$85 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 2/10. 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 Cana2 stops$401
Santo Domingo
Santo Domingo2 stops$449
Montego Bay
Montego Bay1 stop$474
Oranjestad
Oranjestad2 stops$578
Nassau
Nassau1 stop$394
Kingston
Kingston2 stops$689
Simpson Bay
Simpson Bay2 stops$514
Providenciales
Providenciales1 stop$365
George Town
George Town1 stop$443
Willemstad
Willemstad2 stops$573
St. John's
St. John's2 stops$605
Puerto Plata
Puerto Plata2 stops$583
Aguadilla
Aguadilla1 stop$182
Punta Cana
Punta Cana2 stops$401
Santo Domingo
Santo Domingo2 stops$449
Montego Bay
Montego Bay1 stop$474
Oranjestad
Oranjestad2 stops$578
Nassau
Nassau1 stop$394
Kingston
Kingston2 stops$689
Simpson Bay
Simpson Bay2 stops$514
Providenciales
Providenciales1 stop$365
George Town
George Town1 stop$443
Willemstad
Willemstad2 stops$573
St. John's
St. John's2 stops$605
Puerto Plata
Puerto Plata2 stops$583
Aguadilla
Aguadilla1 stop$182

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, Jan 31 - Fri, Feb 6
American Airlines Logo
10:17 am - 11:59 pm
MKE
-
SJU
11h 42m2 stops
American Airlines Logo
6:05 am - 3:57 pm
SJU
-
MKE
11h 52m1 stop
$236American Airlines
Sun, Jan 18 - Sat, Jan 24
Frontier Logo
7:42 pm - 9:25 am
MKE
-
SJU
11h 43m1 stop
Frontier Logo
8:00 am - 6:53 pm
SJU
-
MKE
12h 53m1 stop
$237Frontier
Mon, Feb 2 - Wed, Feb 4
Multiple Airlines Logo
7:01 pm - 4:22 pm
MKE
-
SJU
19h 21m2 stops
Multiple Airlines Logo
6:00 am - 6:01 pm
SJU
-
MKE
14h 01m1 stop
$246Multiple Airlines
Sun, Feb 1 - Mon, Feb 9
United Airlines Logo
11:30 am - 9:00 pm
MKE
-
SJU
7h 30m1 stop
United Airlines Logo
2:05 am - 12:09 pm
SJU
-
MKE
12h 04m2 stops
$254United Airlines
Sat, Feb 28 - Fri, Mar 6
Delta Logo
5:23 am - 12:45 pm
MKE
-
PLS
6h 22m1 stop
Delta Logo
3:50 pm - 11:47 pm
PLS
-
MKE
8h 57m1 stop
$365Delta
Sat, Feb 28 - Fri, Mar 6
Delta Logo
7:00 am - 2:25 pm
MKE
-
PLS
6h 25m1 stop
Delta Logo
1:25 pm - 11:47 pm
PLS
-
MKE
11h 22m2 stops
$370Delta
Mon, Feb 9 - Tue, Feb 17
Multiple Airlines Logo
7:01 pm - 2:52 pm
MKE
-
STT
17h 51m1 stop
Multiple Airlines Logo
3:36 pm - 3:44 pm
STT
-
MKE
26h 08m1 stop
$376Multiple Airlines
Wed, Apr 1 - Wed, Apr 8
United Airlines Logo
5:10 am - 12:45 pm
MKE
-
GCM
7h 35m1 stop
United Airlines Logo
1:50 pm - 10:40 pm
GCM
-
MKE
8h 50m1 stop
$443United Airlines
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
5:40 pm - 12:55 pm
MKE
-
GCM
18h 15m2 stops
Southwest Logo
1:50 pm - 10:15 pm
GCM
-
MKE
9h 25m1 stop
$463Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
5:40 am - 11:35 am
MKE
-
MBJ
5h 55m1 stop
Southwest Logo
12:15 pm - 10:15 pm
MBJ
-
MKE
10h 00m2 stops
$511Southwest
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 Punta Cana, at $497 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 $497.

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 December and November, when the average cost of round-trip tickets is $657 and $519 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 18 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$87
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 3% 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.
8.0
SouthwestOverall score based on 4249 reviews
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

2.0 MediocreMatthew, Jan 2026
DAL - SAN
Read more Southwest reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

A 12 hour flight during the day with one real meal service - are you kidding? Also the breakfast was one of the worst and not what was listed

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

It was great with United overall except for two things. 1) It was a 5-hour flight and we were with kids, so we were asking for extra snacks. They were extremely reticent to dole them out even though there wasn't any meal and the kids were starting to hit their limit towards the end. 2) Baggage didn't arrive until 80 minutes after we landed.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

The staff was hospitable and professional. The seat had a bit of wear. The winner shade was stuck 1/4 open. I received the best of both worlds. The morning sun was able to come in and blind the screen i was trying to use while at the same time it was too low to look out and enjoy the view. Rather embarrassing for a 1st class ticket.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

I’m so sorry, I can’t remember her name, I believe it was Dimpti. She was stellar, also a mature Asian flight attendant, lots of flowers in her hair, just as amazing! But literally the crew was AWESOME . Only downside is there weren’t any charging outlets. Maybe I needed to ask a flight attendant , but it would’ve been nice to have one easily accessible.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

Aircraft was noisy, old and never dimmed the lights on a night flight even on business class! I flew 17 times on United and probably another 40 on other airlines United USA /Europe flights were the worst to include luggage delayed once going to europe and once coming back

Check how old the airframe is, some older ones have inoperable seat back entertainment or power.

The economy seats are very cramped and the food was bizarre. However, I did like the greek yogurt option for breakfast.

While I didn’t watch much tv I would have liked a few more options of TV series from Apple TV or hbo max ..

Everything about the flight was lovely. My only suggestion would be to offer a few more options of tv series from Apple TV or HBO.

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?

They should have allowed for extra time to de-ice the plane before boarding passengers. This delayed us about 10-15 mins after we boarded. Overall experience was fine. Crew was friendly and on top of everything. We didn’t have any issues during the flight.

Experience was good. We were delayed in leaving by 15 mins because the flight was waiting on a family that was late in getting to the gate. Food and drink options were as expected. I highly recommend checking in ahead of time using the airline’s app so that it’s quicker to get your luggage tags as soon as you arrive at the terminal. No more waiting in long lines!

Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!

We never made it due to delays on both ends. Gate attendant said it was mechanical but the system said otherwise, so no compensation. That’s not right.

Our flight from Eagle to Vail was delayed to the point we missed our connection to Savannah. Now we’re a family of 4 in a hotel room with luggage, no toiletries, no clean clothes. Gate attendant said the delay was mechanical but it was put in the system as something else so no compensation. That’s just wrong.

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.

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports