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Cheap flights from Wisconsin to Grand Cayman from $137

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 6/12. 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 Wisconsin to Grand Cayman

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
6:22 pm - 11:25 am
ORD
-
GCM
17h 03m
2 stops
Air Canada Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
$383Air Canada
Sun, Jun 7 - Thu, Jun 11
Air Canada Logo
3:40 pm - 11:25 am
ORD
-
GCM
43h 45m
2 stops
Air Canada Logo
12:25 pm - 2:55 pm
GCM
-
ORD
26h 30m
1 stop
$386Air Canada
Sat, Jun 6 - Thu, Jun 11
Air Canada Logo
8:35 pm - 10:00 am
ORD
-
GCM
13h 25m
1 stop
Air Canada Logo
12:25 pm - 7:45 am
GCM
-
ORD
19h 20m
2 stops
$408Air Canada
Fri, May 29 - Thu, Jun 4
Air Canada Logo
1:05 pm - 11:25 am
MSP
-
GCM
46h 20m
2 stops
Air Canada Logo
10:55 am - 12:10 pm
GCM
-
MSP
25h 15m
1 stop
$416Air Canada
Sat, Jun 6 - Sat, Jun 13
Air Canada Logo
7:00 am - 11:25 am
MSP
-
GCM
28h 25m
1 stop
Air Canada Logo
10:55 am - 12:10 pm
GCM
-
MSP
25h 15m
1 stop
$423Air Canada
Sun, Jun 7 - Sat, Jun 13
Air Canada Logo
3:40 pm - 11:25 am
ORD
-
GCM
43h 45m
2 stops
Air Canada Logo
10:40 am - 9:00 am
GCM
-
ORD
22h 20m
1 stop
$426Air Canada
Tue, Sep 1 - Sat, Sep 5
American Airlines Logo
6:46 pm - 1:10 pm
MKE
-
GCM
18h 24m
2 stops
American Airlines Logo
12:30 pm - 7:49 am
GCM
-
MKE
19h 19m
2 stops
$504American Airlines
Sun, Aug 16 - Fri, Aug 21
American Airlines Logo
8:21 am - 11:30 am
MKE
-
GCM
27h 09m
1 stop
American Airlines Logo
12:30 pm - 7:49 am
GCM
-
MKE
19h 19m
2 stops
$513American Airlines
Sun, Aug 16 - Fri, Aug 21
American Airlines Logo
5:50 pm - 1:10 pm
MKE
-
GCM
19h 20m
2 stops
American Airlines Logo
12:00 pm - 7:49 am
GCM
-
MKE
19h 49m
2 stops
$525American Airlines
Fri, Aug 7 - Thu, Aug 13
Delta Logo
5:34 am - 11:39 am
MKE
-
GCM
6h 05m
1 stop
Delta Logo
1:04 pm - 8:53 pm
GCM
-
MKE
7h 49m
1 stop
$566Delta
Sun, Aug 16 - Fri, Aug 21

United Airlines flights from Wisconsin to Grand Cayman

Our best United Airlines deals on Wisconsin to Grand Cayman flight tickets
United Airlines
Oct 26
MKE8:45 pmMilwaukee-Mitchell
18h 45m
2 stops
GCM3:30 pmGeorge Town Owen Roberts Intl
Oct 30
GCM4:45 pmGeorge Town Owen Roberts Intl
24h 28m
2 stops
MKE5:13 pmMilwaukee-Mitchell
$624
United Airlines
Oct 26
MKE4:00 pmMilwaukee-Mitchell
23h 30m
1 stop
GCM3:30 pmGeorge Town Owen Roberts Intl
Oct 30
GCM4:45 pmGeorge Town Owen Roberts Intl
18h 49m
2 stops
MKE11:34 amMilwaukee-Mitchell
$637
United Airlines
Sep 5
MKE6:00 amMilwaukee-Mitchell
7h 35m
1 stop
GCM1:35 pmGeorge Town Owen Roberts Intl
Sep 12
GCM1:35 pmGeorge Town Owen Roberts Intl
9h 04m
1 stop
MKE10:39 pmMilwaukee-Mitchell
$661

