$152 Find Cheap Flights from Milwaukee to Caribbean - Compare and Save

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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$556
Santo Domingo
Santo Domingo1 stop$660
Montego Bay
Montego Bay1 stop$453
Nassau
Nassau1 stop$478
Simpson Bay
Simpson Bay2 stops$495
Providenciales
Providenciales1 stop$436
Aguadilla
Aguadilla2 stops$568
Puerto Plata
Puerto Plata2 stops$700
St. John's
St. John's1 stop$796
Punta Cana
Punta Cana1 stop$556
Santo Domingo
Santo Domingo1 stop$660
Montego Bay
Montego Bay1 stop$453
Nassau
Nassau1 stop$478
Simpson Bay
Simpson Bay2 stops$495
Providenciales
Providenciales1 stop$436
Aguadilla
Aguadilla2 stops$568
Puerto Plata
Puerto Plata2 stops$700
St. John's
St. John's1 stop$796
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 $425 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 $425.

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 $809 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 $485 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $730 and $714 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

$152
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 10% 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 4219 reviews
7.0Food
8.6Crew
7.4Entertainment
8.0Comfort
8.1Boarding
Airline reviews

The service was fine, about the same as you get on most lower end airlines. I dont understand the perks of flying them much anymore for the cost.

4.0 OkayPatrick, Oct 2026
Read more Southwest reviews

The service was fine, about the same as you get on most lower end airlines. I dont understand the perks of flying them much anymore for the cost.

the flight was significantly delayed. Not much was done by the airline to compensate passengers

the flight itself was totally fine. The crew were great and very helpful. The flight was delayed, however, over an hour without a lot of information as to why.

Had to walk back and forth between concourses to figure out which gate I was supposed to be at. The app and the flight board in the airport had different gates listed. Was told numerous times to check bags only to get on the plane and find that there was plenty of room for bags. The flight was over an hour late which had me landing after the last train departed. WiFi was unusable

My experience was okay I changed my returning flight and I was charged extra money which I dont think should be the case, especially because I experienced small delays from my going flight. And many flights were either canceled or delayed after my original flight time. I believe some customers should have the ability to change flights due to certain situations

I've taken four flights with Southwest within the last three months and every single flight was delayed.

It was great and arrived home a little sooner than expected which is nice.

I fly out every other weekend and this is the 4th time my flight has been delayed at Southwest. I will be flying out twice a month on average for the next 6-7 months. If this is your average ‘on time’ I’ll probably be flying another airline.

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.

I enjoyed the whole flight and the crew was amazing i dont usually fly delta

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.

Worst boarding experience, flight extremely delayed causing super tight connect and deplaning was a disaster as ppl were pushing and shoving to get off. Then after flying over 8 hours had to get off a job to next flight. Limited beverage service in Business class (water or white wine) no food. The plane was very cold (temperature) so uncomfortable

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Seats needs to be wirer and food is very poor

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.

Air was off while waiting on the runway and the temperatures became very uncomfortably hot. Flight attendants were very loud and rude the entire flight.

I booked tickets from San Diego to Cincinnati months in advance to attend my sister’s wedding, a wedding where I was serving as the officiant. At 10:00 PM the night before my 6:00 AM flight (just 8 hours before departure), I received an alert that my first leg to Denver was delayed, causing me to miss my connecting flight to Cincinnati. When I called Frontier customer service, they informed me that they couldn't get me on any other flight that would get me there in time for the Saturday wedding, let alone the rehearsal dinner. Because I had a critical role in the wedding, I was forced to buy a last-minute ticket on another airline for three times the original price, costing me well over $1,000 extra. Even with the emergency flight, I still missed the rehearsal dinner entirely. When I spoke with Frontier, they agreed to refund my original ticket, but showed zero care or accountability for the massive financial burden and distress they caused. Their "compensation" for causing me to spend an extra $1,000+ and miss an irreplaceable family event? A $75 Frontier voucher. Frontier completely dropped the ball. Their customer service showed zero empathy, and their reliability is non-existent. I will never fly Frontier again, and no one else should either if they actually need to get where they want to go. Tip for anyone flying from Denver to Cincinnati: Avoid Frontier connecting flights or layovers at all costs, especially for time-sensitive events. Book direct flights with an airline that actually offers reliable customer support and rebooking options when delays occur.

I booked tickets from San Diego to Cincinnati months in advance to attend my sister’s wedding, a wedding where I was serving as the officiant. At 10:00 PM the night before my 6:00 AM flight (just 8 hours before departure), I received an alert that my first leg to Denver was delayed, causing me to miss my connecting flight to Cincinnati. When I called Frontier customer service, they informed me that they couldn't get me on any other flight that would get me there in time for the Saturday wedding, let alone the rehearsal dinner. Because I had a critical role in the wedding, I was forced to buy a last-minute ticket on another airline for three times the original price, it costing me well over $1,000 extra. Even with the emergency flight, I still missed the rehearsal dinner entirely. When I spoke with Frontier, they agreed to refund my original ticket, but showed zero care or accountability for the massive financial burden and distress they caused. Their "compensation” for causing me to spend an extra $1,000+ and miss an irreplaceable family event? A $75 Frontier voucher. Frontier completely dropped the ball. Their customer service showed zero empathy letting me know that it was Frontier who was the real victim by refunding my ticket price, and their reliability is non-existent. I will never fly Frontier again, and I strongly advise anyone who actually needs to arrive at their destination on time for an important event to book with literally any other airline.

Flight delayed and missed connection. Next available flight was a 10 hour delay.

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.

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