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Grand Cayman

$147+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
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 October 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(Priceline)

One-way from

$147
(Southwest)

Popular in

March

Cheapest in

August

Average price

$602
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. 6% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 6, 2025.

This Priceline deal was found by Cheapflights users on 10/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:05 amORD - GCM
1 stop7h 35mSpirit Airlines
Sat 12/132:35 pmGCM - ORD
1 stop7h 25mSpirit Airlines
Deal found 10/4$320
This American Airlines deal was found by Cheapflights users on 10/4. 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 11/297:30 pmORD - GCM
1 stop15h 43mAmerican Airlines
Wed 12/33:45 pmGCM - ORD
1 stop9h 52mAmerican Airlines
Deal found 10/4$352
This Delta deal was found by Cheapflights users on 10/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/221:35 pmORD - GCM
2 stops22h 02mDelta
Thu 12/251:52 pmGCM - ORD
1 stop11h 10mDelta
Deal found 10/4$357
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Fri 12/126:35 pmORD - GCM
1 stop16h 26mAmerican Airlines
Fri 12/193:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 10/3$367
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Sun 12/145:00 amORD - GCM
1 stop6h 00mAmerican Airlines
Sun 12/213:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 10/3$372
This Delta deal was found by Cheapflights users on 10/3. 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 12/237:55 pmORD - GCM
1 stop15h 42mDelta
Sun 12/283:42 pmGCM - ORD
1 stop9h 20mDelta
Deal found 10/3$377
This Delta deal was found by Cheapflights users on 10/3. 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.
Mon 12/221:35 pmORD - GCM
2 stops22h 02mDelta
Sun 12/283:42 pmGCM - ORD
1 stop6h 32mDelta
Deal found 10/3$382
This Delta deal was found by Cheapflights users on 10/5. 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 12/235:30 amORD - GCM
1 stop6h 07mDelta
Tue 12/301:52 pmGCM - ORD
1 stop8h 22mDelta
Deal found 10/5$385
This Gotogate deal was found by Cheapflights users on 10/4. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/295:55 pmORD - GCM
2 stops17h 30mMultiple Airlines
Sat 12/62:35 pmGCM - ORD
1 stop10h 07mMultiple Airlines
Deal found 10/4$388
This Delta deal was found by Cheapflights users on 10/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:30 amORD - GCM
1 stop6h 07mDelta
Wed 12/243:42 pmGCM - ORD
2 stops18h 19mDelta
Deal found 10/4$390
This United Airlines deal was found by Cheapflights users on 10/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/48:50 amORD - GCM
1 stop6h 40mUnited Airlines
Tue 11/115:45 pmGCM - ORD
1 stop7h 30mUnited Airlines
Deal found 10/5$392
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Fri 12/58:00 amMKE - GCM
1 stop7h 30mUnited Airlines
Mon 12/85:45 pmGCM - MKE
2 stops17h 34mUnited Airlines
Deal found 10/4$484

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 October 6, 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

Thu 2/5

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Thu 2/12

2:25 pm-11:13 pm

1 stop9h 48m

$336

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 12/23

7:55 pm-12:37 pm

1 stop15h 42m

George Town Owen Roberts Intl

Thu 12/25

3:42 pm-12:02 am

1 stop9h 20m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 12/23

7:55 pm-12:37 pm

1 stop15h 42m

George Town Owen Roberts Intl

Sun 12/28

3:42 pm-12:02 am

1 stop9h 20m

$377

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 12/23

9:41 am-12:37 pm

2 stops25h 56m

George Town Owen Roberts Intl

Mon 12/29

1:52 pm-12:02 am

1 stop11h 10m

$382

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 12/23

5:30 am-12:37 pm

1 stop6h 07m

George Town Owen Roberts Intl

Tue 12/30

1:52 pm-9:14 pm

1 stop8h 22m

$385

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 11/4

5:00 am-11:56 am

1 stop5h 56m

George Town Owen Roberts Intl

Sat 11/8

9:00 am-5:15 pm

1 stop9h 15m

$417

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/8

8:48 am-4:35 pm

1 stop6h 47m

George Town Owen Roberts Intl

Mon 11/10

5:45 pm-10:02 am

1 stop17h 17m

$423

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

7:29 am-3:26 pm

1 stop6h 57m

George Town Owen Roberts Intl

Wed 1/7

3:25 pm-6:49 pm

Nonstop4h 24m

$461

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

9:15 pm-4:35 pm

1 stop18h 20m

George Town Owen Roberts Intl

Wed 12/31

5:45 pm-12:14 am

1 stop7h 29m

$464

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 12/22

9:41 am-12:37 pm

2 stops25h 56m

George Town Owen Roberts Intl

Thu 12/25

3:42 pm-12:54 pm

2 stops22h 12m

$466

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/3

Showing 1-10 of 52 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 October 6, 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.

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.

  • How long is the flight from Wisconsin to Grand Cayman?

    For as low as $336, United Airlines can have you in Grand Cayman from Wisconsin in 4h. Airlines will cover a distance of 1613 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $147. Air Canada flights start at $167 while deals on Sun Country Air start at $199 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 October 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$212Average$637FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$613FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$513Average$692FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$648FlexibilityNo cancel feeOn-time63%

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