
KAYAK's insights & trends for Milwaukee to Caribbean Islands flights
Get data-powered insights and trends into flights from Milwaukee to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.
What is the cheapest Milwaukee to Caribbean Islands flight route?
The cheapest ticket to Caribbean Islands from Milwaukee found in the last 5 days was to Punta Cana, at $394 round-trip. The most popular route is from Milwaukee (MKE) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $394.
Can I save money by flying with a layover from Milwaukee to Caribbean Islands?
No, with an average price for the route of $446, prices are generally cheapest when you fly direct.
What is the cheapest month to fly from Milwaukee to Caribbean Islands?
The cheapest month for flights from Milwaukee to Caribbean Islands is April, when tickets cost $588 (return) on average. On the other hand, the most expensive months are November and March, when the average cost of round-trip tickets is $758 and $740 respectively.
How far in advance should I book a flight from Milwaukee to Caribbean Islands?
To get a below average price on the flight from Milwaukee to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.
Good to know
Low season | September |
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High season | March |
FAQs - booking Caribbean Islands flights
Reviews of the top 5 airlines serving from Milwaukee to Caribbean Islands
I liked how it boarded fast. I do not like how the seats are just too narrow, and I’m not a big person.
I liked how it boarded fast. I do not like how the seats are just too narrow, and I’m not a big person.
Stop asking fir people to check carry on and then bind are free. Then the wait to get your luggage is ridiculous. This particular flight came with a 45 min wait, after waiting in tarmac waiting for a gate inhaling jet exhaust. And how about those landings?! Do the pilots not know the earth is coming up under the descending plane?! This is the only airline I get sick on. Every. Time.
I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.
Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.
Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.
One, we were met with more than six hours of delays with no information flowing from the airline to the passenger. I had to continually refresh for updates to departure time - which changed multiple times throughout the day. Updates were never pushed to me nor was an explanation provided for the delay until this morning. Two, while they claim that "due to the short flight" no beverage service would be provided. Our flight was mostly empty. I'd think given the massive inconvenience, SW could have shared a Diet Coke and some peanuts. And BTW, SW used to always make these available on this flight back in the day. Let's be honest, this is cost savings at the customer's expense.
Despite paying for an ‘upgraded’ seat in row 1, I had to put my luggage in the middle of the plane. Snacks were bleh and seat was small and uncomfortable and I am not large. Attendants were fine but not super helpful. Plane just seemed outdated.
It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.
Flight time kept changing and so did the gate. It was very frustrating
We were headed for Florida and anxious to get there. Everything was absolutely the best. This is our first time with Southwest and it’s now our go to airline. Best ever.
Gate agent and flight attendants were efficient, but more stern than warm.
The flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.
The Delta assistsed services were awesome for my aunt. So very helpful.
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.
The flight was for my mom in wheelchair the staff in Newark wer not friendly took a long time to even get a wheelchair she almost missed her flight because they finally got a chair few minutes before boarding they had to rush her to the gate. They took her carryon and checked it as a bag told her don’t worry free of charge but they charge the credit card anyway. She also told me the seats are not comfortable at all as if they were broken she could feel the bars in the seat SFO staff was much better overall she had the worst experience
Wifi is very frustrating - could not connect and therefore unable to work on the trip
Entertainment was great. Seats were good. They did not have my pre-ordered hot food product available but did comp me something cold in place of the item.
Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.
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.
My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.
The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.
The flight could have actually taken place. Canceled flight and no option to rebook that day.
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
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.
My seat was comfortable and I had plenty of leg room.
Boarding and crew were great, but seats are terribly uncomfortable. No food or entertainment options.
Everything went very smoothly! Thanks for a great first experience flying with small children!
Crew members great. Everything else a 0! Got on plane at 530am. Got de boarded for mechanical issue. Supposed to leave by 830 am. Zero communication from gate agents. Then supposed to leave by 230pm. Then delayed till 330pm. Still zero communication with gate agents. All they would say is if you have an issue call the 1800 number. You call and sit on hold minimum 45 minutes for zero answer. Finally board at 345pm didn’t take off till after 4pm! Sat in airport for 11 hours with 4 adults and 3 kids. Finally offered a $100 (we are sorry) voucher for next trip. Missed whole day in Florida had to change reservations in Florida! Absolute joke of an airline! And I usually really like sun country.
Booked through Kayak for $236. They canceled the flight unknown to me; retaining $100 for canceling it. Found out when I went to check in. Rebooked the same flight for $400. Incredibly disappointed. The Sun Country part was as to be expected. Crowded, no food, no arm room but got me where I wanted to go.
3 seperate extremely rude unhelpful staff. Delayed flight. Lost my bag
Sat between 2 big men. I was uncomfortable. Flight was delayed twice. About 2 hours altogether.
It was a good experience. I do wish the seats were roomier. Also, I did not like being charged for my carry on bag
Exceptional take off and landing in snow and wind…thank you to the well skilled pilots!
I liked entertainment system being downloaded on my iPad. The selections were limited but I appreciated being able to use my own screen. The flight was just fine. My only issue was both terminals being far from the main airport. Especially stoning at LAX near midnight and having to wait for a bus to take us to baggage pickup. Very inconvenient.