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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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
May 10 — May 171
Sat 5/10
Sat 5/17
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 May 5, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$442
(Mytrip)

One-way from

$181
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$535
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. 1% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 5, 2025.

This Mytrip deal was found by Cheapflights users on 5/4. 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.
Sat 10/253:11 pmORD - GCM
1 stop20h 29mMultiple Airlines
Sat 11/18:50 amGCM - ORD
1 stop13h 57mMultiple Airlines
Deal found 5/4$442
This Air Canada deal was found by Cheapflights users on 5/4. 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.
Sat 5/316:15 pmORD - GCM
2 stops41h 40mAir Canada
Thu 6/512:50 pmGCM - ORD
1 stop24h 05mAir Canada
Deal found 5/4$513
This American Airlines deal was found by Cheapflights users on 5/4. 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 6/287:24 amMKE - GCM
1 stop6h 36mAmerican Airlines
Wed 7/212:25 pmGCM - MKE
1 stop11h 34mAmerican Airlines
Deal found 5/4$538
This American Airlines deal was found by Cheapflights users on 5/5. 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 12/27:14 amMSN - GCM
1 stop7h 41mAmerican Airlines
Mon 12/82:15 pmGCM - MSN
2 stops21h 06mAmerican Airlines
Deal found 5/5$542
This Delta deal was found by Cheapflights users on 5/5. 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 5/5$558
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 11/266:12 amMSP - GCM
1 stop8h 58mMultiple Airlines
Sun 11/3012:40 pmGCM - MSP
1 stop26h 44mMultiple Airlines
Deal found 5/5$591
This Southwest deal was found by Cheapflights users on 5/4. 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.
Wed 11/126:05 amORD - GCM
1 stop5h 30mSouthwest
Thu 11/201:30 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 5/4$602
This Delta deal was found by Cheapflights users on 5/5. 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 6/35:30 amORD - GCM
1 stop5h 50mDelta
Wed 6/1112:40 pmGCM - ORD
1 stop8h 44mDelta
Deal found 5/5$610
This American Airlines deal was found by Cheapflights users on 5/4. 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 7/25:29 amORD - GCM
2 stops7h 41mAmerican Airlines
Fri 7/1112:10 pmGCM - ORD
2 stops11h 47mAmerican Airlines
Deal found 5/4$614
This American Airlines deal was found by Cheapflights users on 5/5. 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 10/256:42 amMSP - GCM
1 stop5h 53mAmerican Airlines
Sat 11/84:15 pmGCM - MSP
1 stop8h 54mAmerican Airlines
Deal found 5/5$630
This United Airlines deal was found by Cheapflights users on 5/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:00 amORD - GCM
1 stop6h 30mUnited Airlines
Sat 11/11:40 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 5/4$650
This Southwest deal was found by Cheapflights users on 5/4. 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 5/116:00 amMKE - GCM
1 stop5h 50mSouthwest
Sat 5/173:50 pmGCM - MKE
1 stop6h 30mSouthwest
Deal found 5/4$706

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 May 5, 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 10/25

3:11 pm-11:40 am

1 stop20h 29m

George Town Owen Roberts Intl

Sat 11/1

8:50 am-10:47 pm

1 stop13h 57m

$442

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 5/31

6:15 pm-11:55 am

2 stops41h 40m

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-12:55 pm

1 stop24h 05m

$513

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 6/28

7:24 am-2:00 pm

1 stop6h 36m

George Town Owen Roberts Intl

Wed 7/2

12:25 pm-11:59 pm

1 stop11h 34m

$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

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 6/16

5:04 pm-11:04 am

2 stops18h 00m

George Town Owen Roberts Intl

Sat 6/28

3:05 pm-9:20 am

2 stops18h 15m

$586

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Mon 7/7

7:47 am-4:10 pm

3 stops32h 23m

George Town Owen Roberts Intl

Sun 7/13

12:40 pm-2:12 pm

1 stop25h 32m

$602

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 6/3

5:30 am-11:20 am

1 stop5h 50m

George Town Owen Roberts Intl

Tue 6/10

12:40 pm-9:24 pm

1 stop8h 44m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 7/2

6:00 am-1:10 pm

1 stop7h 10m

George Town Owen Roberts Intl

Fri 7/11

12:10 pm-10:51 pm

2 stops10h 41m

$614

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sat 10/25

6:42 am-12:35 pm

1 stop5h 53m

George Town Owen Roberts Intl

Sat 11/8

4:15 pm-12:09 am

1 stop8h 54m

$630

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 10/25

6:00 am-12:30 pm

1 stop6h 30m

George Town Owen Roberts Intl

Sat 11/1

1:40 pm-5:56 pm

Nonstop4h 16m

$650

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

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 May 5, 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 May 5, 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
4,292 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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
4,292 reviews
Southwest
8.0
Very good
4,292 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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
7,941 reviews
Southwest
8.0
Very good
4,292 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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
8,702 reviews
Southwest
8.0
Very good
4,292 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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
4,292 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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!
WestJet
7.2
Good
2,829 reviews
Southwest
8.0
Very good
4,292 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Boarding

8.2

Overall

8.0

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 $212. Delta flights start at $293 while deals on WestJet start at $303 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 May 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$273Average$618FlexibilityNo cancel feeOn-time69%
DeltaCheapest$310Average$621FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$486Average$646FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$668FlexibilityNo cancel feeOn-time63%

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