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Cheap flights from Madison to Grand Cayman from $222

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 Grand Cayman departing on 1/10. 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 Grand Cayman

Cheap round-trip flights

Delta Logo
5:40 am - 11:36 amMSN-GCM
5h 56m1 stop
Delta Logo
12:52 pm - 10:59 pmGCM-MSN
10h 07m1 stop
$499Delta
Find Deal
vie., sep. 12 - vie., sep. 19
American Airlines Logo
6:24 pm - 11:25 amMSN-GCM
17h 01m2 stops
American Airlines Logo
12:25 pm - 11:10 pmGCM-MSN
10h 45m1 stop
$503American Airlines
Find Deal
vie., sep. 12 - vie., sep. 19
Delta Logo
5:45 am - 12:37 pmMSN-GCM
5h 52m1 stop
Delta Logo
2:02 pm - 10:34 pmGCM-MSN
9h 32m1 stop
$548Delta
Find Deal
jue., dic. 4 - lun., dic. 8
American Airlines Logo
4:15 pm - 11:58 amMSN-GCM
19h 43m2 stops
American Airlines Logo
3:14 pm - 11:51 pmGCM-MSN
9h 37m2 stops
$552American Airlines
Find Deal
sáb., nov. 1 - sáb., nov. 8
American Airlines Logo
4:15 pm - 12:40 pmMSN-GCM
20h 25m1 stop
American Airlines Logo
8:45 am - 11:58 pmGCM-MSN
16h 13m1 stop
$558American Airlines
Find Deal
sáb., nov. 1 - sáb., nov. 8
American Airlines Logo
7:09 am - 4:00 pmMSN-GCM
7h 51m1 stop
American Airlines Logo
6:10 pm - 10:23 amGCM-MSN
17h 13m1 stop
$573American Airlines
Find Deal
mar., dic. 23 - mar., dic. 30
United Airlines Logo
6:30 am - 4:30 pmMSN-GCM
9h 00m2 stops
United Airlines Logo
5:45 pm - 2:01 pmGCM-MSN
21h 16m2 stops
$662United Airlines
Find Deal
jue., dic. 4 - mar., dic. 9
United Airlines Logo
8:15 am - 1:45 pmMSN-GCM
28h 30m1 stop
United Airlines Logo
5:45 pm - 1:51 pmGCM-MSN
21h 06m2 stops
$669United Airlines
Find Deal
vie., dic. 5 - dom., dic. 7
Air Canada Logo
12:19 pm - 12:20 pmMSN-GCM
23h 01m2 stops
Air Canada Logo
1:30 pm - 2:54 pmGCM-MSN
26h 24m2 stops
$1,110Air Canada
Find Deal
mié., dic. 3 - mar., dic. 9
Air Canada Logo
12:19 pm - 12:20 pmMSN-GCM
23h 01m2 stops
Air Canada Logo
1:30 pm - 2:54 pmGCM-MSN
26h 24m2 stops
$1,155Air Canada
Find Deal
jue., dic. 4 - mar., dic. 9

Delta flights from Madison to Grand Cayman

Our best Delta deals on Madison to Grand Cayman flight tickets
Delta
Sep 12
MSN5:40 amMadison Truax Field
5h 56m
1 stop
GCM11:36 amGeorge Town Owen Roberts Intl
Sep 19
GCM12:52 pmGeorge Town Owen Roberts Intl
10h 07m
1 stop
MSN10:59 pmMadison Truax Field
$499
Find similar
Delta
Dec 4
MSN5:45 amMadison Truax Field
5h 52m
1 stop
GCM12:37 pmGeorge Town Owen Roberts Intl
Dec 8
GCM2:02 pmGeorge Town Owen Roberts Intl
9h 32m
1 stop
MSN10:34 pmMadison Truax Field
$548
Find similar
Delta
Dec 3
MSN5:50 pmMadison Truax Field
17h 47m
2 stops
GCM12:37 pmGeorge Town Owen Roberts Intl
Dec 8
GCM2:02 pmGeorge Town Owen Roberts Intl
9h 32m
1 stop
MSN10:34 pmMadison Truax Field
$583
Find similar

American Airlines flights from Madison to Grand Cayman

Our best American Airlines deals on Madison to Grand Cayman flight tickets
American Airlines
Sep 12
MSN6:24 pmMadison Truax Field
17h 01m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
Sep 19
GCM12:25 pmGeorge Town Owen Roberts Intl
10h 45m
1 stop
MSN11:10 pmMadison Truax Field
$503
Find similar
American Airlines
Nov 1
MSN4:15 pmMadison Truax Field
19h 43m
2 stops
GCM11:58 amGeorge Town Owen Roberts Intl
Nov 8
GCM3:14 pmGeorge Town Owen Roberts Intl
9h 37m
2 stops
MSN11:51 pmMadison Truax Field
$552
Find similar
American Airlines
Nov 1
MSN4:15 pmMadison Truax Field
20h 25m
1 stop
GCM12:40 pmGeorge Town Owen Roberts Intl
Nov 8
GCM8:45 amGeorge Town Owen Roberts Intl
16h 13m
1 stop
MSN11:58 pmMadison Truax Field
$558
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Grand Cayman 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 julio 31, 2025.
Use the filters below to find and compare flights from Madison to Grand Cayman that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

