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Cheap flights from Wisconsin to Grand Cayman from $126

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Grand Cayman departing on 9/9. 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 Wisconsin to Grand Cayman

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
5:35 pm - 9:45 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 10m1 stop Toronto Pearson Intl
Air Canada Logo
12:25 pm - 2:50 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
26h 25m1 stop Toronto Pearson Intl
$329Air Canada
Fri, Sep 11 - Thu, Sep 17
Air Canada Logo
5:35 pm - 9:45 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 10m1 stop Toronto Pearson Intl
Air Canada Logo
12:25 pm - 2:50 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
26h 25m1 stop Toronto Pearson Intl
$335Air Canada
Fri, Sep 11 - Thu, Sep 17
American Airlines Logo
2:48 pm - 11:27 amMKE  Milwaukee-Mitchell-GCM George Town Owen Roberts Intl
20h 39m2 stops Chicago O'Hare Intl Charlotte Douglas
American Airlines Logo
12:36 pm - 7:33 pmGCM  George Town Owen Roberts Intl-MKE Milwaukee-Mitchell
6h 57m1 stop Charlotte Douglas
$402American Airlines
Thu, Sep 24 - Thu, Oct 1
American Airlines Logo
5:53 pm - 11:00 amMKE  Milwaukee-Mitchell-GCM George Town Owen Roberts Intl
17h 07m2 stops Charlotte Douglas Miami
American Airlines Logo
11:55 am - 8:01 amGCM  George Town Owen Roberts Intl-MKE Milwaukee-Mitchell
20h 06m2 stops Miami Chicago O'Hare Intl
$402American Airlines
Sat, Sep 26 - Sat, Oct 3
United Airlines Logo
6:00 am - 4:30 pmMKE  Milwaukee-Mitchell-GCM George Town Owen Roberts Intl
9h 30m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
United Airlines Logo
2:50 pm - 8:56 pmGCM  George Town Owen Roberts Intl-MKE Milwaukee-Mitchell
7h 06m1 stop Chicago O'Hare Intl
$489United Airlines
Tue, Dec 15 - Sun, Dec 20
United Airlines Logo
6:00 am - 4:30 pmMKE  Milwaukee-Mitchell-GCM George Town Owen Roberts Intl
9h 30m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
United Airlines Logo
5:45 pm - 9:52 amGCM  George Town Owen Roberts Intl-MKE Milwaukee-Mitchell
17h 07m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
$489United Airlines
Tue, Dec 15 - Sun, Dec 20
Sun Country Air Logo
1:25 pm - 6:45 pmMSP  Minneapolis St Paul-GCM George Town Owen Roberts Intl
4h 20mnonstop
Sun Country Air Logo
7:45 pm - 11:23 pmGCM  George Town Owen Roberts Intl-MSP Minneapolis St Paul
4h 38mnonstop
$499Sun Country Air
Sat, Dec 19 - Sat, Dec 26
Sun Country Air Logo
1:25 pm - 6:44 pmMSP  Minneapolis St Paul-GCM George Town Owen Roberts Intl
4h 19mnonstop
Sun Country Air Logo
7:45 pm - 11:23 pmGCM  George Town Owen Roberts Intl-MSP Minneapolis St Paul
4h 38mnonstop
$499Sun Country Air
Sat, Jan 30 - Sat, Feb 6
Delta Logo
5:17 pm - 12:50 pmMSN  Madison Truax Field-GCM George Town Owen Roberts Intl
18h 33m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl
Delta Logo
2:05 pm - 8:50 amGCM  George Town Owen Roberts Intl-MSN Madison Truax Field
19h 45m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$584Delta
Fri, Jan 22 - Thu, Jan 28
Delta Logo
5:50 pm - 12:40 pmMSN  Madison Truax Field-GCM George Town Owen Roberts Intl
17h 50m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
2:05 pm - 8:50 amGCM  George Town Owen Roberts Intl-MSN Madison Truax Field
19h 45m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$584Delta
Sat, Jan 23 - Thu, Jan 28

