Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Milwaukee to the Cayman Islands from $228

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Milwaukee to the Cayman Islands departing on 7/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Milwaukee to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:50 pm - 12:35 pm
MKE
-
GCM
14h 45m
2 stops
Southwest Logo
1:55 pm - 7:25 pm
GCM
-
MKE
6h 30m
1 stop
$484Southwest
Mon, Nov 2 - Sat, Nov 7
Southwest Logo
5:10 am - 12:35 pm
MKE
-
GCM
6h 25m
1 stop
Southwest Logo
1:55 pm - 7:25 pm
GCM
-
MKE
6h 30m
1 stop
$490Southwest
Mon, Nov 2 - Sat, Nov 7
American Airlines Logo
6:48 pm - 2:17 pm
MKE
-
GCM
18h 29m
2 stops
American Airlines Logo
1:00 pm - 11:59 pm
GCM
-
MKE
11h 59m
2 stops
$495American Airlines
Mon, Nov 2 - Sat, Nov 7
American Airlines Logo
6:48 pm - 11:27 am
MKE
-
GCM
16h 39m
2 stops
American Airlines Logo
12:30 pm - 10:59 pm
GCM
-
MKE
10h 29m
1 stop
$500American Airlines
Wed, Aug 19 - Tue, Aug 25
American Airlines Logo
2:49 pm - 11:27 am
MKE
-
GCM
20h 38m
1 stop
American Airlines Logo
12:30 pm - 10:59 pm
GCM
-
MKE
10h 29m
1 stop
$506American Airlines
Wed, Aug 19 - Tue, Aug 25
American Airlines Logo
6:01 am - 8:20 pm
MKE
-
GCM
13h 19m
2 stops
American Airlines Logo
9:00 am - 6:01 pm
GCM
-
MKE
10h 01m
2 stops
$510American Airlines
Wed, Nov 4 - Fri, Nov 13
Southwest Logo
3:35 pm - 12:35 pm
MKE
-
GCM
20h 00m
2 stops
Southwest Logo
1:30 pm - 11:45 pm
GCM
-
MKE
11h 15m
1 stop
$524Southwest
Wed, Nov 4 - Fri, Nov 13
American Airlines Logo
6:35 am - 3:00 pm
MKE
-
GCM
8h 25m
1 stop
American Airlines Logo
12:30 pm - 10:59 pm
GCM
-
MKE
10h 29m
1 stop
$539American Airlines
Sat, Aug 8 - Fri, Aug 14
American Airlines Logo
6:00 pm - 11:00 am
MKE
-
GCM
17h 00m
2 stops
American Airlines Logo
2:10 pm - 10:59 pm
GCM
-
MKE
8h 49m
2 stops
$544American Airlines
Sat, Aug 8 - Fri, Aug 14
Delta Logo
6:00 am - 11:39 am
MKE
-
GCM
5h 39m
1 stop
Delta Logo
1:05 pm - 9:30 pm
GCM
-
MKE
8h 25m
1 stop
$550Delta
Sat, Sep 5 - Sat, Sep 12

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Southwest flights from Milwaukee to Cayman Islands

Our best Southwest deals on Milwaukee to Cayman Islands flight tickets
Southwest
Nov 2
MKE8:50 pmMilwaukee-Mitchell
14h 45m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 7
GCM1:55 pmGeorge Town Owen Roberts Intl
6h 30m
1 stop
MKE7:25 pmMilwaukee-Mitchell
$484
Southwest
Nov 2
MKE5:10 amMilwaukee-Mitchell
6h 25m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 7
GCM1:55 pmGeorge Town Owen Roberts Intl
6h 30m
1 stop
MKE7:25 pmMilwaukee-Mitchell
$490
Southwest
Nov 4
MKE3:35 pmMilwaukee-Mitchell
20h 00m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 13
GCM1:30 pmGeorge Town Owen Roberts Intl
11h 15m
1 stop
MKE11:45 pmMilwaukee-Mitchell
$524

