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Cheap flights from Madison to the Cayman Islands from $361

This is the cheapest one-way 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 1/22. 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
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.
American Airlines Logo
4:47 pm - 11:35 am
MSN
-
GCM
17h 48m1 stop
American Airlines Logo
3:35 pm - 11:26 pm
GCM
-
MSN
8h 51m1 stop
$471American Airlines
Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
4:47 pm - 11:50 am
MSN
-
GCM
18h 03m2 stops
American Airlines Logo
12:53 pm - 10:42 pm
GCM
-
MSN
10h 49m2 stops
$476American Airlines
Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
4:47 pm - 11:26 am
MSN
-
GCM
17h 39m2 stops
American Airlines Logo
3:45 pm - 10:43 am
GCM
-
MSN
19h 58m2 stops
$481American Airlines
Sat, Jan 31 - Sun, Feb 8
American Airlines Logo
6:14 am - 2:50 pm
MSN
-
GCM
8h 36m1 stop
American Airlines Logo
3:50 pm - 11:04 am
GCM
-
MSN
19h 14m1 stop
$483American Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
8:24 pm - 10:40 am
MSN
-
GCM
14h 16m2 stops
American Airlines Logo
3:50 pm - 11:04 am
GCM
-
MSN
19h 14m1 stop
$488American Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
4:30 pm - 11:26 am
MSN
-
GCM
17h 56m1 stop
American Airlines Logo
3:45 pm - 10:43 am
GCM
-
MSN
19h 58m2 stops
$490American Airlines
Sat, Jan 31 - Sun, Feb 8
American Airlines Logo
6:14 am - 3:25 pm
MSN
-
GCM
8h 11m1 stop
American Airlines Logo
3:35 pm - 11:26 pm
GCM
-
MSN
8h 51m1 stop
$510American Airlines
Fri, Feb 20 - Tue, Feb 24
American Airlines Logo
6:14 am - 2:15 pm
MSN
-
GCM
8h 01m1 stop
American Airlines Logo
12:00 pm - 12:35 pm
GCM
-
MSN
24h 35m2 stops
$514American Airlines
Tue, Mar 31 - Tue, Apr 7
American Airlines Logo
7:00 am - 2:14 pm
MSN
-
GCM
6h 14m1 stop
American Airlines Logo
1:05 pm - 11:26 pm
GCM
-
MSN
11h 21m2 stops
$515American Airlines
Fri, Feb 20 - Tue, Feb 24
American Airlines Logo
8:24 pm - 11:05 am
MSN
-
GCM
14h 41m2 stops
American Airlines Logo
7:45 am - 10:42 pm
GCM
-
MSN
14h 57m2 stops
$518American Airlines
Mon, Mar 30 - Mon, Apr 6

American Airlines flights from Madison to Cayman Islands

Our best American Airlines deals on Madison to Cayman Islands flight tickets
American Airlines
Feb 6
MSN4:47 pmMadison Truax Field
17h 48m
1 stop
GCM11:35 amGeorge Town Owen Roberts Intl
Feb 13
GCM3:35 pmGeorge Town Owen Roberts Intl
8h 51m
1 stop
MSN11:26 pmMadison Truax Field
$471
American Airlines
Feb 6
MSN4:47 pmMadison Truax Field
18h 03m
2 stops
GCM11:50 amGeorge Town Owen Roberts Intl
Feb 13
GCM12:53 pmGeorge Town Owen Roberts Intl
10h 49m
2 stops
MSN10:42 pmMadison Truax Field
$476
American Airlines
Jan 31
MSN4:47 pmMadison Truax Field
17h 39m
2 stops
GCM11:26 amGeorge Town Owen Roberts Intl
Feb 8
GCM3:45 pmGeorge Town Owen Roberts Intl
19h 58m
2 stops
MSN10:43 amMadison Truax Field
$481

United Airlines flights from Madison to Cayman Islands

Our best United Airlines deals on Madison to Cayman Islands flight tickets
United Airlines
Mar 2
MSN6:30 amMadison Truax Field
6h 15m
1 stop
GCM1:45 pmGeorge Town Owen Roberts Intl
Mar 5
GCM2:50 pmGeorge Town Owen Roberts Intl
8h 42m
1 stop
MSN10:32 pmMadison Truax Field
$553
United Airlines
Mar 2
MSN6:30 amMadison Truax Field
6h 15m
1 stop
GCM1:45 pmGeorge Town Owen Roberts Intl
Mar 5
GCM5:45 pmGeorge Town Owen Roberts Intl
22h 13m
2 stops
MSN2:58 pmMadison Truax Field
$558
United Airlines
Mar 30
MSN8:30 amMadison Truax Field
28h 15m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
Apr 8
GCM1:50 pmGeorge Town Owen Roberts Intl
7h 26m
1 stop
MSN9:16 pmMadison Truax Field
$559

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 January 11, 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

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 2/6

4:47 pm-11:35 am

1 stop17h 48m

George Town Owen Roberts Intl

Fri 2/13

3:35 pm-11:26 pm

1 stop8h 51m

$471

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 2/6

4:47 pm-11:50 am

2 stops18h 03m

George Town Owen Roberts Intl

Fri 2/13

12:53 pm-10:42 pm

2 stops10h 49m

$476

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/31

4:47 pm-11:26 am

2 stops17h 39m

George Town Owen Roberts Intl

Sun 2/8

3:45 pm-10:43 am

2 stops19h 58m

$481

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 3/30

6:14 am-2:50 pm

1 stop8h 36m

George Town Owen Roberts Intl

Mon 4/6

3:50 pm-11:04 am

1 stop19h 14m

$483

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 3/30

8:24 pm-10:40 am

2 stops14h 16m

George Town Owen Roberts Intl

Mon 4/6

3:50 pm-11:04 am

1 stop19h 14m

$488

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/31

4:30 pm-11:26 am

1 stop17h 56m

George Town Owen Roberts Intl

Sun 2/8

3:45 pm-10:43 am

2 stops19h 58m

$490

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 2/20

6:14 am-3:25 pm

1 stop8h 11m

George Town Owen Roberts Intl

Tue 2/24

3:35 pm-11:26 pm

1 stop8h 51m

$510

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 3/31

6:14 am-2:15 pm

1 stop8h 01m

George Town Owen Roberts Intl

Tue 4/7

12:00 pm-12:35 pm

2 stops24h 35m

$514

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 2/20

7:00 am-2:14 pm

1 stop6h 14m

George Town Owen Roberts Intl

Tue 2/24

1:05 pm-11:26 pm

2 stops11h 21m

$515

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 3/30

8:24 pm-11:05 am

2 stops14h 41m

George Town Owen Roberts Intl

Mon 4/6

7:45 am-10:42 pm

2 stops14h 57m

$518

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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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 16% 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

6h 15m

Direct flights

None
The fastest flight from Madison to Cayman Islands takes 6h 15m
There are no direct flights from Madison to Cayman Islands. There are no popular flight routes from Madison to Cayman Islands.
Search flight deals

  • 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
American AirlinesPriceFrom $524Free CancellationRating
7.2
11,101 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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Popular flights according to clicks in the last 7 days on momondo
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