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Grand Cayman

$181+ Cheap flights from Wisconsin to Grand Cayman

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Apr 30 — May 71
Wed 4/30
Wed 5/7
1 adult, Economy
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Cheap flight deals from Wisconsin to Grand Cayman

Keep the following information in mind while searching for Wisconsin to Grand Cayman flight deals. Data was last updated April 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$465
(Kiwi.com)

One-way from

$181
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$548
Provider with most accurate pricing for Milwaukee-Mitchell-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-George Town Owen Roberts Intl flights.
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From Wisconsin to Grand Cayman
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One-way flight from Wisconsin to Grand Cayman
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Wisconsin to Grand Cayman

Cheapest flights from Wisconsin to Grand Cayman
Explore the most affordable flight options available from Wisconsin to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/183:11 pmORD - GCM
1 stop20h 29mMultiple Airlines
Sat 10/258:50 amGCM - ORD
1 stop13h 57mMultiple Airlines
Deal found 4/24$465
This Air Canada deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
Thu 6/512:50 pmGCM - ORD
1 stop19h 09mAir Canada
Deal found 4/25$491
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:20 amMKE - GCM
1 stop5h 45mAmerican Airlines
Sat 10/113:20 pmGCM - MKE
1 stop7h 43mAmerican Airlines
Deal found 4/25$538
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:29 pmMSN - GCM
2 stops18h 17mAmerican Airlines
Mon 12/82:15 pmGCM - MSN
2 stops21h 06mAmerican Airlines
Deal found 4/25$542
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/295:35 amMKE - GCM
1 stop5h 50mDelta
Wed 7/212:40 pmGCM - MKE
1 stop7h 33mDelta
Deal found 4/24$558
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/155:25 pmORD - GCM
2 stops18h 25mSouthwest
Fri 6/2012:45 pmGCM - ORD
2 stops20h 40mSouthwest
Deal found 4/25$586
This Mytrip deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/26:18 amMSP - GCM
3 stops32h 32mMultiple Airlines
Mon 5/57:00 amGCM - MSP
2 stops30h 40mMultiple Airlines
Deal found 4/25$608
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/245:35 amORD - GCM
1 stop5h 50mDelta
Tue 7/812:50 pmGCM - ORD
1 stop8h 31mDelta
Deal found 4/24$610
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/285:00 amORD - GCM
1 stop8h 10mAmerican Airlines
Tue 6/312:10 pmGCM - ORD
2 stops9h 33mAmerican Airlines
Deal found 4/25$614
This deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/176:50 amMKE - GCM
1 stop6h 40mUnited Airlines
Sat 5/241:45 pmGCM - MKE
1 stop8h 40mUnited Airlines
Deal found 4/23$628
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/175:15 amMSP - GCM
1 stop6h 16mDelta
Sun 8/2412:50 pmGCM - MSP
1 stop8h 42mDelta
Deal found 4/25$630
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/277:16 pmMSP - GCM
2 stops15h 44mAmerican Airlines
Tue 9/212:45 pmGCM - MSP
2 stops11h 03mAmerican Airlines
Deal found 4/25$634

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated April 25, 2025.
Use the filters below to find and compare flights from Wisconsin to Grand Cayman that are best for you.

Fly from

Wisconsin

Fly to

Grand Cayman

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 10/18

3:11 pm-11:40 am

1 stop20h 29m

George Town Owen Roberts Intl

Sat 10/25

8:50 am-10:47 pm

1 stop13h 57m

$465

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-9:52 am

2 stops21h 02m

$491

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 10/4

5:20 am-11:05 am

1 stop5h 45m

George Town Owen Roberts Intl

Sat 10/11

3:20 pm-11:03 pm

1 stop7h 43m

$538

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 6/29

5:35 am-11:25 am

1 stop5h 50m

George Town Owen Roberts Intl

Wed 7/2

12:40 pm-8:13 pm

1 stop7h 33m

$558

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/15

5:25 pm-11:50 am

2 stops18h 25m

George Town Owen Roberts Intl

Fri 6/20

12:45 pm-9:25 am

2 stops20h 40m

$586

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 6/16

8:16 pm-11:15 am

2 stops14h 59m

George Town Owen Roberts Intl

Sat 6/28

3:05 pm-9:20 am

2 stops18h 15m

$586

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 6/24

5:35 am-11:25 am

1 stop5h 50m

George Town Owen Roberts Intl

Tue 7/8

12:50 pm-9:21 pm

1 stop8h 31m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/28

5:00 am-1:10 pm

1 stop8h 10m

George Town Owen Roberts Intl

Tue 6/3

12:10 pm-9:43 pm

2 stops9h 33m

$614

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 5/17

6:50 am-1:30 pm

1 stop6h 40m

George Town Owen Roberts Intl

Sat 5/24

1:45 pm-10:25 pm

1 stop8h 40m

$628

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sun 8/17

5:15 am-11:31 am

1 stop6h 16m

George Town Owen Roberts Intl

Sun 8/24

12:50 pm-9:32 pm

1 stop8h 42m

$630

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 28 results
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Best time to book a flight from Wisconsin to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from Wisconsin with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Wisconsin to Grand Cayman

What is the cheapest month to book a flight from Wisconsin to Grand Cayman?

Currently, January is the cheapest month in which you can book a flight from Wisconsin to Grand Cayman (average of $467). Flying from Wisconsin to Grand Cayman in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from WI to LAW?

Find hourly flight availability from Wisconsin to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 25, 2025.

When flying from Wisconsin to Grand Cayman, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Grand Cayman. Reviews last updated April 25, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Wisconsin to Grand Cayman by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Air Canada
7.0
Good
9,210 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Wisconsin to Grand Cayman one-way?

    To fly one-way, consider booking your trip with Air Canada, which is currently one of the cheapest options available, starting at $184. Delta flights start at $288 while deals on American Airlines start at $292 one-way.

  • Can I find deals for flights from Wisconsin to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Grand Cayman.

  • Can I find deals for business class flights from Wisconsin to Grand Cayman?

    Yes. Cheapflights offers flight deals from Wisconsin to Grand Cayman by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Wisconsin to Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Wisconsin to Grand Cayman (average of $467). Flying from Wisconsin to Grand Cayman in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Wisconsin to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Wisconsin to Grand Cayman

Discover the top 4 airlines that operate flights from Wisconsin to Grand Cayman. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$273Average$614FlexibilityNo cancel feeOn-time69%
DeltaCheapest$310Average$653FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$476Average$651FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$668FlexibilityNo cancel feeOn-time63%

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