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Grand Cayman

$141+ Cheap flights from Wisconsin to Grand Cayman

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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
1 adult, Economy
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Cheap flight deals from Wisconsin to Grand Cayman

Keep the following information in mind while searching for Wisconsin to Grand Cayman flight deals. Data was last updated February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(Sun Country Air)

One-way from

$141
(American Airlines)

Popular in

March

Cheapest in

April

Average price

$527
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 Grand Cayman
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One-way flight from Wisconsin to Grand Cayman
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Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
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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 February 2025
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Find flight deals from Wisconsin to Grand Cayman

Cheapest flights from Wisconsin to Grand Cayman
Explore the most affordable flight options available from Wisconsin to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.

This Sun Country Air deal was found by Cheapflights users on 2/22. 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 2/22$319
This American Airlines deal was found by Cheapflights users on 2/22. 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 3/16:01 amMSP - GCM
1 stop7h 59mAmerican Airlines
Wed 3/51:00 pmGCM - MSP
1 stop11h 21mAmerican Airlines
Deal found 2/22$374
This Mytrip deal was found by Cheapflights users on 2/22. 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 3/11:48 pmMSP - GCM
Nonstop4h 15mMultiple Airlines
Sat 3/88:50 amGCM - MSP
1 stop28h 49mMultiple Airlines
Deal found 2/22$417
This Delta deal was found by Cheapflights users on 2/22. 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 3/15:20 amMSP - GCM
1 stop7h 34mDelta
Sat 3/83:55 pmGCM - MSP
Nonstop4h 48mDelta
Deal found 2/22$464
This Delta deal was found by Cheapflights users on 2/23. 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 5/35:45 amMKE - GCM
1 stop5h 37mDelta
Fri 5/912:35 pmGCM - MKE
1 stop8h 00mDelta
Deal found 2/23$536
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sun 5/118:30 pmMSP - GCM
2 stops15h 20mSouthwest
Sat 5/171:10 pmGCM - MSP
2 stops9h 35mSouthwest
Deal found 2/22$542
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Sun 6/296:46 pmMKE - GCM
1 stop16h 14mAmerican Airlines
Wed 7/23:45 pmGCM - MKE
1 stop7h 16mAmerican Airlines
Deal found 2/22$559
This Southwest deal was found by Cheapflights users on 2/22. 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.
Mon 3/248:25 pmMKE - GCM
2 stops15h 20mSouthwest
Wed 4/212:45 pmGCM - MKE
2 stops9h 45mSouthwest
Deal found 2/22$580
This Mytrip deal was found by Cheapflights users on 2/22. 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 4/95:10 amORD - GCM
2 stops31h 33mMultiple Airlines
Sat 4/127:05 pmGCM - ORD
3 stops35h 28mMultiple Airlines
Deal found 2/22$608
This American Airlines deal was found by Cheapflights users on 2/23. 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 4/97:00 amORD - GCM
1 stop5h 59mAmerican Airlines
Wed 4/1612:35 pmGCM - ORD
1 stop10h 04mAmerican Airlines
Deal found 2/23$609
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 3/264:14 pmMKE - GCM
1 stop26h 26mMultiple Airlines
Fri 4/411:05 amGCM - MKE
1 stop23h 39mMultiple Airlines
Deal found 2/22$624
This United Airlines deal was found by Cheapflights users on 2/22. 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.
Tue 3/255:35 pmMKE - GCM
2 stops21h 50mUnited Airlines
Thu 4/31:35 pmGCM - MKE
2 stops22h 22mUnited Airlines
Deal found 2/22$628

Find flights from Wisconsin to Grand Cayman within your budget

Customize your flight search to find flights from Wisconsin to Grand Cayman 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 February 23, 2025.

Fly from

Wisconsin

Fly to

Grand Cayman

Route

Depart

Return

Price

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sat 4/5

1:48 pm-6:03 pm

Nonstop4h 15m

George Town Owen Roberts Intl

Sat 4/12

7:05 pm-11:54 pm

Nonstop4h 49m

$319

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Tue 3/25

6:00 am-2:00 pm

1 stop8h 00m

George Town Owen Roberts Intl

Tue 4/1

3:00 pm-11:39 pm

1 stop8h 39m

$374

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sat 4/5

5:20 am-11:25 am

1 stop6h 05m

George Town Owen Roberts Intl

Sat 4/12

3:20 pm-8:05 pm

Nonstop4h 45m

$464

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Tue 4/8

1:45 pm-4:10 pm

1 stop26h 25m

George Town Owen Roberts Intl

Tue 4/15

11:30 am-3:35 pm

2 stops28h 05m

$469

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 5/3

5:45 am-11:22 am

1 stop5h 37m

George Town Owen Roberts Intl

Fri 5/9

12:35 pm-8:35 pm

1 stop8h 00m

$536

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sun 5/11

8:30 pm-11:50 am

2 stops15h 20m

George Town Owen Roberts Intl

Sat 5/17

1:10 pm-10:45 pm

2 stops9h 35m

$542

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 6/29

6:46 pm-11:00 am

1 stop16h 14m

George Town Owen Roberts Intl

Wed 7/2

3:45 pm-11:01 pm

1 stop7h 16m

$559

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Mon 3/24

8:25 pm-11:45 am

2 stops15h 20m

George Town Owen Roberts Intl

Wed 4/2

12:45 pm-10:30 pm

2 stops9h 45m

$580

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 4/9

5:10 am-12:43 pm

2 stops31h 33m

George Town Owen Roberts Intl

Sat 4/12

7:05 pm-6:33 am

3 stops35h 28m

$608

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 4/9

7:00 am-12:59 pm

1 stop5h 59m

George Town Owen Roberts Intl

Wed 4/16

12:35 pm-10:39 pm

1 stop10h 04m

$609

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 34 results
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Best time to book a flight from Wisconsin to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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.

Travel insights for flights from Wisconsin to Grand Cayman

Get recent, data-driven insights about flights from Wisconsin to Grand Cayman including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Wisconsin to Grand Cayman?

Currently, January is the cheapest month in which you can book a flight from Wisconsin to Grand Cayman (average of $467). Flying from Wisconsin to Grand Cayman 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 LAW?

Find hourly flight availability from Wisconsin to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 23, 2025.

When flying from Wisconsin to Grand Cayman, 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 Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated February 23, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Wisconsin to Grand Cayman 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
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,385 reviews
Southwest
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

WestJet
7.2
Good
2,796 reviews
Southwest
8.1
Very good
4,385 reviews

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.6

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Grand Cayman. 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 Grand Cayman one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $141. Sun Country Air flights start at $151 while deals on Air Canada start at $216 one-way.

  • Can I find deals for flights from Wisconsin to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Grand Cayman.

  • Can I find deals for business class flights from Wisconsin to Grand Cayman?

    Yes. Cheapflights offers flight deals from Wisconsin to Grand Cayman 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 Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Wisconsin to Grand Cayman (average of $467). Flying from Wisconsin to Grand Cayman 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.

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Alternative routes for Wisconsin to Grand Cayman

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Top 4 airlines flying from Wisconsin to Grand Cayman

Discover the top 4 airlines that operate flights from Wisconsin to Grand Cayman. 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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$212Average$629FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$609FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$492Average$648FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$668FlexibilityNo cancel feeOn-time63%
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