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Cayman Islands

$505+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Jul 22 — Jul 291
Mi 7/22
Mi 7/29
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 Juni 22, 2026.

This American Airlines deal was found by Cheapflights users on 6/21. 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.
Sa 8/226:40 am
MSN
-
GCM
1 stop8h 20m
American Airlines
Mi 8/2612:30 pm
GCM
-
MSN
1 stop10h 39m
American Airlines
Deal found 6/21$505
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Mo 11/308:25 pm
MSN
-
GCM
2 stops19h 05m
United Airlines
Di 12/85:45 pm
GCM
-
MSN
2 stops16h 08m
United Airlines
Deal found 6/17$514
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Di 11/247:08 am
MSN
-
GCM
2 stops12h 12m
American Airlines
Di 12/812:55 pm
GCM
-
MSN
1 stop11h 54m
American Airlines
Deal found 6/18$535
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Sa 12/56:00 am
MSN
-
GCM
1 stop5h 56m
American Airlines
Mo 12/143:14 pm
GCM
-
MSN
1 stop9h 35m
American Airlines
Deal found 6/21$551
This United Airlines deal was found by Cheapflights users on 6/21. 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.
Sa 12/56:30 am
MSN
-
GCM
2 stops9h 05m
United Airlines
Mo 12/145:45 pm
GCM
-
MSN
2 stops21h 05m
United Airlines
Deal found 6/21$556
This United Airlines deal was found by Cheapflights users on 6/19. 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.
Di 12/85:00 am
MSN
-
GCM
2 stops10h 30m
United Airlines
Do 12/105:45 pm
GCM
-
MSN
2 stops30h 08m
United Airlines
Deal found 6/19$584
This Delta deal was found by Cheapflights users on 6/20. 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.
Do 8/275:43 am
MSN
-
GCM
1 stop5h 56m
Delta
Di 9/11:04 pm
GCM
-
MSN
1 stop9h 34m
Delta
Deal found 6/20$588

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 Juni 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$505
(American Airlines)
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

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 Juni 22, 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

Sa 8/22

6:40 am-3:00 pm

1 stop8h 20m

George Town Owen Roberts Intl

Mi 8/26

12:30 pm-11:09 pm

1 stop10h 39m

$505

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mo 11/30

8:25 pm-4:30 pm

2 stops19h 05m

George Town Owen Roberts Intl

Di 12/8

5:45 pm-8:53 am

2 stops16h 08m

$514

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mo 11/30

3:55 pm-11:58 am

2 stops19h 03m

George Town Owen Roberts Intl

Di 12/8

1:25 pm-10:57 pm

2 stops10h 32m

$535

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sa 12/5

6:00 am-12:56 pm

1 stop5h 56m

George Town Owen Roberts Intl

Mo 12/14

3:14 pm-11:49 pm

1 stop9h 35m

$551

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sa 12/5

6:30 am-4:35 pm

2 stops9h 05m

George Town Owen Roberts Intl

Mo 12/14

5:45 pm-1:50 pm

2 stops21h 05m

$556
Quickest round-trip

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Do 8/27

5:43 am-11:39 am

1 stop5h 56m

George Town Owen Roberts Intl

Di 9/1

1:04 pm-10:38 pm

1 stop9h 34m

$588

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

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
No data available for this route at this time. Please check back soon.

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 Juni 22, 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
9,875 reviews

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,875 reviews
United Airlines
7.4
Good
9,875 reviews

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
American Airlines
7.1
Good
11,739 reviews
United Airlines
7.4
Good
9,875 reviews

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 $505, American Airlines can have you in Cayman Islands from Madison in 8h 20m. 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.

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 Juni 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$383Average$487FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$470Average$601FlexibilityNo cancel feeOn-time71%

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