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Cheap flights from Madison to the Cayman Islands from $499

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to the Cayman Islands departing on 8/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Madison to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:43 am - 11:39 am
MSN
-
GCM
5h 56m
1 stop
Delta Logo
1:04 pm - 10:32 pm
GCM
-
MSN
9h 28m
1 stop
$499Delta
Tue, Aug 11 - Tue, Aug 18
American Airlines Logo
6:53 pm - 11:00 am
MSN
-
GCM
16h 07m
2 stops
American Airlines Logo
12:00 pm - 11:09 pm
GCM
-
MSN
11h 09m
2 stops
$504American Airlines
Tue, Aug 11 - Tue, Aug 18
American Airlines Logo
11:33 am - 11:27 am
MSN
-
GCM
23h 54m
1 stop
American Airlines Logo
2:10 pm - 11:09 pm
GCM
-
MSN
8h 59m
2 stops
$514American Airlines
Tue, Aug 25 - Tue, Sep 1
American Airlines Logo
6:30 am - 3:00 pm
MSN
-
GCM
8h 30m
1 stop
American Airlines Logo
12:30 pm - 11:09 pm
GCM
-
MSN
10h 39m
1 stop
$541American Airlines
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
6:50 am - 1:36 pm
MSN
-
GCM
6h 46m
1 stop
American Airlines Logo
12:00 pm - 9:26 am
GCM
-
MSN
21h 26m
2 stops
$546American Airlines
Fri, Jul 31 - Fri, Aug 7
American Airlines Logo
6:30 am - 3:00 pm
MSN
-
GCM
8h 30m
1 stop
American Airlines Logo
12:30 pm - 11:09 pm
GCM
-
MSN
10h 39m
1 stop
$551American Airlines
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
6:53 pm - 1:10 pm
MSN
-
GCM
18h 17m
2 stops
American Airlines Logo
12:00 pm - 11:09 pm
GCM
-
MSN
11h 09m
2 stops
$556American Airlines
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
7:05 am - 2:20 pm
MSN
-
GCM
7h 15m
1 stop
American Airlines Logo
3:20 pm - 11:23 am
GCM
-
MSN
20h 03m
1 stop
$577American Airlines
Sat, Oct 17 - Sat, Oct 31
American Airlines Logo
5:11 pm - 10:23 am
MSN
-
GCM
17h 12m
1 stop
American Airlines Logo
12:30 pm - 11:09 pm
GCM
-
MSN
10h 39m
1 stop
$583American Airlines
Fri, Jul 31 - Fri, Aug 7
Delta Logo
5:43 am - 11:39 am
MSN
-
GCM
5h 56m
1 stop
Delta Logo
1:04 pm - 10:32 pm
GCM
-
MSN
9h 28m
1 stop
$675Delta
Fri, Aug 28 - Wed, Sep 2

Delta flights from Madison to Cayman Islands

Our best Delta deals on Madison to Cayman Islands flight tickets
Delta
Aug 11
MSN5:43 amMadison Truax Field
5h 56m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
Aug 18
GCM1:04 pmGeorge Town Owen Roberts Intl
9h 28m
1 stop
MSN10:32 pmMadison Truax Field
$499
Delta
Aug 28
MSN5:43 amMadison Truax Field
5h 56m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
Sep 2
GCM1:04 pmGeorge Town Owen Roberts Intl
9h 28m
1 stop
MSN10:32 pmMadison Truax Field
$675
Delta
Aug 28
MSN5:43 amMadison Truax Field
5h 56m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
Sep 2
GCM1:04 pmGeorge Town Owen Roberts Intl
9h 56m
2 stops
MSN11:00 pmMadison Truax Field
$680

American Airlines flights from Madison to Cayman Islands

Our best American Airlines deals on Madison to Cayman Islands flight tickets
American Airlines
Aug 11
MSN6:53 pmMadison Truax Field
16h 07m
2 stops
GCM11:00 amGeorge Town Owen Roberts Intl
Aug 18
GCM12:00 pmGeorge Town Owen Roberts Intl
11h 09m
2 stops
MSN11:09 pmMadison Truax Field
$504
American Airlines
Aug 25
MSN11:33 amMadison Truax Field
23h 54m
1 stop
GCM11:27 amGeorge Town Owen Roberts Intl
Sep 1
GCM2:10 pmGeorge Town Owen Roberts Intl
8h 59m
2 stops
MSN11:09 pmMadison Truax Field
$514
American Airlines
Aug 22
MSN6:30 amMadison Truax Field
8h 30m
1 stop
GCM3:00 pmGeorge Town Owen Roberts Intl
Aug 26
GCM12:30 pmGeorge Town Owen Roberts Intl
10h 39m
1 stop
MSN11:09 pmMadison Truax Field
$541

momondo 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, momondo users made 832,500 searches. Data last updated June 6, 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
Quickest round-trip

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 8/11

5:43 am-11:39 am

1 stop5h 56m

George Town Owen Roberts Intl

Tue 8/18

1:04 pm-10:32 pm

1 stop9h 28m

$499

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 8/11

6:53 pm-11:00 am

2 stops16h 07m

George Town Owen Roberts Intl

Tue 8/18

12:00 pm-11:09 pm

2 stops11h 09m

$504

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 8/25

11:33 am-11:27 am

1 stop23h 54m

George Town Owen Roberts Intl

Tue 9/1

2:10 pm-11:09 pm

2 stops8h 59m

$514

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 8/22

6:30 am-3:00 pm

1 stop8h 30m

George Town Owen Roberts Intl

Wed 8/26

12:30 pm-11:09 pm

1 stop10h 39m

$541

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 7/31

6:50 am-1:36 pm

1 stop6h 46m

George Town Owen Roberts Intl

Fri 8/7

12:00 pm-9:26 am

2 stops21h 26m

$546

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 8/22

6:30 am-3:00 pm

1 stop8h 30m

George Town Owen Roberts Intl

Wed 8/26

12:30 pm-11:09 pm

1 stop10h 39m

$551

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 8/22

6:53 pm-1:10 pm

2 stops18h 17m

George Town Owen Roberts Intl

Wed 8/26

12:00 pm-11:09 pm

2 stops11h 09m

$556

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 10/17

7:05 am-2:20 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sat 10/31

3:20 pm-11:23 am

1 stop20h 03m

$577

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 7/31

5:11 pm-10:23 am

1 stop17h 12m

George Town Owen Roberts Intl

Fri 8/7

12:30 pm-11:09 pm

1 stop10h 39m

$583

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 8/28

5:43 am-11:39 am

1 stop5h 56m

George Town Owen Roberts Intl

Wed 9/2

1:04 pm-10:32 pm

1 stop9h 28m

$675

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from Madison to Cayman Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Madison to Cayman Islands flights?

You could potentially save up to 12% on your flight if you consider stops on a Madison to Cayman Islands flight.

Cheap Madison to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Cayman Islands

Fastest flight time

5h 56m

Direct flights

None
The fastest flight from Madison to Cayman Islands takes 5h 56m
There are no direct flights from Madison to Cayman Islands. There are no popular flight routes from Madison to Cayman Islands.
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Frequently asked questions about flying from Madison to the Cayman Islands

  • When did momondo last update prices for flights from Madison Truax Field Airport to Cayman Islands?

    Prices for flights from Madison Truax Field Airport to Cayman Islands are updated daily.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Cayman Islands?

  • How old do you have to be to fly from Madison Truax Field Airport to Cayman Islands?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Madison Truax Field Airport to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The travel and health documents you'll need for your trip to Cayman Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cayman Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Madison to Cayman Islands

Compare and see reviews for airlines that fly from Madison to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $383Free CancellationRating
7.4
9,777 reviews
Search United Airlines flights
American AirlinesPriceFrom $470Free CancellationRating
7.1
11,651 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Cayman Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Madison to Cayman Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Madison to Cayman Islands with flexible booking policies on momondo?

All flight searches from Madison to Cayman Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Madison to Cayman Islands?

momondo helps you find the best flight between Madison and Cayman Islands by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Madison to Cayman Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Madison to Cayman Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Cayman Islands and let you know when they change.

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Find better results for your trip to the Cayman Islands

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