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Cheap flights from Madison to the Cayman Islands from $277

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 3/21. 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
5:37 pm - 11:31 am
MSN
-
GCM
17h 54m
2 stops
American Airlines Logo
12:35 pm - 11:55 pm
GCM
-
MSN
11h 20m
1 stop
$364American Airlines
Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
11:35 am - 11:31 am
MSN
-
GCM
23h 56m
1 stop
American Airlines Logo
12:35 pm - 11:55 pm
GCM
-
MSN
11h 20m
1 stop
$367American Airlines
Sat, Apr 11 - Wed, Apr 15
United Airlines Logo
6:00 am - 12:45 pm
MSN
-
GCM
6h 45m
1 stop
United Airlines Logo
1:35 pm - 8:57 am
GCM
-
MSN
19h 22m
2 stops
$382United Airlines
Wed, Apr 15 - Thu, Apr 23
United Airlines Logo
6:00 am - 12:45 pm
MSN
-
GCM
6h 45m
1 stop
United Airlines Logo
1:50 pm - 8:57 am
GCM
-
MSN
19h 07m
1 stop
$383United Airlines
Wed, Apr 15 - Thu, Apr 23
United Airlines Logo
8:35 pm - 12:45 pm
MSN
-
GCM
16h 10m
1 stop
United Airlines Logo
1:50 pm - 11:49 pm
GCM
-
MSN
9h 59m
1 stop
$384United Airlines
Thu, Apr 16 - Thu, Apr 23
American Airlines Logo
4:12 pm - 11:00 am
MSN
-
GCM
18h 48m
2 stops
American Airlines Logo
12:35 pm - 11:54 pm
GCM
-
MSN
11h 19m
1 stop
$389American Airlines
Wed, May 13 - Wed, May 20
American Airlines Logo
11:35 am - 11:31 am
MSN
-
GCM
23h 56m
1 stop
American Airlines Logo
12:35 pm - 11:54 pm
GCM
-
MSN
11h 19m
1 stop
$393American Airlines
Wed, May 13 - Wed, May 20
United Airlines Logo
5:00 am - 12:45 pm
MSN
-
GCM
7h 45m
1 stop
United Airlines Logo
1:50 pm - 9:16 pm
GCM
-
MSN
7h 26m
1 stop
$445United Airlines
Tue, Apr 21 - Fri, Apr 24
American Airlines Logo
5:37 pm - 11:31 am
MSN
-
GCM
17h 54m
2 stops
American Airlines Logo
12:35 pm - 11:55 pm
GCM
-
MSN
11h 20m
1 stop
$450American Airlines
Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
5:08 pm - 11:31 am
MSN
-
GCM
18h 23m
1 stop
American Airlines Logo
12:35 pm - 11:55 pm
GCM
-
MSN
11h 20m
1 stop
$454American Airlines
Sat, Apr 11 - Wed, Apr 15

American Airlines flights from Madison to Cayman Islands

Our best American Airlines deals on Madison to Cayman Islands flight tickets
American Airlines
Apr 11
MSN5:37 pmMadison Truax Field
17h 54m
2 stops
GCM11:31 amGeorge Town Owen Roberts Intl
Apr 15
GCM2:05 pmGeorge Town Owen Roberts Intl
18h 40m
2 stops
MSN8:45 amMadison Truax Field
$364
American Airlines
Apr 11
MSN11:35 amMadison Truax Field
23h 56m
1 stop
GCM11:31 amGeorge Town Owen Roberts Intl
Apr 15
GCM12:35 pmGeorge Town Owen Roberts Intl
11h 20m
1 stop
MSN11:55 pmMadison Truax Field
$367
American Airlines
May 13
MSN4:12 pmMadison Truax Field
18h 48m
2 stops
GCM11:00 amGeorge Town Owen Roberts Intl
May 20
GCM12:35 pmGeorge Town Owen Roberts Intl
11h 19m
1 stop
MSN11:54 pmMadison Truax Field
$389

United Airlines flights from Madison to Cayman Islands

Our best United Airlines deals on Madison to Cayman Islands flight tickets
United Airlines
Apr 15
MSN6:00 amMadison Truax Field
6h 45m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
Apr 23
GCM1:35 pmGeorge Town Owen Roberts Intl
19h 22m
2 stops
MSN8:57 amMadison Truax Field
$382
United Airlines
Apr 15
MSN6:00 amMadison Truax Field
6h 45m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
Apr 23
GCM1:50 pmGeorge Town Owen Roberts Intl
19h 07m
1 stop
MSN8:57 amMadison Truax Field
$383
United Airlines
Apr 16
MSN8:35 pmMadison Truax Field
15h 55m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Apr 23
GCM1:50 pmGeorge Town Owen Roberts Intl
9h 59m
1 stop
MSN11:49 pmMadison Truax Field
$384

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 March 2, 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

Sat 4/11

5:37 pm-11:31 am

2 stops17h 54m

George Town Owen Roberts Intl

Wed 4/15

12:35 pm-11:55 pm

1 stop11h 20m

$364

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 4/11

11:35 am-11:31 am

1 stop23h 56m

George Town Owen Roberts Intl

Wed 4/15

12:35 pm-11:55 pm

1 stop11h 20m

$367

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 4/15

6:00 am-12:45 pm

1 stop6h 45m

George Town Owen Roberts Intl

Thu 4/23

1:35 pm-8:57 am

2 stops19h 22m

$382

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 4/15

6:00 am-12:45 pm

1 stop6h 45m

George Town Owen Roberts Intl

Thu 4/23

1:50 pm-8:57 am

1 stop19h 07m

$383

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 4/16

8:35 pm-12:45 pm

1 stop16h 10m

George Town Owen Roberts Intl

Thu 4/23

1:50 pm-11:49 pm

1 stop9h 59m

$384

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 5/13

4:12 pm-11:00 am

2 stops18h 48m

George Town Owen Roberts Intl

Wed 5/20

12:35 pm-11:54 pm

1 stop11h 19m

$389

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 5/13

11:35 am-11:31 am

1 stop23h 56m

George Town Owen Roberts Intl

Wed 5/20

12:35 pm-11:54 pm

1 stop11h 19m

$393

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 4/21

5:00 am-12:45 pm

1 stop7h 45m

George Town Owen Roberts Intl

Fri 4/24

1:50 pm-9:16 pm

1 stop7h 26m

$445

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 4/11

5:37 pm-11:31 am

2 stops17h 54m

George Town Owen Roberts Intl

Wed 4/15

12:35 pm-11:55 pm

1 stop11h 20m

$450

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 4/11

5:08 pm-11:31 am

1 stop18h 23m

George Town Owen Roberts Intl

Wed 4/15

12:35 pm-11:55 pm

1 stop11h 20m

$454

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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

7h 00m

Direct flights

None
The fastest flight from Madison to Cayman Islands takes 7h 00m
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
United AirlinesPriceFrom $383Free CancellationRating
7.4
9,375 reviews
Search United Airlines flights
American AirlinesPriceFrom $484Free CancellationRating
7.1
11,369 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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