$364 Find Cheap Flights from Milwaukee to Grand Cayman

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 Grand Cayman departing on 2/25. 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

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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Flight Deals

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

Sat, Apr 25 - Fri, May 15
American Airlines Logo
6:32 pm - 11:33 am
MKE
-
GCM
17h 01m
1 stop
American Airlines Logo
12:35 pm - 10:43 am
GCM
-
MKE
22h 08m
2 stops
$364American Airlines
Sat, Apr 18 - Tue, Apr 21
American Airlines Logo
6:32 pm - 11:33 am
MKE
-
GCM
17h 01m
1 stop
American Airlines Logo
12:35 pm - 9:57 pm
GCM
-
MKE
9h 22m
1 stop
$379American Airlines
Sat, Apr 18 - Tue, Apr 21
American Airlines Logo
6:32 pm - 11:33 am
MKE
-
GCM
17h 01m
1 stop
American Airlines Logo
2:10 pm - 7:41 am
GCM
-
MKE
17h 31m
2 stops
$384American Airlines
Wed, Apr 1 - Wed, Apr 8
United Airlines Logo
6:50 am - 12:45 pm
MKE
-
GCM
5h 55m
1 stop
United Airlines Logo
1:50 pm - 10:20 pm
GCM
-
MKE
8h 30m
1 stop
$415United Airlines
Fri, Apr 10 - Thu, Apr 16
Delta Logo
5:45 am - 11:47 am
MKE
-
GCM
6h 02m
1 stop
Delta Logo
1:25 pm - 8:35 pm
GCM
-
MKE
7h 10m
1 stop
$430Delta
Wed, Apr 8 - Wed, Apr 22
American Airlines Logo
6:42 pm - 11:33 am
MKE
-
GCM
16h 51m
1 stop
American Airlines Logo
2:05 pm - 10:59 am
GCM
-
MKE
20h 54m
2 stops
$435American Airlines
Tue, Apr 21 - Mon, Apr 27
American Airlines Logo
5:00 pm - 11:33 am
MKE
-
GCM
18h 33m
2 stops
American Airlines Logo
12:35 pm - 10:57 pm
GCM
-
MKE
10h 22m
1 stop
$455American Airlines
Sat, Apr 25 - Fri, May 15
American Airlines Logo
6:32 pm - 11:33 am
MKE
-
GCM
17h 01m
1 stop
American Airlines Logo
12:35 pm - 10:47 pm
GCM
-
MKE
10h 12m
1 stop
$459American Airlines
Thu, Mar 19 - Wed, Mar 25
United Airlines Logo
7:00 am - 12:45 pm
MKE
-
GCM
5h 45m
1 stop
United Airlines Logo
1:50 pm - 10:43 pm
GCM
-
MKE
8h 53m
1 stop
$471United Airlines
Wed, Apr 1 - Wed, Apr 8
American Airlines Logo
6:20 am - 7:15 pm
MKE
-
GCM
12h 55m
2 stops
American Airlines Logo
2:10 pm - 10:59 am
GCM
-
MKE
20h 49m
2 stops
$476American Airlines
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 $413, 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 September, when the average cost of round-trip tickets is $820 and $685 respectively.

Good to know

Low seasonSeptember
Cheapest flight$215
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly with an average 34% 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.

Reviews of the top 3 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.
7.9
DeltaOverall score based on 8207 reviews
7.8Entertainment
7.2Food
7.9Comfort
8.1Boarding
8.5Crew
Airline reviews

First flight out and was 85 minutes delayed. Notification came out way too late

4.0 OkayJason, Feb 2026
SEA - SLC
Read more Delta reviews

First flight out and was 85 minutes delayed. Notification came out way too late

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

Once boarding started it was pretty quick. Food was inedible; cold and salty..

Entertainment kept turning itself off. Gave up on watching a movie.

Both the WIFI and entertainment did not work for 2.5h

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.

No Snacks or Entertainment. The flight was short, snacks should still be given.

We lost a day of our vacation because AA did not get the plane to the gate on time. Even though the gate attendant was very clear that it was not weather related, AA would do nothing because there was some snow that day. They basically said the gate attendant was wrong even though she was on the front line of the situation and they were not.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports