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Cayman Islands

$548+ 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
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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 septiembre 15, 2025.

Round-trip from

$548
(Delta)

Popular in

November

Cheapest in

October
From Madison Truax Field to Cayman Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($42 potential savings vs. average RT price).
Search Deals

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 septiembre 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 12/24:12 pmMSN - GCM
2 stops19h 12mAmerican Airlines
lun. 12/88:45 amGCM - MSN
2 stops15h 41mAmerican Airlines
Deal found 9/14$552
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/213:47 pmMSN - GCM
2 stops19h 33mAmerican Airlines
dom. 10/268:25 amGCM - MSN
2 stops15h 26mAmerican Airlines
Deal found 9/14$601

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 septiembre 15, 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

vie. 2/6

6:15 am-2:30 pm

1 stop7h 15m

George Town Owen Roberts Intl

vie. 2/13

3:45 pm-10:08 pm

1 stop7h 23m

$548

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

jue. 3/12

7:20 am-1:20 pm

1 stop6h 00m

George Town Owen Roberts Intl

jue. 3/19

3:15 pm-10:18 am

2 stops19h 03m

$552

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

mar. 12/2

4:12 pm-12:24 pm

2 stops19h 12m

George Town Owen Roberts Intl

lun. 12/8

8:45 am-11:26 pm

2 stops15h 41m

$552

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

vie. 2/6

4:17 pm-11:41 am

2 stops18h 24m

George Town Owen Roberts Intl

vie. 2/13

1:35 pm-9:26 pm

1 stop8h 51m

$552

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

jue. 1/29

3:49 pm-12:00 pm

2 stops19h 11m

George Town Owen Roberts Intl

dom. 2/8

4:15 pm-10:27 am

2 stops19h 12m

$557

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

vie. 1/30

7:55 am-7:51 pm

2 stops10h 56m

George Town Owen Roberts Intl

dom. 2/8

4:15 pm-10:18 am

2 stops19h 03m

$557

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

sáb. 1/31

6:13 am-7:51 pm

2 stops12h 38m

George Town Owen Roberts Intl

dom. 2/8

4:15 pm-10:27 am

2 stops19h 12m

$557

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, 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.

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 septiembre 15, 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
10,000 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

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 $552, Delta can have you in Cayman Islands from Madison in 6h. Airlines will cover a distance of 1710 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$537Average$631FlexibilityNo cancel feeOn-time71%

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