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Air Canada flights from Wisconsin to Grand Cayman

Our best Air Canada deals on Wisconsin to Grand Cayman flight tickets
Air Canada
Sep 11
ORD5:35 pmChicago O'Hare Intl
16h 10m
1 stop
GCM9:45 amGeorge Town Owen Roberts Intl
Sep 17
GCM12:25 pmGeorge Town Owen Roberts Intl
26h 25m
1 stop
ORD2:50 pmChicago O'Hare Intl
$329
Air Canada
Sep 11
ORD5:35 pmChicago O'Hare Intl
16h 10m
1 stop
GCM9:45 amGeorge Town Owen Roberts Intl
Sep 17
GCM12:25 pmGeorge Town Owen Roberts Intl
26h 25m
1 stop
ORD2:50 pmChicago O'Hare Intl
$335
Air Canada
Oct 16
ORD3:45 pmChicago O'Hare Intl
19h 45m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
Oct 25
GCM12:10 pmGeorge Town Owen Roberts Intl
8h 03m
1 stop
ORD8:13 pmChicago O'Hare Intl
$346

American Airlines flights from Wisconsin to Grand Cayman

Our best American Airlines deals on Wisconsin to Grand Cayman flight tickets
American Airlines
Sep 24
MKE5:11 pmMilwaukee-Mitchell
18h 16m
2 stops
GCM11:27 amGeorge Town Owen Roberts Intl
Oct 1
GCM12:36 pmGeorge Town Owen Roberts Intl
19h 25m
2 stops
MKE8:01 amMilwaukee-Mitchell
$402
American Airlines
Sep 24
MKE2:02 pmMilwaukee-Mitchell
21h 25m
1 stop
GCM11:27 amGeorge Town Owen Roberts Intl
Oct 1
GCM12:36 pmGeorge Town Owen Roberts Intl
6h 57m
1 stop
MKE7:33 pmMilwaukee-Mitchell
$405
American Airlines
Jan 8
MSN6:16 amMadison Truax Field
7h 19m
1 stop
GCM2:35 pmGeorge Town Owen Roberts Intl
Jan 23
GCM4:40 pmGeorge Town Owen Roberts Intl
20h 27m
1 stop
MSN12:07 pmMadison Truax Field
$406

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 August 13, 2026.
Use the filters below to find and compare flights from Wisconsin to Grand Cayman that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Fri 9/11

