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Cayman Islands

$127+ Cheap flights from Wisconsin to the Cayman Islands

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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Wisconsin to Cayman Islands

Keep the following information in mind while searching for Wisconsin to Cayman Islands flight deals. Data was last updated August 20, 2025.

Round-trip from

$357
(FlightHub)

One-way from

$127
(Booking.com)

Popular in

March

Cheapest in

August

Average price

$483
From Wisconsin to Cayman Islands
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One-way flight from Wisconsin to Cayman Islands
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Highest demand for flights based on searches. 9% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Wisconsin to Cayman Islands

Cheapest flights from Wisconsin to Cayman Islands
Explore the most affordable flight options available from Wisconsin to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Southwest deal was found by Cheapflights users on 8/20. 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 11/28:25 pmMSP - GCM
2 stops15h 10mSouthwest
Tue 11/41:30 pmGCM - MSP
2 stops9h 45mSouthwest
Deal found 8/20$436
This Orbitz deal was found by Cheapflights users on 8/18. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:15 pmORD - GCM
1 stop15h 05mAir Canada
Sun 11/21:30 pmGCM - ORD
1 stop20h 43mAir Canada
Deal found 8/18$443
This Booking.com deal was found by Cheapflights users on 8/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/128:25 pmORD - GCM
1 stop15h 30mAir Canada
Mon 10/2012:50 pmGCM - ORD
1 stop24h 24mAir Canada
Deal found 8/18$462
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Thu 10/910:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Tue 10/1411:30 amGCM - ORD
1 stop21h 52mMultiple Airlines
Deal found 8/20$463
This Mytrip deal was found by Cheapflights users on 8/18. 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.
Thu 10/210:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Thu 10/94:45 pmGCM - ORD
1 stop16h 37mMultiple Airlines
Deal found 8/18$467
This United Airlines deal was found by Cheapflights users on 8/20. 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 11/45:00 amMKE - GCM
2 stops10h 30mUnited Airlines
Sat 11/82:50 pmGCM - MKE
1 stop7h 00mUnited Airlines
Deal found 8/20$467
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 9/1910:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Sun 9/214:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Deal found 8/17$474
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Fri 10/310:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Fri 10/104:45 pmGCM - ORD
1 stop15h 33mMultiple Airlines
Deal found 8/19$475
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Tue 9/210:27 amORD - GCM
1 stop29h 43mMultiple Airlines
Tue 9/911:30 amGCM - ORD
1 stop21h 48mMultiple Airlines
Deal found 8/18$478
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/310:27 amORD - GCM
1 stop25h 13mMultiple Airlines
Mon 9/84:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Deal found 8/18$481
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Tue 9/210:27 amORD - GCM
1 stop29h 43mMultiple Airlines
Mon 9/84:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Deal found 8/18$486
This Southwest deal was found by Cheapflights users on 8/19. 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.
Sat 11/154:35 pmMSP - GCM
2 stops19h 00mSouthwest
Fri 11/211:30 pmGCM - MSP
2 stops8h 55mSouthwest
Deal found 8/19$489

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Cayman Islands 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 August 20, 2025.
Use the filters below to find and compare flights from Wisconsin to the Cayman Islands that are best for you.

Fly from

Wisconsin

Fly to

Cayman Islands

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-9:00 pm

1 stop10h 05m

$357

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/31

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 2/7

11:55 am-9:00 pm

1 stop10h 05m

$357

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 1/21

5:45 am-12:35 pm

1 stop5h 50m

George Town Owen Roberts Intl

Fri 1/30

2:00 pm-11:27 pm

1 stop10h 27m

$396

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 1/18

5:45 am-12:35 pm

1 stop5h 50m

George Town Owen Roberts Intl

Wed 1/28

2:00 pm-11:27 pm

1 stop10h 27m

$396

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

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 1/18

5:45 am-12:35 pm

1 stop5h 50m

George Town Owen Roberts Intl

Fri 1/30

2:00 pm-11:27 pm

1 stop10h 27m

$396

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 1/21

5:45 am-12:35 pm

1 stop5h 50m

George Town Owen Roberts Intl

Wed 1/28

2:00 pm-11:27 pm

1 stop10h 27m

$396

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 1/18

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

Sat 1/17

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 1/24

11:55 am-11:42 pm

1 stop12h 47m

$433

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sun 11/2

8:25 pm-12:35 pm

2 stops15h 10m

George Town Owen Roberts Intl

Tue 11/4

1:30 pm-10:15 pm

2 stops9h 45m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 42 results
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Best time to book a flight from Wisconsin to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands 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 the Cayman Islands

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

Currently, January is the cheapest month in which you can book a flight from Wisconsin to Cayman Islands (average of $467). Flying from Wisconsin to Cayman Islands 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 KY?

Find hourly flight availability from Wisconsin to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 20, 2025.

When flying from Wisconsin to Cayman Islands, 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 Cayman Islands. 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 Cayman Islands?

    Airlines like Spirit Airlines, Delta, and Southwest fly from Wisconsin to Cayman Islands in about 5h 50m. The time it takes to get you to your destination can typically vary by up to 10h 11m. The distance from Wisconsin to Cayman Islands is about 1677 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $127. Users have also found prices from $164 and $218 on Southwest and Sun Country Air, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Wisconsin to Cayman Islands 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 Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Wisconsin to Cayman Islands (average of $467). Flying from Wisconsin to Cayman Islands 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 Cayman Islands

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 Cayman Islands

Discover the top 4 airlines that operate flights from Wisconsin to Cayman Islands. 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$273Average$613FlexibilityNo cancel feeOn-time69%
DeltaCheapest$310Average$641FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$497Average$673FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$650FlexibilityNo cancel feeOn-time63%

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