$105 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 11/7. 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

Wed, Oct 15 - Wed, Oct 22
American Airlines Logo
5:30 am - 4:04 pmSJU-MKE
11h 34m1 stop
American Airlines Logo
1:43 pm - 11:59 pmMKE-SJU
9h 16m1 stop
$215American Airlines
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Wed, Sep 10 - Sun, Sep 14
American Airlines Logo
4:43 pm - 10:04 amSJU-MKE
18h 21m2 stops
American Airlines Logo
6:23 pm - 12:47 pmMKE-SJU
17h 24m2 stops
$220American Airlines
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Thu, Nov 6 - Tue, Nov 11
Delta Logo
6:43 pm - 11:55 pmSJU-MKE
7h 12m1 stop
Delta Logo
7:00 am - 5:10 pmMKE-SJU
8h 10m1 stop
$225Delta
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Wed, Aug 13 - Sun, Aug 17
Spirit Airlines Logo
4:05 pm - 11:06 pmSJU-MKE
8h 01m1 stop
Spirit Airlines Logo
6:00 am - 3:10 pmMKE-SJU
8h 10m1 stop
$273Spirit Airlines
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Fri, Dec 5 - Wed, Dec 10
Delta Logo
2:26 pm - 8:07 pmSJU-MKE
7h 41m1 stop
Delta Logo
7:00 am - 5:10 pmMKE-SJU
8h 10m1 stop
$285Delta
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Fri, Aug 22 - Mon, Aug 25
Spirit Airlines Logo
4:05 pm - 11:06 pmSJU-MKE
8h 01m1 stop
Spirit Airlines Logo
6:00 am - 11:57 pmMKE-SJU
16h 57m1 stop
$314Spirit Airlines
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Wed, Aug 27 - Sat, Sep 6
Southwest Logo
11:50 am - 9:30 pmSJU-MKE
10h 40m1 stop
Southwest Logo
10:15 am - 9:50 pmMKE-SJU
10h 35m1 stop
$340Southwest
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Wed, Aug 13 - Sat, Sep 13
Southwest Logo
3:05 pm - 9:50 pmSJU-MKE
7h 45m1 stop
Southwest Logo
5:05 am - 4:25 pmMKE-SJU
10h 20m1 stop
$343Southwest
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Thu, Dec 4 - Wed, Dec 10
United Airlines Logo
4:52 pm - 10:30 pmSJU-MKE
7h 38m1 stop
United Airlines Logo
7:00 am - 9:26 pmMKE-SJU
12h 26m2 stops
$355United Airlines
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Fri, Oct 3 - Sat, Oct 18
United Airlines Logo
12:30 am - 5:08 pmPOS-MKE
17h 38m1 stop
United Airlines Logo
10:18 am - 11:23 pmMKE-POS
12h 05m1 stop
$637United Airlines
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Good to know

Low seasonMarch
Cheapest flight$105
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 22% 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.

Reviews of the 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 7980 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

Check in process was terrible. Lady at counter didn’t know what she was doing

4.0 OkayAnonymous, Jul 2025ICN - SEA
Read more Delta reviews

Check in process was terrible. Lady at counter didn’t know what she was doing

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

The crew was amazing; Von, Vera and Guadalupe were very friendly and attentive throughout the entire flight. They were friendly and welcoming to everyone. A solid and dedicated team for sure!

Terrible. I was bumped off of my original flight and spent the next six days fighting to get back on it. I lost hours of my vacation trying to get this situation corrected.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

International baggage recheck process in Philadelphia was a disaster. Waited 1 hour and 45 minutes to receive our bags. Waited 15 minutes to recheck bags, flight notification boards were blank so we asked an AA representative for our connecting gate and we were directed to the wrong terminal and gate. Our connection window was over 3 hours and we made our flight by 5 minutes. We pulled away from the gate and sat on the runway for 1 1/2 hours. 1 of our 4 bags didn’t make it to Phoenix. The mobile app for lost baggage didn’t work, the AA rep had to manually fix.

I miss my flight and they could not rebook me that day because the other flight was full, and for the next day I had to pay a whole new fee again which I think is unprofessional

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

Everything you need to know for your flight to Milwaukee

Information on the airport you'll fly into in Milwaukee

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