$470 Find Cheap Flights from Madison to Grand Cayman

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 2/6. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Grand Cayman

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Grand Cayman, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Grand Cayman, as well as popular online travel agencies
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Flight Deals

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, Feb 6 - Fri, Feb 13
American Airlines Logo
4:47 pm - 11:35 amMSN-GCM
17h 48m1 stop
American Airlines Logo
3:36 pm - 11:29 pmGCM-MSN
8h 53m1 stop
$470American Airlines
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Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
4:47 pm - 11:35 amMSN-GCM
17h 48m1 stop
American Airlines Logo
8:45 am - 10:51 pmGCM-MSN
15h 06m2 stops
$475American Airlines
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Wed, Feb 18 - Mon, Feb 23
United Airlines Logo
3:58 pm - 1:45 pmMSN-GCM
20h 47m1 stop
United Airlines Logo
2:50 pm - 9:07 pmGCM-MSN
7h 17m1 stop
$476United Airlines
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Thu, Jan 29 - Sun, Feb 8
American Airlines Logo
5:22 pm - 11:26 amMSN-GCM
17h 04m2 stops
American Airlines Logo
3:45 pm - 10:11 amGCM-MSN
19h 26m2 stops
$480American Airlines
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Wed, Feb 18 - Mon, Feb 23
American Airlines Logo
4:45 pm - 11:50 amMSN-GCM
18h 05m2 stops
American Airlines Logo
3:36 pm - 9:10 amGCM-MSN
18h 34m1 stop
$481American Airlines
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Thu, Jan 29 - Sun, Feb 8
American Airlines Logo
5:22 pm - 2:35 pmMSN-GCM
20h 13m1 stop
American Airlines Logo
3:45 pm - 10:11 amGCM-MSN
19h 26m2 stops
$486American Airlines
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Sat, Jan 31 - Sun, Feb 8
American Airlines Logo
4:30 pm - 11:26 amMSN-GCM
17h 56m1 stop
American Airlines Logo
3:45 pm - 10:11 amGCM-MSN
19h 26m2 stops
$489American Airlines
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Sat, Jan 17 - Sat, Jan 24
United Airlines Logo
6:30 am - 1:45 pmMSN-GCM
6h 15m1 stop
United Airlines Logo
2:25 pm - 11:44 pmGCM-MSN
10h 19m1 stop
$580United Airlines
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Thu, Jan 29 - Sun, Feb 8
United Airlines Logo
6:30 am - 1:45 pmMSN-GCM
6h 15m1 stop
United Airlines Logo
2:50 pm - 10:10 amGCM-MSN
20h 20m1 stop
$586United Airlines
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Thu, Feb 5 - Sun, Feb 8
Delta Logo
5:38 am - 12:40 pmMSN-GCM
6h 02m1 stop
Delta Logo
2:05 pm - 10:37 pmGCM-MSN
9h 32m1 stop
$868Delta
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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 $404, prices are generally cheapest when you fly direct.

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Good to know

Low seasonOctober
Cheapest flight$470
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 1% lower on average.
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.

  • What is the cheapest time of day to fly to Grand Cayman?

    The cheapest time of day to fly to Grand Cayman is generally in the evening, when round-trip flights cost $580 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Grand Cayman is generally in the morning, which is peak travel time and where the average cost of a ticket is $637.

Reviews of the top airline 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.
7.2
American AirlinesOverall score based on 11037 reviews
6.9Entertainment
6.4Food
7.5Boarding
7.2Comfort
8.0Crew
Airline reviews

We loved the steward on the plane. He made the night enjoyable

10.0 Excellentchloe, Nov 2025ORD - ATW
Read more American Airlines reviews

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports

Madison (MSN)

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