HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Mar 19 — Mar 261
Wed 3/19
Wed 3/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Grand Cayman 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
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 Grand Cayman

Keep the following information in mind while searching for Madison to Grand Cayman flight deals. Data was last updated March 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$542
(American Airlines)

Popular in

August

Cheapest in

June

Average price

$694
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 Grand Cayman
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals

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 March 14, 2025.

This American Airlines deal was found by Cheapflights users on 3/13. 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 4/66:43 pmMSN - GCM
2 stops16h 52mAmerican Airlines
Fri 4/112:00 pmGCM - MSN
2 stops20h 38mAmerican Airlines
Deal found 3/13$542
This Delta deal was found by Cheapflights users on 3/13. 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.
Wed 4/165:45 amMSN - GCM
1 stop5h 37mDelta
Mon 4/2112:47 pmGCM - MSN
1 stop9h 45mDelta
Deal found 3/13$948

Find flights from Madison to Grand Cayman within your budget

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 March 14, 2025.

Fly from

Madison

Fly to

Grand Cayman

Route

Depart

Return

Price

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 4/6

6:43 pm-11:35 am

2 stops16h 52m

George Town Owen Roberts Intl

Fri 4/11

2:00 pm-10:38 am

2 stops20h 38m

$542

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 4/16

5:45 am-11:22 am

1 stop5h 37m

George Town Owen Roberts Intl

Mon 4/21

12:47 pm-10:32 pm

1 stop9h 45m

$948

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

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.

Travel insights for flights from Madison to Grand Cayman

Get recent, data-driven insights about flights from Madison to Grand Cayman including ideal travel times, pricing trends, and more.

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 March 14, 2025.
Delta
8.0
Very good
7,944 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

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
7,944 reviews
Delta
8.0
Very good
7,944 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

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
7,944 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

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 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Minneapolis to George Town flights
Milwaukee to George Town flights
Madison to George Town flights
O'Hare Intl to Cayman Brac flights

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 March 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$512Average$673FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$547Average$605FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.