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Cayman Islands

$197+ Cheap flights from Madison (MSN) to the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
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 March 23, 2026.

This United Airlines deal was found by Cheapflights users on 3/19. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/53:56 pm
MSN
-
GCM
2 stops20h 34m
United Airlines
Tue 5/121:35 pm
GCM
-
MSN
2 stops19h 21m
United Airlines
Deal found 3/19$384
This American Airlines deal was found by Cheapflights users on 3/19. 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.
Tue 5/54:51 pm
MSN
-
GCM
1 stop18h 40m
American Airlines
Tue 5/1212:35 pm
GCM
-
MSN
1 stop10h 21m
American Airlines
Deal found 3/19$387
This American Airlines deal was found by Cheapflights users on 3/23. 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 9/136:35 pm
MSN
-
GCM
2 stops16h 35m
American Airlines
Thu 9/1712:35 pm
GCM
-
MSN
1 stop11h 46m
American Airlines
Deal found 3/23$466
This United Airlines deal was found by Cheapflights users on 3/19. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:55 pm
MSN
-
GCM
2 stops15h 35m
United Airlines
Thu 5/71:35 pm
GCM
-
MSN
2 stops33h 19m
United Airlines
Deal found 3/19$510
This United Airlines deal was found by Cheapflights users on 3/19. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
MSN
-
GCM
1 stop6h 45m
United Airlines
Wed 4/151:50 pm
GCM
-
MSN
1 stop7h 31m
United Airlines
Deal found 3/19$523
This American Airlines deal was found by Cheapflights users on 3/19. 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.
Sat 4/185:08 pm
MSN
-
GCM
1 stop18h 23m
American Airlines
Sat 4/254:03 pm
GCM
-
MSN
1 stop7h 53m
American Airlines
Deal found 3/19$531
This American Airlines deal was found by Cheapflights users on 3/19. 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.
Wed 4/88:24 pm
MSN
-
GCM
2 stops16h 46m
American Airlines
Wed 4/152:05 pm
GCM
-
MSN
2 stops18h 40m
American Airlines
Deal found 3/19$533

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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$384
(United Airlines)

One-way from

$197
(KAYAK)

Popular in

November

Cheapest in

April

Average price

$517
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
Search Deals
One-way flight from Madison Truax Field to Cayman Islands
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 23, 2026.
Use the filters below to find and compare flights from Madison to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 5/5

3:56 pm-12:30 pm

2 stops20h 34m

George Town Owen Roberts Intl

Tue 5/12

1:35 pm-8:56 am

2 stops19h 21m

$384

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 9/13

6:35 pm-11:10 am

2 stops16h 35m

George Town Owen Roberts Intl

Thu 9/17

12:35 pm-12:21 am

1 stop11h 46m

$466

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 5/4

8:55 pm-12:30 pm

2 stops15h 35m

George Town Owen Roberts Intl

Thu 5/7

1:35 pm-10:54 pm

2 stops33h 19m

$510
Quickest round-trip

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 4/8

6:00 am-12:45 pm

1 stop6h 45m

George Town Owen Roberts Intl

Wed 4/15

1:50 pm-9:21 pm

1 stop7h 31m

$523

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 4/18

5:08 pm-11:31 am

1 stop18h 23m

George Town Owen Roberts Intl

Sat 4/25

4:03 pm-11:56 pm

1 stop7h 53m

$531

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 5/5

5:30 am-12:00 pm

1 stop6h 30m

George Town Owen Roberts Intl

Tue 5/12

1:19 pm-10:44 pm

1 stop9h 25m

$579

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 7/3

5:11 pm-10:23 am

1 stop17h 12m

George Town Owen Roberts Intl

Fri 7/10

5:12 pm-7:49 am

2 stops14h 37m

$584

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 6/22

6:46 am-1:35 pm

1 stop6h 49m

George Town Owen Roberts Intl

Sun 6/28

5:12 pm-12:37 pm

2 stops19h 25m

$589
Cheapest one-way
Quickest one-way

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 4/15

6:22 pm-12:00 pm

2 stops17h 38m

$197

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 4/15

11:35 am-11:31 am

1 stop23h 56m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/18

Sorted by cheapest first

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, November is the cheapest month in which you can book a flight from Madison to Cayman Islands (average of $376). Flying from Madison to Cayman Islands in June is currently the most expensive (average of $597). 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 March 23, 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
9,460 reviews

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Boarding

7.7

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
9,460 reviews
United Airlines
7.4
Good
9,460 reviews

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Boarding

7.7

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
7.1
Good
11,489 reviews
United Airlines
7.4
Good
9,460 reviews

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Boarding

7.7

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 $466, United Airlines can have you in Cayman Islands from Madison in 16h 35m. 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, November is the cheapest month in which you can book a flight from Madison to Cayman Islands (average of $376). Flying from Madison to Cayman Islands in June is currently the most expensive (average of $597). 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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$383Average$487FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$484Average$581FlexibilityNo cancel feeOn-time71%

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