$470 Find Cheap Flights from Milwaukee to Grand Cayman

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 Grand Cayman departing on 1/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Grand Cayman

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Grand Cayman, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Grand Cayman, as well as popular online travel agencies
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Cheap Flights from Milwaukee to Grand Cayman

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stop$470
George Town
George Town1 stop$470

Book Cheap Milwaukee to Grand Cayman 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 Grand Cayman 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 Grand Cayman

Tue, Jan 20 - Wed, Jan 28
Delta Logo
5:45 am - 12:35 pmMKE-GCM
5h 50m1 stop
Delta Logo
2:00 pm - 11:27 pmGCM-MKE
10h 27m1 stop
$470Delta
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Sun, Sep 28 - Mon, Oct 6
Delta Logo
5:40 am - 11:36 amMKE-GCM
5h 56m1 stop
Delta Logo
12:55 pm - 11:55 pmGCM-MKE
11h 00m1 stop
$504Delta
Find Deal
Thu, Jan 22 - Tue, Jan 27
Delta Logo
5:45 am - 12:35 pmMKE-GCM
5h 50m1 stop
Delta Logo
2:00 pm - 11:27 pmGCM-MKE
10h 27m1 stop
$514Delta
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Fri, Jan 23 - Fri, Jan 30
Delta Logo
12:20 pm - 12:50 pmMKE-GCM
23h 30m2 stops
Delta Logo
2:00 pm - 11:27 pmGCM-MKE
10h 27m1 stop
$518Delta
Find Deal
Sat, Nov 29 - Sat, Dec 6
United Airlines Logo
5:00 am - 1:45 pmMKE-GCM
7h 45m1 stop
United Airlines Logo
5:30 pm - 11:29 amGCM-MKE
18h 59m2 stops
$542United Airlines
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Mon, Dec 1 - Sat, Dec 6
Southwest Logo
8:15 pm - 12:35 pmMKE-GCM
15h 20m2 stops
Southwest Logo
1:55 pm - 10:15 pmGCM-MKE
9h 20m1 stop
$547Southwest
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Sat, Jan 17 - Sat, Jan 24
American Airlines Logo
6:19 am - 12:56 pmMKE-GCM
5h 37m1 stop
American Airlines Logo
4:40 pm - 11:04 pmGCM-MKE
7h 24m1 stop
$548American Airlines
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Tue, Jan 20 - Tue, Jan 27
American Airlines Logo
6:58 am - 2:00 pmMKE-GCM
6h 02m1 stop
American Airlines Logo
8:30 am - 11:04 pmGCM-MKE
15h 34m2 stops
$552American Airlines
Find Deal
Sat, Feb 21 - Fri, Feb 27
Southwest Logo
6:00 pm - 12:55 pmMKE-GCM
17h 55m2 stops
Southwest Logo
1:50 pm - 11:50 pmGCM-MKE
11h 00m2 stops
$620Southwest
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Sun, Jan 18 - Sun, Jan 25
United Airlines Logo
6:00 am - 1:45 pmMKE-GCM
6h 45m1 stop
United Airlines Logo
2:50 pm - 8:48 pmGCM-MKE
6h 58m1 stop
$668United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Milwaukee to Grand Cayman flights

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

Can I save money by flying with a layover from Milwaukee to Grand Cayman?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $601, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Grand Cayman, 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 Grand Cayman 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 $716 respectively.

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

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 Grand Cayman, 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 Grand Cayman, 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$470
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 Grand Cayman flights

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

    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 Grand Cayman.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman?

    The cheapest time of day to fly to Grand Cayman 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 Grand Cayman 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 Grand Cayman

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Grand Cayman. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Milwaukee to Grand Cayman? 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 4241 reviews
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

6.0 GoodCarl, Aug 2025MSY - BWI
Read more Southwest reviews

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

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.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

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!

Great service on board. Boarding a bit slow due to process. Food was pretty average.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

I flew with my dog and had already purchased my dog’s ticket. Even that morning I had called costumer service to insure that my husband and I had seats together since the website was giving me an error when choosing our seats and the representative mentioned our dog. I showed up early to the airport and when I got to the gate and we started boarding I was help back and told that I was supposed to have a yellow tag and that I should have checked in at the counter for them to give me that tag. I was not aware of this, the representative on the phone did not say anything. Nor did I see it anywhere in the checking process online, so if you travel with a pet and are not checking in luggage, just know that you still have to go to the check in counter when arriving at the airport unless you want to be the last one to board and not have room for your carry on in the overhead bins. Other than that, I had a great experience.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

From the first moment you interact with United Airlines, you can expect nothing less but extreme frustration. The baggage handler at the bag drop seems completely unbothered by the presence of customers waiting in line. No help was extended to load the baggage whatsoever. And if any of your bags is overweight by 0.01 pound they will make you re-distribute everything in your suitcase just to play power trip. When it was time to board no help was extended to customers to locate their seats. Moreover. It was a chaotic mess at the gate when it was unclear who should board first and everyone just bunched up, trying to get on the plane. I am sure the crew was doing their best to perform their jobs while being paid their wages however it shouldn’t be that hard to smile once or twice when you’re in the business if serving customers. It is a shame for the United States of America to have a flagship carrier of such low caliber. Our flight was also delayed by about an hour and a half due to further delays prior to our inbound flight. Being someone who has travelled for both business and leisure in Asia, Europe, and South America I have never experienced such poor quality of service.

Very small cramped plane for an international flight. Everything else was good, but it was maybe the smallest comfort-wise I've ever been on for longer than 3-4 hours and the trip was 7.5

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

Our bags took a long time to get unloaded once we landed.

Boarding: Boarding was a bit of a mess. Our tickets indicated "BC" for Business Class, but we and many others were confused as that was not indicated anywhere in the airport, so we didn't know when we're supposed to board. The airplane: The airplane was nice. However, we sat near the back of the business class cabin and the flight attendants and passengers from other cabins would constantly move the curtain (which was very loud), preventing me from fallling asleep on my 8 hour flight. The flight crew: Amazing, generally. However, they nearly forgot to serve breakfast to me. The flight food: I was able to select my meal for dinner, which was really good. Breakfast was a bit of a mess, however. The crew forgot to serve me breakfast until the last minute. Very little was available by the time they remembered. The entertainment: Paltry, underwhelming, and dated. Not one new movie was available. Bottom line: For the money, you might want to consider other options for your international business class flights.

We fly American Airlines quite a bit. And we always fly business class when traveling internationally. We were a bit disappointed with the comfort of this particular plane as well as the entertainment options.

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

Did not get the seat I selected and paid for.

We arrived 4 hours early and still almost missed the flight because they weren’t able to access one of the boarding tickets. They then sent hour bags late and we were all of our without clothing and eventually had to take an expensive cab back and forth to the airport as they wouldn’t deliver the bag which arrived late at night that day and we would have to wait until noon the began day (messing up a second day of plans). Also, all the food has dairy or pork. No vegan or even vegetarian option in the flight—even for purchase.

The flight was canceled 3 hours after original take off time

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