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Grand Cayman

$77+ 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 4/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Feb 10 — Feb 171
Tue 2/10
Tue 2/17
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 January 11, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$325
(Kiwi.com)

One-way from

$77
(FlightHub)

Popular in

March

Cheapest in

August

Average price

$557
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. 10% potential increase in price ($68 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 11, 2026.

This Mytrip deal was found by Cheapflights users on 1/10. 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 1/1712:44 pmORD - GCM
3 stops24h 09mSpirit Airlines
Sat 1/242:34 pmGCM - ORD
1 stop7h 29mSpirit Airlines
Deal found 1/10$324
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 2/184:43 pmORD - GCM
1 stop20h 00mMultiple Airlines
Tue 2/2411:30 amGCM - ORD
1 stop23h 09mMultiple Airlines
Deal found 1/10$325
This Kiwi.com deal was found by Cheapflights users on 1/9. 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 2/45:32 pmORD - GCM
1 stop19h 21mMultiple Airlines
Wed 2/1811:30 amGCM - ORD
1 stop23h 09mMultiple Airlines
Deal found 1/9$326
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 2/184:43 pmORD - GCM
1 stop20h 00mMultiple Airlines
Sun 2/224:45 pmGCM - ORD
1 stop17h 54mMultiple Airlines
Deal found 1/10$327
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Sun 2/85:15 amORD - GCM
1 stop7h 38mMultiple Airlines
Tue 2/1711:30 amGCM - ORD
1 stop23h 09mMultiple Airlines
Deal found 1/10$328
This Kiwi.com deal was found by Cheapflights users on 1/10. 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.
Sun 2/85:15 amORD - GCM
1 stop7h 38mMultiple Airlines
Wed 2/1811:30 amGCM - ORD
1 stop23h 09mMultiple Airlines
Deal found 1/10$329
This Mytrip deal was found by Cheapflights users on 1/10. 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 1/2410:07 amORD - GCM
3 stops26h 46mSpirit Airlines
Sat 1/312:34 pmGCM - ORD
1 stop8h 29mSpirit Airlines
Deal found 1/10$330
This FlightHub deal was found by Cheapflights users on 1/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/225:15 amORD - GCM
1 stop7h 38mSpirit Airlines
Sun 2/12:49 pmGCM - ORD
1 stop9h 58mSpirit Airlines
Deal found 1/9$334
This Expedia deal was found by Cheapflights users on 1/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/148:00 amORD - GCM
1 stop27h 25mMultiple Airlines
Sat 1/172:34 pmGCM - ORD
1 stop10h 12mMultiple Airlines
Deal found 1/9$339
This Travelocity deal was found by Cheapflights users on 1/11. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/117:20 amORD - GCM
1 stop5h 33mMultiple Airlines
Tue 1/131:30 pmGCM - ORD
1 stop21h 36mMultiple Airlines
Deal found 1/11$340
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 2/75:15 amORD - GCM
1 stop7h 23mMultiple Airlines
Mon 2/164:45 pmGCM - ORD
1 stop17h 54mMultiple Airlines
Deal found 1/10$341
This Trip.com deal was found by Cheapflights users on 1/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/41:48 pmMSP - GCM
Nonstop4h 16mMultiple Airlines
Fri 4/107:00 amGCM - MSP
1 stop9h 06mMultiple Airlines
Deal found 1/9$348

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 January 11, 2026.
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 1/24

10:07 am-1:53 pm

3 stops26h 46m

George Town Owen Roberts Intl

Sat 1/31

2:34 pm-10:03 pm

1 stop8h 29m

$330

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 4/16

8:20 pm-11:10 am

1 stop14h 50m

George Town Owen Roberts Intl

Sun 4/19

12:30 pm-10:03 pm

1 stop9h 33m

$364

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 3/28

6:25 pm-11:10 am

1 stop16h 45m

George Town Owen Roberts Intl

Fri 4/3

12:30 pm-1:00 pm

1 stop24h 30m

$367

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/21

6:04 am-2:35 pm

1 stop7h 31m

George Town Owen Roberts Intl

Sat 2/28

3:40 pm-10:59 pm

1 stop8h 19m

$425

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 3/30

2:00 pm-11:10 am

1 stop21h 10m

George Town Owen Roberts Intl

Mon 4/6

4:45 pm-8:41 am

1 stop15h 56m

$438

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Wed 2/18

6:15 pm-12:55 pm

2 stops17h 40m

George Town Owen Roberts Intl

Tue 2/24

1:50 pm-9:50 pm

2 stops9h 00m

$440

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/7

8:07 pm-11:26 am

1 stop14h 19m

George Town Owen Roberts Intl

Thu 2/12

3:35 pm-6:45 pm

Nonstop4h 10m

$443

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/10

5:30 am-12:40 pm

1 stop6h 10m

George Town Owen Roberts Intl

Fri 2/13

1:54 pm-9:01 pm

1 stop8h 07m

$453

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/26

5:30 am-12:40 pm

1 stop6h 10m

George Town Owen Roberts Intl

Wed 2/4

2:05 pm-9:41 am

2 stops20h 36m

$458

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 2/19

2:50 pm-6:04 pm

Nonstop4h 14m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/9

Showing 1-10 of 54 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, March is the cheapest month in which you can book a flight from Wisconsin to Grand Cayman (average of $212). Flying from Wisconsin to Grand Cayman in September is currently the most expensive (average of $685). 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.

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 $425, Spirit Airlines can have you in Grand Cayman from Wisconsin in 7h 31m. 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.

  • 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, March is the cheapest month in which you can book a flight from Wisconsin to Grand Cayman (average of $212). Flying from Wisconsin to Grand Cayman in September is currently the most expensive (average of $685). 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 3 airlines flying from Wisconsin to Grand Cayman

Discover the top 3 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 January 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$310Average$628FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$390Average$537FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$470Average$697FlexibilityNo cancel feeOn-time71%

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