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Cayman Islands

$168+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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 April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$451
(American Airlines)

One-way from

$168
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$593
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. 3% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 2, 2025.

This Sun Country Air deal was found by Cheapflights users on 4/2. 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 4/51:48 pmMSP - GCM
Nonstop4h 15mSun Country Air
Sat 4/127:05 pmGCM - MSP
Nonstop4h 49mSun Country Air
Deal found 4/2$319
This American Airlines deal was found by Cheapflights users on 4/1. 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 9/64:41 pmMKE - GCM
2 stops19h 54mAmerican Airlines
Sat 9/1312:45 pmGCM - MKE
2 stops10h 24mAmerican Airlines
Deal found 4/1$451
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/121:48 pmMSP - GCM
Nonstop4h 16mMultiple Airlines
Mon 4/147:00 amGCM - MSP
2 stops30h 40mMultiple Airlines
Deal found 4/1$453
This Delta deal was found by Cheapflights users on 4/2. 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.
Sat 4/55:20 amMSP - GCM
1 stop6h 05mDelta
Sat 4/123:20 pmGCM - MSP
Nonstop4h 45mDelta
Deal found 4/2$464
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/45:43 pmMSP - GCM
1 stop17h 12mAmerican Airlines
Wed 4/92:00 pmGCM - MSP
2 stops18h 42mAmerican Airlines
Deal found 4/1$478
This Delta deal was found by Cheapflights users on 3/31. 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 5/135:40 amMKE - GCM
1 stop5h 40mDelta
Tue 5/2012:35 pmGCM - MKE
1 stop8h 00mDelta
Deal found 3/31$482
This Mytrip deal was found by Cheapflights users on 4/1. 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 5/35:55 amORD - GCM
2 stops29h 45mMultiple Airlines
Sat 5/108:50 amGCM - ORD
1 stop8h 51mMultiple Airlines
Deal found 4/1$492
This Air Canada deal was found by Cheapflights users on 4/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
Thu 6/512:50 pmGCM - ORD
2 stops21h 02mAir Canada
Deal found 4/1$518
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/163:30 pmMSN - GCM
2 stops19h 39mAmerican Airlines
Mon 4/212:00 pmGCM - MSN
2 stops20h 38mAmerican Airlines
Deal found 4/1$578
This Delta deal was found by Cheapflights users on 4/1. 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 4/65:45 amMSN - GCM
1 stop5h 40mDelta
Fri 4/112:45 pmGCM - MSN
1 stop8h 15mDelta
Deal found 4/1$604
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/285:00 amORD - GCM
1 stop6h 20mAmerican Airlines
Tue 6/32:10 pmGCM - ORD
2 stops10h 01mAmerican Airlines
Deal found 4/1$614
This Delta deal was found by Cheapflights users on 4/1. 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 5/155:30 amORD - GCM
1 stop5h 50mDelta
Thu 5/2212:35 pmGCM - ORD
1 stop8h 45mDelta
Deal found 4/1$635

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 April 2, 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

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 9/6

4:41 pm-12:35 pm

2 stops19h 54m

George Town Owen Roberts Intl

Sat 9/13

12:45 pm-11:09 pm

2 stops10h 24m

$451

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sat 4/12

1:48 pm-6:04 pm

Nonstop4h 16m

George Town Owen Roberts Intl

Mon 4/14

7:00 am-1:40 pm

2 stops30h 40m

$453

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Tue 5/13

5:40 am-11:20 am

1 stop5h 40m

George Town Owen Roberts Intl

Tue 5/20

12:35 pm-8:35 pm

1 stop8h 00m

$482

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 5/3

5:55 am-11:40 am

2 stops29h 45m

George Town Owen Roberts Intl

Sat 5/10

8:50 am-5:41 pm

1 stop8h 51m

$492

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-9:52 am

2 stops21h 02m

$518

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Wed 4/16

3:30 pm-11:09 am

2 stops19h 39m

George Town Owen Roberts Intl

Mon 4/21

2:00 pm-10:38 am

2 stops20h 38m

$578

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/28

5:00 am-11:20 am

1 stop6h 20m

George Town Owen Roberts Intl

Tue 6/3

2:10 pm-12:11 am

2 stops10h 01m

$614

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 5/15

5:30 am-11:20 am

1 stop5h 50m

George Town Owen Roberts Intl

Thu 5/22

12:35 pm-9:20 pm

1 stop8h 45m

$635

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sun 8/17

6:46 am-12:50 pm

1 stop6h 04m

George Town Owen Roberts Intl

Sun 8/24

12:45 pm-9:53 pm

1 stop9h 08m

$635

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sat 8/23

6:00 am-1:30 pm

1 stop7h 30m

George Town Owen Roberts Intl

Sat 8/30

1:35 pm-8:59 am

2 stops19h 24m

$644

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 26 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 April 2, 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.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated April 2, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Wisconsin to Cayman Islands by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,616 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
WestJet
7.2
Good
2,789 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Comfort

8.0

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $213. Users have also found prices from $231 and $293 on Southwest and Delta, 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$273Average$614FlexibilityNo cancel feeOn-time69%
DeltaCheapest$310Average$648FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$486Average$653FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$668FlexibilityNo cancel feeOn-time63%

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