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Cayman Islands

$691+ Cheap flights from Madison (MSN) to the Cayman Islands

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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Madison to Cayman Islands

Keep the following information in mind while searching for Madison to Cayman Islands flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$691
(American Airlines)

Popular in

August

Cheapest in

June

Average price

$708
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 Cayman Islands
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Madison to Cayman Islands

Cheapest flights from Madison to Cayman Islands
Explore the most affordable flight options available from Madison to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/19. 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.
Sun 4/63:02 pmMSN - GCM
2 stops20h 07mAmerican Airlines
Fri 4/1112:35 pmGCM - MSN
2 stops22h 03mAmerican Airlines
Deal found 2/19$691
This United deal was found by Cheapflights users on 2/19. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/66:30 amMSN - GCM
1 stop6h 10mUnited Airlines
Fri 4/111:10 pmGCM - MSN
2 stops20h 57mUnited Airlines
Deal found 2/19$701
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/216:10 amMSN - GCM
1 stop7h 23mDelta
Fri 3/283:00 pmGCM - MSN
1 stop8h 04mDelta
Deal found 2/20$1,483

Find flights from Madison to Cayman Islands within your budget

Customize your flight search to find flights from Madison to Cayman Islands 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 February 20, 2025.

Fly from

Madison

Fly to

Cayman Islands

Route

Depart

Return

Price

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 4/6

3:02 pm-11:09 am

2 stops20h 07m

George Town Owen Roberts Intl

Fri 4/11

12:35 pm-10:38 am

2 stops22h 03m

$691

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 4/6

6:30 am-12:40 pm

1 stop6h 10m

George Town Owen Roberts Intl

Fri 4/11

1:10 pm-10:07 am

2 stops20h 57m

$701

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 3/21

6:10 am-1:33 pm

1 stop7h 23m

George Town Owen Roberts Intl

Fri 3/28

3:00 pm-11:04 pm

1 stop8h 04m

$1,483

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Best time to book a flight from Madison to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands 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.

Travel insights for flights from Madison to Cayman Islands

Get recent, data-driven insights about flights from Madison to Cayman Islands including ideal travel times, pricing trends, and more.

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

Currently, January is the cheapest month in which you can book a flight from Madison to Cayman Islands (average of $467). Flying from Madison to Cayman Islands 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.

What is the cheapest time of day to fly from MSN to KY?

Find hourly flight availability from Madison to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Cayman Islands as you normally would.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. 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 Cayman Islands. Reviews last updated February 20, 2025.
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,219 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
8,765 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,219 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Madison to Cayman Islands. 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 Cayman Islands?

    If you book a flight to Cayman Islands from Madison, you will be flying from Truax Field, which is the city’s only airport. Madison Truax Field (MSN) is located 5.4 mi from the center of Madison.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison to Cayman Islands 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 Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Madison to Cayman Islands (average of $467). Flying from Madison to Cayman Islands 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.

See more FAQs

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Top 3 airlines flying from Madison to Cayman Islands

Discover the top 3 airlines that operate flights from Madison to Cayman Islands. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$494Average$610FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$512Average$667FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$547Average$605FlexibilityNo cancel feeOn-time69%
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