$228 Find Cheap Flights from Milwaukee to the Cayman Islands - Compare and Save

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

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Book Cheap Milwaukee to the Cayman Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to the Cayman Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milwaukee to the Cayman Islands

Mon, Nov 2 - Sat, Nov 7
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
Wed, Aug 19 - Tue, Aug 25
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
Sat, Aug 8 - Fri, Aug 14
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, Sep 5 - Sat, Sep 12
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
American Airlines Logo
7:00 am - 2:17 pm
MKE
-
GCM
7h 17m
1 stop
American Airlines Logo
11:55 am - 8:01 am
GCM
-
MKE
20h 06m
2 stops
$555American Airlines
Sat, Sep 5 - Sat, Sep 12
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
$561Delta
Booking Insights

KAYAK's insights & trends for Milwaukee to the Cayman Islands flights

Get data-powered insights and trends into flights from Milwaukee to the Cayman Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Milwaukee to the Cayman Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Milwaukee to the Cayman Islands is March, when tickets cost $359 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $888 and $810 respectively.

Good to know

Low seasonMay
Cheapest flight$228
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from Milwaukee to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Milwaukee to the Cayman Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Milwaukee to the Cayman Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to the Cayman Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to the Cayman Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Milwaukee to the Cayman Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Milwaukee to the Cayman Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milwaukee to the Cayman Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Milwaukee to the Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Milwaukee to the Cayman Islands

 
Need help choosing which airline to fly with from Milwaukee to the Cayman Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8465 reviews
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
7.8Comfort
Airline reviews

My flight home from Knoxville, TN, included a layover in Atlanta. I boarded the aircraft in Zone 5 and although there was limited overhead space, I was able to put my 'backpack' style roller-bag above my seat. Unfortunately, due to continued bad weather, we had to deplane. There were many people who would have missed their connection, so they rebooked. When we were re-boarding, the gate agent welcomed zone 5 and then made an announcement: All roller-bags for zone 5 passengers and higher will need to be gate checked. I promptly pushed the telescoping handle in and held my bag like a backpack. I was able to bring it on board, which was a relief. Upon entering the aircraft it became apparent that there was easily 40% open overhead space. There were audible signs of angry passengers who felt duped into checking their bags when in fact there were noticeably LESS passengers on the aircraft and TONS of overhead space. I'm not sure what kinds of parameters are used to determine when to cut off roller-bags from being brought on board, but it seemed deceptive and underhanded to have so many people get stuck checking their bags when clearly there was ample room for at least one more zone.

4.0 OkayErnest, Jul 2026
TYS - ATL
Read more Delta reviews

My flight home from Knoxville, TN, included a layover in Atlanta. I boarded the aircraft in Zone 5 and although there was limited overhead space, I was able to put my 'backpack' style roller-bag above my seat. Unfortunately, due to continued bad weather, we had to deplane. There were many people who would have missed their connection, so they rebooked. When we were re-boarding, the gate agent welcomed zone 5 and then made an announcement: All roller-bags for zone 5 passengers and higher will need to be gate checked. I promptly pushed the telescoping handle in and held my bag like a backpack. I was able to bring it on board, which was a relief. Upon entering the aircraft it became apparent that there was easily 40% open overhead space. There were audible signs of angry passengers who felt duped into checking their bags when in fact there were noticeably LESS passengers on the aircraft and TONS of overhead space. I'm not sure what kinds of parameters are used to determine when to cut off roller-bags from being brought on board, but it seemed deceptive and underhanded to have so many people get stuck checking their bags when clearly there was ample room for at least one more zone.

Flight was delayed and then "they did not have time to load food". No snack or drink at all for 1.5 how flight. Somebody wasn't prepared.

No Internet, no backseat screen, no nothing. I bought a Delta ticket and ended up on American Airlines. How did that happen?

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

Worst service- attendants dont want to help and sat us in front of bathroom

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

Our flight was great with an unexpected upgrade. However, four days into our travel we are still without a piece of luggage. The bag tracker has not been accurate, the airline is not communicating with me or the luggage delivery service and no one is willing to take responsibility or guarantee any kind of support or reimbursement. Unfortunately, we do not have the option to easily shop to replace items as we are currently on a cruise. I have been very disappointed by United Airlines response.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

Initial flight had an engine overheat - returned to DFW. Had another plane ready, but crew timed out. Had to wait 5h for boarding. Fully boarded and pilot says plane is not flight worthy. Deplane and go to the other end of the terminal. Wait an hour to board third plane because the crew couldn’t leave the second plane because no wheelchairs were brought to remove passengers. Finally take off and there is no catering (in flight service) even in first class. Very much an AA failure.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

Flight left more than 5 hours late. American's policy did not allow flight to be fueled or bags to be loaded due to intermittent lightning. We were on the plane for hours before having to deplane. They then changed the departure time to an earlier than expected time. We re-boarded and had to wait another 1.5 hours on the plane before it finally took off. Flight crew did not serve any food or drinks while airborne.

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

Boarding was relatively fast and easy and the crew was attentive throughout.

Everything you need to know for your flight from Milwaukee to the Cayman Islands

Information on your arrival and departure airports