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Grand Cayman

$470+ Cheap flights from Milwaukee (MKE) to Grand Cayman

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — GCM
Dez 21 — Dez 281
So 12/21
So 12/28
1 adult, Economy
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Cheap flight deals from Milwaukee to Grand Cayman

Keep the following information in mind while searching for Milwaukee to Grand Cayman flight deals. Data was last updated November 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$447
(American Airlines)

Popular in

March

Cheapest in

August

Average price

$608
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 Grand Cayman
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Highest demand for flights based on searches. 5% potential increase in price ($33 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 November 2025
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Find flight deals from Milwaukee to Grand Cayman

Cheapest flights from Milwaukee to Grand Cayman
Explore the most affordable flight options available from Milwaukee to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2025.

This Delta deal was found by Cheapflights users on 11/20. 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.
So 12/215:40 amMKE - GCM
1 stop5h 56mDelta
Do 12/253:42 pmGCM - MKE
1 stop8h 01mDelta
Deal found 11/20$470
This United Airlines deal was found by Cheapflights users on 11/20. 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.
So 12/215:00 amMKE - GCM
2 stops10h 35mUnited Airlines
Do 12/255:45 pmGCM - MKE
2 stops18h 42mUnited Airlines
Deal found 11/20$489
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Sa 12/208:02 pmMKE - GCM
2 stops14h 55mAmerican Airlines
Mi 12/247:30 amGCM - MKE
2 stops15h 26mAmerican Airlines
Deal found 11/20$589
This United Airlines deal was found by Cheapflights users on 11/20. 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.
Sa 12/206:36 amMKE - GCM
2 stops32h 59mUnited Airlines
Sa 12/275:45 pmGCM - MKE
2 stops28h 26mUnited Airlines
Deal found 11/20$600
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Sa 12/208:02 pmMKE - GCM
1 stop17h 33mAmerican Airlines
Sa 12/273:45 pmGCM - MKE
1 stop9h 14mAmerican Airlines
Deal found 11/20$673

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee 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 November 21, 2025.
Use the filters below to find and compare flights from Milwaukee to Grand Cayman that are best for you.

Fly from

Milwaukee

Fly to

Grand Cayman

Route

Depart

Return

Price

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sa 1/17

7:00 am-2:00 pm

1 stop6h 00m

George Town Owen Roberts Intl

Sa 1/24

2:05 pm-7:58 pm

1 stop6h 53m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sa 1/17

5:00 am-4:20 pm

2 stops10h 20m

George Town Owen Roberts Intl

Sa 1/24

2:50 pm-10:56 pm

1 stop9h 06m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Fr 2/6

7:32 am-2:35 pm

1 stop6h 03m

George Town Owen Roberts Intl

Fr 2/13

12:54 pm-10:48 pm

1 stop10h 54m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sa 1/24

5:15 am-2:00 pm

1 stop7h 45m

George Town Owen Roberts Intl

Sa 1/31

3:25 pm-11:46 pm

1 stop9h 21m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

So 12/21

5:40 am-12:36 pm

1 stop5h 56m

George Town Owen Roberts Intl

Do 12/25

3:42 pm-10:43 pm

1 stop8h 01m

$470

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sa 2/7

5:00 am-4:35 pm

2 stops10h 35m

George Town Owen Roberts Intl

Sa 2/14

5:30 pm-10:30 am

2 stops18h 00m

$475

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Best time to book a flight from Milwaukee to Grand Cayman

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

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

Currently, March is the cheapest month in which you can book a flight from Milwaukee to Grand Cayman (average of $212). Flying from Milwaukee to Grand Cayman 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 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 November 21, 2025.
Read through reviews of airlines operating flights from Milwaukee to Grand Cayman, such as Southwest, Delta, and United Airlines. 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
4,251 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

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
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

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
8,002 reviews
Southwest
8.0
Very good
4,251 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

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
9,028 reviews
Southwest
8.0
Very good
4,251 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

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
11,047 reviews
Southwest
8.0
Very good
4,251 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

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 Grand Cayman. 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 Grand Cayman?

    Milwaukee-Mitchell (MKE) is the airport you will fly out of if you book a flight from Milwaukee to Grand Cayman. 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 Grand Cayman?

    Delta and United Airlines can get you from Milwaukee to Grand Cayman in just under 6h. Your travel time can differ by up to 4h 20m. There are 1677 mi between Milwaukee and Grand Cayman. This flight may include one or multiple stops.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Milwaukee to Grand Cayman (average of $212). Flying from Milwaukee to Grand Cayman 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 Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to George Town flights
Minneapolis to George Town flights
Milwaukee to George Town flights
Madison to George Town flights
O'Hare Intl to Cayman Brac flights

Top 4 airlines flying from Milwaukee to Grand Cayman

Discover the top 4 airlines that operate flights from Milwaukee 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 November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$212Average$581FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$613FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$513Average$814FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$526Average$631FlexibilityNo cancel feeOn-time63%

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