$163 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 6/18. 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 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, May 21 - Sat, Sep 12
American Airlines Logo
2:31 pm - 11:59 pm
MBJ
-
MKE
9h 28m
1 stop
American Airlines Logo
4:33 pm - 10:50 am
MKE
-
MBJ
18h 17m
2 stops
$321American Airlines
Thu, Aug 27 - Mon, Aug 31
Delta Logo
2:59 pm - 8:53 pm
SJU
-
MKE
6h 54m
1 stop
Delta Logo
5:55 am - 1:30 pm
MKE
-
SJU
6h 35m
1 stop
$326Delta
Thu, Jul 30 - Wed, Aug 12
American Airlines Logo
7:00 am - 11:44 pm
SJU
-
MKE
17h 44m
1 stop
American Airlines Logo
2:46 pm - 11:59 pm
MKE
-
SJU
8h 13m
1 stop
$331American Airlines
Thu, May 28 - Sun, May 31
American Airlines Logo
6:20 am - 5:23 pm
SJU
-
MKE
12h 03m
1 stop
American Airlines Logo
6:00 am - 11:01 pm
MKE
-
SJU
16h 01m
1 stop
$335American Airlines
Tue, May 19 - Tue, May 26
United Airlines Logo
2:40 pm - 7:01 pm
MBJ
-
MKE
28h 21m
2 stops
United Airlines Logo
5:00 am - 3:10 pm
MKE
-
MBJ
10h 10m
2 stops
$348United Airlines
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
8:55 pm - 8:55 am
SJU
-
MKE
13h 00m
1 stop
Southwest Logo
5:45 am - 4:55 pm
MKE
-
SJU
10h 10m
2 stops
$365Southwest
Wed, Aug 5 - Fri, Aug 14
American Airlines Logo
1:38 pm - 11:23 pm
SJU
-
MKE
10h 45m
2 stops
American Airlines Logo
6:16 am - 10:24 pm
MKE
-
SJU
15h 08m
1 stop
$366American Airlines
Sun, Jul 26 - Mon, Aug 3
Southwest Logo
6:05 am - 5:45 pm
SJU
-
MKE
12h 40m
1 stop
Southwest Logo
3:15 pm - 11:35 pm
MKE
-
SJU
7h 20m
1 stop
$387Southwest
Mon, Jun 15 - Wed, Aug 19
Delta Logo
3:29 pm - 11:59 pm
STT
-
MKE
9h 30m
1 stop
Delta Logo
5:34 am - 1:34 pm
MKE
-
STT
7h 00m
1 stop
$643Delta
Wed, Aug 26 - Sat, Aug 29
United Airlines Logo
1:50 pm - 10:00 am
PUJ
-
MKE
21h 10m
2 stops
United Airlines Logo
7:30 am - 3:00 pm
MKE
-
PUJ
6h 30m
1 stop
$659United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$163
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 10% 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 4302 reviews
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

10.0 ExcellentChristopher, May 2026
CLE - LAS
Read more Southwest reviews

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Everything could and should be better. We are paying for, it's not a favor, it's a service and should involve quality, responsibility and respect.

Seats were comfortable, 8 hours. One flight attendant was not appropriate in his verbal response: "Please, DON'T touch me.", after being tapped near his elbow after being made unaware he skipped serving me & had passed further down the aisle.

Boarding in Amsterdam is always chaotic. More complicated than needs to be ( boarding pass checked twice, once for general security, then by the airline). The bathrooms on this flight are dirty, and smelly. The food was mediocre at best The crew was decent

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

Round trip flight to Canada and back to the US was smooth and efficient.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

Spanish speaker flight attendants were incredibly rude. A male flight attendant named Allen, grabbed my bag out of the overhead bin and moved it without my permission. When I asked what he was doing, he informed me that the overhead bins were public space? It would be easy to ignore this comment, as you don’t know the whole story, but the flight attendants were militant and rude. Delta, you can do better!

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Seats very comfortable; service efficient and pleasant; flight was on-time; boarding organized.

Seats were not super comfortable and food was not good at all. If I had a chance I would definitely fly a different airline. Of course they are better than any budget airline, but not by much.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

Very friendly and helpful staff on board and United was excellent when I missed my onward flight due to the delay in London. Very well organised meant much less stress

Flew steerage class. Short on leg room unless you pay more. No window unless you pay more. Etc. United is trying to squeeze every cent from you. It doesn’t make for any loyalty.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

The small flights with Valet Luggage has a poor service

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

Everything was fine except the end of the flight. We spent more than an hour circling around Miami due to weather conditions. That was not good.

They lost my bag. ... And I asked them 3 times to 3 different people if my checked bag will maKe it all the way - they all confirmed and at the end it was left at the connection... Bravo

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Delayed due to weather in Dallas (arriving flight arrived late), then boarded the plane only to deboard immediately afterwards, tire needed to be replaced. Flight supposed to depart at 6:15pm but departed at 9:35pm.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

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