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Cayman Islands

$419+ 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
Sep 6 — Sep 131
Sun 9/6
Sun 9/13
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 August 7, 2026.

This United Airlines deal was found by Cheapflights users on 8/5. 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 10/246:39 pm -
2 stops20h 51m
Sat 10/311:55 pm -
1 stop7h 10m
Deal found 8/5$419
This American Airlines deal was found by Cheapflights users on 8/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:00 am -
1 stop7h 17m
Wed 9/912:00 pm -
2 stops20h 14m
Deal found 8/3$424
This American Airlines deal was found by Cheapflights users on 8/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/122:17 pm -
1 stop21h 13m
Sat 9/2612:36 pm -
2 stops19h 38m
Deal found 8/3$432
This American Airlines deal was found by Cheapflights users on 8/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/94:21 pm -
2 stops18h 39m
Fri 10/308:00 am -
2 stops12h 08m
Deal found 8/3$494
This American Airlines deal was found by Cheapflights users on 8/6. 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 10/48:05 pm -
2 stops17h 05m
Sun 10/1112:35 pm -
1 stop11h 22m
Deal found 8/6$499
This American Airlines deal was found by Cheapflights users on 8/5. 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 10/241:24 pm -
1 stop22h 06m
Sat 10/313:15 pm -
1 stop7h 32m
Deal found 8/5$500
This American Airlines deal was found by Cheapflights users on 8/2. 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 11/126:38 pm -
1 stop15h 45m
Sat 11/213:18 pm -
1 stop9h 39m
Deal found 8/2$509
This American Airlines deal was found by Cheapflights users on 8/2. 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 11/127:05 am -
2 stops11h 53m
Sun 11/2212:59 pm -
2 stops20h 25m
Deal found 8/2$519
This United Airlines deal was found by Cheapflights users on 8/6. 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 10/277:00 pm -
2 stops20h 30m
Thu 10/294:45 pm -
2 stops28h 20m
Deal found 8/6$544

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 August 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$419
(United 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 August 7, 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 Madison Truax Field - GCM George Town Owen Roberts Intl

MSNGCM

Madison Truax Field

Sat 10/24

6:39 pm-3:30 pm

2 stops20h 51m

George Town Owen Roberts Intl

Sat 10/31

1:55 pm-9:05 pm

1 stop7h 10m

$419
Quickest round-trip

MadisonGeorge Town

MSN Madison Truax Field - GCM George Town Owen Roberts Intl

MSNGCM

Madison Truax Field

Sat 1/9

7:05 pm-12:05 pm

2 stops16h 00m

George Town Owen Roberts Intl

Sat 1/23

1:05 pm-10:59 pm

2 stops10h 54m

$424

MadisonGeorge Town

MSN Madison Truax Field - GCM George Town Owen Roberts Intl

MSNGCM

Madison Truax Field

Fri 1/8

4:47 pm-12:05 pm

2 stops18h 18m

George Town Owen Roberts Intl

Sat 1/16

3:40 pm-12:12 am

2 stops9h 32m

$494

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

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 August 7, 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
10,085 reviews

Crew

8.1

Food

6.7

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
United Airlines
7.4
Good
10,085 reviews
United Airlines
7.4
Good
10,085 reviews

Crew

8.1

Food

6.7

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
American Airlines
7.1
Good
11,883 reviews
United Airlines
7.4
Good
10,085 reviews

Crew

8.1

Food

6.7

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

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 $424, United Airlines can have you in Cayman Islands from Madison in 16h. 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 August 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$383Average$487FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$470Average$570FlexibilityNo cancel feeOn-time71%

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