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Grand Cayman

$222+ Cheap flights from Madison (MSN) to Grand Cayman

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Aug 31 — Sep 71
Sun 8/31
Sun 9/7
1 adult, Economy
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Cheap flight deals from Madison to Grand Cayman

Keep the following information in mind while searching for Madison to Grand Cayman flight deals. Data was last updated August 26, 2025.

Round-trip from

$548
(American Airlines)

One-way from

$222
(American Airlines)

Popular in

November

Cheapest in

October

Average price

$765
From Madison Truax Field to Grand Cayman
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One-way flight from Madison Truax Field to Grand Cayman
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Highest demand for flights based on searches. 7% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Madison to Grand Cayman

Cheapest flights from Madison to Grand Cayman
Explore the most affordable flight options available from Madison to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2025.

This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/215:46 pmMSN - GCM
2 stops17h 34mAmerican Airlines
Sun 10/262:00 pmGCM - MSN
2 stops20h 15mAmerican Airlines
Deal found 8/24$557
This American Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:00 amMSN - GCM
1 stop10h 14mAmerican Airlines
Sat 11/296:15 pmGCM - MSN
1 stop17h 08mAmerican Airlines
Deal found 8/25$836

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Grand Cayman that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 26, 2025.
Use the filters below to find and compare flights from Madison to Grand Cayman that are best for you.

Fly from

Madison

Fly to

Grand Cayman

Route

Depart

Return

Price

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 1/14

6:19 am-12:56 pm

1 stop5h 37m

George Town Owen Roberts Intl

Wed 1/21

1:40 pm-11:42 pm

1 stop11h 02m

$548

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/17

6:19 am-12:56 pm

1 stop5h 37m

George Town Owen Roberts Intl

Sat 1/24

2:00 pm-1:26 pm

1 stop24h 26m

$554

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 1/29

4:17 pm-11:41 am

2 stops18h 24m

George Town Owen Roberts Intl

Sun 2/8

4:15 pm-10:18 am

2 stops19h 03m

$557

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 10/21

5:46 pm-11:20 am

2 stops17h 34m

George Town Owen Roberts Intl

Sun 10/26

2:00 pm-10:15 am

2 stops20h 15m

$557

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/31

7:07 am-7:51 pm

2 stops11h 44m

George Town Owen Roberts Intl

Sun 2/8

4:15 pm-10:06 am

2 stops18h 51m

$557

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 10/22

5:46 pm-1:10 pm

2 stops19h 24m

$222

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 10/22

2:14 pm-4:10 pm

3 stops49h 56m

$3,426

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/25

Best time to book a flight from Madison to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to Grand Cayman

What is the cheapest month to book a flight from Madison to Grand Cayman?

Currently, January is the cheapest month in which you can book a flight from Madison to Grand Cayman (average of $467). Flying from Madison to Grand Cayman in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Grand Cayman. Reviews last updated August 26, 2025.
Read reviews from past customers who have flown American Airlines from Madison to Grand Cayman. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Crew

8.0

Boarding

7.5

Food

6.5

Comfort

7.2

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Crew

8.0

Boarding

7.5

Food

6.5

Comfort

7.2

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Madison to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Grand Cayman?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Grand Cayman. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to Grand Cayman?

    A quick flight from Madison to Grand Cayman can take about 5h 37m. American Airlines provides one of the quickest options available for as low as $548. The distance from Madison to Grand Cayman is about 1710 mi.

  • Can I find deals for flights from Madison to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Madison to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Grand Cayman.

  • Can I find deals for business class flights from Madison to Grand Cayman?

    Yes. Cheapflights offers flight deals from Madison to Grand Cayman by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Madison to Grand Cayman (average of $467). Flying from Madison to Grand Cayman in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Madison to Grand Cayman

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Top airline flying from Madison to Grand Cayman

Discover the top airline that operate flights from Madison to Grand Cayman. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$537Average$635FlexibilityNo cancel feeOn-time71%

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