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Cayman Islands

$183+ Cheap flights from Milwaukee (MKE) 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Milwaukee to Cayman Islands

Keep the following information in mind while searching for Milwaukee to Cayman Islands flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$470
(Delta)

One-way from

$322
(American Airlines)

Popular in

March

Cheapest in

August

Average price

$602
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 Milwaukee-Mitchell to Cayman Islands
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One-way flight from Milwaukee-Mitchell to Cayman Islands
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Highest demand for flights based on searches. 6% potential increase in price ($46 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 October 2025
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Find flight deals from Milwaukee to Cayman Islands

Cheapest flights from Milwaukee to Cayman Islands
Explore the most affordable flight options available from Milwaukee to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Delta deal was found by Cheapflights users on 10/27. 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 12/115:45 amMKE - GCM
1 stop5h 50mDelta
Thu 12/181:50 pmGCM - MKE
1 stop11h 04mDelta
Deal found 10/27$470
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/115:00 amMKE - GCM
2 stops8h 44mAmerican Airlines
Thu 12/183:11 pmGCM - MKE
2 stops20h 18mAmerican Airlines
Deal found 10/27$475
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:05 amMKE - GCM
1 stop6h 40mUnited Airlines
Thu 11/275:45 pmGCM - MKE
2 stops24h 32mUnited Airlines
Deal found 10/28$533
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:48 pmMKE - GCM
2 stops16h 25mAmerican Airlines
Thu 11/271:25 pmGCM - MKE
2 stops25h 47mAmerican Airlines
Deal found 10/28$673
This Mytrip deal was found by Cheapflights users on 10/27. 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.
Thu 12/1110:34 amMKE - GCM
3 stops24h 01mMultiple Airlines
Thu 12/182:40 pmGCM - MKE
3 stops27h 47mMultiple Airlines
Deal found 10/27$1,162
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/225:45 amMKE - GCM
1 stop5h 40mDelta
Sat 11/291:50 pmGCM - MKE
1 stop11h 06mDelta
Deal found 10/28$2,076

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee 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 October 29, 2025.
Use the filters below to find and compare flights from Milwaukee to the Cayman Islands that are best for you.

Fly from

Milwaukee

Fly to

Cayman Islands

Route

Depart

Return

Price

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Fri 12/19

5:00 am-1:45 pm

1 stop7h 45m

George Town Owen Roberts Intl

Wed 12/24

2:50 pm-9:11 pm

1 stop7h 21m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 1/24

7:32 am-2:51 pm

1 stop6h 19m

George Town Owen Roberts Intl

Sat 1/31

3:51 pm-10:02 pm

1 stop7h 11m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Thu 12/11

5:45 am-12:35 pm

1 stop5h 50m

George Town Owen Roberts Intl

Thu 12/18

1:50 pm-11:54 pm

1 stop11h 04m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Thu 12/11

5:00 am-4:30 pm

2 stops10h 30m

George Town Owen Roberts Intl

Thu 12/18

2:50 pm-9:11 pm

1 stop7h 21m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 2/4

6:30 am-8:25 pm

1 stop12h 55m

George Town Owen Roberts Intl

Wed 2/11

12:16 pm-11:23 pm

1 stop12h 07m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Fri 2/6

6:00 am-1:45 pm

1 stop6h 45m

George Town Owen Roberts Intl

Sat 2/21

5:45 pm-10:30 am

2 stops17h 45m

$475

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Fri 2/6

3:53 pm-11:50 am

2 stops18h 57m

George Town Owen Roberts Intl

Fri 2/13

1:00 pm-11:30 pm

2 stops11h 30m

$475

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Thu 12/11

5:00 am-2:44 pm

2 stops8h 44m

George Town Owen Roberts Intl

Thu 12/18

3:11 pm-10:29 am

2 stops20h 18m

$475

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sun 2/15

6:00 am-2:30 pm

1 stop7h 30m

$183

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Fri 3/20

6:50 pm-10:45 am

2 stops15h 55m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 13 results
1
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Best time to book a flight from Milwaukee to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Milwaukee 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 Milwaukee to the Cayman Islands

What is the cheapest month to book a flight from Milwaukee to Cayman Islands?

Currently, March is the cheapest month in which you can book a flight from Milwaukee to Cayman Islands (average of $212). Flying from Milwaukee to Cayman Islands in September is currently the most expensive (average of $650). 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.

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 October 29, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Milwaukee to the Cayman Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,992 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,999 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Milwaukee 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 airport do you fly from for flights from Milwaukee to Cayman Islands?

    Milwaukee-Mitchell (MKE) is the airport you will fly out of if you book a flight from Milwaukee to Cayman Islands. It is only a 6.4 mi journey to Milwaukee-Mitchell (MKE) from Milwaukee’s city center.

  • How long is the flight from Milwaukee to Cayman Islands?

    There are many flights that can get you from Milwaukee to Cayman Islands in 6h 19m. Fly via United Airlines or American Airlines to get the fastest option. The distance between Milwaukee and Cayman Islands is about 1677 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Milwaukee to Cayman Islands that include hotel bookings?

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

  • How can I find direct flights from Milwaukee to Cayman Islands?

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

  • Can I find deals for business class flights from Milwaukee to Cayman Islands?

    Yes. Cheapflights offers flight deals from Milwaukee 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 Milwaukee to Cayman Islands?

    Currently, March is the cheapest month in which you can book a flight from Milwaukee to Cayman Islands (average of $212). Flying from Milwaukee to Cayman Islands in September is currently the most expensive (average of $650). 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 Milwaukee 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 Milwaukee to Cayman Islands

Discover the top 4 airlines that operate flights from Milwaukee 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$212Average$581FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$613FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$513Average$818FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$631FlexibilityNo cancel feeOn-time63%

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