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Grand Cayman

$406+ Cheap flights from Madison (MSN) to Grand Cayman

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Madison to Grand Cayman

Best flights from Madison to Grand Cayman
Discover carefully curated flight deals from Madison to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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.
Fri 2/67:20 amMSN - GCM
1 stop6h 15mAmerican Airlines
Fri 2/133:36 pmGCM - MSN
1 stop8h 52mAmerican Airlines
Deal found 12/16$406
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Fri 1/306:00 amMSN - GCM
1 stop7h 35mAmerican Airlines
Fri 2/63:30 pmGCM - MSN
1 stop7h 35mAmerican Airlines
Deal found 12/16$406
This American Airlines deal was found by Cheapflights users on 12/16. 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 1/314:47 pmMSN - GCM
2 stops17h 39mAmerican Airlines
Sun 2/83:45 pmGCM - MSN
2 stops19h 58mAmerican Airlines
Deal found 12/16$416
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 1/2911:29 amMSN - GCM
1 stop26h 06mAmerican Airlines
Sun 2/83:45 pmGCM - MSN
2 stops20h 10mAmerican Airlines
Deal found 12/16$451

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$406
(American Airlines)

Popular in

April

Cheapest in

March

Average price

$631
Provider with most accurate pricing for Madison Truax Field-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-George Town Owen Roberts Intl flights.
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From Madison Truax Field to Grand Cayman
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Highest demand for flights based on searches. 1% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 18, 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

Fri 2/6

7:20 am-2:35 pm

1 stop6h 15m

George Town Owen Roberts Intl

Fri 2/13

3:36 pm-11:28 pm

1 stop8h 52m

$406

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 1/30

6:00 am-2:35 pm

1 stop7h 35m

George Town Owen Roberts Intl

Fri 2/6

3:30 pm-10:05 pm

1 stop7h 35m

$406

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/31

4:47 pm-11:26 am

2 stops17h 39m

George Town Owen Roberts Intl

Sun 2/8

3:45 pm-10:43 am

2 stops19h 58m

$416

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 1/29

11:29 am-2:35 pm

1 stop26h 06m

George Town Owen Roberts Intl

Sun 2/8

3:45 pm-10:55 am

2 stops20h 10m

$451

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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, March is the cheapest month in which you can book a flight from Madison to Grand Cayman (average of $212). Flying from Madison to Grand Cayman in September is currently the most expensive (average of $685). 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 December 18, 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
11,055 reviews

Crew

8.0

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,055 reviews
American Airlines
7.2
Good
11,055 reviews

Crew

8.0

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 6h 15m. American Airlines provides one of the quickest options available for as low as $406. 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, March is the cheapest month in which you can book a flight from Madison to Grand Cayman (average of $212). Flying from Madison to Grand Cayman in September is currently the most expensive (average of $685). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$524Average$606FlexibilityNo cancel feeOn-time71%

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