$267+ 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 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Cayman Islands with Cheapflights
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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Best
Last-minute
One-way
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 November 4, 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 November 4, 2026.
This United Airlines deal was found by Cheapflights users on 11/1. 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 12/15:38 pm -
2 stops21h 52m
Tue 12/222:55 pm -
1 stop9h 04m
Deal found 11/1![United Airlines logo]()
$510
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/16:33 pm -
1 stop15h 53m
Tue 12/225:45 pm -
1 stop15h 27m
Deal found 11/1![American Airlines logo]()
$545
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/175:51 am -
1 stop9h 54m
Thu 12/245:45 pm -
1 stop15h 27m
Deal found 11/2![American Airlines logo]()
$580
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/167:10 pm -
1 stop20h 35m
Sun 12/205:45 pm -
1 stop15h 27m
Deal found 11/1![American Airlines logo]()
$596
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:40 am -
2 stops25h 29m
Thu 12/2412:40 pm -
3 stops26h 20m
Deal found 11/2![Multiple Airlines logo]()
$1,263
This United Airlines deal was found by Cheapflights users on 10/31. 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 12/306:06 am -
1 stop6h 39m
Sat 1/25:45 pm -
2 stops18h 56m
Deal found 10/31![United Airlines logo]()
$1,642
This American Airlines deal was found by Cheapflights users on 10/31. 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 12/307:00 am -
1 stop6h 50m
Sat 1/23:31 pm -
1 stop20h 13m
Deal found 10/31![American Airlines logo]()
$1,645
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 November 4, 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 November 4, 2026.
This American Airlines deal was found by Cheapflights users on 11/1. 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 1/95:37 pm -
2 stops17h 11m
Sat 1/163:32 pm -
1 stop9h 42m
Deal found 11/1![American Airlines logo]()
$584
This United Airlines deal was found by Cheapflights users on 10/30. 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 2/66:35 am -
1 stop6h 10m
Wed 2/102:25 pm -
1 stop8h 13m
Deal found 10/30![United Airlines logo]()
$675
This American Airlines deal was found by Cheapflights users on 11/1. 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 1/95:10 pm -
2 stops17h 54m
Sat 1/233:32 pm -
1 stop9h 42m
Deal found 11/1![American Airlines logo]()
$584
This United Airlines deal was found by Cheapflights users on 11/1. 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 4/26:45 am -
1 stop6h 00m
Tue 4/61:50 pm -
1 stop9h 15m
Deal found 11/1![United Airlines logo]()
$675
This United Airlines deal was found by Cheapflights users on 11/1. 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 3/236:39 pm -
2 stops20h 51m
Wed 4/71:50 pm -
1 stop9h 15m
Deal found 11/1![United Airlines logo]()
$679
This United Airlines deal was found by Cheapflights users on 11/1. 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 3/246:39 pm -
2 stops20h 51m
Wed 4/71:50 pm -
1 stop7h 04m
Deal found 11/1![United Airlines logo]()
$679
This United Airlines deal was found by Cheapflights users on 11/2. 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 2/136:39 pm -
2 stops20h 56m
Sat 2/205:45 pm -
2 stops28h 14m
Deal found 11/2![United Airlines logo]()
$714
Last-minute flights from Madison to Cayman IslandsDiscover last-minute flight deals from Madison to Cayman Islands. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Cayman Islands. Data last updated November 4, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 11/1. 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 12/15:38 pm -
2 stops21h 52m
Tue 12/222:55 pm -
1 stop9h 04m
Deal found 11/1![United Airlines logo]()
$510
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/16:33 pm -
1 stop15h 53m
Tue 12/225:45 pm -
1 stop15h 27m
Deal found 11/1![American Airlines logo]()
$545
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/167:10 pm -
1 stop20h 35m
Sun 12/205:45 pm -
1 stop15h 27m
Deal found 11/1![American Airlines logo]()
$596
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/175:51 am -
1 stop9h 54m
Thu 12/245:45 pm -
1 stop15h 27m
Deal found 11/2![American Airlines logo]()
$580
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:40 am -
2 stops25h 29m
Thu 12/2412:40 pm -
3 stops26h 20m
Deal found 11/2![Multiple Airlines logo]()
$1,263
This United Airlines deal was found by Cheapflights users on 10/31. 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 12/306:06 am -
1 stop6h 39m
Sat 1/25:45 pm -
2 stops18h 56m
Deal found 10/31![United Airlines logo]()
$1,642
This American Airlines deal was found by Cheapflights users on 10/31. 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 12/307:00 am -
1 stop6h 50m
Sat 1/23:31 pm -
1 stop20h 13m
Deal found 10/31![American Airlines logo]()
$1,645
One-way flights from Madison to Cayman IslandsSearch for one-way flight options from Madison to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Madison to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/295:00 am -
2 stops10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![United Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Tue 12/293:02 pm -
3 stops43h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$545
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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $510 (United Airlines) |
One-way from | $267 (United 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 November 4, 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
Tue 12/29
5:00 am-4:45 pm
1 stop10h 45m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$267
Quickest round-trip
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Tue 12/29
5:00 am-4:35 pm
2 stops10h 35m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$267
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Tue 12/29
3:02 pm-11:35 am
3 stops43h 33m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$545
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Sat 1/9
5:37 pm-11:48 am
2 stops17h 11m
George Town Owen Roberts Intl
Sat 1/16
3:32 pm-12:14 am
1 stop9h 42m
$584
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Sat 1/9
5:10 pm-12:04 pm
2 stops17h 54m
George Town Owen Roberts Intl
Sat 1/23
3:32 pm-12:14 am
1 stop9h 42m
$584
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Sat 2/6
6:35 am-1:45 pm
1 stop6h 10m
George Town Owen Roberts Intl
Wed 2/10
2:25 pm-9:38 pm
1 stop8h 13m
$675
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Fri 4/2
6:45 am-12:45 pm
1 stop6h 00m
George Town Owen Roberts Intl
Tue 4/6
1:50 pm-11:05 pm
1 stop9h 15m
$675
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Tue 3/23
6:39 pm-3:30 pm
2 stops20h 51m
George Town Owen Roberts Intl
Wed 4/7
1:50 pm-11:05 pm
1 stop9h 15m
$679
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Wed 3/24
6:39 pm-3:30 pm
2 stops20h 51m
George Town Owen Roberts Intl
Wed 4/7
1:50 pm-8:54 pm
1 stop7h 04m
$679
MadisonGeorge Town
MSN Madison Truax Field - GCM George Town Owen Roberts Intl
MSNGCM
Madison Truax Field
Sat 2/13
6:39 pm-4:35 pm
2 stops20h 56m
George Town Owen Roberts Intl
Sat 2/20
5:45 pm-8:59 pm
2 stops28h 14m
$714
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.
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 November 4, 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.
Overall
7.3
Entertainment
7.1
Boarding
7.7
Food
6.7
Crew
8.1
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentAsha,Sep 2026
LGA - IAH
Overall
7.3
Entertainment
7.1
Boarding
7.7
Food
6.7
Crew
8.1
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentAsha,Sep 2026
LGA - IAH
Overall
7.3
Entertainment
7.1
Boarding
7.7
Food
6.7
Crew
8.1
Comfort
7.3
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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Alternative routes for Madison to Cayman Islands
See prices for flight routes from nearby airports that may be better suited for you.
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 November 4, 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 November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$383 | Average$487 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$457 | Average$611 | FlexibilityNo cancel fee | On-time71% |