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Cheap flights from Madison to the Cayman Islands from $470

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 2/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Madison to the Cayman Islands

Cheap round-trip flights

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Delta Logo
5:38 am - 12:40 pmMSN-GCM
6h 02m1 stop
Delta Logo
2:00 pm - 10:37 pmGCM-MSN
9h 37m1 stop
$470Delta
Find Deal
Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
4:30 pm - 11:50 amMSN-GCM
18h 20m2 stops
American Airlines Logo
3:36 pm - 11:29 pmGCM-MSN
8h 53m1 stop
$475American Airlines
Find Deal
Fri, Feb 6 - Fri, Feb 13
American Airlines Logo
7:00 am - 3:25 pmMSN-GCM
7h 25m1 stop
American Airlines Logo
3:45 pm - 10:11 amGCM-MSN
19h 26m2 stops
$480American Airlines
Find Deal
Sat, Jan 31 - Sun, Feb 8
American Airlines Logo
1:16 pm - 2:35 pmMSN-GCM
24h 19m1 stop
American Airlines Logo
3:45 pm - 10:11 amGCM-MSN
19h 26m2 stops
$486American Airlines
Find Deal
Thu, Jan 29 - Sun, Feb 8
American Airlines Logo
8:00 am - 8:25 pmMSN-GCM
11h 25m2 stops
American Airlines Logo
3:45 pm - 10:19 amGCM-MSN
19h 34m2 stops
$500American Airlines
Find Deal
Sat, Jan 17 - Sat, Jan 24
American Airlines Logo
8:10 am - 11:26 amMSN-GCM
26h 16m1 stop
American Airlines Logo
3:45 pm - 10:19 amGCM-MSN
19h 34m2 stops
$510American Airlines
Find Deal
Sat, Jan 17 - Sat, Jan 24
American Airlines Logo
7:20 am - 1:20 pmMSN-GCM
6h 00m1 stop
American Airlines Logo
1:00 pm - 2:02 pmGCM-MSN
25h 02m1 stop
$528American Airlines
Find Deal
Thu, Mar 12 - Thu, Mar 19
United Airlines Logo
6:40 am - 1:45 pmMSN-GCM
6h 05m1 stop
United Airlines Logo
2:25 pm - 11:44 pmGCM-MSN
10h 19m1 stop
$548United Airlines
Find Deal
Sun, Jan 4 - Thu, Jan 8
American Airlines Logo
6:20 am - 6:51 pmMSN-GCM
12h 31m2 stops
American Airlines Logo
3:15 pm - 10:18 amGCM-MSN
19h 03m2 stops
$552American Airlines
Find Deal
Thu, Mar 12 - Thu, Mar 19
Delta Logo
5:50 pm - 11:24 amMSN-GCM
17h 34m2 stops
Delta Logo
12:45 pm - 10:35 pmGCM-MSN
9h 50m1 stop
$553Delta
Find Deal
Mon, Apr 20 - Wed, Apr 22

Delta flights from Madison to Cayman Islands

Our best Delta deals on Madison to Cayman Islands flight tickets
Delta
Feb 6
MSN5:38 amMadison Truax Field
6h 02m
1 stop
GCM12:40 pmGeorge Town Owen Roberts Intl
Feb 13
GCM2:00 pmGeorge Town Owen Roberts Intl
9h 37m
1 stop
MSN10:37 pmMadison Truax Field
$470
Find similar
Delta
Apr 20
MSN5:50 pmMadison Truax Field
17h 34m
2 stops
GCM11:24 amGeorge Town Owen Roberts Intl
Apr 22
GCM12:45 pmGeorge Town Owen Roberts Intl
9h 50m
1 stop
MSN10:35 pmMadison Truax Field
$553
Find similar
Delta
Apr 20
MSN5:45 amMadison Truax Field
5h 39m
1 stop
GCM11:24 amGeorge Town Owen Roberts Intl
Apr 22
GCM12:45 pmGeorge Town Owen Roberts Intl
9h 50m
1 stop
MSN10:35 pmMadison Truax Field
$614
Find similar

American Airlines flights from Madison to Cayman Islands

Our best American Airlines deals on Madison to Cayman Islands flight tickets
American Airlines
Feb 6
MSN4:30 pmMadison Truax Field
18h 20m
2 stops
GCM11:50 amGeorge Town Owen Roberts Intl
Feb 13
GCM3:36 pmGeorge Town Owen Roberts Intl
8h 53m
1 stop
MSN11:29 pmMadison Truax Field
$475
Find similar
American Airlines
Jan 31
MSN7:00 amMadison Truax Field
7h 25m
1 stop
GCM3:25 pmGeorge Town Owen Roberts Intl
Feb 8
GCM3:45 pmGeorge Town Owen Roberts Intl
19h 26m
2 stops
MSN10:11 amMadison Truax Field
$480
Find similar
American Airlines
Jan 29
MSN1:16 pmMadison Truax Field
24h 19m
1 stop
GCM2:35 pmGeorge Town Owen Roberts Intl
Feb 8
GCM3:45 pmGeorge Town Owen Roberts Intl
19h 26m
2 stops
MSN10:11 amMadison Truax Field
$486
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 November 13, 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

Fri 2/6

5:38 am-12:40 pm

1 stop6h 02m

George Town Owen Roberts Intl

Fri 2/13

2:00 pm-10:37 pm

1 stop9h 37m

$470

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 2/6

4:30 pm-11:50 am

2 stops18h 20m

George Town Owen Roberts Intl

Fri 2/13

3:36 pm-11:29 pm

1 stop8h 53m

$475

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/31

7:00 am-3:25 pm

1 stop7h 25m

George Town Owen Roberts Intl

Sun 2/8

3:45 pm-10:11 am

2 stops19h 26m

$480

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 1/29

1:16 pm-2:35 pm

1 stop24h 19m

George Town Owen Roberts Intl

Sun 2/8

3:45 pm-10:11 am

2 stops19h 26m

$486

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/17

8:00 am-8:25 pm

2 stops11h 25m

George Town Owen Roberts Intl

Sat 1/24

3:45 pm-10:19 am

2 stops19h 34m

$500

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/17

8:10 am-11:26 am

1 stop26h 16m

George Town Owen Roberts Intl

Sat 1/24

3:45 pm-10:19 am

2 stops19h 34m

$510

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 3/12

7:20 am-1:20 pm

1 stop6h 00m

George Town Owen Roberts Intl

Thu 3/19

1:00 pm-2:02 pm

1 stop25h 02m

$528

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 1/4

6:40 am-1:45 pm

1 stop6h 05m

George Town Owen Roberts Intl

Thu 1/8

2:25 pm-11:44 pm

1 stop10h 19m

$548

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 3/12

6:20 am-6:51 pm

2 stops12h 31m

George Town Owen Roberts Intl

Thu 3/19

3:15 pm-10:18 am

2 stops19h 03m

$552

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 4/20

5:50 pm-11:24 am

2 stops17h 34m

George Town Owen Roberts Intl

Wed 4/22

12:45 pm-10:35 pm

1 stop9h 50m

$553

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.

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

Direct flights

None
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 $537Free CancellationRating
7.2
11,051 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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