vie. 9/12

5:40 am-11:36 am

1 stop5h 56m

George Town Owen Roberts Intl

vie. 9/19

12:52 pm-10:59 pm

1 stop10h 07m

$499

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

vie. 9/12

6:24 pm-11:25 am

2 stops17h 01m

George Town Owen Roberts Intl

vie. 9/19

12:25 pm-11:10 pm

1 stop10h 45m

$503

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

jue. 12/4

5:45 am-12:37 pm

1 stop5h 52m

George Town Owen Roberts Intl

lun. 12/8

2:02 pm-10:34 pm

1 stop9h 32m

$548

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

sáb. 11/1

4:15 pm-11:58 am

2 stops19h 43m

George Town Owen Roberts Intl

sáb. 11/8

3:14 pm-11:51 pm

2 stops9h 37m

$552

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

sáb. 11/1

4:15 pm-12:40 pm

1 stop20h 25m

George Town Owen Roberts Intl

sáb. 11/8

8:45 am-11:58 pm

1 stop16h 13m

$558

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

mar. 12/23

7:09 am-4:00 pm

1 stop7h 51m

George Town Owen Roberts Intl

mar. 12/30

6:10 pm-10:23 am

1 stop17h 13m

$573

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

jue. 12/4

6:30 am-4:30 pm

2 stops9h 00m

George Town Owen Roberts Intl

mar. 12/9

5:45 pm-2:01 pm

2 stops21h 16m

$662

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

vie. 12/5

8:15 am-1:45 pm

1 stop28h 30m

George Town Owen Roberts Intl

dom. 12/7

5:45 pm-1:51 pm

2 stops21h 06m

$669

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

mié. 12/3

12:19 pm-12:20 pm

2 stops23h 01m

George Town Owen Roberts Intl

mar. 12/9

1:30 pm-2:54 pm

2 stops26h 24m

$1,110

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

jue. 12/4

12:19 pm-12:20 pm

2 stops23h 01m

George Town Owen Roberts Intl

mar. 12/9

1:30 pm-2:54 pm

2 stops26h 24m

$1,155

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 Grand Cayman from

How to get the cheapest flight ticket from Madison to Grand Cayman

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 Grand Cayman?

The cheapest day to depart from Madison to Grand Cayman is on a Monday when prices can be found for as low as $577. On the other hand, Sunday is the most expensive day to depart from Madison because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $655.

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

Our most recent data shows that the best time of day to fly to Grand Cayman is in the afternoon. Flights from Madison to Grand Cayman during this time can be as low as $580. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $637 on average. Flights to Grand Cayman 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 Grand Cayman flights?

No. A direct flight is the cheapest option for a flight between Madison to Grand Cayman.

Cheap Madison to Grand Cayman flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Grand Cayman

Best Price Found

$222

Fastest flight time

5h 52m

Direct flights

None

Airports in Grand Cayman

1 airport
The best one-way flight to Grand Cayman from Madison in the past 72 hours is $222. The best round-trip flight deal from Madison to Grand Cayman found on momondo in the last 72 hours is $499.
The fastest flight from Madison to Grand Cayman takes 5h 52m
There are no direct flights from Madison to Grand Cayman. Popular non-direct route for this connection is Madison Truax Field Airport - George Town Owen Roberts Intl Airport.
There is 1 airport near Grand Cayman: George Town Owen Roberts Intl (GCM)
Search flight deals

  • When did momondo last update prices for flights from Madison Truax Field Airport to Grand Cayman?

    Prices for flights from Madison Truax Field Airport to Grand Cayman are updated daily.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Grand Cayman?

  • How old do you have to be to fly from Madison Truax Field Airport to Grand Cayman?

    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 Grand Cayman.

  • What documentation or ID do you need to fly to Grand Cayman?

    The travel and health documents you'll need for your trip to Grand Cayman 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 Grand Cayman. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Madison to Grand Cayman?

Best airlines flying from Madison to Grand Cayman

Compare and see reviews for airlines that fly from Madison to Grand Cayman with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $513Free CancellationRating
8.0
7,981 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 Grand Cayman?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Madison to Grand Cayman. momondo saves you time and could save you money on your trip.

Can I find flights from Madison to Grand Cayman with flexible booking policies on momondo?

Yes. All flights to Grand Cayman from Madison on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Madison to Grand Cayman?

momondo helps you find the best flight between Madison and Grand Cayman 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 Grand Cayman right now. Can momondo alert me if prices change?

Price alerts on flights to Grand Cayman from Madison are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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