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Cayman Islands

$56+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$323
(Expedia)

One-way from

$56
(Orbitz)

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 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. 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 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 January 8, 2026.

This Expedia deal was found by Cheapflights users on 1/7. 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 1/211:55 pmORD - GCM
2 stops45h 30mMultiple Airlines
Sun 1/252:49 pmGCM - ORD
1 stop9h 57mMultiple Airlines
Deal found 1/7$323
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/184:43 pmORD - GCM
1 stop20h 00mSpirit Airlines
Sun 2/222:49 pmGCM - ORD
2 stops18h 05mSpirit Airlines
Deal found 1/5$324
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/184:43 pmORD - GCM
1 stop20h 00mMultiple Airlines
Mon 2/234:45 pmGCM - ORD
1 stop17h 54mMultiple Airlines
Deal found 1/5$325
This Mytrip deal was found by Cheapflights users on 1/7. 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 1/249:23 amORD - GCM
3 stops27h 30mSpirit Airlines
Sat 1/312:34 pmGCM - ORD
2 stops19h 38mSpirit Airlines
Deal found 1/7$327
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 2/410:07 amORD - GCM
2 stops26h 46mMultiple Airlines
Mon 2/94:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Deal found 1/8$329
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/55:15 amORD - GCM
1 stop7h 38mMultiple Airlines
Sun 2/82:49 pmGCM - ORD
2 stops31h 38mMultiple Airlines
Deal found 1/7$333
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/1110:07 amORD - GCM
2 stops26h 36mMultiple Airlines
Wed 2/2511:30 amGCM - ORD
1 stop23h 09mMultiple Airlines
Deal found 1/6$334
This FlightHub deal was found by Cheapflights users on 1/8. 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 1/8$335
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/68:43 pmORD - GCM
1 stop15h 55mMultiple Airlines
Fri 2/137:00 amGCM - ORD
1 stop9h 18mMultiple Airlines
Deal found 1/6$338
This Mytrip deal was found by Cheapflights users on 1/7. 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 2/55:15 amORD - GCM
1 stop7h 38mMultiple Airlines
Wed 2/115:10 pmGCM - ORD
1 stop17h 12mMultiple Airlines
Deal found 1/7$339
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/1111:30 amGCM - ORD
1 stop23h 09mMultiple Airlines
Deal found 1/7$340
This FlightHub deal was found by Cheapflights users on 1/7. 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.
Sat 5/25:15 amORD - GCM
1 stop7h 28mSpirit Airlines
Sat 5/91:40 pmGCM - ORD
1 stop10h 01mSpirit Airlines
Deal found 1/7$341

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 January 8, 2026.
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

Sun 1/18

3:35 pm-12:25 pm

2 stops19h 50m

George Town Owen Roberts Intl

Fri 1/23

1:30 pm-8:05 am

2 stops19h 35m

$422

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 2/25

5:23 am-12:29 pm

1 stop6h 06m

George Town Owen Roberts Intl

Wed 3/4

1:54 pm-8:13 pm

1 stop7h 19m

$447

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/17

5:25 am-12:29 pm

1 stop6h 04m

George Town Owen Roberts Intl

Fri 2/20

1:54 pm-9:01 pm

1 stop8h 07m

$453

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 3/19

6:00 am-1:44 pm

1 stop7h 44m

George Town Owen Roberts Intl

Tue 3/24

7:45 am-9:04 pm

2 stops13h 19m

$462

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 2/23

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 2/28

2:50 pm-6:04 pm

Nonstop4h 14m

$469

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 2/6

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 2/13

2:50 pm-6:04 pm

Nonstop4h 14m

$469

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 2/25

6:14 am-3:25 pm

1 stop8h 11m

George Town Owen Roberts Intl

Wed 3/4

3:35 pm-11:26 pm

1 stop8h 51m

$471

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 2/21

5:00 am-1:45 pm

1 stop7h 45m

George Town Owen Roberts Intl

Sat 2/28

2:25 pm-10:26 pm

1 stop9h 01m

$471

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 4/19

8:45 am-12:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Thu 4/23

1:50 pm-6:13 pm

Nonstop4h 23m

$473

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 2/25

5:00 am-8:15 pm

2 stops14h 15m

George Town Owen Roberts Intl

Wed 3/4

3:45 pm-11:14 pm

1 stop8h 29m

$476

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 54 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, March is the cheapest month in which you can book a flight from Wisconsin to Cayman Islands (average of $212). Flying from Wisconsin to Cayman Islands 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 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 Air Canada, Delta, and American Airlines fly from Wisconsin to Cayman Islands in about 6h 06m. The time it takes to get you to your destination can typically vary by up to 13h 44m. 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.

  • 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, March is the cheapest month in which you can book a flight from Wisconsin to Cayman Islands (average of $212). Flying from Wisconsin to Cayman Islands 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

Browse thousands of different options on Cheapflights for your next trip

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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 3 airlines flying from Wisconsin to Cayman Islands

Discover the top 3 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$310Average$638FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$390Average$533FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$470Average$696FlexibilityNo cancel feeOn-time71%

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