$162 Find Cheap Flights from Milwaukee to Caribbean - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Caribbean departing on 10/31. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Milwaukee to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$530
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$372
Oranjestad
Oranjestad1 stop$476
Nassau
Nassau1 stop$470
Kingston
Kingston2 stops$666
Simpson Bay
Simpson Bay2 stops$470
Providenciales
Providenciales1 stop$499
George Town
George Town2 stops$424
Willemstad
Willemstad2 stops$703
Aguadilla
Aguadilla2 stops$326
Puerto Plata
Puerto Plata2 stops$829
St. John's
St. John's2 stops$760
Punta Cana
Punta Cana1 stop$530
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$372
Oranjestad
Oranjestad1 stop$476
Nassau
Nassau1 stop$470
Kingston
Kingston2 stops$666
Simpson Bay
Simpson Bay2 stops$470
Providenciales
Providenciales1 stop$499
George Town
George Town2 stops$424
Willemstad
Willemstad2 stops$703
Aguadilla
Aguadilla2 stops$326
Puerto Plata
Puerto Plata2 stops$829
St. John's
St. John's2 stops$760

Book Cheap Milwaukee to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milwaukee to Caribbean

Sat, Aug 22 - Tue, Aug 25
Delta Logo
7:03 am - 4:38 pm
MKE
-
SJU
8h 35m
1 stop
Delta Logo
5:49 pm - 11:53 pm
SJU
-
MKE
7h 04m
1 stop
$326Delta
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
8:20 am - 11:15 pm
MKE
-
SJU
13h 55m
1 stop
American Airlines Logo
6:00 am - 5:00 pm
SJU
-
MKE
12h 00m
2 stops
$331American Airlines
Mon, Oct 5 - Fri, Oct 30
American Airlines Logo
6:27 pm - 12:09 pm
MKE
-
SJU
16h 42m
1 stop
American Airlines Logo
12:13 pm - 11:57 pm
SJU
-
MKE
12h 44m
1 stop
$332American Airlines
Mon, Oct 5 - Fri, Oct 30
American Airlines Logo
6:27 pm - 11:31 am
MKE
-
SJU
16h 04m
2 stops
American Airlines Logo
6:00 am - 9:49 pm
SJU
-
MKE
16h 49m
1 stop
$333American Airlines
Wed, Sep 2 - Mon, Sep 7
American Airlines Logo
5:00 am - 6:33 pm
MKE
-
SJU
12h 33m
2 stops
American Airlines Logo
7:03 am - 9:06 pm
SJU
-
MKE
15h 03m
1 stop
$337American Airlines
Wed, Sep 30 - Wed, Oct 21
Delta Logo
12:44 pm - 10:19 pm
MKE
-
SJU
8h 35m
1 stop
Delta Logo
7:30 am - 5:42 pm
SJU
-
MKE
11h 12m
1 stop
$345Delta
Sat, Nov 7 - Tue, Nov 10
United Airlines Logo
10:37 am - 9:00 pm
MKE
-
SJU
8h 23m
1 stop
United Airlines Logo
8:05 am - 5:38 pm
SJU
-
MKE
11h 33m
2 stops
$348United Airlines
Wed, Sep 2 - Mon, Sep 7
United Airlines Logo
6:15 am - 8:38 pm
MKE
-
SJU
13h 23m
2 stops
United Airlines Logo
1:00 am - 10:00 am
SJU
-
MKE
10h 00m
2 stops
$351United Airlines
Sat, Oct 10 - Sun, Oct 25
United Airlines Logo
10:42 am - 11:50 pm
MKE
-
SJU
12h 08m
2 stops
United Airlines Logo
3:55 pm - 10:45 pm
SJU
-
MKE
7h 50m
1 stop
$353United Airlines
Sat, Sep 19 - Sun, Oct 4
United Airlines Logo
5:00 am - 8:38 pm
MKE
-
SJU
14h 38m
2 stops
United Airlines Logo
3:56 pm - 10:59 pm
SJU
-
MKE
8h 03m
1 stop
$354United Airlines
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Milwaukee found in the last 5 days was to Punta Cana, at $628 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 $628.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $680, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Milwaukee to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Milwaukee to Caribbean is April, when tickets cost $101 (return) on average. On the other hand, the most expensive months are March and February, when the average cost of round-trip tickets is $1,063 and $892 respectively.

How far in advance should I book a flight from Milwaukee to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Milwaukee to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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 13 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$162
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 Montego Bay

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 4250 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

8.0 ExcellentAnonymous, Jul 2026
PHL - BNA
Read more Southwest reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

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.

Everything about this flight was good except for the very end when I reached my destination. Everyone from the tune to the wheelchair escorts were great with the case were great but I miss you with people at the check in this at the very end. I need help from the chicken desk because I forgot my pillow on the plane The female worker at the chicken desk said that they found my pillow and she was going to retrieve it for me. She left a 30 minutes without any update and her so she saw me walking back and forth waiting for her and they didn't even bother calling her or radioing her for any updates. They were busy because they were behind schedule and they were overwhelmed but thanks because at least glanced me and try to give me an update just a quick radio check or phone call. I don't care about the pillow but if you tell me to wait, I waited for at least half an hour before I said something and I just left because they wouldn't bother talking to me so I could, so everything's going in the review. I took pictures of the two men that were left working at the check-in counter. The totally ignored me despite the signals I've been giving them. I don't see any offers in the kayak review to add pictures or screenshots so I'm going to post another review I don't know their name but I'm pretty sure Delta will find other names when they see the review. Google with pictures. There was another guy at the chicken counter bring an orange workers vest who finally left after telling me that the girl that was retrieving my pillow is working the gates now. That would have been if they just told me that's what happened. But I had no update. Make me wait for nothing. Thank you Delta airlines!

We had a great experience with Delta. They helped us from the start at the kiosk all the way to our final destination, including help reassigning and upgrading our seats free of charge at the gates, escorts with the wheelchair for my brother and even getting our luggage at baggage claim for us. I also had special help because I forgot my pillow on the plane. The wheelchair escort contacted for associates at the check-in desk all the way back to the plane and retrieved my pillow for me.

Crew was real good, flight was smooth and came in early.

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 delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Staff could’ve been a little more cordial. The men were much more friendlier than the women. My daughter and I also missed the 2nd to last meal as we were sleeping but that is on us.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

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.

I found the seats ergonomically uncomfortable forcing the body to seat slightly hunched. For a short flight I worked on adjustments but for a longer flight, it would be difficult.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

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.

It was awful everything about it terrible I will never ever ever ride it again

It was awful ....my first time flying on it and I will NEVER fly it again ....everything about it was terrible .....most especially the flight attendants

Crew was kind of grumpy and there was no beverage service at all. Sodas were $4. Disappointing.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports