$193 Find Cheap Flights from Madison to the Cayman Islands - Compare and Save

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 12/5. 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

Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
6:40 am - 3:00 pm
MSN
-
GCM
8h 20m
1 stop
American Airlines Logo
12:30 pm - 11:09 pm
GCM
-
MSN
10h 39m
1 stop
$455American Airlines
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
6:40 am - 3:00 pm
MSN
-
GCM
8h 20m
1 stop
American Airlines Logo
12:00 pm - 11:09 pm
GCM
-
MSN
11h 09m
2 stops
$460American Airlines
Thu, Aug 27 - Tue, Sep 1
American Airlines Logo
11:33 am - 11:27 am
MSN
-
GCM
23h 54m
1 stop
American Airlines Logo
2:10 pm - 9:17 am
GCM
-
MSN
19h 07m
2 stops
$469American Airlines
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
6:40 am - 3:00 pm
MSN
-
GCM
8h 20m
1 stop
American Airlines Logo
12:30 pm - 11:09 pm
GCM
-
MSN
10h 39m
1 stop
$475American Airlines
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
6:53 pm - 1:10 pm
MSN
-
GCM
18h 17m
2 stops
American Airlines Logo
12:00 pm - 11:09 pm
GCM
-
MSN
11h 09m
2 stops
$480American Airlines
Thu, Aug 27 - Tue, Sep 1
American Airlines Logo
11:33 am - 11:27 am
MSN
-
GCM
23h 54m
1 stop
American Airlines Logo
2:10 pm - 9:17 am
GCM
-
MSN
19h 07m
2 stops
$489American Airlines
Sat, Sep 5 - Wed, Sep 9
American Airlines Logo
7:00 am - 2:17 pm
MSN
-
GCM
7h 17m
1 stop
American Airlines Logo
12:36 pm - 8:50 pm
GCM
-
MSN
8h 14m
1 stop
$490American Airlines
Sat, Dec 5 - Sat, Dec 12
United Airlines Logo
6:30 am - 1:45 pm
MSN
-
GCM
6h 15m
1 stop
United Airlines Logo
2:50 pm - 8:49 pm
GCM
-
MSN
6h 59m
1 stop
$491United Airlines
Sat, Sep 5 - Wed, Sep 9
American Airlines Logo
5:00 am - 1:10 pm
MSN
-
GCM
8h 10m
2 stops
American Airlines Logo
12:00 pm - 11:15 pm
GCM
-
MSN
11h 15m
2 stops
$495American Airlines
Sat, Dec 5 - Mon, Dec 14
American Airlines Logo
8:08 pm - 2:24 pm
MSN
-
GCM
17h 16m
2 stops
American Airlines Logo
3:14 pm - 11:49 pm
GCM
-
MSN
9h 35m
1 stop
$496American 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.

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$193
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 9896 reviews
7.1Entertainment
7.7Boarding
8.1Crew
7.3Comfort
6.6Food
Airline reviews

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

8.0 ExcellentNico, Jun 2026
LAX - HNL
Read more United Airlines reviews

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

I was very disappointed with my experience at the United Airlines baggage check. The representative was rude and unhelpful. I was required to remove approximately 1.5 pounds from my two checked bags, even though it was a very small amount over the limit. The interaction was unnecessarily unpleasant, and I expected much better customer service. I hope United will review this incident and provide additional customer service training to its staff.

No extra snacks were available. Meals quality is terrible. Crew was not friendly.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

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.

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

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