
Cheap Flights from Milwaukee to Caribbean
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook Cheap Milwaukee to Caribbean Plane Tickets
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KAYAK's insights & trends for Milwaukee to Caribbean flights
Get data-powered insights and trends into flights from Milwaukee to Caribbean to help you find the cheapest flights, the best time to fly and much more.
What is the cheapest Milwaukee to Caribbean flight route?
The cheapest ticket to Caribbean 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?
No, with an average price for the route of $835, prices are generally cheapest when you fly direct.
What is the cheapest month to fly from Milwaukee to Caribbean?
The cheapest month for flights from Milwaukee to Caribbean is January, when tickets cost $477 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $747 and $692 respectively.
How far in advance should I book a flight from Milwaukee to Caribbean?
To get a below average price on the flight from Milwaukee to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.
Which airlines fly non-stop between Milwaukee and Caribbean?
There are 3 airlines that fly nonstop from Milwaukee to Caribbean. They are: American Airlines, Sun Country Air and United Airlines. The cheapest price of all airlines flying this route was found with United Airlines at $235 for a round-trip flight to San Juan Luis Munoz Marin Intl Airport (SJU). On average, American Airlines offers the best prices for nonstop flights between Milwaukee and Caribbean.
Which airlines provide the cheapest flights from Milwaukee to Caribbean?
In the past 5 days, the cheapest round-trip tickets from Milwaukee to Caribbean were found on Southwest ($322) and United Airlines ($354).
How long does a flight from Milwaukee to Caribbean take?
The duration of a flight to Caribbean depends on your arrival airport. The shortest routes to Caribbean from Milwaukee are to Punta Cana, which takes 4h 32m, Nassau, which takes 5h 20m, and Montego Bay, which takes 6h 48m.
Which cabin class options are there for flights between Milwaukee and Caribbean?
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
Good to know
Low season | September |
|---|---|
High season | March |
Cheapest flight | $100 |
FAQs - booking Caribbean flights
Reviews of the top 5 airlines serving from Milwaukee to Caribbean
Flight attendant skipped about 6 rows for drink service. I got a side eye when I asked for a drink - like it was an inconvenience or my mistake. He shouldn't be on a flight if he doesn't like his job and doesn't have customer service first attitude.
Flight attendant skipped about 6 rows for drink service. I got a side eye when I asked for a drink - like it was an inconvenience or my mistake. He shouldn't be on a flight if he doesn't like his job and doesn't have customer service first attitude.
The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.
They did not fix the wifi that they knew was an issue on an earlier flight. The flight was filled with business people that were clearly frustrated not being able to work. That can’t happen on a 3 1/2 hour flight. Would rather have been delayed a bit.
The WiFi did not work three hours of productivity lost. 15 people from the firm were on the flight. Loss of revenue
Very rude stewardess; there was a senior citizen woman next to me who asked the stewardess for help getting her purse out of the overhead bin, and it was as though she asked the stewardess for $1M . . . . I was shocked how rude that stewardess was. The stewardess also refused to get the senior citizen woman a drink about half way thru the flight, telling her that we were almost landing . . . . that stewardess made my flight (and in particular the flight of the senior citizen next to me) very uncomfortable
Overall good experience...exception: very cold temp in teh cabin.
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.
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.
There was overbooking that delayed boarding. Then an airport emergency lockdown that caused further delays in boarding. However the time was made up during flight and there was a minimal delay in landing. Everything else was excellent.
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.
typical but they have finally enhanced the wifi on some UA flights. Boy, its such a huge improvement
This was a small aircraft (relatively) and we were delayed half an hour on takeoff, which is not the airlines fault.
Return flight was perfect. All on time and no hiccups. However, going was another story. I don't blame United for the weather, but I am rather disappointed in its response to my getting stranded in my layover city for the night. United gave me a $20 food voucher. That's it. But besides this policy, the employees were incredibly helpful rerouting me to my final destination in Fort Lauderdale, FL. So overall, 8 out of 10. 10 out of 10 for flight comfort, inflight service and before flight service. 5 out of 10 for layover handling.
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.
Great flight, no problems. I wish they would increase the checked bag weight limit. Packing was very stressful.
My experience with Frontier was terrible. We were delayed for 2 hours. At one point during the wait at the gate I left to go get a sandwich - I was gone probably 15 minutes. In my absence, they decided to move our flight up, boarded and left. When I came back the two attendants were very rude and I unavoidably had to purchase another ticket on the next flight. During this whole time, the Frontier app did not update the departure time, so I was SOL.
Flight delayed 9 hours. On tarmac for over an hour after arrival. Will never book with Frontier under any circumstances ever again.
My ATL–CVG Frontier flight was disappointing due to both an operational issue and unprofessional customer service. After everyone had boarded and the aircraft had pushed back from the gate, we were delayed because the passenger count did not match the flight manifest. The crew counted passengers approximately six times before the aircraft returned to the gate and gate agents boarded to help resolve the discrepancy. We were ultimately advised that a family had been allowed to board but not all of their boarding passes had been properly scanned. This resulted in a departure delay of nearly an hour. I did appreciate that the pilot kept passengers informed and tried to reassure us that some of the delay could be recovered during the flight. My greater concern was the customer-service experience. I am a Frontier Elite Platinum member and was seated within the first five rows. When I boarded, the overhead bins near my seat were already closed. I opened two bins to see whether my small backpack would fit. A female flight attendant sharply told me that a closed bin meant it was full, although the second bin clearly had available space. When I tried to ask whether I could simply place my backpack in that available space, she ignored me. Later, while the gate agents were working to resolve the passenger-count problem, I heard the same flight attendant make jokes about how many gate agents it takes to count passengers. She then made unnecessary comments about the male gate agent doing the count, men thinking they can do things better than women, and women knowing better and outliving men. Later in the flight, she also commented that passengers should know that the first thing they need to do is always be nice to the flight attendants. Courtesy absolutely should go both ways. Flight attendants deserve respect from passengers, but passengers also deserve respectful and professional treatment from the crew. Joking about colleagues who were actively trying to correct an operational problem, making gender-based comments in front of passengers, and being dismissive toward a passenger asking a simple baggage question were unnecessary and unprofessional. I fly enough to understand that delays and mistakes happen. What determines the quality of the experience is how those situations are handled. Unfortunately, the customer-service attitude on this flight made an already frustrating operational delay considerably worse.
Did not get on the flight, they had a gate change and my app never updated me! Trying to get flight credit
Flight was delayed by about an hour, once we arrived at LAX we had to take a shuttle to the baggage claim - it was completely disorganized. The agents at the shuttles were rude and unable to provide any information. Frontier charges extra for everything from bags to drinks - at the end it ends up being more expensive than flying the better airlines
Sat in the airport waiting for my flight for 5 hours. Finally got on the plane only to be thrown off and told that my flight was cancelled. Zero customer service. Nobody spoke to us. Just the worst
Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck
It was a no frills flight. Would have liked to be able to charge my device
Both flights were delayed. The sizing of bags is crazy. I know it is advertised as a no frills cheaper option but it does feel like you are being extorted for money the whole way-- $20 dollars to talk to a gate agent? Charging for soda a pretzels? I don't think I will be flying Frontier again if I can help it. That said, all the staff were wonderful.