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Cayman Islands

$223+ 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 7/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
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Cheap 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 April 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$586
(American Airlines)

One-way from

$223
(American Airlines)

Popular in

August

Cheapest in

July

Average price

$736
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
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One-way flight from Madison Truax Field to Cayman Islands
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Highest demand for flights based on searches. 1% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find 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 April 22, 2025.

This American Airlines deal was found by Cheapflights users on 4/22. 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 11/27:14 amMSN - GCM
1 stop7h 41mAmerican Airlines
Fri 11/71:45 pmGCM - MSN
1 stop8h 39mAmerican Airlines
Deal found 4/22$538
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/182:27 pmMSN - GCM
2 stops22h 03mUnited Airlines
Sat 5/244:45 pmGCM - MSN
2 stops17h 26mUnited Airlines
Deal found 4/22$596
This Delta deal was found by Cheapflights users on 4/22. 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.
Sun 5/185:30 amMSN - GCM
1 stop5h 50mDelta
Sat 5/241:03 pmGCM - MSN
1 stop8h 28mDelta
Deal found 4/22$626

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 April 22, 2025.
Use the filters below to find and compare flights from Madison to the Cayman Islands that are best for you.

Fly from

Madison

Fly to

Cayman Islands

Route

Depart

Return

Price

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 6/16

8:16 pm-11:04 am

2 stops14h 48m

George Town Owen Roberts Intl

Sat 6/28

3:30 pm-11:30 pm

1 stop8h 00m

$586

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 5/18

2:27 pm-12:30 pm

2 stops22h 03m

George Town Owen Roberts Intl

Sat 5/24

4:45 pm-10:11 am

2 stops17h 26m

$596

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 5/18

5:30 am-11:20 am

1 stop5h 50m

George Town Owen Roberts Intl

Sat 5/24

1:03 pm-9:31 pm

1 stop8h 28m

$626

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 7/6

8:27 pm-1:10 pm

2 stops16h 43m

$223

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 7/6

5:40 am-11:25 am

1 stop5h 45m

$261

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 7/6

6:30 am-12:30 pm

3 stops54h 00m

$2,767

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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, January is the cheapest month in which you can book a flight from Madison to Cayman Islands (average of $467). Flying from Madison to Cayman Islands in March is currently the most expensive (average of $594). 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 April 22, 2025.
Delta
8.0
Very good
7,920 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,683 reviews
Delta
8.0
Very good
7,920 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,920 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • What are the cheapest airlines to fly from Madison to Cayman Islands one-way?

    $223 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $261 and $2,767, respectively.

  • 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, January is the cheapest month in which you can book a flight from Madison to Cayman Islands (average of $467). Flying from Madison to Cayman Islands in March is currently the most expensive (average of $594). 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$512Average$658FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$547Average$605FlexibilityNo cancel feeOn-time69%

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