5:35 pm-9:45 am

1 stop16h 10m

George Town Owen Roberts Intl

Thu 9/17

12:25 pm-2:50 pm

1 stop26h 25m

$329

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Fri 9/11

5:35 pm-9:45 am

1 stop16h 10m

George Town Owen Roberts Intl

Thu 9/17

12:25 pm-2:50 pm

1 stop26h 25m

$335

MilwaukeeGeorge Town

MKE Milwaukee-Mitchell - GCM George Town Owen Roberts Intl

MKEGCM

Milwaukee-Mitchell

Thu 9/24

2:48 pm-11:27 am

2 stops20h 39m

George Town Owen Roberts Intl

Thu 10/1

12:36 pm-7:33 pm

1 stop6h 57m

$402

MilwaukeeGeorge Town

MKE Milwaukee-Mitchell - GCM George Town Owen Roberts Intl

MKEGCM

Milwaukee-Mitchell

Sat 9/26

5:53 pm-11:00 am

2 stops17h 07m

George Town Owen Roberts Intl

Sat 10/3

11:55 am-8:01 am

2 stops20h 06m

$402

MilwaukeeGeorge Town

MKE Milwaukee-Mitchell - GCM George Town Owen Roberts Intl

MKEGCM

Milwaukee-Mitchell

Tue 12/15

6:00 am-4:30 pm

2 stops9h 30m

George Town Owen Roberts Intl

Sun 12/20

2:50 pm-8:56 pm

1 stop7h 06m

$489

MilwaukeeGeorge Town

MKE Milwaukee-Mitchell - GCM George Town Owen Roberts Intl

MKEGCM

Milwaukee-Mitchell

Tue 12/15

6:00 am-4:30 pm

2 stops9h 30m

George Town Owen Roberts Intl

Sun 12/20

5:45 pm-9:52 am

2 stops17h 07m

$489

MinneapolisGeorge Town

MSP Minneapolis St Paul - GCM George Town Owen Roberts Intl

MSPGCM

Minneapolis St Paul

Sat 12/19

1:25 pm-6:45 pm

Nonstop4h 20m

George Town Owen Roberts Intl

Sat 12/26

7:45 pm-11:23 pm

Nonstop4h 38m

$499
Quickest round-trip

MinneapolisGeorge Town

MSP Minneapolis St Paul - GCM George Town Owen Roberts Intl

MSPGCM

Minneapolis St Paul

Sat 1/30

1:25 pm-6:44 pm

Nonstop4h 19m

George Town Owen Roberts Intl

Sat 2/6

7:45 pm-11:23 pm

Nonstop4h 38m

$499

MadisonGeorge Town

MSN Madison Truax Field - GCM George Town Owen Roberts Intl

MSNGCM

Madison Truax Field

Fri 1/22

5:17 pm-12:50 pm

2 stops18h 33m

George Town Owen Roberts Intl

Thu 1/28

2:05 pm-8:50 am

2 stops19h 45m

$584

MadisonGeorge Town

MSN Madison Truax Field - GCM George Town Owen Roberts Intl

MSNGCM

Madison Truax Field

Sat 1/23

5:50 pm-12:40 pm

2 stops17h 50m

George Town Owen Roberts Intl

Thu 1/28

2:05 pm-8:50 am

2 stops19h 45m

$584

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Grand Cayman from

How to get the cheapest flight ticket from Wisconsin 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 month to fly to Grand Cayman?

The cheapest month to fly to Grand Cayman from Wisconsin is in September. Flight prices, which tend to average around $531, are often lower during this time because this is during the off-season. If you don’t want to visit Grand Cayman in September, then you should wait until October to fly from Wisconsin, when ticket prices are also cheap, with an average price of $547.

Can stopping save me money on Wisconsin to Grand Cayman flights?

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

Cheap Wisconsin to Grand Cayman flight deals and tips

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

Fastest flight time

3h 46m

Direct flights

Every day

Airports in Grand Cayman

1 airport
The fastest flight from Wisconsin to Grand Cayman takes 3h 46m
Direct flights go from Wisconsin to Grand Cayman every day.
There is 1 airport in Grand Cayman. From Wisconsin there are direct flights to George Town Owen Roberts Intl (GCM).
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Frequently asked questions about flying from Wisconsin to Grand Cayman

  • When did momondo last update prices for flights from Wisconsin to Grand Cayman?

    Prices for flights from Wisconsin to Grand Cayman refresh daily.

  • How many operators does momondo search for flights from Wisconsin to Grand Cayman?

  • How old do you have to be to fly from Wisconsin to Grand Cayman?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Grand Cayman.

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

    The required travel and health documents for your Grand Cayman trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Grand Cayman. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from Wisconsin to Grand Cayman

Compare and see reviews for airlines that fly from Wisconsin to Grand Cayman with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $383Free CancellationRating
7.4
10,111 reviews
Search United Airlines flights
DeltaPriceFrom $406Free CancellationRating
7.8
8,505 reviews
Search Delta flights
American AirlinesPriceFrom $470Free CancellationRating
7.1
11,911 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Grand Cayman?

Finding the right flight to Grand Cayman from Wisconsin is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Grand Cayman quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Grand Cayman from Wisconsin with this policy.

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

momondo provides multiple filters to help you find the best flight to Grand Cayman from Wisconsin. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Wisconsin to Grand Cayman right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Wisconsin to Grand Cayman flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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