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Cayman Islands

$95+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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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 November 20, 2025.

This United Airlines deal was found by Cheapflights users on 11/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:45 amORD - GCM
1 stop6h 50mUnited Airlines
Sat 12/132:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 11/18$344
This United Airlines deal was found by Cheapflights users on 11/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Fri 12/265:45 pmGCM - ORD
1 stop7h 29mUnited Airlines
Deal found 11/17$350
This Delta deal was found by Cheapflights users on 11/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:30 amORD - GCM
1 stop6h 06mDelta
Mon 12/293:42 pmGCM - ORD
1 stop9h 20mDelta
Deal found 11/17$354
This Delta deal was found by Cheapflights users on 11/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:00 amORD - GCM
2 stops28h 36mDelta
Mon 12/293:42 pmGCM - ORD
2 stops18h 19mDelta
Deal found 11/17$359
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:24 amORD - GCM
Nonstop4h 11mAmerican Airlines
Wed 12/313:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 11/19$365
This United Airlines deal was found by Cheapflights users on 11/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Sat 12/62:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 11/18$370
This Mytrip deal was found by Cheapflights users on 11/18. 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.
Wed 12/32:01 pmORD - GCM
3 stops22h 44mSpirit Airlines
Sun 12/72:40 pmGCM - ORD
1 stop10h 29mSpirit Airlines
Deal found 11/18$372
This Mytrip deal was found by Cheapflights users on 11/18. 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.
Sat 12/64:38 pmORD - GCM
2 stops20h 07mSpirit Airlines
Sat 12/135:56 pmGCM - ORD
3 stops27h 13mSpirit Airlines
Deal found 11/18$379
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Sat 12/137:12 amMSP - GCM
1 stop8h 43mMultiple Airlines
Sat 12/205:56 pmGCM - MSP
1 stop28h 19mMultiple Airlines
Deal found 11/18$408
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:40 amMKE - GCM
1 stop5h 56mDelta
Thu 12/253:42 pmGCM - MKE
1 stop8h 01mDelta
Deal found 11/20$470
This United Airlines deal was found by Cheapflights users on 11/20. 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.
Sun 12/215:00 amMKE - GCM
2 stops10h 35mUnited Airlines
Thu 12/255:45 pmGCM - MKE
2 stops18h 42mUnited Airlines
Deal found 11/20$489
This Sun Country Air deal was found by Cheapflights users on 11/19. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/201:36 pmMSP - GCM
Nonstop4h 20mSun Country Air
Sat 12/278:00 pmGCM - MSP
Nonstop4h 45mSun Country Air
Deal found 11/19$498

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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$343
(Kiwi.com)

One-way from

$95
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$608
Provider with most accurate pricing for Milwaukee-Mitchell-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-George Town Owen Roberts Intl flights.
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From Wisconsin to Cayman Islands
Search Deals
One-way flight from Wisconsin to Cayman Islands
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
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 November 2025
Search Deals

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 November 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

Wed 12/17

7:35 am-4:30 pm

1 stop7h 55m

George Town Owen Roberts Intl

Wed 12/24

2:50 pm-6:04 pm

Nonstop4h 14m

$344

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 12/23

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Mon 12/29

5:10 pm-11:44 pm

1 stop7h 34m

$350

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/13

7:10 am-4:55 pm

1 stop8h 45m

George Town Owen Roberts Intl

Wed 12/17

7:00 am-8:09 pm

2 stops14h 09m

$354

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/14

5:30 am-12:40 pm

1 stop6h 10m

George Town Owen Roberts Intl

Thu 1/15

2:05 pm-11:59 pm

1 stop10h 54m

$354

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/18

5:30 am-12:40 pm

1 stop6h 10m

George Town Owen Roberts Intl

Wed 1/21

2:05 pm-11:56 pm

1 stop10h 51m

$354

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

5:30 am-12:36 pm

1 stop6h 06m

George Town Owen Roberts Intl

Wed 12/31

1:52 pm-7:38 pm

1 stop6h 46m

$354

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 12/25

5:30 am-12:36 pm

1 stop6h 06m

George Town Owen Roberts Intl

Mon 12/29

3:42 pm-9:14 pm

1 stop6h 32m

$354

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/21

5:30 am-2:27 pm

1 stop7h 57m

George Town Owen Roberts Intl

Wed 12/31

3:42 pm-9:01 am

2 stops18h 19m

$359

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 3/9

10:35 am-11:35 am

2 stops25h 00m

George Town Owen Roberts Intl

Thu 3/12

1:00 pm-9:14 pm

1 stop8h 14m

$359

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 3/23

7:00 am-11:35 am

2 stops28h 35m

George Town Owen Roberts Intl

Tue 3/31

1:00 pm-7:29 pm

1 stop6h 29m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 57 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.

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 November 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 29% on flights from Wisconsin to Cayman Islands by exploring options for tickets in the afternoon.

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 United Airlines, Delta, and American Airlines fly from Wisconsin to Cayman Islands in about 6h 10m. The time it takes to get you to your destination can typically vary by up to 12h 10m. The distance from Wisconsin to Cayman Islands is about 1613 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

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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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$212Average$636FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$613FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$513Average$694FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$631FlexibilityNo cancel feeOn-time63%

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