$364 Find Cheap Flights from Madison to the Cayman Islands

This is the cheapest round-trip 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 4/11. 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

sáb., abr. 11 - mié., abr. 15
American Airlines Logo
5:37 pm - 11:31 am
MSN
-
GCM
17h 54m
2 stops
American Airlines Logo
2:05 pm - 8:45 am
GCM
-
MSN
18h 40m
2 stops
$364American Airlines
sáb., abr. 11 - mié., abr. 15
American Airlines Logo
11:35 am - 11:31 am
MSN
-
GCM
23h 56m
1 stop
American Airlines Logo
12:35 pm - 11:55 pm
GCM
-
MSN
11h 20m
1 stop
$367American Airlines
mié., abr. 15 - jue., abr. 23
United Airlines Logo
6:00 am - 12:45 pm
MSN
-
GCM
6h 45m
1 stop
United Airlines Logo
1:35 pm - 8:57 am
GCM
-
MSN
19h 22m
2 stops
$382United Airlines
mié., abr. 15 - jue., abr. 23
United Airlines Logo
6:00 am - 12:45 pm
MSN
-
GCM
6h 45m
1 stop
United Airlines Logo
1:50 pm - 8:57 am
GCM
-
MSN
19h 07m
1 stop
$383United Airlines
mié., abr. 15 - jue., abr. 23
American Airlines Logo
5:08 pm - 1:10 pm
MSN
-
GCM
20h 02m
2 stops
American Airlines Logo
2:10 pm - 9:48 am
GCM
-
MSN
19h 38m
2 stops
$389American Airlines
mar., abr. 21 - vie., abr. 24
United Airlines Logo
5:00 am - 12:45 pm
MSN
-
GCM
7h 45m
1 stop
United Airlines Logo
1:50 pm - 9:16 pm
GCM
-
MSN
7h 26m
1 stop
$445United Airlines
sáb., abr. 11 - mié., abr. 15
American Airlines Logo
8:24 pm - 11:31 am
MSN
-
GCM
15h 07m
2 stops
American Airlines Logo
12:00 pm - 11:55 pm
GCM
-
MSN
11h 55m
2 stops
$450American Airlines
sáb., abr. 11 - mar., abr. 14
American Airlines Logo
5:08 pm - 11:31 am
MSN
-
GCM
18h 23m
1 stop
American Airlines Logo
12:35 pm - 11:01 pm
GCM
-
MSN
10h 26m
1 stop
$454American Airlines
dom., abr. 12 - mar., abr. 14
United Airlines Logo
8:35 pm - 12:30 pm
MSN
-
GCM
15h 55m
2 stops
United Airlines Logo
1:50 pm - 9:21 pm
GCM
-
MSN
7h 31m
1 stop
$469United Airlines
sáb., abr. 11 - mié., abr. 15
United Airlines Logo
5:00 am - 3:05 pm
MSN
-
GCM
10h 05m
2 stops
United Airlines Logo
1:50 pm - 9:16 pm
GCM
-
MSN
7h 26m
1 stop
$470United 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.

Which airlines provide the cheapest flights from Madison to the Cayman Islands?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Madison to the Cayman Islands were found on United Airlines ($382) and American Airlines ($389).

Good to know

Low seasonMarch
Cheapest flight$364
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 18% lower on average.
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 9370 reviews
6.6Food
7.1Entertainment
8.1Crew
7.7Boarding
7.3Comfort
Airline reviews

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

8.0 ExcellentAnonymous, Mar 2026
EWR - PIT
Read more United Airlines reviews

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

There was no WiFi available, there were mechanical problems with the plane and we landed at C 124, then the gate was switched to A 26, then all the way back to C126! For a 75 yo woman traveling alone, this was a difficult journey, indeed!

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Terrible because it was cancelled due to volcanic ash clouds in Guatemala while all other airlines kept flying. Had to pay for a hotel to stay overnight in Houston and try to fly next day.

Flight delayed for more than 16 hrs and no effort was spent to provide an alternate

We got delayed three hours and nobody thought to have the bathroom fixed while we were sitting waiting to board? took a full hour to have maintenance come and check it off. Had to shut the bathroom down twice so that the pilots could go to the bathroom. Everyone missed their connections.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

It was good experience this time. The flight was on time.

I very rarely fly American and my experience today reenforces that is the correct decision. While the staff were all very courteous, our flight was first thing in the morning so there was no reason to be delayed, yet appropriate maintenance checks weren’t completed prior to our flight so we were delayed multiple times. Not a great showing, American Airlines.

It's very confusing because Kayak has it as American Airlines, but it was Hawaiian Airlines, but operated by Alaska Airlines. I had to go to the airport for my boarding pass because American said I didn't have any trips.

Smooth flight. From the early boarding and all were on board before departure time and arrived early in ONT. Great crew. Thank you!!!!

Small plane, poor meal choices for first class, bad terminal and boarding experience at LAX

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

Information on your arrival and departure airports