$119 Find Cheap Flights from Milwaukee to Caribbean - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Milwaukee to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$630
Santo Domingo
Santo Domingo1 stop$640
Montego Bay
Montego Bay1 stop$433
Nassau
Nassau2 stops$599
Simpson Bay
Simpson Bay1 stop$539
Providenciales
Providenciales2 stops$520
Aguadilla
Aguadilla2 stops$418
Puerto Plata
Puerto Plata1 stop$730
St. John's
St. John's1 stop$781
Punta Cana
Punta Cana1 stop$630
Santo Domingo
Santo Domingo1 stop$640
Montego Bay
Montego Bay1 stop$433
Nassau
Nassau2 stops$599
Simpson Bay
Simpson Bay1 stop$539
Providenciales
Providenciales2 stops$520
Aguadilla
Aguadilla2 stops$418
Puerto Plata
Puerto Plata1 stop$730
St. John's
St. John's1 stop$781
Booking Insights

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?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $788 on average.

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 $741 and $700 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 3 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low season

September

Cheapest flight

$119
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 7% increase in price.
Flight from Milwaukee to San Juan

FAQs - booking Caribbean flights

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

    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 Caribbean.

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

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

    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 Caribbean 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 Caribbean?

    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 Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Milwaukee to Caribbean

 
Need help choosing which airline to fly with from Milwaukee to Caribbean? 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
SouthwestOverall score based on 4216 reviews
8.1Boarding
7.4Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

A List preferred boarding was nice Asked for a mask and cheerfully received Denver bag check-in is tricky. Not near other checking desk. Have to navigate to east security and up to level six for bag checkin. TSA busy and 20 minutes process thru pre lines Denver train to gates quick but one more thing to plan time for and long concourse walk to gate

10.0 ExcellentRon, Oct 2026
Read more Southwest reviews

A List preferred boarding was nice Asked for a mask and cheerfully received Denver bag check-in is tricky. Not near other checking desk. Have to navigate to east security and up to level six for bag checkin. TSA busy and 20 minutes process thru pre lines Denver train to gates quick but one more thing to plan time for and long concourse walk to gate

Not exactly Southwest’s problem, but the new Burbank airport is not great. No restaurants open and tons of work still to be completed. Can’t believe they opened the airport in that condition.

You made me miss my connecting flight. I can not go to Cleveland on teh revised flight you are sending as I will the entire meeting. I have no option that to fly back. I hope you compensate me for the loss.

Overall great! Internet was a little slow but no other issues.

Horrible communication from Southwest. No accountability. Flight was delayed for 4 hours and TSA closed in the interim. We were not allowed to our gate. Southwest knew this information and did not relay to their customers to arrive to the airport earlier.

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

Your computers were down and took a long time to check baggage

Southwest has lost most of what made it special. The flight attendants all used to seem fun and like they were having fun. Now they seem just miserable. They do NOT seem happy to give you your pretzels and drinks. They stick it in your hand or on your tray like it's an annoyance. They bark safety instructions at you. It's not just this flight but the last few SW flights I've had to SNA and SAN as well and it's not just me. I've informally surveyed my colleagues (business and leisure travelers) and these feelings are consistent. The tickets are similarly priced to other carriers and the seat assignments make boarding slower. The free luggage and free ability to change flights is still a differentiator. You lose that and there's virtually nothing special left.

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.

First, off the bat, the Delta gate attendant was rude, inattentive and gave us an attitude when we asked for clarification of our seats for this rebooked flight as we missed our connecting flight due to the delay from Berlin. Flight attendants were all but friendly, rushed through for water refills so you couldn’t even catch them to request more water. Snacks were just OK. Headphones for the movies were so bad that with the airplane noise, the volume of the movie wouldn’t go up enough to even understand the voices. I had to turn on CC to even know what was being said.

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 WiFi went out an hour before the flight was due to land so I did not get my money's worth.

I have been flying united for a long time but now I’m done

It's not United, but TSA security at Terminal A in Newark is a disaster and seriously makes me consider switching to flying out of JFK. The touchless TSA pre-check had a line of over 50 people and the bag screening was so slow that it limited the flow of people through the facial recognition process. It is the only airport that I frequent that has this issue and makes me reconsider whether I should fly out of Newark given the wasted time and frustration it causes. As I said, it is not a United issue but will impact United if people choose to stop utilizing Newark airport because of the poor experience.

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.

It got me to my destination? However we were an hour delayed departing, and we never received any updates or notifications from staff. Poor communication and customer service.

Frontier didn’t give us enough notice that our flight had been delayed. I was just entering the airport when I received the notice, less than 2hrs before my scheduled flight. They delayed it 1hr 22min because another jet left late out of Vegas. Frontier needs better communication with customers because I could have eaten at home and had someone drive me instead of paying for an Uber.

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

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.

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental