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Cheap flights from Wisconsin to Grand Cayman from $71

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 3/1. 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.
Spirit Airlines Logo
6:51 pm - 1:43 pm
ORD
-
GCM
17h 52m
2 stops
Spirit Airlines Logo
2:49 pm - 12:40 am
GCM
-
ORD
10h 51m
2 stops
$358Spirit Airlines
Sat, Feb 21 - Thu, Feb 26
Multiple Airlines Logo
4:15 pm - 11:10 am
ORD
-
GCM
18h 55m
1 stop
Multiple Airlines Logo
1:52 pm - 11:17 pm
GCM
-
ORD
9h 25m
1 stop
$362Multiple Airlines
Mon, Apr 6 - Thu, Apr 9
American Airlines Logo
8:22 pm - 1:44 pm
MSN
-
GCM
16h 22m
1 stop
American Airlines Logo
2:35 pm - 9:08 am
GCM
-
MSN
18h 33m
2 stops
$364American Airlines
Sat, Mar 7 - Tue, Mar 10
Multiple Airlines Logo
8:16 pm - 1:43 pm
ORD
-
GCM
16h 27m
1 stop
Multiple Airlines Logo
2:49 pm - 2:30 pm
GCM
-
ORD
24h 41m
2 stops
$364Multiple Airlines
Wed, Feb 25 - Sun, Mar 1
American Airlines Logo
8:22 pm - 1:44 pm
MSN
-
GCM
16h 22m
1 stop
American Airlines Logo
2:44 pm - 9:08 am
GCM
-
MSN
18h 24m
1 stop
$365American Airlines
Sat, Mar 7 - Tue, Mar 10
Spirit Airlines Logo
7:17 am - 12:57 pm
ORD
-
GCM
5h 40m
1 stop
Spirit Airlines Logo
1:52 pm - 10:20 am
GCM
-
ORD
20h 28m
2 stops
$365Spirit Airlines
Sun, Mar 15 - Thu, Mar 19
Delta Logo
5:55 pm - 1:01 pm
MKE
-
GCM
18h 06m
1 stop
Delta Logo
1:54 pm - 11:47 pm
GCM
-
MKE
10h 53m
1 stop
$424Delta
Fri, Feb 27 - Wed, Mar 4
Delta Logo
6:20 am - 2:40 pm
MSN
-
GCM
7h 20m
1 stop
Delta Logo
1:54 pm - 10:24 pm
GCM
-
MSN
9h 30m
1 stop
$424Delta
Fri, Feb 27 - Wed, Mar 4
United Airlines Logo
6:50 am - 12:45 pm
MKE
-
GCM
5h 55m
1 stop
United Airlines Logo
1:50 pm - 10:15 pm
GCM
-
MKE
8h 25m
1 stop
$461United Airlines
Wed, Apr 1 - Wed, Apr 8
Sun Country Air Logo
1:24 pm - 6:40 pm
MSP
-
GCM
4h 16mnonstop
Sun Country Air Logo
7:41 pm - 11:24 pm
GCM
-
MSP
4h 43mnonstop
$499Sun Country Air
Sat, Feb 21 - Sat, Feb 28

Spirit Airlines flights from Wisconsin to Grand Cayman

Our best Spirit Airlines deals on Wisconsin to Grand Cayman flight tickets
Spirit Airlines
Feb 21
ORD6:51 pmChicago O'Hare Intl
17h 52m
2 stops
GCM1:43 pmGeorge Town Owen Roberts Intl
Feb 26
GCM2:49 pmGeorge Town Owen Roberts Intl
10h 51m
2 stops
ORD12:40 amChicago O'Hare Intl
$358
Spirit Airlines
Mar 15
ORD7:17 amChicago O'Hare Intl
5h 40m
1 stop
GCM12:57 pmGeorge Town Owen Roberts Intl
Mar 19
GCM1:52 pmGeorge Town Owen Roberts Intl
20h 28m
2 stops
ORD10:20 amChicago O'Hare Intl
$365
Spirit Airlines
Mar 14
ORD5:05 amChicago O'Hare Intl
7h 15m
1 stop
GCM12:20 pmGeorge Town Owen Roberts Intl
Mar 19
GCM1:52 pmGeorge Town Owen Roberts Intl
9h 25m
1 stop
ORD11:17 pmChicago O'Hare Intl
$382

