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Cheap flights from Wisconsin to Grand Cayman from $97

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 12/6. 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
7:10 am - 4:55 pmORD-GCM
8h 45m1 stop
Spirit Airlines Logo
5:56 pm - 12:09 amGCM-ORD
7h 13m1 stop
$272Spirit Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 13
Spirit Airlines Logo
7:10 am - 4:55 pmORD-GCM
8h 45m1 stop
Spirit Airlines Logo
2:40 pm - 8:01 pmGCM-ORD
6h 21m1 stop
$286Spirit Airlines
Find Deal
Sat, Dec 6 - Thu, Dec 11
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$338United Airlines
Find Deal
Sat, Nov 29 - Sat, Dec 6
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$342United Airlines
Find Deal
Sat, Jan 24 - Fri, Jan 30
American Airlines Logo
7:11 am - 2:28 pmORD-GCM
6h 17m1 stop
American Airlines Logo
1:01 pm - 8:26 pmGCM-ORD
8h 25m1 stop
$344American Airlines
Find Deal
Sat, Nov 29 - Sat, Dec 6
Multiple Airlines Logo
5:32 pm - 1:39 pmORD-GCM
19h 07m1 stop
Multiple Airlines Logo
2:34 pm - 11:35 pmGCM-ORD
10h 01m2 stops
$345Multiple Airlines
Find Deal
Wed, Jan 21 - Sun, Feb 1
American Airlines Logo
5:00 am - 12:00 pmORD-GCM
6h 00m1 stop
American Airlines Logo
3:35 pm - 6:45 pmGCM-ORD
4h 10mnonstop
$347American Airlines
Find Deal
Sun, Dec 14 - Sun, Dec 21
Delta Logo
8:02 pm - 12:35 pmORD-GCM
15h 33m1 stop
Delta Logo
1:50 pm - 8:04 amGCM-ORD
19h 14m2 stops
$357Delta
Find Deal
Wed, Nov 26 - Wed, Dec 3
Delta Logo
7:59 pm - 10:57 amORD-GCM
13h 58m1 stop
Delta Logo
2:05 pm - 9:40 amGCM-ORD
20h 35m2 stops
$361Delta
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Fri, Jan 23 - Mon, Jan 26
Multiple Airlines Logo
5:15 am - 1:39 pmORD-GCM
7h 24m1 stop
Multiple Airlines Logo
2:34 pm - 11:35 pmGCM-ORD
10h 01m2 stops
$364Multiple Airlines
Find Deal
Sat, Jan 24 - Sun, Feb 1

Southwest flights from Wisconsin to Grand Cayman

Our best Southwest deals on Wisconsin to Grand Cayman flight tickets
Southwest
Jan 31
MSP4:40 pmMinneapolis St Paul
19h 15m
2 stops
GCM12:55 pmGeorge Town Owen Roberts Intl
Feb 3
GCM1:50 pmGeorge Town Owen Roberts Intl
9h 00m
2 stops
MSP9:50 pmMinneapolis St Paul
$526
Find similar
Southwest
Feb 6
MSP6:20 pmMinneapolis St Paul
17h 10m
2 stops
GCM12:30 pmGeorge Town Owen Roberts Intl
Feb 11
GCM1:50 pmGeorge Town Owen Roberts Intl
9h 00m
2 stops
MSP9:50 pmMinneapolis St Paul
$561
Find similar
Southwest
Nov 14
MSP4:30 pmMinneapolis St Paul
19h 30m
2 stops
GCM1:00 pmGeorge Town Owen Roberts Intl
Dec 4
GCM1:30 pmGeorge Town Owen Roberts Intl
9h 15m
2 stops
MSP9:45 pmMinneapolis St Paul
$650
Find similar

United Airlines flights from Wisconsin to Grand Cayman

Our best United Airlines deals on Wisconsin to Grand Cayman flight tickets
United Airlines
Nov 29
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
Dec 6
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
$338
Find similar
United Airlines
Jan 24
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
Jan 30
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
$342
Find similar
United Airlines
Jan 24
ORD5:37 amChicago O'Hare Intl
9h 43m
1 stop
GCM4:20 pmGeorge Town Owen Roberts Intl
Jan 29
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
$346
Find similar

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 November 6, 2025.
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 12/6

7:10 am-4:55 pm

1 stop8h 45m

George Town Owen Roberts Intl

Sat 12/13

5:56 pm-12:09 am

1 stop7h 13m

$272

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/6

7:10 am-4:55 pm

1 stop8h 45m

George Town Owen Roberts Intl

Thu 12/11

2:40 pm-8:01 pm

1 stop6h 21m

$286

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/29

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 12/6

2:50 pm-6:04 pm

Nonstop4h 14m

$338

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 1/30

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/29

7:11 am-2:28 pm

1 stop6h 17m

George Town Owen Roberts Intl

Sat 12/6

1:01 pm-8:26 pm

1 stop8h 25m

$344

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/21

5:32 pm-1:39 pm

1 stop19h 07m

George Town Owen Roberts Intl

Sun 2/1

2:34 pm-11:35 pm

2 stops10h 01m

$345

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

5:00 am-12:00 pm

1 stop6h 00m

George Town Owen Roberts Intl

Sun 12/21

3:35 pm-6:45 pm

Nonstop4h 10m

$347

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 11/26

8:02 pm-12:35 pm

1 stop15h 33m

George Town Owen Roberts Intl

Wed 12/3

1:50 pm-8:04 am

2 stops19h 14m

$357

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 1/23

7:59 pm-10:57 am

1 stop13h 58m

George Town Owen Roberts Intl

Mon 1/26

2:05 pm-9:40 am

2 stops20h 35m

$361

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

5:15 am-1:39 pm

1 stop7h 24m

George Town Owen Roberts Intl

Sun 2/1

2:34 pm-11:35 pm

2 stops10h 01m

$364

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.

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

The cheapest day to depart from Wisconsin to Grand Cayman is on a Tuesday when prices can be found for as low as $526. On the other hand, Sunday is the most expensive day to depart from Wisconsin because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $742.

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 Wisconsin to Grand Cayman during this time can be as low as $558. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $612 on average. Flights to Grand Cayman from Wisconsin in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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 near Grand Cayman: 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
8,001 reviews
Search Delta flights
United AirlinesPriceFrom $273Free CancellationRating
7.4
9,007 reviews
Search United Airlines flights
American AirlinesPriceFrom $513Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
SouthwestPriceFrom $526Free CancellationRating
8.0
4,241 reviews
Search Southwest 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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