$218 Find Cheap Flights from Milwaukee to the Cayman Islands

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 6/15. 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

Sat, Aug 29 - Sat, Sep 5
American Airlines Logo
7:00 am - 2:17 pm
MKE
-
GCM
7h 17m
1 stop
American Airlines Logo
3:17 pm - 10:57 pm
GCM
-
MKE
7h 40m
1 stop
$499American Airlines
Sat, Aug 29 - Sat, Sep 5
American Airlines Logo
6:48 pm - 11:00 am
MKE
-
GCM
16h 12m
2 stops
American Airlines Logo
12:30 pm - 7:44 am
GCM
-
MKE
19h 14m
2 stops
$504American Airlines
Wed, Nov 4 - Sat, Nov 7
American Airlines Logo
6:48 pm - 2:17 pm
MKE
-
GCM
18h 29m
2 stops
American Airlines Logo
9:00 am - 11:59 pm
GCM
-
MKE
15h 59m
2 stops
$509American Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
4:12 pm - 1:10 pm
MKE
-
GCM
20h 58m
2 stops
American Airlines Logo
11:55 am - 12:51 pm
GCM
-
MKE
24h 56m
2 stops
$523American Airlines
Fri, Jun 12 - Mon, Jun 15
Delta Logo
5:40 am - 11:34 am
MKE
-
GCM
5h 54m
1 stop
Delta Logo
12:59 pm - 11:59 pm
GCM
-
MKE
11h 00m
1 stop
$541Delta
Fri, Jun 12 - Mon, Jun 15
American Airlines Logo
5:53 pm - 10:55 am
MKE
-
GCM
17h 02m
2 stops
American Airlines Logo
12:01 pm - 11:47 pm
GCM
-
MKE
11h 46m
2 stops
$546American Airlines
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 - 11:27 am
GCM
-
MKE
23h 32m
2 stops
$567American Airlines
Wed, Nov 11 - Sun, Nov 15
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
$568Southwest
Wed, Nov 11 - Sun, Nov 15
American Airlines Logo
5:00 am - 8:20 pm
MKE
-
GCM
14h 20m
2 stops
American Airlines Logo
3:14 pm - 9:38 am
GCM
-
MKE
19h 24m
2 stops
$577American Airlines
Wed, Nov 4 - Sun, Nov 8
American Airlines Logo
6:48 pm - 11:58 am
MKE
-
GCM
16h 10m
2 stops
American Airlines Logo
1:40 pm - 8:00 am
GCM
-
MKE
19h 20m
2 stops
$582American Airlines
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 $857 and $625 respectively.

Good to know

Low seasonOctober
Cheapest flight$218
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 30% 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.
7.9
DeltaOverall score based on 8412 reviews
8.1Boarding
8.5Crew
7.8Comfort
7.2Food
7.8Entertainment
Airline reviews

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

8.0 Excellentsondra, May 2026
SRQ - LGA
Read more Delta reviews

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

The crew were efficient. The pilots seemed professional. It was a bit chilly in our seats. The sheet provided weren’t very helpful.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

It was a short flight so I was expecting too much

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Lost of requested seat assignments. Lost my husband's meal choice

They made nearly everyone check their bag because the overhead bins are way too small. Extremely inconvenient

Delayed delayed. Poor professionalism. Our seats changed and we pay for them

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

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

Information on your arrival and departure airports