United Airlines flights from Wisconsin to Grand Cayman

Our best United Airlines deals on Wisconsin to Grand Cayman flight tickets
United Airlines
Apr 1
MKE6:50 amMilwaukee-Mitchell
5h 55m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
Apr 8
GCM1:50 pmGeorge Town Owen Roberts Intl
8h 25m
1 stop
MKE10:15 pmMilwaukee-Mitchell
$461
United Airlines
Mar 12
MSN6:30 amMadison Truax Field
6h 15m
1 stop
GCM12:45 pmGeorge Town Owen Roberts Intl
Mar 22
GCM4:45 pmGeorge Town Owen Roberts Intl
18h 53m
2 stops
MSN11:38 amMadison Truax Field
$507
United Airlines
Feb 9
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
Feb 13
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
$535

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 February 4, 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

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/21

6:51 pm-1:43 pm

2 stops17h 52m

George Town Owen Roberts Intl

Thu 2/26

2:49 pm-12:40 am

2 stops10h 51m

$358

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 4/6

4:15 pm-11:10 am

1 stop18h 55m

George Town Owen Roberts Intl

Thu 4/9

1:52 pm-11:17 pm

1 stop9h 25m

$362

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 3/7

8:22 pm-1:44 pm

1 stop16h 22m

George Town Owen Roberts Intl

Tue 3/10

2:35 pm-9:08 am

2 stops18h 33m

$364

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/25

8:16 pm-1:43 pm

1 stop16h 27m

George Town Owen Roberts Intl

Sun 3/1

2:49 pm-2:30 pm

2 stops24h 41m

$364

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Sat 3/7

8:22 pm-1:44 pm

1 stop16h 22m

George Town Owen Roberts Intl

Tue 3/10

2:44 pm-9:08 am

1 stop18h 24m

$365

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/15

7:17 am-12:57 pm

1 stop5h 40m

George Town Owen Roberts Intl

Thu 3/19

1:52 pm-10:20 am

2 stops20h 28m

$365

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Fri 2/27

5:55 pm-1:01 pm

1 stop18h 06m

George Town Owen Roberts Intl

Wed 3/4

1:54 pm-11:47 pm

1 stop10h 53m

$424

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Fri 2/27

6:20 am-2:40 pm

1 stop7h 20m

George Town Owen Roberts Intl

Wed 3/4

1:54 pm-10:24 pm

1 stop9h 30m

$424

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 4/1

6:50 am-12:45 pm

1 stop5h 55m

George Town Owen Roberts Intl

Wed 4/8

1:50 pm-10:15 pm

1 stop8h 25m

$461

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sat 2/21

1:24 pm-6:40 pm

Nonstop4h 16m

George Town Owen Roberts Intl

Sat 2/28

7:41 pm-11:24 pm

Nonstop4h 43m

$499

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 August. Flight prices, which tend to average around $483, are often lower during this time because this is during the off-season. If you don’t want to visit Grand Cayman in August, then you should wait until May to fly from Wisconsin, when ticket prices are also cheap, with an average price of $535.

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 59m

Direct flights

Every day

Airports in Grand Cayman

1 airport
The fastest flight from Wisconsin to Grand Cayman takes 3h 59m
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).
Search flight deals

  • 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
DeltaPriceFrom $212Free CancellationRating
7.9
8,144 reviews
Search Delta flights
United AirlinesPriceFrom $321Free CancellationRating
7.4
9,236 reviews
Search United Airlines flights
American AirlinesPriceFrom $470Free CancellationRating
7.2
11,222 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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