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Cheap flights from Madison to the Cayman Islands from $548

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 12/6. 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

American Airlines Logo
7:00 am - 1:55 pmMSN-GCM
5h 55m1 stop
American Airlines Logo
4:15 pm - 11:59 pmGCM-MSN
8h 44m1 stop
$548American Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 13
American Airlines Logo
5:46 pm - 12:40 pmMSN-GCM
18h 54m2 stops
American Airlines Logo
8:45 am - 11:51 pmGCM-MSN
16h 06m2 stops
$552American Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
American Airlines Logo
8:25 pm - 11:25 amMSN-GCM
15h 00m2 stops
American Airlines Logo
2:00 pm - 10:15 amGCM-MSN
20h 15m2 stops
$557American Airlines
Find Deal
Wed, Oct 22 - Sun, Oct 26
American Airlines Logo
12:35 pm - 3:20 pmMSN-GCM
26h 45m1 stop
American Airlines Logo
1:25 pm - 11:58 pmGCM-MSN
11h 33m1 stop
$558American Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
American Airlines Logo
8:09 am - 11:25 amMSN-GCM
27h 16m1 stop
American Airlines Logo
12:25 pm - 11:51 pmGCM-MSN
11h 26m1 stop
$563American Airlines
Find Deal
Wed, Oct 22 - Sun, Oct 26
American Airlines Logo
12:19 pm - 12:00 pmMSN-GCM
22h 41m1 stop
American Airlines Logo
4:15 pm - 10:29 amGCM-MSN
19h 14m2 stops
$568American Airlines
Find Deal
Thu, Jan 29 - Sun, Feb 8
American Airlines Logo
3:55 pm - 12:40 pmMSN-GCM
19h 45m1 stop
American Airlines Logo
1:40 pm - 11:41 pmGCM-MSN
11h 01m1 stop
$604American Airlines
Find Deal
Mon, Dec 1 - Mon, Dec 8
American Airlines Logo
4:17 pm - 12:00 pmMSN-GCM
18h 43m1 stop
American Airlines Logo
1:40 pm - 10:29 amGCM-MSN
21h 49m1 stop
$613American Airlines
Find Deal
Sat, Jan 31 - Sun, Feb 8
United Airlines Logo
7:00 am - 1:45 pmMSN-GCM
5h 45m1 stop
United Airlines Logo
2:50 pm - 8:54 pmGCM-MSN
7h 04m1 stop
$668United Airlines
Find Deal
Thu, Jan 29 - Sun, Feb 8
United Airlines Logo
6:20 am - 12:45 pmMSN-GCM
6h 25m1 stop
United Airlines Logo
2:50 pm - 8:35 pmGCM-MSN
6h 45m1 stop
$712United Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8

American Airlines flights from Madison to Cayman Islands

Our best American Airlines deals on Madison to Cayman Islands flight tickets
American Airlines
Dec 6
MSN7:00 amMadison Truax Field
5h 55m
1 stop
GCM1:55 pmGeorge Town Owen Roberts Intl
Dec 13
GCM4:15 pmGeorge Town Owen Roberts Intl
8h 44m
1 stop
MSN11:59 pmMadison Truax Field
$548
Find similar
American Airlines
Nov 1
MSN5:46 pmMadison Truax Field
18h 54m
2 stops
GCM12:40 pmGeorge Town Owen Roberts Intl
Nov 8
GCM8:45 amGeorge Town Owen Roberts Intl
16h 06m
2 stops
MSN11:51 pmMadison Truax Field
$552
Find similar
American Airlines
Oct 22
MSN8:25 pmMadison Truax Field
15h 00m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
Oct 26
GCM2:00 pmGeorge Town Owen Roberts Intl
20h 15m
2 stops
MSN10:15 amMadison Truax Field
$557
Find similar

United Airlines flights from Madison to Cayman Islands

Our best United Airlines deals on Madison to Cayman Islands flight tickets
United Airlines
Jan 29
MSN7:00 amMadison Truax Field
5h 45m
1 stop
GCM1:45 pmGeorge Town Owen Roberts Intl
Feb 8
GCM2:50 pmGeorge Town Owen Roberts Intl
7h 04m
1 stop
MSN8:54 pmMadison Truax Field
$668
Find similar
United Airlines
Nov 1
MSN6:20 amMadison Truax Field
6h 25m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
Nov 8
GCM2:50 pmGeorge Town Owen Roberts Intl
6h 45m
1 stop
MSN8:35 pmMadison Truax Field
$712
Find similar

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 August 7, 2025.
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 12/6

7:00 am-1:55 pm

1 stop5h 55m

George Town Owen Roberts Intl

Sat 12/13

4:15 pm-11:59 pm

1 stop8h 44m

$548

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 11/1

5:46 pm-12:40 pm

2 stops18h 54m

George Town Owen Roberts Intl

Sat 11/8

8:45 am-11:51 pm

2 stops16h 06m

$552

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 10/22

8:25 pm-11:25 am

2 stops15h 00m

George Town Owen Roberts Intl

Sun 10/26

2:00 pm-10:15 am

2 stops20h 15m

$557

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 11/1

12:35 pm-3:20 pm

1 stop26h 45m

George Town Owen Roberts Intl

Sat 11/8

1:25 pm-11:58 pm

1 stop11h 33m

$558

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 10/22

8:09 am-11:25 am

1 stop27h 16m

George Town Owen Roberts Intl

Sun 10/26

12:25 pm-11:51 pm

1 stop11h 26m

$563

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 1/29

12:19 pm-12:00 pm

1 stop22h 41m

George Town Owen Roberts Intl

Sun 2/8

4:15 pm-10:29 am

2 stops19h 14m

$568

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 12/1

3:55 pm-12:40 pm

1 stop19h 45m

George Town Owen Roberts Intl

Mon 12/8

1:40 pm-11:41 pm

1 stop11h 01m

$604

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/31

4:17 pm-12:00 pm

1 stop18h 43m

George Town Owen Roberts Intl

Sun 2/8

1:40 pm-10:29 am

1 stop21h 49m

$613

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 1/29

7:00 am-1:45 pm

1 stop5h 45m

George Town Owen Roberts Intl

Sun 2/8

2:50 pm-8:54 pm

1 stop7h 04m

$668

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 11/1

6:20 am-12:45 pm

1 stop6h 25m

George Town Owen Roberts Intl

Sat 11/8

2:50 pm-8:35 pm

1 stop6h 45m

$712

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

What is the cheapest day to depart on your flight to Cayman Islands?

Our data shows that Monday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $577. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Sunday is $655.

What is the cheapest time of day to depart on your flight to Cayman Islands?

According to our data, the cheapest time of day to fly to Cayman Islands is in the afternoon. momondo users have found flights departing from Madison to Cayman Islands in the afternoon for as low as $580. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $637 on average. Flights to Cayman Islands from Madison in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

Best Price Found

$548

Fastest flight time

5h 45m

Direct flights

None

Airports in Cayman Islands

1 airport
The best flight deal from Madison to Cayman Islands found on momondo in the last 72 hours is $548
The fastest flight from Madison to Cayman Islands takes 5h 45m
There are no direct flights from Madison to Cayman Islands. Popular non-direct route for this connection is Madison Truax Field Airport - George Town Owen Roberts Intl Airport.
There is 1 airport near Cayman Islands: George Town Owen Roberts Intl (GCM)
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
DeltaPriceFrom $513Free CancellationRating
8.0
7,985 reviews
Search Delta flights
American AirlinesPriceFrom $531Free CancellationRating
7.2
10,000 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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