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Grand Cayman

$542+ Cheap flights from Madison (MSN) to Grand Cayman

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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
May 10 — May 171
Sat 5/10
Sat 5/17
1 adult, Economy
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Cheap flight deals from Madison to Grand Cayman

Keep the following information in mind while searching for Madison to Grand Cayman flight deals. Data was last updated May 5, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$586
(American Airlines)

Popular in

August

Cheapest in

June

Average price

$607
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 Grand Cayman
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Highest demand for flights based on searches. 2% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Find flight deals from Madison to Grand Cayman

Cheapest flights from Madison to Grand Cayman
Explore the most affordable flight options available from Madison to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2025.

This American Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 12/27:14 amMSN - GCM
1 stop7h 41mAmerican Airlines
Mon 12/82:15 pmGCM - MSN
2 stops21h 06mAmerican Airlines
Deal found 5/5$542

Cheapflights Fare Finder

Customize your flight search to find flights from Madison to Grand Cayman 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 May 5, 2025.
Use the filters below to find and compare flights from Madison to Grand Cayman that are best for you.

Fly from

Madison

Fly to

Grand Cayman

Route

Depart

Return

Price

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 6/16

5:04 pm-11:04 am

2 stops18h 00m

George Town Owen Roberts Intl

Sat 6/28

3:05 pm-9:20 am

2 stops18h 15m

$586

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Best time to book a flight from Madison to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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 Grand Cayman

What is the cheapest month to book a flight from Madison to Grand Cayman?

Currently, January is the cheapest month in which you can book a flight from Madison to Grand Cayman (average of $467). Flying from Madison to Grand Cayman 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 Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated May 5, 2025.
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Boarding

7.5

Food

6.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Andrew,May 2025

LAX - MIA

2 hour delay. Discovered an engine problem late, we boarded the plane and they asked us to come off. To add insult to injury nothing was given to passengers to make amends. No free drink. No extra food or snacks. No free WiFi. Gimme a break
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Boarding

7.5

Food

6.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Andrew,May 2025

LAX - MIA

2 hour delay. Discovered an engine problem late, we boarded the plane and they asked us to come off. To add insult to injury nothing was given to passengers to make amends. No free drink. No extra food or snacks. No free WiFi. Gimme a break

Related info for your journey

Find useful and relevant information for your journey from Madison to Grand Cayman. 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 Grand Cayman?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Grand Cayman. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • Can I find deals for flights from Madison to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Madison to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Grand Cayman.

  • Can I find deals for business class flights from Madison to Grand Cayman?

    Yes. Cheapflights offers flight deals from Madison to Grand Cayman 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 Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Madison to Grand Cayman (average of $467). Flying from Madison to Grand Cayman 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.

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Alternative routes for Madison to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to George Town flights
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Top 2 airlines flying from Madison to Grand Cayman

Discover the top 2 airlines that operate flights from Madison to Grand Cayman. 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 May 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$512Average$622FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$547Average$612FlexibilityNo cancel feeOn-time69%

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