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Cayman Islands

$499+ 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
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/29. 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 2/65:38 am
MSN
-
GCM
1 stop6h 02m
Delta
Fri 2/133:55 pm
GCM
-
MSN
1 stop7h 53m
Delta
Deal found 1/29$499
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 2/67:25 am
MSN
-
GCM
2 stops11h 55m
American Airlines
Fri 2/1312:53 pm
GCM
-
MSN
2 stops10h 49m
American Airlines
Deal found 1/27$504
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/266:30 am
MSN
-
GCM
1 stop7h 55m
American Airlines
Wed 4/111:40 am
GCM
-
MSN
2 stops11h 09m
American Airlines
Deal found 1/27$515
This United Airlines deal was found by Cheapflights users on 1/26. 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 3/26:30 am
MSN
-
GCM
1 stop6h 15m
United Airlines
Thu 3/52:50 pm
GCM
-
MSN
1 stop24h 12m
United Airlines
Deal found 1/26$525
This United Airlines deal was found by Cheapflights users on 1/27. 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 3/306:00 am
MSN
-
GCM
2 stops30h 30m
United Airlines
Mon 4/61:35 pm
GCM
-
MSN
2 stops31h 41m
United Airlines
Deal found 1/27$546
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/126:15 am
MSN
-
GCM
1 stop7h 29m
American Airlines
Thu 3/192:15 pm
GCM
-
MSN
1 stop9h 20m
American Airlines
Deal found 1/27$559

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$515
(American Airlines)

Popular in

April

Cheapest in

March

Average price

$585
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.
Search Deals
From Madison Truax Field to Cayman Islands
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Thu 3/26

6:30 am-2:25 pm

1 stop7h 55m

George Town Owen Roberts Intl

Wed 4/1

11:40 am-10:49 pm

2 stops11h 09m

$515

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 3/2

6:30 am-1:45 pm

1 stop6h 15m

George Town Owen Roberts Intl

Thu 3/5

2:50 pm-2:02 pm

1 stop24h 12m

$525

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 3/30

6:00 am-12:30 pm

2 stops30h 30m

George Town Owen Roberts Intl

Mon 4/6

1:35 pm-9:16 pm

2 stops31h 41m

$546

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 3/12

6:15 am-1:44 pm

1 stop7h 29m

George Town Owen Roberts Intl

Thu 3/19

2:15 pm-11:35 pm

1 stop9h 20m

$559

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 3/13

6:15 am-1:44 pm

1 stop7h 29m

George Town Owen Roberts Intl

Fri 3/20

7:45 am-9:39 pm

2 stops13h 54m

$564

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 7/17

6:30 pm-1:00 pm

2 stops18h 30m

George Town Owen Roberts Intl

Sun 7/26

2:10 pm-10:39 am

2 stops20h 29m

$569

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 January 29, 2026.
Read reviews from past customers who have flown United Airlines and 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.
United Airlines
7.4
Good
9,214 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,214 reviews
United Airlines
7.4
Good
9,214 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,205 reviews
United Airlines
7.4
Good
9,214 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 $525, American Airlines can have you in Cayman Islands from Madison in 6h 15m. 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, 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 2 airlines flying from Madison to Cayman Islands

Discover the top 2 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$383Average$490FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$484Average$581FlexibilityNo cancel feeOn-time71%

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