$176 Find Cheap Flights from Madison to the Cayman Islands

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 7/13. 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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Flight Deals

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

Wed, May 13 - Tue, May 19
American Airlines Logo
5:08 pm - 1:10 pm
MSN
-
GCM
20h 02m
2 stops
American Airlines Logo
12:35 pm - 10:56 pm
GCM
-
MSN
10h 21m
1 stop
$499American Airlines
Wed, May 13 - Tue, May 19
American Airlines Logo
11:35 am - 11:31 am
MSN
-
GCM
23h 56m
1 stop
American Airlines Logo
12:35 pm - 10:56 pm
GCM
-
MSN
10h 21m
1 stop
$505American Airlines
Tue, Oct 20 - Sun, Oct 25
American Airlines Logo
2:01 pm - 11:00 am
MSN
-
GCM
20h 59m
1 stop
American Airlines Logo
3:30 pm - 9:16 am
GCM
-
MSN
17h 46m
2 stops
$571American Airlines
Sat, May 30 - Wed, Jun 3
United Airlines Logo
5:00 am - 3:35 pm
MSN
-
GCM
10h 35m
2 stops
United Airlines Logo
1:35 pm - 8:55 am
GCM
-
MSN
19h 20m
2 stops
$614United Airlines
Sat, May 30 - Wed, Jun 3
United Airlines Logo
5:00 am - 3:35 pm
MSN
-
GCM
10h 35m
2 stops
United Airlines Logo
1:35 pm - 8:55 am
GCM
-
MSN
19h 20m
2 stops
$617United Airlines
Tue, Oct 20 - Sun, Oct 25
American Airlines Logo
2:01 pm - 11:00 am
MSN
-
GCM
20h 59m
1 stop
American Airlines Logo
12:40 pm - 11:31 pm
GCM
-
MSN
10h 51m
1 stop
$639American Airlines
Sat, May 30 - Wed, Jun 3
United Airlines Logo
5:00 am - 3:10 pm
MSN
-
GCM
10h 10m
2 stops
United Airlines Logo
1:35 pm - 11:05 pm
GCM
-
MSN
33h 30m
2 stops
$668United Airlines
Sat, May 30 - Wed, Jun 3
United Airlines Logo
6:30 am - 1:30 pm
MSN
-
GCM
7h 00m
1 stop
United Airlines Logo
1:35 pm - 11:05 pm
GCM
-
MSN
33h 30m
2 stops
$671United 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.

What is the cheapest month to fly from Madison to the Cayman Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Madison to the Cayman Islands is May, when tickets cost $0 (return) on average. On the other hand, the most expensive months are August and June, when the average cost of round-trip tickets is $687 and $581 respectively.

Find deals

Good to know

Low seasonApril
Cheapest flight$176
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 15% 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 9682 reviews
6.6Food
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
Airline reviews

I liked that my son and I were reseated next to each other (we had different bookings). I liked that it was a directg flight and mostly on time. I liked that you provided pillows and blankets. Flight attendants were generally courteous. The messaging through wifi did not work well. The food was not good. Seats are very narrow and I felt slightly claustraphobic in the window seat.

8.0 ExcellentLILLY, May 2026
SFO - HKG
Read more United Airlines reviews

I liked that my son and I were reseated next to each other (we had different bookings). I liked that it was a directg flight and mostly on time. I liked that you provided pillows and blankets. Flight attendants were generally courteous. The messaging through wifi did not work well. The food was not good. Seats are very narrow and I felt slightly claustraphobic in the window seat.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

Some crew were unfriendly or in some cases just straight up rude.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

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

Information on your arrival and departure airports

Madison (MSN)