Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Madison to the Cayman Islands from $419

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 10/24. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Madison to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
6:39 pm - 3:30 pm
MSN
-
GCM
20h 51m
2 stops
United Airlines Logo
1:55 pm - 9:05 pm
GCM
-
MSN
7h 10m
1 stop
$419United Airlines
Sat, Oct 24 - Sat, Oct 31
American Airlines Logo
6:16 am - 2:35 pm
MSN
-
GCM
7h 19m
1 stop
American Airlines Logo
3:25 pm - 12:12 am
GCM
-
MSN
9h 47m
1 stop
$419American Airlines
Fri, Jan 8 - Sat, Jan 16
American Airlines Logo
7:05 pm - 2:45 pm
MSN
-
GCM
18h 40m
2 stops
American Airlines Logo
3:25 pm - 12:12 am
GCM
-
MSN
9h 47m
1 stop
$424American Airlines
Fri, Jan 8 - Sat, Jan 16
American Airlines Logo
7:05 pm - 12:05 pm
MSN
-
GCM
16h 00m
2 stops
American Airlines Logo
1:05 pm - 10:59 pm
GCM
-
MSN
10h 54m
2 stops
$424American Airlines
Sat, Jan 9 - Sat, Jan 23
United Airlines Logo
5:43 pm - 4:30 pm
MSN
-
GCM
21h 47m
2 stops
United Airlines Logo
5:45 pm - 9:50 am
GCM
-
MSN
17h 05m
2 stops
$424United Airlines
Tue, Nov 3 - Sun, Nov 8
United Airlines Logo
7:15 pm - 4:30 pm
MSN
-
GCM
20h 15m
2 stops
United Airlines Logo
5:45 pm - 9:44 am
GCM
-
MSN
16h 59m
2 stops
$424United Airlines
Thu, Dec 10 - Sun, Dec 13
United Airlines Logo
7:00 pm - 4:30 pm
MSN
-
GCM
20h 30m
2 stops
United Airlines Logo
5:45 pm - 11:51 am
GCM
-
MSN
19h 06m
2 stops
$492United Airlines
Mon, Nov 30 - Mon, Dec 7
Delta Logo
5:43 am - 11:39 am
MSN
-
GCM
5h 56m
1 stop
Delta Logo
1:00 pm - 10:41 pm
GCM
-
MSN
9h 41m
1 stop
$499Delta
Sat, Sep 5 - Wed, Sep 9
Delta Logo
5:50 am - 11:40 am
MSN
-
GCM
5h 50m
1 stop
Delta Logo
1:00 pm - 10:41 pm
GCM
-
MSN
9h 41m
1 stop
$499Delta
Sun, Sep 27 - Sun, Oct 4
Delta Logo
5:43 am - 11:39 am
MSN
-
GCM
5h 56m
1 stop
Delta Logo
1:00 pm - 10:41 pm
GCM
-
MSN
9h 41m
1 stop
$575Delta
Sat, Sep 5 - Wed, Sep 9

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Delta flights from Madison to Cayman Islands

Our best Delta deals on Madison to Cayman Islands flight tickets
Delta
Sep 27
MSN5:50 amMadison Truax Field
5h 50m
1 stop
GCM11:40 amGeorge Town Owen Roberts Intl
Oct 4
GCM1:00 pmGeorge Town Owen Roberts Intl
9h 41m
1 stop
MSN10:41 pmMadison Truax Field
$499
Delta
Sep 5
MSN5:43 amMadison Truax Field
5h 56m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
Sep 9
GCM1:00 pmGeorge Town Owen Roberts Intl
9h 41m
1 stop
MSN10:41 pmMadison Truax Field
$575
Delta
Sep 5
MSN5:43 amMadison Truax Field
5h 56m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
Sep 9
GCM1:00 pmGeorge Town Owen Roberts Intl
9h 41m
1 stop
MSN10:41 pmMadison Truax Field
$579

American Airlines flights from Madison to Cayman Islands

Our best American Airlines deals on Madison to Cayman Islands flight tickets
American Airlines
Jan 8
MSN6:16 amMadison Truax Field
7h 19m
1 stop
GCM2:35 pmGeorge Town Owen Roberts Intl
Jan 16
GCM3:25 pmGeorge Town Owen Roberts Intl
9h 47m
1 stop
MSN12:12 amMadison Truax Field
$419
American Airlines
Jan 9
MSN7:05 pmMadison Truax Field
16h 00m
2 stops
GCM12:05 pmGeorge Town Owen Roberts Intl
Jan 23
GCM1:05 pmGeorge Town Owen Roberts Intl
10h 54m
2 stops
MSN10:59 pmMadison Truax Field
$424
American Airlines
Jan 9
MSN12:20 pmMadison Truax Field
25h 15m
1 stop
GCM2:35 pmGeorge Town Owen Roberts Intl
Jan 16
GCM3:25 pmGeorge Town Owen Roberts Intl
9h 47m
1 stop
MSN12:12 amMadison Truax Field
$425

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 July 29, 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

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 10/24

6:39 pm-3:30 pm

2 stops20h 51m

George Town Owen Roberts Intl

Sat 10/31

1:55 pm-9:05 pm

1 stop7h 10m

$419

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 1/8

6:16 am-2:35 pm

1 stop7h 19m

George Town Owen Roberts Intl

Sat 1/16

3:25 pm-12:12 am

1 stop9h 47m

$419

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 1/8

7:05 pm-2:45 pm

2 stops18h 40m

George Town Owen Roberts Intl

Sat 1/16

3:25 pm-12:12 am

1 stop9h 47m

$424

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 1/9

7:05 pm-12:05 pm

2 stops16h 00m

George Town Owen Roberts Intl

Sat 1/23

1:05 pm-10:59 pm

2 stops10h 54m

$424

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 11/3

5:43 pm-4:30 pm

2 stops21h 47m

George Town Owen Roberts Intl

Sun 11/8

5:45 pm-9:50 am

2 stops17h 05m

$424

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 12/10

7:15 pm-4:30 pm

2 stops20h 15m

George Town Owen Roberts Intl

Sun 12/13

5:45 pm-9:44 am

2 stops16h 59m

$424

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 11/30

7:00 pm-4:30 pm

2 stops20h 30m

George Town Owen Roberts Intl

Mon 12/7

5:45 pm-11:51 am

2 stops19h 06m

$492

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 9/5

5:43 am-11:39 am

1 stop5h 56m

George Town Owen Roberts Intl

Wed 9/9

1:00 pm-10:41 pm

1 stop9h 41m

$499
Quickest round-trip

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sun 9/27

5:50 am-11:40 am

1 stop5h 50m

George Town Owen Roberts Intl

Sun 10/4

1:00 pm-10:41 pm

1 stop9h 41m

$499

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 9/5

5:43 am-11:39 am

1 stop5h 56m

George Town Owen Roberts Intl

Wed 9/9

1:00 pm-10:41 pm

1 stop9h 41m

$575

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 15% 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 50m

Direct flights

None
The fastest flight from Madison to Cayman Islands takes 5h 50m
There are no direct flights from Madison to Cayman Islands. There are no popular flight routes from Madison to Cayman Islands.
Search flight deals

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
10,052 reviews
Search United Airlines flights
American AirlinesPriceFrom $470Free CancellationRating
7.1
11,839 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.

An easier way to manage your Cayman Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 8/28
Fri 9/4
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Cayman Islands

Popular cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to George Townfrom $267
Flights to Cayman Bracfrom $343
Flights to Little Caymanfrom $359