$422+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Oct 21 — Oct 281
Round-trip
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Madison to Cayman Islands
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Cheapest flights from Madison to Cayman IslandsExplore 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 September 21, 2026.
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 September 21, 2026.
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:05 pm -
2 stops16h 25m
Fri 10/3012:25 pm -
1 stop11h 32m
Deal found 9/17![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/19. 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 12/56:02 am -
1 stop7h 39m
Sat 12/123:45 pm -
1 stop9h 14m
Deal found 9/19![American Airlines logo]()
$539
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/309:32 am -
1 stop6h 13m
Tue 1/55:45 pm -
1 stop7h 30m
Deal found 9/16![American Airlines logo]()
$644
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:38 am -
2 stops26h 57m
Fri 10/3011:25 am -
1 stop22h 33m
Deal found 9/20![Multiple Airlines logo]()
$680
This Booking.com deal was found by Cheapflights users on 9/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:39 pm -
2 stops22h 31m
Fri 10/3012:10 pm -
2 stops34h 57m
Deal found 9/20![Air Canada logo]()
$1,663
Best flights from Madison to Cayman IslandsDiscover carefully curated flight deals from Madison to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
Discover carefully curated flight deals from Madison to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
This American Airlines deal was found by Cheapflights users on 9/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/225:57 pm -
2 stops16h 51m
Wed 1/2712:48 pm -
2 stops12h 19m
Deal found 9/20![American Airlines logo]()
$521
This United Airlines deal was found by Cheapflights users on 9/16. 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 1/206:40 am -
1 stop6h 05m
Fri 1/292:55 pm -
1 stop9h 15m
Deal found 9/16![United Airlines logo]()
$527
This United Airlines deal was found by Cheapflights users on 9/16. 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 1/266:09 pm -
1 stop18h 36m
Fri 1/292:55 pm -
1 stop7h 08m
Deal found 9/16![United Airlines logo]()
$533
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Sat 1/98:36 pm -
2 stops17h 39m
Sat 1/233:34 pm -
1 stop9h 33m
Deal found 9/21![American Airlines logo]()
$544
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/225:00 am -
1 stop7h 45m
Wed 1/272:55 pm -
1 stop9h 15m
Deal found 9/20![United Airlines logo]()
$536
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sat 1/2312:30 pm -
1 stop24h 15m
Wed 2/32:55 pm -
1 stop9h 15m
Deal found 9/17![United Airlines logo]()
$580
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Sun 1/246:00 am -
1 stop6h 45m
Wed 2/32:55 pm -
1 stop9h 15m
Deal found 9/19![United Airlines logo]()
$613
This United Airlines deal was found by Cheapflights users on 9/19. 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 1/205:00 am -
1 stop7h 45m
Tue 2/22:25 pm -
2 stops24h 40m
Deal found 9/19![United Airlines logo]()
$618
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 1/296:40 am -
1 stop6h 05m
Sun 2/72:55 pm -
1 stop9h 15m
Deal found 9/16![United Airlines logo]()
$619
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 1/226:00 am -
1 stop6h 45m
Sun 1/312:55 pm -
1 stop9h 15m
Deal found 9/16![United Airlines logo]()
$619
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sat 1/233:40 pm -
1 stop21h 05m
Sun 1/312:55 pm -
1 stop7h 08m
Deal found 9/17![United Airlines logo]()
$626
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/246:40 am -
1 stop6h 05m
Mon 2/12:55 pm -
1 stop7h 08m
Deal found 9/20![United Airlines logo]()
$641
Last-minute flights from Madison to Cayman IslandsDiscover last-minute flight deals from Madison to Cayman Islands. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Cayman Islands. Data last updated September 21, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:05 pm -
2 stops16h 25m
Fri 10/3012:25 pm -
2 stops10h 47m
Deal found 9/17![American Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:38 am -
2 stops26h 57m
Fri 10/3011:25 am -
1 stop22h 33m
Deal found 9/20![Multiple Airlines logo]()
$680
This Booking.com deal was found by Cheapflights users on 9/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:39 pm -
2 stops22h 31m
Fri 10/3012:10 pm -
2 stops34h 57m
Deal found 9/20![Air Canada logo]()
$1,663
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 September 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $422 (American Airlines) |
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 7,457,451 searches. Data last updated September 21, 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
Cheapest round-trip
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Fri 1/22
5:57 pm-11:48 am
2 stops16h 51m
George Town Owen Roberts Intl
Wed 1/27
12:48 pm-12:07 am
2 stops12h 19m
$521
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Wed 1/20
6:40 am-1:45 pm
1 stop6h 05m
George Town Owen Roberts Intl
Fri 1/29
2:55 pm-11:10 pm
1 stop9h 15m
$527
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Tue 1/26
6:09 pm-1:45 pm
1 stop18h 36m
George Town Owen Roberts Intl
Fri 1/29
2:55 pm-9:03 pm
1 stop7h 08m
$533
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Fri 1/22
5:00 am-1:45 pm
1 stop7h 45m
George Town Owen Roberts Intl
Wed 1/27
2:55 pm-11:10 pm
1 stop9h 15m
$536
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Sat 1/9
8:36 pm-3:15 pm
2 stops17h 39m
George Town Owen Roberts Intl
Sat 1/23
3:34 pm-12:07 am
1 stop9h 33m
$544
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Sat 1/23
12:30 pm-1:45 pm
1 stop24h 15m
George Town Owen Roberts Intl
Wed 2/3
2:55 pm-11:10 pm
1 stop9h 15m
$580
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Sun 1/24
6:00 am-1:45 pm
1 stop6h 45m
George Town Owen Roberts Intl
Wed 2/3
2:55 pm-11:10 pm
1 stop9h 15m
$613
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Wed 1/20
5:00 am-1:45 pm
1 stop7h 45m
George Town Owen Roberts Intl
Tue 2/2
2:25 pm-2:05 pm
2 stops24h 40m
$618
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Fri 1/29
6:40 am-1:45 pm
1 stop6h 05m
George Town Owen Roberts Intl
Sun 2/7
2:55 pm-11:10 pm
1 stop9h 15m
$619
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Fri 1/22
6:00 am-1:45 pm
1 stop6h 45m
George Town Owen Roberts Intl
Sun 1/31
2:55 pm-11:10 pm
1 stop9h 15m
$619
Showing 1-10 of 12 resultsSorted 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.
MSN-GCM
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
MSN-KY0
MSN-GCM
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 September 21, 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.
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Crew
8.1
Food
6.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAsha,Sep 2026
LGA - IAH
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Crew
8.1
Food
6.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAsha,Sep 2026
LGA - IAH
Comfort
7.3
Entertainment
7.1
Boarding
7.7
Crew
8.1
Food
6.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAsha,Sep 2026
LGA - IAH
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.
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Complete your trip
Complete your trip to Cayman Islands by adding a car rental and/or hotel reservation to your travel itinerary.
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Madison and Cayman Islands flights
Browse other Madison and Cayman Islands flight options. Last updated on September 21, 2026.
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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 7,457,451 searches. Data last updated September 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$383 | Average$487 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$470 | Average$611 | FlexibilityNo cancel fee | On-time71% |