$113 Find Cheap Flights from Caribbean Islands 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 9/4. 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

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Cheap Flights from Caribbean Islands to Milwaukee

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

Thu, Sep 4 - Thu, Sep 18
Delta Logo
12:50 pm - 11:36 pmSJU-MKE
11h 46m1 stop
Delta Logo
12:20 pm - 10:08 pmMKE-SJU
8h 48m1 stop
$225Delta
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Wed, Sep 10 - Wed, Sep 24
American Airlines Logo
4:42 pm - 10:04 amSJU-MKE
18h 22m2 stops
American Airlines Logo
3:47 pm - 11:11 amMKE-SJU
18h 24m2 stops
$230American Airlines
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Wed, Sep 10 - Wed, Sep 24
American Airlines Logo
4:42 pm - 10:04 amSJU-MKE
18h 22m2 stops
American Airlines Logo
5:46 pm - 11:11 amMKE-SJU
16h 25m2 stops
$231American Airlines
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Thu, Jul 10 - Mon, Jul 14
Spirit Airlines Logo
1:37 am - 8:50 amSJU-MKE
8h 13m1 stop
Spirit Airlines Logo
4:37 pm - 1:35 amMKE-SJU
7h 58m1 stop
$284Spirit Airlines
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Sun, Jul 13 - Mon, Jul 21
Spirit Airlines Logo
1:37 am - 8:50 amSJU-MKE
8h 13m1 stop
Spirit Airlines Logo
4:37 pm - 1:35 amMKE-SJU
7h 58m1 stop
$295Spirit Airlines
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Thu, Sep 18 - Sun, Sep 21
Delta Logo
5:19 pm - 11:25 pmSJU-MKE
7h 06m1 stop
Delta Logo
6:00 am - 4:08 pmMKE-SJU
9h 08m1 stop
$302Delta
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Tue, Sep 9 - Wed, Sep 24
United Airlines Logo
1:05 am - 10:13 amSJU-MKE
10h 08m2 stops
United Airlines Logo
10:50 am - 11:57 pmMKE-SJU
12h 07m2 stops
$405United Airlines
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Sat, Jul 5 - Mon, Aug 25
United Airlines Logo
2:17 pm - 11:54 pmMBJ-MKE
9h 37m1 stop
United Airlines Logo
5:40 pm - 1:10 pmMKE-MBJ
19h 30m2 stops
$445United Airlines
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Thu, Jul 3 - Sat, Jul 5
Southwest Logo
11:25 am - 10:00 pmSJU-MKE
11h 35m1 stop
Southwest Logo
8:20 am - 4:15 pmMKE-SJU
6h 55m1 stop
$470Southwest
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Mon, Jul 14 - Mon, Jul 21
Southwest Logo
7:40 pm - 8:05 amSJU-MKE
13h 25m1 stop
Southwest Logo
8:40 pm - 9:05 amMKE-SJU
11h 25m1 stop
$480Southwest
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Good to know

Low seasonMarch
High seasonJuly
Cheapest flight$113
Best time to beat the crowds but there is an average 9% increase 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 Islands to Milwaukee

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Milwaukee from Caribbean Islands 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 Islands 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 Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands 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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top airlines flying from Caribbean Islands to Milwaukee

 
Need help choosing which airline to fly with from Caribbean Islands 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
DeltaOverall score based on 7963 reviews
7.9Entertainment
7.9Comfort
7.3Food
8.2Boarding
8.5Crew
Airline reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

4.0 OkayKoonj, Jun 2025MSP - AUS
Read more Delta reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The flight crew were friendly and attentive. Food was good and they passed out ice cream and drinks awhile after Lunch was done. The ice cream was a nice treat! I found several movies to watch during the flight. There was many movies and tv shows to choose from. We flew Premium economy and there was enough leg room to be comfortable. The seats were also comfortable. I would fly AA again if the airfare isn’t expensive.

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Everything you need to know for your flight to Milwaukee

Information on the airport you'll fly into in Milwaukee

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