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Cayman Islands

$169+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
May 5 — May 121
Mon 5/5
Mon 5/12
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 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$473
(Kiwi.com)

One-way from

$195
(Trip.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. 1% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 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 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/29. 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 10/43:11 pmORD - GCM
1 stop20h 29mMultiple Airlines
Wed 10/811:30 amGCM - ORD
1 stop11h 17mMultiple Airlines
Deal found 4/29$464
This Air Canada deal was found by Cheapflights users on 4/29. 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
1 stop9h 15mAir Canada
Deal found 4/29$511
This American Airlines deal was found by Cheapflights users on 4/29. 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 6/287:24 amMKE - GCM
1 stop6h 36mAmerican Airlines
Wed 7/212:25 pmGCM - MKE
1 stop11h 34mAmerican Airlines
Deal found 4/29$538
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 12/27:14 amMSN - GCM
1 stop7h 41mAmerican Airlines
Mon 12/84:15 pmGCM - MSN
2 stops19h 05mAmerican Airlines
Deal found 4/29$542
This Southwest deal was found by Cheapflights users on 4/29. 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 9/66:00 amORD - GCM
1 stop6h 10mSouthwest
Sat 9/131:10 pmGCM - ORD
1 stop8h 20mSouthwest
Deal found 4/29$576
This Delta deal was found by Cheapflights users on 4/29. 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.
Mon 7/145:35 amORD - GCM
1 stop5h 50mDelta
Tue 7/2212:40 pmGCM - ORD
1 stop8h 50mDelta
Deal found 4/29$610
This American Airlines deal was found by Cheapflights users on 4/29. 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 10mAmerican Airlines
Tue 6/312:10 pmGCM - ORD
2 stops11h 46mAmerican Airlines
Deal found 4/29$614
This American Airlines deal was found by Cheapflights users on 4/29. 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 10/256:20 pmMSP - GCM
1 stop16h 45mAmerican Airlines
Sat 11/81:10 pmGCM - MSP
1 stop8h 30mAmerican Airlines
Deal found 4/29$630
This United Airlines deal was found by Cheapflights users on 4/29. 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 7/269:26 amORD - GCM
Nonstop4h 04mUnited Airlines
Sat 8/21:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 4/29$645
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Mon 6/96:42 amMSP - GCM
1 stop10h 38mMultiple Airlines
Wed 6/1811:30 amGCM - MSP
2 stops29h 57mMultiple Airlines
Deal found 4/28$665
This Southwest deal was found by Cheapflights users on 4/29. 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 5/105:45 amMSP - GCM
2 stops9h 05mSouthwest
Sat 5/171:10 pmGCM - MSP
2 stops9h 35mSouthwest
Deal found 4/29$670
This WestJet deal was found by Cheapflights users on 4/29. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/131:40 pmORD - GCM
2 stops47h 05mWestJet
Tue 7/221:45 pmGCM - ORD
2 stops26h 59mWestJet
Deal found 4/29$792

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 30, 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 10/4

3:11 pm-11:40 am

1 stop20h 29m

George Town Owen Roberts Intl

Wed 10/8

11:30 am-10:47 pm

1 stop11h 17m

$464

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-10:05 pm

1 stop9h 15m

$511

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 6/28

7:24 am-2:00 pm

1 stop6h 36m

George Town Owen Roberts Intl

Wed 7/2

12:25 pm-11:59 pm

1 stop11h 34m

$538

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 6/16

6:40 pm-1:10 pm

2 stops18h 30m

George Town Owen Roberts Intl

Sat 6/28

3:05 pm-9:20 am

2 stops18h 15m

$542

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 9/6

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Sat 9/13

1:10 pm-9:30 pm

1 stop8h 20m

$576

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 7/14

5:35 am-11:25 am

1 stop5h 50m

George Town Owen Roberts Intl

Wed 7/23

12:40 pm-9:30 pm

1 stop8h 50m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/28

5:00 am-11:10 am

1 stop6h 10m

George Town Owen Roberts Intl

Tue 6/3

12:10 pm-11:56 pm

2 stops11h 46m

$614

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sat 10/25

6:20 pm-11:05 am

1 stop16h 45m

George Town Owen Roberts Intl

Sat 11/8

1:10 pm-8:40 pm

1 stop8h 30m

$630

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 7/26

9:26 am-1:30 pm

Nonstop4h 04m

George Town Owen Roberts Intl

Sat 8/2

1:45 pm-6:07 pm

Nonstop4h 22m

$645

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Mon 6/9

6:42 am-5:20 pm

1 stop10h 38m

George Town Owen Roberts Intl

Wed 6/18

11:30 am-5:27 pm

2 stops29h 57m

$665

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 30, 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 30, 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
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $197. Users have also found prices from $242 and $288 on WestJet 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$273Average$618FlexibilityNo cancel feeOn-time69%
DeltaCheapest$310Average$647FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$476Average$652FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$668FlexibilityNo cancel feeOn-time63%

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