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

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Cheap Flights from Milwaukee to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$521
Santo Domingo
Santo Domingo1 stop$570
Montego Bay
Montego Bay1 stop$412
Nassau
Nassau1 stop$478
Simpson Bay
Simpson Bay2 stops$484
Providenciales
Providenciales1 stop$435
Aguadilla
Aguadilla1 stop$367
St. John's
St. John's1 stop$755
Puerto Plata
Puerto Plata2 stops$789
Punta Cana
Punta Cana1 stop$521
Santo Domingo
Santo Domingo1 stop$570
Montego Bay
Montego Bay1 stop$412
Nassau
Nassau1 stop$478
Simpson Bay
Simpson Bay2 stops$484
Providenciales
Providenciales1 stop$435
Aguadilla
Aguadilla1 stop$367
St. John's
St. John's1 stop$755
Puerto Plata
Puerto Plata2 stops$789
Booking Insights

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 $656 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 $656.

Can I save money by flying with a layover from Milwaukee to Caribbean Islands?

No, with an average price for the route of $423, 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 $589 (return) on average. On the other hand, the most expensive months are November and March, when the average cost of round-trip tickets is $764 and $757 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 13 weeks before departure.

Good to know

Low season

September

Cheapest flight

$119
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Milwaukee to San Juan

FAQs - booking Caribbean Islands flights

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

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

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

 
Need help choosing which airline to fly with from Milwaukee to Caribbean 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.
8.0
SouthwestOverall score based on 4215 reviews
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

4.0 OkayMather, Aug 2026
Read more Southwest reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

Flight left on time and was early landing. Seats not comfortable and not enough space…

Flight left on time. Seat spacing is way too small…

It would have been better if the flight was on time

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

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 no food, so :( to that one. The flight was delayed by 3 hours. Not Delta's fault. Not the crew's fault. Considering how tired all us passengers were, everything went surprisingly well. The flight crew were very helpful, friendly, and professional. I always 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.

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

Polaris seat is plush and conducive to sleep. Cabin crew was experienced, highly attentive and helpful when any need arose, such as finding a lost phone in the seat mechanism. Food was a disappointment, especially the Japanese items coming out of Newark all seemed a bit overcooked, though the empanada snacks served midway were a hit.

The flight was excellent. Their was no service as we boarded, the flight attendants spent about 30 minutes just taking and not really caring that the cabin was about 80 degrees and did not offered any beverage to first class passengers or any passenger. The flight from DEN to ONT is not long but not under an hour, we received one drink and bag of chips if you were lucky. I was in first class…. I did leave my hat on the plane and it only took less than five minutes for a United rep to locate and bring it to me.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

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.

Plane had mechanical issues. We had to de plane and board a different plane and were an hour late

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.

Boarding was relatively fast and easy and the crew was attentive throughout.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports