$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 12/4. 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
$180
Typical prices: $264-$325
Frontier
Thu 2/19Mon 2/23
SJU - MKE • 1 stop
Cheapest non-stop
$719
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, Feb 19 - Mon, Feb 23
Frontier Logo
9:37 pm - 6:45 pmSJU-MKE
23h 08m1 stop
Frontier Logo
7:40 pm - 9:55 amMKE-SJU
12h 15m1 stop
$180Frontier
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Sat, Feb 14 - Sat, Feb 21
Frontier Logo
11:05 am - 5:04 pmSJU-MKE
7h 59m1 stop
Frontier Logo
6:02 pm - 2:50 amMKE-SJU
6h 48m1 stop
$181Frontier
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Sun, Dec 21 - Wed, Dec 31
American Airlines Logo
1:30 am - 11:03 amSJU-MKE
11h 33m1 stop
American Airlines Logo
7:10 am - 9:51 pmMKE-SJU
12h 41m1 stop
$235American Airlines
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Thu, Jan 29 - Mon, Feb 2
American Airlines Logo
6:00 am - 3:57 pmSJU-MKE
11h 57m1 stop
American Airlines Logo
7:32 am - 9:39 pmMKE-SJU
12h 07m1 stop
$240American Airlines
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Wed, Feb 18 - Mon, Feb 23
Frontier Logo
3:55 am - 6:45 pmSJU-MKE
16h 50m1 stop
Frontier Logo
7:40 pm - 2:50 amMKE-SJU
29h 10m1 stop
$251Frontier
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Thu, Feb 19 - Mon, Feb 23
Southwest Logo
5:00 pm - 10:35 pmSJU-MKE
7h 35m1 stop
Southwest Logo
12:10 pm - 12:40 amMKE-SJU
10h 30m2 stops
$266Southwest
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Thu, Jan 29 - Sun, Feb 1
Delta Logo
4:55 pm - 11:46 pmPUJ-MKE
8h 51m1 stop
Delta Logo
7:05 am - 4:21 pmMKE-PUJ
7h 16m1 stop
$391Delta
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Thu, Jan 29 - Sun, Feb 1
United Airlines Logo
12:56 pm - 10:56 pmPUJ-MKE
12h 00m2 stops
United Airlines Logo
6:00 am - 5:25 pmMKE-PUJ
9h 25m2 stops
$396United Airlines
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Thu, Jan 29 - Sun, Feb 1
United Airlines Logo
2:55 pm - 1:53 pmPUJ-MKE
24h 58m1 stop
United Airlines Logo
2:32 pm - 4:02 pmMKE-PUJ
23h 30m1 stop
$402United Airlines
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Thu, Jan 29 - Sun, Feb 1
Delta Logo
4:45 pm - 11:46 pmMBJ-MKE
8h 01m1 stop
Delta Logo
7:00 am - 3:20 pmMKE-MBJ
7h 20m1 stop
$437Delta
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Useful Info

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 4 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 4251 reviews
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
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.

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.

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.

the over had ligth did not work'd for the all way

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.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

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.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

United has come a long way, it’s been a fantastic experience traveling with them.

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

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.

Great crew, excellent landing, good food. Over all great experience. Thank you!

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.

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.

flight was good until we arrived at cmh ten minutes early but then sat on tarmac for twenty minutes because a plane was at our gate, so we had to wait despite the pilot tellling us 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.

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

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