American Airlines flights from Milwaukee to Cayman Islands

Our best American Airlines deals on Milwaukee to Cayman Islands flight tickets
American Airlines
Nov 2
MKE7:19 pmMilwaukee-Mitchell
17h 58m
2 stops
GCM2:17 pmGeorge Town Owen Roberts Intl
Nov 7
GCM3:18 pmGeorge Town Owen Roberts Intl
9h 41m
1 stop
MKE11:59 pmMilwaukee-Mitchell
$495
American Airlines
Aug 19
MKE6:48 pmMilwaukee-Mitchell
16h 39m
2 stops
GCM11:27 amGeorge Town Owen Roberts Intl
Aug 25
GCM12:30 pmGeorge Town Owen Roberts Intl
10h 29m
1 stop
MKE10:59 pmMilwaukee-Mitchell
$500
American Airlines
Aug 19
MKE2:49 pmMilwaukee-Mitchell
20h 38m
1 stop
GCM11:27 amGeorge Town Owen Roberts Intl
Aug 25
GCM12:30 pmGeorge Town Owen Roberts Intl
10h 29m
1 stop
MKE10:59 pmMilwaukee-Mitchell
$506

momondo 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, momondo users made 832,500 searches. Data last updated July 15, 2026.
Use the filters below to find and compare flights from Milwaukee to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Mon 11/2

8:50 pm-12:35 pm

2 stops14h 45m

George Town Owen Roberts Intl

Sat 11/7

1:55 pm-7:25 pm

1 stop6h 30m

$484
Quickest round-trip

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Mon 11/2

5:10 am-12:35 pm

1 stop6h 25m

George Town Owen Roberts Intl

Sat 11/7

1:55 pm-7:25 pm

1 stop6h 30m

$490

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Mon 11/2

6:48 pm-2:17 pm

2 stops18h 29m

George Town Owen Roberts Intl

Sat 11/7

1:00 pm-11:59 pm

2 stops11h 59m

$495

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 8/19

6:48 pm-11:27 am

2 stops16h 39m

George Town Owen Roberts Intl

Tue 8/25

12:30 pm-10:59 pm

1 stop10h 29m

$500

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 8/19

2:49 pm-11:27 am

1 stop20h 38m

George Town Owen Roberts Intl

Tue 8/25

12:30 pm-10:59 pm

1 stop10h 29m

$506

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 11/4

6:01 am-8:20 pm

2 stops13h 19m

George Town Owen Roberts Intl

Fri 11/13

9:00 am-6:01 pm

2 stops10h 01m

$510

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 11/4

3:35 pm-12:35 pm

2 stops20h 00m

George Town Owen Roberts Intl

Fri 11/13

1:30 pm-11:45 pm

1 stop11h 15m

$524

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 8/8

6:35 am-3:00 pm

1 stop8h 25m

George Town Owen Roberts Intl

Fri 8/14

12:30 pm-10:59 pm

1 stop10h 29m

$539

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 8/8

6:00 pm-11:00 am

2 stops17h 00m

George Town Owen Roberts Intl

Fri 8/14

2:10 pm-10:59 pm

2 stops8h 49m

$544

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 9/5

6:00 am-11:39 am

1 stop5h 39m

George Town Owen Roberts Intl

Sat 9/12

1:05 pm-9:30 pm

1 stop8h 25m

$550

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from Milwaukee to Cayman Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Cayman Islands?

If you aren’t able to travel to Cayman Islands during the month of March, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $390.

Cheap Milwaukee to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milwaukee to Cayman Islands

Fastest flight time

5h 39m

Direct flights

None
The fastest flight from Milwaukee to Cayman Islands takes 5h 39m
There are no direct flights from Milwaukee to Cayman Islands. There are no popular flight routes from Milwaukee to Cayman Islands.
Search flight deals

Frequently asked questions about flying from Milwaukee to the Cayman Islands

  • When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Cayman Islands?

    Prices for flights from Milwaukee-Mitchell Airport to Cayman Islands were last updated today.

  • How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Cayman Islands?

  • How old do you have to be to fly from Milwaukee-Mitchell Airport to Cayman Islands?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milwaukee-Mitchell Airport to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The travel and health documents required for your trip to Cayman Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Cayman Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Milwaukee to Cayman Islands

Compare and see reviews for airlines that fly from Milwaukee to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $399Free CancellationRating
7.4
9,988 reviews
Search United Airlines flights
DeltaPriceFrom $406Free CancellationRating
7.8
8,469 reviews
Search Delta flights
American AirlinesPriceFrom $470Free CancellationRating
7.1
11,806 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Milwaukee to Cayman Islands?

It is quick and easy to find Milwaukee to Cayman Islands flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Cayman Islands that suits you.

Can I find flights from Milwaukee to Cayman Islands with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Cayman Islands from Milwaukee with this policy.

How can momondo help me find flights from Milwaukee to Cayman Islands?

Once you have performed a search for Milwaukee to Cayman Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Milwaukee to Cayman Islands right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Cayman Islands from Milwaukee. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Cayman Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 8/14
Fri 8/21
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Cayman Islands

Popular cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to George Townfrom $268
Flights to Cayman Bracfrom $375
Flights to Little Caymanfrom $394