$90 Find Cheap Flights from Milwaukee to Caribbean

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 2/14. 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.
1 adult
1 adult, Economy, 0 bags

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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$365
Santo Domingo
Santo Domingo1 stop$518
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$572
Nassau
Nassau1 stop$393
Kingston
Kingston1 stop$753
Simpson Bay
Simpson Bay1 stop$501
Providenciales
Providenciales2 stops$358
George Town
George Town1 stop$412
Willemstad
Willemstad1 stop$570
St. John's
St. John's1 stop$599
Puerto Plata
Puerto Plata1 stop$582
Aguadilla
Aguadilla2 stops$235
Punta Cana
Punta Cana1 stop$365
Santo Domingo
Santo Domingo1 stop$518
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$572
Nassau
Nassau1 stop$393
Kingston
Kingston1 stop$753
Simpson Bay
Simpson Bay1 stop$501
Providenciales
Providenciales2 stops$358
George Town
George Town1 stop$412
Willemstad
Willemstad1 stop$570
St. John's
St. John's1 stop$599
Puerto Plata
Puerto Plata1 stop$582
Aguadilla
Aguadilla2 stops$235

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

Mon, Dec 29 - Tue, Dec 30
Frontier Logo
12:08 pm - 2:50 amMKE-SJU
12h 42m1 stop
Frontier Logo
6:00 am - 6:26 pmSJU-MKE
14h 26m1 stop
$301Frontier
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Sat, Jan 31 - Wed, Feb 11
Multiple Airlines Logo
7:48 pm - 9:47 amMKE-SJU
11h 59m1 stop
Multiple Airlines Logo
8:40 am - 6:45 pmSJU-MKE
36h 05m2 stops
$302Multiple Airlines
Find Deal
Sun, Feb 8 - Sat, Feb 14
Delta Logo
7:00 am - 5:17 pmMKE-SJU
8h 17m1 stop
Delta Logo
7:30 am - 5:21 pmSJU-MKE
11h 51m1 stop
$305Delta
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Wed, Jan 28 - Thu, Feb 5
Delta Logo
10:15 am - 8:58 pmMKE-SJU
8h 43m1 stop
Delta Logo
6:27 pm - 11:44 pmSJU-MKE
7h 17m1 stop
$306Delta
Find Deal
Sat, Jan 31 - Mon, Feb 9
American Airlines Logo
6:00 am - 3:48 pmMKE-SJU
7h 48m1 stop
American Airlines Logo
6:00 am - 3:57 pmSJU-MKE
11h 57m1 stop
$308American Airlines
Find Deal
Sat, Jan 31 - Thu, Feb 12
United Airlines Logo
2:32 pm - 6:11 amMKE-SJU
13h 39m2 stops
United Airlines Logo
8:35 am - 2:05 pmSJU-MKE
7h 30m1 stop
$309United Airlines
Find Deal
Sun, Dec 14 - Sun, Dec 21
American Airlines Logo
6:50 pm - 2:25 pmMKE-PLS
18h 35m2 stops
American Airlines Logo
11:17 am - 11:00 pmPLS-MKE
12h 43m2 stops
$374American Airlines
Find Deal
Thu, Dec 18 - Tue, Dec 23
Spirit Airlines Logo
8:15 pm - 2:28 pmMKE-STT
16h 13m1 stop
Spirit Airlines Logo
3:23 pm - 7:20 pmSTT-MKE
29h 57m1 stop
$406Spirit Airlines
Find Deal
Thu, Dec 18 - Wed, Dec 24
Spirit Airlines Logo
8:15 pm - 2:28 pmMKE-STT
16h 13m1 stop
Spirit Airlines Logo
3:23 pm - 7:20 pmSTT-MKE
29h 57m1 stop
$408Spirit Airlines
Find Deal
Tue, Jan 27 - Sun, Feb 1
United Airlines Logo
2:32 pm - 1:50 pmMKE-AUA
21h 18m2 stops
United Airlines Logo
3:00 pm - 8:48 pmAUA-MKE
7h 48m1 stop
$604United Airlines
Find Deal
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 72 hours was to Montego Bay, at $540 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 72 hours was $687.

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 September, when tickets cost $315 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $559 and $532 respectively.

What’s the cheapest day of the week to fly from Milwaukee to Caribbean?

The average price of all round-trip flights from Milwaukee to Caribbean clicked on KAYAK for each day over the last 12 months.

When flying from Milwaukee to Caribbean, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Milwaukee, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

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 18 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$90
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 5% 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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $360 on average. Morning departures are around 13% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $458.

  • How many flights are there between Milwaukee and Caribbean per day?

    There is a maximum of 1 nonstop flight a day that takes off from Milwaukee and lands in Caribbean, with an average flight time of 4h 27m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 2 flights.

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.
8.0
SouthwestOverall score based on 4252 reviews
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Great. Seamless. Check in agent at kiosk international was amazing and extremely helpful.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

This was an older airplane. The cabin was constantly warm to hot throughout the 10 hour flight and there were no vents to personalize air flow. Also since it was an older plane, the material and comfort of the chairs were very uncomfortable. I left my flight with major soreness on my tailbone.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Even though we were delayed, we were able to make our connection

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

Always wish for more healthy, gluten free options. We have to bring our own.

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

I had a positive experience on American. I'm blind and traveling with a guide dog and the flight attendants were so kind, friendly, and helpful towards us. They checked in on us during the flight and they made us feel comfortable and welcomed. There was an hour delay before depature, but overall the flight was a smooth ride. I appreciate that there were no issues on this long flight back home.

We were told the flight was delayed 5 times, then it was moved to the next day.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

Just fine but comfort is always an issue since the seats are so close

The Flight was fine, the staff treated me well, the flight got delayed over 5 1/2 hours for maintenance issues....but it worked out OK,, they were very apologetic about it, and it is better to not fly if there is any issue than endanger peoples lives, so in reality that was a good thing, It did cost me extra for parking because I went beyond the time I had purchased for parking at MSP. But all in all, Good flight

I did not take this flight because the reservation made by Kayak was wrong! Kayak owes me a trip from Minneapolis to Duluth.

When I got to the airport in Seattle, they told me the flight "did not exist". Kayak reserved me a seat on a flight that did not exist. This is inexcusable. I was able to change my reservation to a flight that actually did exist, but the flight was later and then I didn't make it in time for the next leg of my trip from Minneapolis to Duluth. Kayak owes me a trip from Minneapolis to Duluth, and a big apology for messing up my reservation.

The plane was freezing cold. Asked for a blanket and there were none. Was told twice that the pilots would warm the plane and it never happened Worst experience flying ever

Multiple delays because they screwed up on the crew schedule and had to wait for over an hour for more people to come.

The Wi-Fi was off, the arm rests are hard plastic.

The assistance with the wheel chairs was fabulous. All the people were so very friendly and helpful. I want to thank them all.

We almost missed our return flight. We got to the gate one minute from closing the cabin door, and the agent got us aboard the plane! We are so very grateful!!!!!

I already filled out a survey for this flight. We booked through KAYAK with airfare assist, and airfare assist did not confirm or honor our flight. Therefore, we had to go to a different place with a different travel agency. I tried very hard with airfare assist, They also promoted this on cheapair.com, but it was a bait and switch in both instances.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports