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Cayman Islands

$179+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$467
(Mytrip)

One-way from

$179
(Trip.com)

Popular in

March

Cheapest in

August

Average price

$571
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. 2% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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.
mar. 7/81:43 pmORD - GCM
1 stop26h 27mMultiple Airlines
lun. 7/144:45 pmGCM - ORD
1 stop23h 26mMultiple Airlines
Deal found 6/11$467
This Air Canada deal was found by Cheapflights users on 6/10. 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.
dom. 10/196:20 pmORD - GCM
1 stop17h 35mAir Canada
jue. 10/3012:35 pmGCM - ORD
1 stop24h 16mAir Canada
Deal found 6/10$515
This Delta deal was found by Cheapflights users on 6/11. 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.
mié. 12/106:00 amMKE - GCM
1 stop5h 37mDelta
mié. 12/313:45 pmGCM - MKE
1 stop9h 08mDelta
Deal found 6/11$516
This Delta deal was found by Cheapflights users on 6/11. 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.
mié. 12/106:00 amORD - GCM
1 stop5h 37mDelta
mar. 1/132:00 pmGCM - ORD
1 stop10h 54mDelta
Deal found 6/11$520
This American Airlines deal was found by Cheapflights users on 6/11. 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.
dom. 9/148:44 pmORD - GCM
1 stop14h 41mAmerican Airlines
vie. 9/1912:10 pmGCM - ORD
2 stops11h 02mAmerican Airlines
Deal found 6/11$524
This Sun Country Air deal was found by Cheapflights users on 6/12. 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.
sáb. 12/201:36 pmMSP - GCM
Nonstop4h 20mSun Country Air
sáb. 12/278:00 pmGCM - MSP
Nonstop4h 45mSun Country Air
Deal found 6/12$535
This United Airlines deal was found by Cheapflights users on 6/10. 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.
mar. 7/293:45 pmMKE - GCM
2 stops20h 45mUnited Airlines
lun. 8/41:35 pmGCM - MKE
1 stop7h 39mUnited Airlines
Deal found 6/10$538
This Southwest deal was found by Cheapflights users on 6/11. 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.
mié. 11/196:05 amORD - GCM
1 stop5h 30mSouthwest
mar. 12/21:30 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 6/11$543
This American Airlines deal was found by Cheapflights users on 6/12. 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.
mar. 7/296:20 amMKE - GCM
1 stop8h 09mAmerican Airlines
lun. 8/412:25 pmGCM - MKE
1 stop11h 39mAmerican Airlines
Deal found 6/12$548
This American Airlines deal was found by Cheapflights users on 6/12. 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.
mar. 12/24:53 pmMSN - GCM
2 stops17h 53mAmerican Airlines
lun. 12/88:30 amGCM - MSN
2 stops13h 56mAmerican Airlines
Deal found 6/12$552
This Southwest deal was found by Cheapflights users on 6/9. 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.
dom. 7/68:15 pmMSP - GCM
2 stops15h 35mSouthwest
jue. 7/1012:45 pmGCM - MSP
2 stops11h 10mSouthwest
Deal found 6/9$576
This Mytrip deal was found by Cheapflights users on 6/10. 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.
lun. 7/77:47 amMSP - GCM
3 stops32h 23mMultiple Airlines
dom. 7/134:45 pmGCM - MSP
2 stops24h 07mMultiple Airlines
Deal found 6/10$578

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 junio 12, 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

mar. 7/8

1:43 pm-4:10 pm

1 stop26h 27m

George Town Owen Roberts Intl

lun. 7/14

4:45 pm-4:11 pm

1 stop23h 26m

$467

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 10/19

6:20 pm-11:55 am

1 stop17h 35m

George Town Owen Roberts Intl

dom. 10/26

12:35 pm-10:58 am

1 stop22h 23m

$515

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 10/20

6:00 am-11:42 am

1 stop5h 42m

George Town Owen Roberts Intl

vie. 10/24

1:02 pm-9:12 pm

1 stop8h 10m

$520

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 9/14

8:44 pm-11:25 am

1 stop14h 41m

George Town Owen Roberts Intl

vie. 9/19

12:10 pm-11:12 pm

2 stops11h 02m

$524

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

mar. 7/29

3:45 pm-12:30 pm

2 stops20h 45m

George Town Owen Roberts Intl

lun. 8/4

1:35 pm-9:14 pm

1 stop7h 39m

$538

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 11/19

6:05 am-12:35 pm

1 stop5h 30m

George Town Owen Roberts Intl

mar. 12/2

1:30 pm-9:50 pm

1 stop9h 20m

$543

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

mar. 7/29

6:20 am-2:29 pm

1 stop8h 09m

George Town Owen Roberts Intl

lun. 8/4

12:25 pm-12:04 am

1 stop11h 39m

$548

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

mar. 12/2

4:53 pm-11:46 am

2 stops17h 53m

George Town Owen Roberts Intl

lun. 12/8

8:30 am-9:26 pm

2 stops13h 56m

$552

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

lun. 7/7

5:40 am-11:22 am

1 stop5h 42m

George Town Owen Roberts Intl

lun. 7/14

12:37 pm-8:46 pm

1 stop8h 09m

$569

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

dom. 7/6

8:15 pm-11:50 am

2 stops15h 35m

George Town Owen Roberts Intl

jue. 7/10

12:45 pm-11:55 pm

2 stops11h 10m

$576

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 25 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 junio 12, 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 junio 12, 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
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,868 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $237. Users have also found prices from $313 and $403 on American Airlines and United Airlines, 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

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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$273Average$623FlexibilityNo cancel feeOn-time69%
DeltaCheapest$310Average$641FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$486Average$656FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$668FlexibilityNo cancel feeOn-time63%

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