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Cayman Islands

$470+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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.
Mon 11/175:29 amMSN - GCM
1 stop6h 06mDelta
Mon 11/241:50 pmGCM - MSN
1 stop9h 42mDelta
Deal found 10/28$553
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Mon 11/175:00 amMSN - GCM
2 stops8h 46mAmerican Airlines
Mon 11/2412:55 pmGCM - MSN
2 stops10h 28mAmerican Airlines
Deal found 10/28$558
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Mon 11/104:34 pmMSN - GCM
2 stops18h 22mAmerican Airlines
Mon 11/179:00 amGCM - MSN
2 stops14h 05mAmerican Airlines
Deal found 10/27$597
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/66:50 amMSN - GCM
1 stop6h 24mAmerican Airlines
Thu 11/133:10 pmGCM - MSN
1 stop9h 41mAmerican Airlines
Deal found 10/27$676
This United Airlines deal was found by Cheapflights users on 10/27. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:50 pmMSN - GCM
2 stops20h 40mUnited Airlines
Thu 11/135:45 pmGCM - MSN
2 stops17h 15mUnited Airlines
Deal found 10/27$681
This United Airlines deal was found by Cheapflights users on 10/27. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:30 amMSN - GCM
2 stops9h 00mUnited Airlines
Mon 11/175:45 pmGCM - MSN
3 stops24h 05mUnited Airlines
Deal found 10/27$4,576

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$470
(American Airlines)

Popular in

November

Cheapest in

October

Average price

$563
Provider with most accurate pricing for Madison Truax Field-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-George Town Owen Roberts Intl flights.
Search Deals
From Madison Truax Field to Cayman Islands
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
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 October 30, 2025.
Use the filters below to find and compare flights from Madison to the Cayman Islands that are best for you.

Fly from

Madison

Fly to

Cayman Islands

Route

Depart

Return

Price

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 2/6

4:47 pm-11:35 am

1 stop17h 48m

George Town Owen Roberts Intl

Fri 2/13

3:36 pm-11:29 pm

1 stop8h 53m

$470

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 1/29

4:30 pm-12:05 pm

2 stops18h 35m

George Town Owen Roberts Intl

Sun 2/8

3:45 pm-10:11 am

2 stops19h 26m

$480

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/31

5:07 pm-11:26 am

2 stops17h 19m

George Town Owen Roberts Intl

Sun 2/8

3:45 pm-10:11 am

2 stops19h 26m

$480

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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.

Cheapflights Insights

Everything you need to know about your flight from Madison to the Cayman Islands

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

Currently, March is the cheapest month in which you can book a flight from Madison to Cayman Islands (average of $212). Flying from Madison to Cayman Islands 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 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 October 30, 2025.
Read reviews from past customers who have flown American Airlines from Madison to the Cayman Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,034 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,034 reviews
American Airlines
7.2
Good
11,034 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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.

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

    For as low as $470, American Airlines can have you in Cayman Islands from Madison in 17h 48m. Airlines will cover a distance of 1710 mi.

  • 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, March is the cheapest month in which you can book a flight from Madison to Cayman Islands (average of $212). Flying from Madison to Cayman Islands 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.

See more FAQs

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Top airline flying from Madison to Cayman Islands

Discover the top airline 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$537Average$612FlexibilityNo cancel feeOn-time71%

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