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$141+ 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 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 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 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. 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 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 February 20, 2025.

This Sun Country Air deal was found by Cheapflights users on 2/20. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/11:48 pmMSP - GCM
Nonstop4h 15mSun Country Air
Sat 3/88:05 pmGCM - MSP
Nonstop4h 45mSun Country Air
Deal found 2/20$319
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 3/66:15 amMSP - GCM
1 stop6h 40mAmerican Airlines
Tue 3/113:00 pmGCM - MSP
1 stop8h 39mAmerican Airlines
Deal found 2/19$374
This Mytrip deal was found by Cheapflights users on 2/18. 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 3/11:48 pmMSP - GCM
Nonstop4h 15mMultiple Airlines
Sun 3/92:00 pmGCM - MSP
1 stop23h 39mMultiple Airlines
Deal found 2/18$408
This Delta deal was found by Cheapflights users on 2/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/289:05 amMSP - GCM
Nonstop4h 30mDelta
Sat 3/13:55 pmGCM - MSP
Nonstop4h 48mDelta
Deal found 2/18$459
This United Airlines deal was found by Cheapflights users on 2/20. 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 4/66:45 amMKE - GCM
1 stop5h 55mUnited Airlines
Sun 4/131:45 pmGCM - MKE
1 stop8h 30mUnited Airlines
Deal found 2/20$536
This American Airlines deal was found by Cheapflights users on 2/20. 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 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 stop18h 49mAmerican Airlines
Deal found 2/20$545
This Delta deal was found by Cheapflights users on 2/20. 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.
Sat 5/35:45 amMKE - GCM
1 stop5h 37mDelta
Fri 5/912:51 pmGCM - MKE
1 stop10h 35mDelta
Deal found 2/20$558
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/236:30 pmORD - GCM
1 stop17h 15mAmerican Airlines
Thu 4/312:00 pmGCM - ORD
1 stop12h 20mAmerican Airlines
Deal found 2/20$610
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/64:41 pmMKE - GCM
3 stops44h 49mMultiple Airlines
Sun 4/1311:30 amGCM - MKE
2 stops31h 23mMultiple Airlines
Deal found 2/20$612
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/252:00 pmORD - GCM
1 stop21h 55mMultiple Airlines
Sat 5/3111:30 amGCM - ORD
3 stops34h 58mMultiple Airlines
Deal found 2/19$615
This United Airlines deal was found by Cheapflights users on 2/20. 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 4/68:45 amORD - GCM
Nonstop3h 55mUnited Airlines
Sun 4/131:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 2/20$620
This Priceline deal was found by Cheapflights users on 2/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/226:15 pmORD - GCM
2 stops17h 40mAir Canada
Thu 6/2612:50 pmGCM - ORD
2 stops19h 05mAir Canada
Deal found 2/20$632

Find flights from Wisconsin to Cayman Islands within your budget

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 February 20, 2025.

Fly from

Wisconsin

Fly to

Cayman Islands

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

Thu 3/6

6:15 am-1:55 pm

1 stop6h 40m

George Town Owen Roberts Intl

Tue 3/11

3:00 pm-11:39 pm

1 stop8h 39m

$374

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sat 4/5

5:54 am-4:10 pm

1 stop10h 16m

George Town Owen Roberts Intl

Sat 4/12

7:05 pm-11:54 pm

Nonstop4h 49m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 4/6

6:45 am-12:40 pm

1 stop5h 55m

George Town Owen Roberts Intl

Sun 4/13

1:45 pm-10:15 pm

1 stop8h 30m

$536

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-10:34 am

1 stop18h 49m

$545

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

12:51 pm-11:26 pm

1 stop10h 35m

$558

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sat 4/5

5:20 am-1:20 pm

1 stop8h 00m

George Town Owen Roberts Intl

Sat 4/12

3:20 pm-8:05 pm

Nonstop4h 45m

$564

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/23

6:30 pm-11:45 am

1 stop17h 15m

George Town Owen Roberts Intl

Thu 4/3

12:00 pm-12:20 am

1 stop12h 20m

$610

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 4/6

4:41 pm-1:30 pm

3 stops44h 49m

George Town Owen Roberts Intl

Sun 4/13

11:30 am-6:53 pm

2 stops31h 23m

$612

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 3/20

9:57 pm-11:40 am

2 stops13h 43m

George Town Owen Roberts Intl

Thu 3/27

2:00 pm-11:37 pm

1 stop9h 37m

$616

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 37 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.

Travel insights for flights from Wisconsin to Cayman Islands

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

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 February 20, 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 February 20, 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
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
2,801 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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 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 American Airlines. According to our data, you can fly for as low as $141. Users have also found prices from $211 and $217 on Air Canada and Southwest, 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.

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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 February 20, 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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