HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cayman Islands

$578+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — GCM
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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 Cayman Islands

Keep the following information in mind while searching for Madison to Cayman Islands flight deals. Data was last updated April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$578
(American Airlines)

Popular in

August

Cheapest in

June

Average price

$675
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
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 April 2025
Search Deals

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 2, 2025.

This American Airlines deal was found by Cheapflights users on 4/1. 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 4/163:30 pmMSN - GCM
2 stops19h 39mAmerican Airlines
Mon 4/212:00 pmGCM - MSN
2 stops20h 38mAmerican Airlines
Deal found 4/1$578
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/65:45 amMSN - GCM
1 stop5h 40mDelta
Fri 4/112:45 pmGCM - MSN
1 stop8h 15mDelta
Deal found 4/1$604

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 2, 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

Wed 4/16

3:30 pm-11:09 am

2 stops19h 39m

George Town Owen Roberts Intl

Mon 4/21

2:00 pm-10:38 am

2 stops20h 38m

$578

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

$1,312

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

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 2, 2025.
To help decide which airline to fly from Madison to Cayman Islands, see what other customers have to say about Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

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
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

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
7,899 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

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 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.

  • 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

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 Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
Minneapolis to Luis Munoz Marin Intl flights
O'Hare Intl to Nassau flights
Minneapolis to Punta Cana flights
Milwaukee to Luis Munoz Marin Intl flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Santo Domingo flights
Minneapolis to Oranjestad flights
Minneapolis to Montego Bay flights
O'Hare Intl to Willemstad flights
Minneapolis to Saint Thomas Island flights
O'Hare Intl to Castries flights
O'Hare Intl to Christiansted flights
Madison to Luis Munoz Marin Intl flights
Minneapolis to Nassau flights
O'Hare Intl to George Town flights
Milwaukee to Punta Cana flights
O'Hare Intl to Puerto Plata flights
Minneapolis to Providenciales flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Bridgetown flights
Appleton to Luis Munoz Marin Intl flights
Milwaukee to Oranjestad flights
Minneapolis to George Town flights
O'Hare Intl to Kingston flights
O'Hare Intl to Ponce flights
Minneapolis to Willemstad flights
Milwaukee to Montego Bay flights
O'Hare Intl to Road Town flights
Milwaukee to Nassau flights
Minneapolis to Simpson Bay flights
Minneapolis to Castries flights
O'Hare Intl to St. John's flights
O'Hare Intl to Gregory Town flights
Milwaukee to Saint Thomas Island flights
O'Hare Intl to Santiago de los Caballeros flights
Green Bay to Luis Munoz Marin Intl flights
Milwaukee to George Town flights
O'Hare Intl to Port of Spain flights
Milwaukee to Castries flights
Madison to Punta Cana flights
O'Hare Intl to Basseterre flights
Milwaukee to Providenciales flights
Minneapolis to Georgetown flights
O'Hare Intl to St. George's flights
Appleton to Nassau flights

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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$512Average$677FlexibilityNo 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.