$526 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 4/9. 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, Apr 9 - Tue, Apr 14
American Airlines Logo
8:24 pm - 11:00 am
MSN
-
GCM
14h 36m
2 stops
American Airlines Logo
12:35 pm - 11:01 pm
GCM
-
MSN
10h 26m
1 stop
$526American Airlines
Thu, Apr 9 - Tue, Apr 14
American Airlines Logo
5:08 pm - 11:33 am
MSN
-
GCM
18h 25m
1 stop
American Airlines Logo
12:35 pm - 11:01 pm
GCM
-
MSN
10h 26m
1 stop
$532American Airlines
Mon, May 18 - Thu, May 28
Delta Logo
6:19 pm - 11:54 am
MSN
-
GCM
17h 35m
2 stops
Delta Logo
1:19 pm - 8:49 am
GCM
-
MSN
19h 30m
2 stops
$564Delta
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
5:17 pm - 10:40 am
MSN
-
GCM
17h 23m
1 stop
American Airlines Logo
3:50 pm - 11:05 am
GCM
-
MSN
19h 15m
1 stop
$570American Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
8:24 pm - 11:09 am
MSN
-
GCM
14h 45m
2 stops
American Airlines Logo
3:50 pm - 11:05 am
GCM
-
MSN
19h 15m
1 stop
$574American Airlines
Tue, May 19 - Thu, May 28
Delta Logo
5:43 am - 11:54 am
MSN
-
GCM
6h 11m
1 stop
Delta Logo
1:19 pm - 10:31 pm
GCM
-
MSN
9h 12m
1 stop
$592Delta
Mon, May 18 - Thu, May 28
Delta Logo
6:19 pm - 11:54 am
MSN
-
GCM
17h 35m
2 stops
Delta Logo
1:19 pm - 10:31 pm
GCM
-
MSN
9h 12m
1 stop
$597Delta
Sat, Jun 6 - Sun, Jun 14
American Airlines Logo
5:52 pm - 11:02 am
MSN
-
GCM
17h 10m
2 stops
American Airlines Logo
5:11 pm - 7:45 am
GCM
-
MSN
14h 34m
2 stops
$613American Airlines
Wed, May 20 - Wed, May 27
American Airlines Logo
4:12 pm - 11:02 am
MSN
-
GCM
18h 50m
2 stops
American Airlines Logo
12:33 pm - 11:59 pm
GCM
-
MSN
11h 26m
1 stop
$614American Airlines
Wed, May 20 - Wed, May 27
American Airlines Logo
11:35 am - 11:28 am
MSN
-
GCM
23h 53m
1 stop
American Airlines Logo
2:45 pm - 11:06 pm
GCM
-
MSN
8h 21m
1 stop
$620American 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 American Airlines ($526) and United Airlines ($674).

Good to know

Low seasonMarch
Cheapest flight$526
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 9344 reviews
6.6Food
7.3Comfort
7.1Entertainment
8.1Crew
7.7Boarding
Airline reviews

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.

10.0 ExcellentAnonymous, Feb 2026
DEN - RSW
Read more United Airlines reviews

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.

Flight on time. Excellent service in Premium Economy. Great food served and cleaned up promptly. Unfortunately the climate control was malfunctioning and it was very cold and felt a bit like camping. Cold helps with sleep though so not complaining too much. Slept well. It asks to rate "entertainment". I do not like any IFE, don't shove a big screen in my face—I have my own phone if I want it. So this will always get low ratings.

We had turbulence ever 1/2 hr or so and the captains announcements were SOOOO LOUD

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

Overall we had a good experience during our flight from San Francisco to Houston.

Airport terminal was outdated, flight was on a small jet with no wifi

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

it was a very short flight so my expectations were low.

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

I am an AA flyer for a very long time... AA has yet to disappoint.

Flight was delayed. Not much information on when the flight would take off. Eventually we were told it was maintenance. App was not giving updates.

Never ontime and always delays. Long waits for customer service and often app doesn’t work

Arriving plane went to wrong gate. Flight Attendant was late. Was in no Hurry when he arrived. Flight was fine. Plane had to wait 20 minutes to get assigned a gate due to designated gate tied up. barely connected.. Boarded extremely late on final leg of trip.

We arrived 25 minutes early only to be told our gate was occupied and so we sat for close to 30 minutes to pull into a gate. That’s not an early arrival!

Experience was great. The best part is the free Wi-Fi connection which helps me to work on the flight

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

The TSA check in took 1.5 hours to get through in Austin and I missed my flights back to DC

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

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

Information on your arrival and departure airports