Air Canada flights from Wisconsin to Grand Cayman

Our best Air Canada deals on Wisconsin to Grand Cayman flight tickets
Air Canada
Jun 7
ORD6:22 pmChicago O'Hare Intl
17h 03m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
Jun 11
GCM12:25 pmGeorge Town Owen Roberts Intl
20h 35m
1 stop
ORD9:00 amChicago O'Hare Intl
$383
Air Canada
Jun 6
ORD3:40 pmChicago O'Hare Intl
43h 45m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
Jun 11
GCM12:25 pmGeorge Town Owen Roberts Intl
26h 30m
1 stop
ORD2:55 pmChicago O'Hare Intl
$386
Air Canada
May 29
ORD8:35 pmChicago O'Hare Intl
13h 25m
1 stop
GCM10:00 amGeorge Town Owen Roberts Intl
Jun 4
GCM12:25 pmGeorge Town Owen Roberts Intl
19h 20m
2 stops
ORD7:45 amChicago O'Hare Intl
$408

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 May 19, 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 - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/7

6:22 pm-11:25 am

2 stops17h 03m

George Town Owen Roberts Intl

Thu 6/11

12:25 pm-9:00 am

1 stop20h 35m

$383

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 6/6

3:40 pm-11:25 am

2 stops43h 45m

George Town Owen Roberts Intl

Thu 6/11

12:25 pm-2:55 pm

1 stop26h 30m

$386

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 5/29

8:35 pm-10:00 am

1 stop13h 25m

George Town Owen Roberts Intl

Thu 6/4

12:25 pm-7:45 am

2 stops19h 20m

$408

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sat 6/6

1:05 pm-11:25 am

2 stops46h 20m

George Town Owen Roberts Intl

Sat 6/13

10:55 am-12:10 pm

1 stop25h 15m

$416

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sun 6/7

7:00 am-11:25 am

1 stop28h 25m

George Town Owen Roberts Intl

Sat 6/13

10:55 am-12:10 pm

1 stop25h 15m

$423

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 9/1

3:40 pm-11:25 am

2 stops43h 45m

George Town Owen Roberts Intl

Sat 9/5

10:40 am-9:00 am

1 stop22h 20m

$426

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 8/16

6:46 pm-1:10 pm

2 stops18h 24m

George Town Owen Roberts Intl

Fri 8/21

12:30 pm-7:49 am

2 stops19h 19m

$504

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 8/16

8:21 am-11:30 am

1 stop27h 09m

George Town Owen Roberts Intl

Fri 8/21

12:30 pm-7:49 am

2 stops19h 19m

$513

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Fri 8/7

5:50 pm-1:10 pm

2 stops19h 20m

George Town Owen Roberts Intl

Thu 8/13

12:00 pm-7:49 am

2 stops19h 49m

$525
Quickest round-trip

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 8/16

5:34 am-11:39 am

1 stop6h 05m

George Town Owen Roberts Intl

Fri 8/21

1:04 pm-8:53 pm

1 stop7h 49m

$566

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 March. Flight prices, which tend to average around $359, are often lower during this time because this is during the off-season. If you don’t want to visit Grand Cayman in March, then you should wait until February to fly from Wisconsin, when ticket prices are also cheap, with an average price of $390.

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

4h 00m

Direct flights

Sun

Airports in Grand Cayman

1 airport
The fastest flight from Wisconsin to Grand Cayman takes 4h 00m
Direct flights go from Wisconsin to Grand Cayman on Sunday. There are no airlines offering direct flights.
There is 1 airport in Grand Cayman. From Wisconsin there are direct flights to George Town Owen Roberts Intl (GCM).
Search flight deals

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
9,733 reviews
Search United Airlines flights
DeltaPriceFrom $406Free CancellationRating
7.9
8,452 reviews
Search Delta flights
American AirlinesPriceFrom $470Free CancellationRating
7.1
11,645 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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