$90 Find Cheap Flights from Caribbean to Milwaukee

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Milwaukee departing on 2/25. 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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Everything you should know

Cheapest round-trip
$242
Typical prices: $267-$362
American Airlines
Thu 1/29Mon 2/2
SJU - MKE • 1 stop
Cheapest non-stop
$754
Sun Country Air
Thu 1/29Sun 2/1
PUJ - MKE • Non-stop
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Flight Deals

Cheap Flights from Caribbean to Milwaukee

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Milwaukee 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 Caribbean to Milwaukee

Thu, Jan 29 - Mon, Feb 2
American Airlines Logo
8:20 am - 3:20 pmSJU-MKE
9h 00m1 stop
American Airlines Logo
10:17 am - 11:56 pmMKE-SJU
11h 39m1 stop
$242American Airlines
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Thu, Dec 18 - Mon, Jan 5
Frontier Logo
3:55 am - 6:26 pmSJU-MKE
16h 31m1 stop
Frontier Logo
10:48 am - 10:15 pmMKE-SJU
9h 27m1 stop
$268Frontier
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Sun, Dec 28 - Mon, Jan 5
Frontier Logo
3:55 am - 11:13 amSJU-MKE
9h 18m1 stop
Frontier Logo
10:48 am - 10:15 pmMKE-SJU
9h 27m1 stop
$284Frontier
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Sun, Dec 21 - Mon, Dec 29
Frontier Logo
3:55 am - 11:13 amSJU-MKE
9h 18m1 stop
Frontier Logo
12:08 pm - 2:50 amMKE-SJU
12h 42m1 stop
$294Frontier
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Fri, Dec 19 - Mon, Jan 5
Multiple Airlines Logo
6:00 am - 6:26 pmSJU-MKE
14h 26m2 stops
Multiple Airlines Logo
8:15 pm - 2:50 amMKE-SJU
28h 35m1 stop
$323Multiple Airlines
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Tue, Jan 13 - Sun, Jan 18
United Airlines Logo
2:05 am - 12:09 pmSJU-MKE
12h 04m2 stops
United Airlines Logo
7:50 am - 9:26 pmMKE-SJU
11h 36m1 stop
$325United Airlines
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Thu, Jan 29 - Sun, Feb 1
Delta Logo
2:19 pm - 7:58 pmMBJ-MKE
6h 39m1 stop
Delta Logo
6:29 pm - 11:13 amMKE-MBJ
15h 44m1 stop
$437Delta
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Thu, Jan 29 - Sun, Feb 1
Delta Logo
12:38 pm - 7:58 pmMBJ-MKE
8h 20m1 stop
Delta Logo
6:29 pm - 12:32 pmMKE-MBJ
17h 03m2 stops
$441Delta
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Thu, Jan 29 - Sun, Feb 1
United Airlines Logo
2:55 pm - 9:59 pmPUJ-MKE
9h 04m1 stop
United Airlines Logo
6:00 am - 5:25 pmMKE-PUJ
9h 25m2 stops
$445United Airlines
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Thu, Jan 29 - Sun, Feb 1
Sun Country Air Logo
3:19 pm - 6:36 pmPUJ-MKE
5h 17mnonstop
Sun Country Air Logo
8:00 am - 2:19 pmMKE-PUJ
4h 19mnonstop
$754Sun Country Air
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Good to know

Low seasonMarch
Cheapest flight$90
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 18% increase in price.
Flight from San Juan to Milwaukee

FAQs for booking flights from Caribbean to Milwaukee

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

    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 Caribbean to Milwaukee.

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

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

    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 to Milwaukee with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Milwaukee?

    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 to Milwaukee from 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 Caribbean to Milwaukee

 
Need help choosing which airline to fly with from Caribbean to Milwaukee? 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 4253 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
Airline reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

10.0 ExcellentDavid, Nov 2025BUF - PHX
Read more Southwest reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

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.

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

One of the best airlines that I flew on, the flight attendants were very attentive and professional.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

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.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

We boarded late. The crew at the airport was dismissive. The seat cushion on the plane was uncomfortable.

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.

Overall, an average flight; food options were not the best, and there were bugs on the plane.

My flight was delayed about three hours. I got home at 3:30 in the morning very bad experience.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

I like how the crew and pilot kept us updated Even though our flight was slightly delayed. We made up time for it in the air. I really did enjoy my seat and amenities and my trip and value overall.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

The inflight staff is never the issue always the extra and charges american charges! Literally 30 bucks for WiFi! Is insane and then it’s choppy and slow. If you pay for it once you don’t need to pay again for switching aircraft especially when there is flight delays

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.

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

Excellent! No complaints! All the staff from the counter to the airplane crew, was just amazing and pleasing to talk to

My baby was crying uncontrollably for the longest time and the entire crew was SO supportive, I’m so appreciative of them. Thank you so much for the support during an exhausting moment. We got very lucky.

I didn't eat, so I can't rate the food. Delayed set off was beyond

No free snacks or drinks. Freezing. Uncomfortable. No plugs or entertainment. If you fly to LA the make you change terminals with a slow bus. Awful trip that took forever. Terrible airline- maybe the worst I’ve ever flown.

I hope you continue to be one of the great company

Crew are always very angry and dismissive like they seem they are being forced to work. In addition, there was a long line for the bathrooms, and only one was allowed to be used. No reason was given for only one bathroom being available; apparently, the stewardess was more interested in using the jumpseat instead of allowing the customers to use the bathroom.

Very positive in both directions. Safe travels, nice staff, lost and found in fact found my phone under my chair! I was out of cash after my NYC trip otherwise I would've offered a reward for helping my day out immensly! Thanks you so much Spirit staff!

I stopped flying spirit as much because they are crooks and thieves. It's not like other airlines where you can at least get credits they just take your money.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

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