$396 Find Cheap Flights from Milwaukee to the Cayman Islands

This is the cheapest round-trip 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 9/7. 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

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Cheap Flights from Milwaukee to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stop$396
George Town
George Town1 stop$396

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.
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Sun, Sep 7 - Fri, Sep 12
Delta Logo
5:25 am - 11:37 amMKE-GCM
6h 12m1 stop
Delta Logo
12:52 pm - 8:49 pmGCM-MKE
7h 57m1 stop
$396Delta
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Mon, Jan 26 - Mon, Feb 2
United Airlines Logo
7:00 am - 1:45 pmMKE-GCM
5h 45m1 stop
United Airlines Logo
2:50 pm - 8:45 pmGCM-MKE
6h 55m1 stop
$451United Airlines
Find Deal
Sun, Sep 7 - Mon, Sep 15
Delta Logo
5:25 am - 11:37 amMKE-GCM
6h 12m1 stop
Delta Logo
12:52 pm - 8:49 pmGCM-MKE
7h 57m1 stop
$467Delta
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Tue, Nov 4 - Sat, Nov 8
Southwest Logo
5:50 am - 12:35 pmMKE-GCM
5h 45m1 stop
Southwest Logo
1:55 pm - 10:15 pmGCM-MKE
9h 20m1 stop
$505Southwest
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Mon, Dec 1 - Sat, Dec 6
Southwest Logo
8:10 pm - 12:35 pmMKE-GCM
15h 25m2 stops
Southwest Logo
1:55 pm - 10:15 pmGCM-MKE
9h 20m1 stop
$535Southwest
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Fri, Sep 5 - Sun, Sep 14
Delta Logo
5:25 am - 11:31 amMKE-GCM
6h 06m1 stop
Delta Logo
12:52 pm - 8:49 pmGCM-MKE
7h 57m1 stop
$538Delta
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Sat, Nov 29 - Sat, Dec 6
American Airlines Logo
5:00 am - 12:56 pmMKE-GCM
6h 56m1 stop
American Airlines Logo
4:15 pm - 10:05 pmGCM-MKE
6h 50m1 stop
$548American Airlines
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Sat, Oct 4 - Sat, Oct 11
American Airlines Logo
2:23 pm - 11:22 amMKE-GCM
20h 59m2 stops
American Airlines Logo
12:25 pm - 12:14 amGCM-MKE
11h 49m1 stop
$552American Airlines
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Tue, Nov 4 - Sat, Nov 8
United Airlines Logo
5:00 am - 4:30 pmMKE-GCM
10h 30m2 stops
United Airlines Logo
5:45 pm - 11:24 amGCM-MKE
18h 39m2 stops
$581United Airlines
Find Deal
Wed, Oct 15 - Mon, Oct 20
Air Canada Logo
12:05 pm - 11:55 amMKE-GCM
23h 50m2 stops
Air Canada Logo
12:50 pm - 5:06 pmGCM-MKE
28h 16m2 stops
$1,423Air Canada
Find Deal
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 August, when tickets cost $483 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $820 and $689 respectively.

How far in advance should I book a flight from Milwaukee to the Cayman Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Milwaukee to the Cayman Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$396
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 33% 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.

  • What is the cheapest time of day to fly to the Cayman Islands?

    The cheapest time of day to fly to the Cayman Islands is generally in the evening, when round-trip flights cost $558 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $612.

Reviews of the top 4 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.
8.0
SouthwestOverall score based on 4244 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

Southwest's seats are the least comfortable I have ever sat in.

4.0 OkayDavid, Aug 2025DTW - STL
Read more Southwest reviews

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

They made us board and then deboard due to mechanical issue which delayed the departure by almost 2 hours and we barely made our connecting flight. These quality checks should've been done before boarding not after.

Having to up charge for a seat assignment is not good. Delta can do better

I liked the friendliness of the staff. The cleanliness of all 3 planes.

Was charged for my luggage despite having been on one ticket from an international flight. Too tired to argue after 15 hours on flight. Was charged for rechecking it at JFK airport. Not sure why those off Kenya Airways were required to do that.

Plane was crowded and even when we hit altitude, the plane was hot, not enough air flow.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

The pilots were late and it made us 1 hour late. The meat was tough and bok choy was also tough.

Flight was delayed 3 hours. No food and drink vouchers was provided. They offered a mini pretzel bag and water .

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

The service was good, the food could have been better.

Staff was rude. Didn’t give water for 2 hours. Worst service

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

This flight was perfect. No complaints and only the highest regard for the crew and ground staff and how they executed perfectly. I fly a lot with United and would request predictability and transparency in their operations instead of last minute changes.

This is for UA2274 from Houston to Sacramento. The flight was delayed arriving due to mechanical issues so we left about 3 hours later than scheduled. When boarding the plane the temperature inside was excessive - likely close to 100. Pilot apologized and said it was going to improve at altitude, which it did. But before that I honestly thought there might have been more delays removing passengers made ill from the heat. We were delayed leaving due to another mechanical issue. There was not water on the plane due to a panel that was not secured. They did that quickly, but the combination of mechanical issues was rather disturbing and did not reflect well on United.

The comfort of the seats was great, the crew eased my child’s anxieties and the fact that I had full cans of my beverage choice was great.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

Sat on the ground in Cincinnati for 50 minutes before deplaning

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Crew should be nicer and emphatic with customers. Same cookies as the past 20 years. Seat are ok and the plane was clean though it was delayed.

Was not able to watch most shows on the entertainment site. They would not load

As smooth as you can expect. Some issues with boarding because the previous plane took forever to deplane but overall, a good experience.

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

There is no room, no gluten free options, or any free internet/entertainment. You have to bring your own tablet or smartphone because there are no screens.

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