$466 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 5/7. 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

Thu, May 7 - Thu, May 14
United Airlines Logo
8:55 pm - 12:30 pm
MSN
-
GCM
15h 35m
2 stops
United Airlines Logo
1:35 pm - 8:56 am
GCM
-
MSN
19h 21m
2 stops
$466United Airlines
Fri, May 8 - Tue, May 12
American Airlines Logo
4:12 pm - 10:55 am
MSN
-
GCM
18h 43m
2 stops
American Airlines Logo
12:35 pm - 10:11 pm
GCM
-
MSN
9h 36m
2 stops
$525American Airlines
Fri, May 8 - Tue, May 12
American Airlines Logo
1:20 pm - 3:03 pm
MSN
-
GCM
25h 43m
1 stop
American Airlines Logo
12:35 pm - 10:56 pm
GCM
-
MSN
10h 21m
1 stop
$531American Airlines
Thu, May 7 - Thu, May 14
American Airlines Logo
5:08 pm - 11:31 am
MSN
-
GCM
18h 23m
1 stop
American Airlines Logo
12:35 pm - 11:54 pm
GCM
-
MSN
11h 19m
1 stop
$577American Airlines
Sat, Jun 6 - Sat, Jun 13
American Airlines Logo
7:00 am - 3:07 pm
MSN
-
GCM
8h 07m
1 stop
American Airlines Logo
12:40 pm - 10:29 pm
GCM
-
MSN
9h 49m
1 stop
$579American Airlines
Fri, Jul 3 - Fri, Jul 10
American Airlines Logo
5:11 pm - 10:56 am
MSN
-
GCM
17h 45m
2 stops
American Airlines Logo
5:12 pm - 10:56 am
GCM
-
MSN
17h 44m
2 stops
$584American Airlines
Tue, May 5 - Thu, May 7
United Airlines Logo
5:34 pm - 12:30 pm
MSN
-
GCM
18h 56m
2 stops
United Airlines Logo
1:35 pm - 10:54 pm
GCM
-
MSN
33h 19m
2 stops
$604United Airlines
Tue, May 5 - Thu, May 7
United Airlines Logo
3:56 pm - 12:30 pm
MSN
-
GCM
20h 34m
2 stops
United Airlines Logo
1:35 pm - 10:54 pm
GCM
-
MSN
33h 19m
2 stops
$624United Airlines
Sat, Jun 6 - Sat, Jun 13
United Airlines Logo
5:00 am - 3:35 pm
MSN
-
GCM
10h 35m
2 stops
United Airlines Logo
4:45 pm - 8:55 am
GCM
-
MSN
16h 10m
2 stops
$626United Airlines
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
8:26 pm - 11:25 am
MSN
-
GCM
14h 59m
2 stops
American Airlines Logo
12:25 pm - 9:22 am
GCM
-
MSN
20h 57m
2 stops
$628American 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 ($466) and American Airlines ($525).

Good to know

Low seasonApril
Cheapest flight$466
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 14% 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 9562 reviews
7.1Entertainment
7.3Comfort
6.6Food
8.1Crew
7.7Boarding
Airline reviews

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

4.0 OkayAllison, Apr 2026
DCA - ORD
Read more United Airlines reviews

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

All good flight was 35 minutes early when arriving in Edinburgh

Flights were on time actually early service was good and crew cheerful

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

Boarding was again a "free for all". We were boarding group 4, and almost the entire plane was able to board before us. It's a shame that someone who follows the rules, gets the short end of the stick. Not fair.

Flight left on time, arrived early, pleasant staff provided water, coffee, etc. access to bathrooms was reasonable and were well maintained. blankets were available, lots of entertainment options. LUGGAGE SERVICE WAS GREAT. I got my one checked bag quickly and was able to make a bus connection for a 2 hour bus ride saving me from waiting another 1.5 hours.

The boarding process was straightforward. One pertinent observation regarding all boarding procedures is that if an individual requires assistance or possesses a special status and is part of preboarding, it is advisable to limit the number of passengers who can preboard with them, rather than the entire, sometimes large, companion groups. The seats are uncomfortable, and the entertainment options are significantly inferior compared to other airlines. During the snack service, I requested an additional bag of snacks, but my request was denied. Initially, the flight attendant agreed to my request.becoming a strange accurate moment. The flight duration was four hours.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

there are no options s for snack besides cookies would ve nice to have a salty option n

We did not have enough time to make our connecting flight. As a result, we were put onto a different airline for our second leg. The different airline was NOT comparable to British Airlines, and our arrival was significantly delayed. The actual flight on BA was amazing.

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

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

Information on your arrival and departure airports