearly 3 hours late...so that was not a good experience. We boarded and then ended up about 1 hour stuck at the gate. Not a good experience.

2.0 MediocreMartin, Nov 2026
Read more United Airlines reviews

We left nearly 3 hours late...so that was not a good experience. We boarded and then ended up about 1 hour stuck at the gate. Not a good experience.

It is completely insane to me that first class does not include WiFi. Also does not include lounge access. Port for phone charging did not work. The crew was absolutely lovely, and the food was excellent.

I appreciate how quickly and kindly the people at the gate at DCA accommodated several of us who wanted to switch from the 6pm flight to the 5pm flight at the last minute. The flight crew was helpful to us too (dealing with luggage).

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 to Grand Cayman

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