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Cheap flights from Wisconsin to Grand Cayman from $164

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 11/16. 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

Spirit Airlines Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Spirit Airlines Logo
11:55 am - 11:42 pmGCM-ORD
12h 47m1 stop
$377Spirit Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
Spirit Airlines Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Spirit Airlines Logo
11:55 am - 11:42 pmGCM-ORD
12h 47m1 stop
$379Spirit Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
Delta Logo
5:45 am - 12:35 pmMKE-GCM
5h 50m1 stop
Delta Logo
2:00 pm - 11:27 pmGCM-MKE
10h 27m1 stop
$396Delta
Find Deal
Tue, Jan 20 - Tue, Jan 27
Air Canada Logo
12:00 pm - 11:55 amORD-GCM
23h 55m1 stop
Air Canada Logo
12:50 pm - 10:53 amGCM-ORD
22h 03m1 stop
$413Air Canada
Find Deal
Sun, Sep 14 - Mon, Sep 22
Air Canada Logo
8:25 pm - 11:55 amORD-GCM
15h 30m1 stop
Air Canada Logo
12:50 pm - 9:51 amGCM-ORD
21h 01m2 stops
$441Air Canada
Find Deal
Sun, Sep 14 - Mon, Sep 22
Logo
10:27 am - 11:40 amORD-GCM
25h 13m1 stop
Logo
4:45 pm - 9:18 amGCM-ORD
16h 33m1 stop
$451
Find Deal
Wed, Sep 10 - Fri, Sep 12
Logo
10:27 am - 9:20 pmORD-GCM
10h 53m1 stop
Logo
4:45 pm - 9:22 amGCM-ORD
16h 37m1 stop
$467
Find Deal
Thu, Oct 2 - Thu, Oct 9
Southwest Logo
6:05 am - 12:55 pmORD-GCM
5h 50m1 stop
Southwest Logo
1:50 pm - 9:50 pmGCM-ORD
9h 00m1 stop
$476Southwest
Find Deal
Mon, Jan 26 - Fri, Jan 30
Southwest Logo
6:45 pm - 12:35 pmMSP-GCM
16h 50m2 stops
Southwest Logo
1:30 pm - 11:20 pmGCM-MSP
10h 50m2 stops
$503Southwest
Find Deal
Mon, Dec 8 - Fri, Dec 12
Delta Logo
5:40 am - 12:30 pmORD-GCM
5h 50m1 stop
Delta Logo
3:45 pm - 11:58 pmGCM-ORD
9h 13m1 stop
$520Delta
Find Deal
Wed, Dec 24 - Wed, Dec 31

Sun Country Air flights from Wisconsin to Grand Cayman

Our best Sun Country Air deals on Wisconsin to Grand Cayman flight tickets
Sun Country Air
Jan 10
MSP1:24 pmMinneapolis St Paul
4h 15m
GCM6:39 pmGeorge Town Owen Roberts Intl
Jan 17
GCM7:40 pmGeorge Town Owen Roberts Intl
4h 38m
MSP11:18 pmMinneapolis St Paul
$497
Find similar
Sun Country Air
Feb 14
MSP1:24 pmMinneapolis St Paul
4h 15m
GCM6:39 pmGeorge Town Owen Roberts Intl
Feb 21
GCM7:41 pmGeorge Town Owen Roberts Intl
4h 43m
MSP11:24 pmMinneapolis St Paul
$516
Find similar
Sun Country Air
Dec 20
MSP1:36 pmMinneapolis St Paul
4h 20m
GCM6:56 pmGeorge Town Owen Roberts Intl
Dec 27
GCM8:00 pmGeorge Town Owen Roberts Intl
4h 45m
MSP11:45 pmMinneapolis St Paul
$557
Find similar

Southwest flights from Wisconsin to Grand Cayman

Our best Southwest deals on Wisconsin to Grand Cayman flight tickets
Southwest
Jan 26
ORD6:05 amChicago O'Hare Intl
5h 50m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Jan 30
GCM1:50 pmGeorge Town Owen Roberts Intl
9h 00m
1 stop
ORD9:50 pmChicago O'Hare Intl
$476
Find similar
Southwest
Dec 8
MSP6:45 pmMinneapolis St Paul
16h 50m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
Dec 12
GCM1:30 pmGeorge Town Owen Roberts Intl
10h 50m
2 stops
MSP11:20 pmMinneapolis St Paul
$503
Find similar
Southwest
Dec 6
MSP4:35 pmMinneapolis St Paul
19h 00m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
Dec 15
GCM1:30 pmGeorge Town Owen Roberts Intl
9h 15m
2 stops
MSP9:45 pmMinneapolis St Paul
$542
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 August 18, 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 1/24

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 1/31

11:55 am-11:42 pm

1 stop12h 47m

$377

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 1/31

11:55 am-11:42 pm

1 stop12h 47m

$379

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Tue 1/20

5:45 am-12:35 pm

1 stop5h 50m

George Town Owen Roberts Intl

Tue 1/27

2:00 pm-11:27 pm

1 stop10h 27m

$396

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 9/14

12:00 pm-11:55 am

1 stop23h 55m

George Town Owen Roberts Intl

Mon 9/22

12:50 pm-10:53 am

1 stop22h 03m

$413

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 9/14

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Mon 9/22

12:50 pm-9:51 am

2 stops21h 01m

$441

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 9/10

10:27 am-11:40 am

1 stop25h 13m

George Town Owen Roberts Intl

Fri 9/12

4:45 pm-9:18 am

1 stop16h 33m

$451

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 10/2

10:27 am-9:20 pm

1 stop10h 53m

George Town Owen Roberts Intl

Thu 10/9

4:45 pm-9:22 am

1 stop16h 37m

$467

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/26

6:05 am-12:55 pm

1 stop5h 50m

George Town Owen Roberts Intl

Fri 1/30

1:50 pm-9:50 pm

1 stop9h 00m

$476

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Mon 12/8

6:45 pm-12:35 pm

2 stops16h 50m

George Town Owen Roberts Intl

Fri 12/12

1:30 pm-11:20 pm

2 stops10h 50m

$503

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

5:40 am-12:30 pm

1 stop5h 50m

George Town Owen Roberts Intl

Wed 12/31

3:45 pm-11:58 pm

1 stop9h 13m

$520

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.

How far in advance should I book a flight to Grand Cayman?

You are more likely to see cheaper flights to Grand Cayman from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Grand Cayman for around $612 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Grand Cayman from Wisconsin for as low as $529 on momondo.

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

Best Price Found

$164

Fastest flight time

3h 46m

Direct flights

Mon, Tue, Sat and Sun

Airports in Grand Cayman

1 airport
The best one-way flight to Grand Cayman from Wisconsin in the past 72 hours is $164. The best round-trip flight deal from Wisconsin to Grand Cayman found on momondo in the last 72 hours is $377.
The fastest flight from Wisconsin to Grand Cayman takes 3h 46m
Direct flights go from Wisconsin to Grand Cayman on Monday, Tuesday, Saturday and Sunday. Airlines offering direct flights are: United Airlines, Delta and American Airlines.
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
United AirlinesPriceFrom $273Free CancellationRating
7.4
8,925 reviews
Search United Airlines flights
DeltaPriceFrom $310Free CancellationRating
8.0
7,981 reviews
Search Delta flights
American AirlinesPriceFrom $497Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $526Free CancellationRating
8.0
4,246 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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Find better results for your trip to Grand Cayman

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