$419 Find Cheap Flights from Madison to Grand Cayman - Compare and Save

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 Grand Cayman departing on 1/8. 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 Grand Cayman 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 Grand Cayman 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 Grand Cayman

Fri, Jan 8 - Sat, Jan 16
American Airlines Logo
5:00 am - 2:35 pm
MSN
-
GCM
8h 35m
1 stop
American Airlines Logo
3:25 pm - 10:46 pm
GCM
-
MSN
8h 21m
1 stop
$419American Airlines
Thu, Sep 24 - Mon, Sep 28
American Airlines Logo
4:23 pm - 11:27 am
MSN
-
GCM
19h 04m
2 stops
American Airlines Logo
12:36 pm - 10:51 am
GCM
-
MSN
22h 15m
2 stops
$424American Airlines
Tue, Nov 3 - Sun, Nov 8
United Airlines Logo
5:00 am - 4:30 pm
MSN
-
GCM
10h 30m
2 stops
United Airlines Logo
5:45 pm - 9:44 am
GCM
-
MSN
16h 59m
2 stops
$430United Airlines
Fri, Jan 8 - Sat, Jan 16
American Airlines Logo
5:00 am - 2:35 pm
MSN
-
GCM
8h 35m
1 stop
American Airlines Logo
3:25 pm - 10:46 pm
GCM
-
MSN
8h 21m
1 stop
$431American Airlines
Thu, Sep 24 - Mon, Sep 28
American Airlines Logo
4:23 pm - 11:27 am
MSN
-
GCM
19h 04m
2 stops
American Airlines Logo
12:36 pm - 1:33 pm
GCM
-
MSN
24h 57m
1 stop
$432American Airlines
Sat, Jan 9 - Sat, Jan 23
American Airlines Logo
7:05 pm - 2:35 pm
MSN
-
GCM
18h 30m
1 stop
American Airlines Logo
4:40 pm - 10:43 am
GCM
-
MSN
19h 03m
1 stop
$434American Airlines
Sat, Jan 9 - Sat, Jan 23
American Airlines Logo
7:27 am - 8:23 pm
MSN
-
GCM
11h 56m
2 stops
American Airlines Logo
3:25 pm - 12:12 am
GCM
-
MSN
9h 47m
1 stop
$436American Airlines
Thu, Sep 24 - Mon, Sep 28
American Airlines Logo
8:15 am - 11:27 am
MSN
-
GCM
27h 12m
1 stop
American Airlines Logo
12:36 pm - 1:33 pm
GCM
-
MSN
24h 57m
1 stop
$437American Airlines
Sat, Oct 24 - Sat, Oct 31
United Airlines Logo
6:06 am - 12:15 pm
MSN
-
GCM
30h 09m
1 stop
United Airlines Logo
1:50 pm - 8:49 pm
GCM
-
MSN
6h 59m
1 stop
$440United Airlines
Sat, Jan 9 - Sat, Jan 23
American Airlines Logo
12:20 pm - 2:35 pm
MSN
-
GCM
25h 15m
1 stop
American Airlines Logo
1:05 pm - 10:59 pm
GCM
-
MSN
10h 54m
2 stops
$442American Airlines
Booking Insights

KAYAK's insights & trends for Madison to Grand Cayman flights

Get data-powered insights and trends into flights from Madison to Grand Cayman to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Madison to Grand Cayman?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $462, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight

$419
Flight from Madison to George Town

FAQs - booking Grand Cayman flights

  • How does KAYAK find such low prices on flights from Madison to Grand Cayman?

    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 Grand Cayman.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Grand Cayman?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison to Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman

 
See real verified KAYAK customer reviews for airlines flying from Madison to Grand Cayman. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Madison to Grand Cayman? 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 10026 reviews
6.6Food
7.7Boarding
7.3Comfort
7.1Entertainment
8.1Crew
Airline reviews

The international portion was good. Food and beverage options were good. The sustainable wooden eatery was less than desirable. Your Star Alliance partner ANA provided real silverware. I'm 6'3" & 198 lbs and felt cramped in the exit row. How can that be? Flight attendant all had a pleasant disposition which is always good.

8.0 ExcellentWaymon, Jul 2026
GPT - IAH
Read more United Airlines reviews

The international portion was good. Food and beverage options were good. The sustainable wooden eatery was less than desirable. Your Star Alliance partner ANA provided real silverware. I'm 6'3" & 198 lbs and felt cramped in the exit row. How can that be? Flight attendant all had a pleasant disposition which is always good.

Flight was late to take off Plane broke down Had to move everyone to another plane Told we weren’t going to LGA but Newark Also told we would be taken to NY But United lied and we ended up at Newark at 2 in the morning Horrible experience. And the experience of trying to get compensation from United is just as bad. They could not care less about their passengers Never again!

Flight was late, the only reason I almost missed my flight was that my connection was also late.

Staff on the plane was incredible. Check-in was very complicated with no staff to help at the airport. I was charged for a second bag even though my ticket says 2 bags are free

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.

Patrons with larger bags were asked to check the bags when boarding. Seems like the most effective, and least costly way, way to successfully use the cramped space.

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 to Grand Cayman

Information on your arrival and departure airports