$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 1/16. 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
$199
Typical prices: $239-$381
Frontier
Wed 1/14Mon 1/19
SJU - MKE • 1 stop
Cheapest non-stop
$648
Sun Country Air
Thu 2/26Mon 3/2
PUJ - MKE • Non-stop
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Flight Deals
Useful Info
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

Wed, Jan 14 - Mon, Jan 19
Frontier Logo
7:34 pm - 6:47 pm
SJU
-
MKE
25h 13m1 stop
Frontier Logo
7:37 pm - 3:26 pm
MKE
-
SJU
17h 49m1 stop
$199Frontier
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
8:30 am - 5:47 pm
SJU
-
MKE
11h 17m2 stops
American Airlines Logo
6:37 pm - 10:40 am
MKE
-
SJU
15h 03m1 stop
$235American Airlines
Thu, Jan 29 - Mon, Feb 2
American Airlines Logo
5:55 pm - 11:35 pm
SJU
-
MKE
7h 40m1 stop
American Airlines Logo
6:10 am - 8:50 pm
MKE
-
SJU
12h 40m2 stops
$240American Airlines
Thu, Jan 29 - Mon, Feb 2
American Airlines Logo
7:07 am - 5:05 pm
SJU
-
MKE
11h 58m1 stop
American Airlines Logo
6:10 am - 8:50 pm
MKE
-
SJU
12h 40m2 stops
$241American Airlines
Fri, Feb 13 - Mon, Feb 16
American Airlines Logo
8:30 am - 5:47 pm
SJU
-
MKE
11h 17m2 stops
American Airlines Logo
12:14 pm - 5:00 am
MKE
-
SJU
14h 46m1 stop
$265American Airlines
Thu, Jan 22 - Mon, Jan 26
United Airlines Logo
2:05 am - 1:53 pm
SJU
-
MKE
13h 48m2 stops
United Airlines Logo
11:30 am - 9:00 pm
MKE
-
SJU
7h 30m1 stop
$325United Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
2:55 pm - 10:28 pm
PUJ
-
MKE
9h 33m1 stop
United Airlines Logo
6:00 am - 4:02 pm
MKE
-
PUJ
8h 02m1 stop
$472United Airlines
Thu, Feb 26 - Mon, Mar 2
Sun Country Air Logo
3:35 pm - 6:51 pm
PUJ
-
MKE
5h 16mnonstop
Sun Country Air Logo
8:00 am - 2:35 pm
MKE
-
PUJ
4h 35mnonstop
$648Sun Country Air
Mon, Jan 5 - Wed, Mar 25
Delta Logo
2:19 pm - 7:57 pm
MBJ
-
MKE
6h 38m1 stop
Delta Logo
5:49 pm - 12:42 pm
MKE
-
MBJ
18h 53m2 stops
$822Delta
Mon, Jan 5 - Sat, Mar 28
Delta Logo
2:19 pm - 7:57 pm
MBJ
-
MKE
6h 38m1 stop
Delta Logo
4:48 pm - 12:42 pm
MKE
-
MBJ
19h 54m2 stops
$847Delta
Useful Info

Good to know

Low seasonMarch
Cheapest flight$90
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 29% 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 4257 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

10.0 ExcellentAnonymous, Dec 2025
DAL - CHS
Read more Southwest reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

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.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Premium economy is like the forgotten class. Aside from meal service never saw a flight attendant. Any additional beverages required going to the very back of the plane to request and there was rarely an attendant there. Seat leg / foot rest hardly elevates and not well suite for someone under 5’6. Bulky armrests

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

Flight was operated by Virgin Atlantic and it was up to their usual high standard. Minor grips about some issues, but they are really first world issues and as a whole, was an excellent flight.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Delta One upgrade it would have been great if my tray extended (it was jammed and wouldn’t pull out), seatbelt had too much slack & my little cabin door didn’t close properly

I paid for a business class ticket on Delta. It was sourced to Virgin Atlantic. They changed out the aircraft which had fewer upper class tickets. Even though I'd checked into the lounge, was receiving alerts via kayak about the delay and changes; no one informed me that the seat would be changed - until I attempted to board and was told that I would have an economy seat or they could search to put me on another airline. Even the flight crew were informed of this change (10 passengers were bumped out of Upper Class) around 2 pm (1400) time. Hours would have helped to consider alternatives instead of making a last minute change. There needs to be compensation from both Delta and Virgin given this change in service/experience.

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

everything was pretty good. Houston airport is awful. Unnecessarily inefficient; people working there are rude. Badly run

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

They did the one thing that really matters - got to Chicago early.

I liked the snacks and the flight attendants were friendly.

The flight was delayed for 1:30 hours for maintenance issues. They should give more information about connecting flights. For a Business Cabin the Crew was mediocre.

Very turbulent trip made it pretty bearable, plus the lack of refreshments served and the lack of any air conditioning before takeoff which took an hour or more.

Flight was late - I was downgraded from first class to coach

Not good - outbound flight was delayed and missed my connection even though I got to the gate after running through the airport - the agent would not let me on because the door was closed (flight had not left). There was no notification from United - overall experience was very disappointing. Additionally, I was downgraded from first class to coach on the alternative flight

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

Did not understand a single word the attendant said on the pa system. I was glad it was not an emergency.

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

I'd have like to check my bag and not toss my hair products.sears are very uncomfortable. And that even water isn't free really sucks. The ticket was almost $400

Loved that all flights were om time or early. Hated all the additional costs for a seat and luggage.

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Terrible they canceled the flight very sheepishly and ended up costing me 1200 dollars and kayak and xcover are doing nothing

It’s Spirit need I say more? Thank this little airline because without it the other airlines would raise their prices so much I wouldn’t be able to fly anywhere. It’s affordable and gets you where you need to go! I’m not flying to get a free bag of chips, y’know?

Spirit cancelled the flight very late last night, I was on the way to the airport when I found out

First time in a decade I threw up on the flight, turbulence was terrible!! The staff were kinda rude at times.

Boarding was good, clearly explained and efficient. Staff were helpful, I would've liked a place to get coffee that wasn't Starbucks

I really liked the personalized treatment at the MDE airport, where someone from SPIRIT received me at the entrance of the counter line to ask if the weight of my luggage was accurate or if I wanted a better seat, gave me a name tag for my luggage and walked me to the counter. Thank you.

The most horrible flight ever not only Spirit delayed our flight 2 hours departure time for a 1 hour flight — that I could have driven FLL to TPA and spend less time on the road —- and they did the same on the return with 2-hr delay again!!! Then to top all, the rubber like and most unconfortable seats in the industry with no leg room!!! There should be an award for these kinds of companies measuring % of returning customers!!!

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