$91 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 1/27. 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
$232
Typical prices: $239-$356
Frontier
Thu 1/29Mon 2/2
SJU - MKE • 1 stop
Cheapest non-stop
$543
Sun Country Air
Fri 1/23Mon 1/26
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

Thu, Jan 29 - Mon, Feb 2
Frontier Logo
8:00 am - 6:16 pm
SJU
-
MKE
12h 16m
1 stop
Frontier Logo
7:01 pm - 3:26 pm
MKE
-
SJU
18h 25m
1 stop
$232Frontier
Tue, Feb 24 - Tue, Mar 17
American Airlines Logo
6:33 am - 11:56 am
SJU
-
MKE
7h 23m
1 stop
American Airlines Logo
5:00 am - 3:28 pm
MKE
-
SJU
9h 28m
1 stop
$236American Airlines
Wed, Feb 11 - Wed, Feb 18
Frontier Logo
5:25 pm - 7:40 am
SJU
-
MKE
16h 15m
1 stop
Frontier Logo
4:39 pm - 11:53 pm
MKE
-
SJU
29h 14m
1 stop
$239Frontier
Fri, Feb 13 - Tue, Feb 17
American Airlines Logo
5:18 pm - 11:55 pm
SJU
-
MKE
8h 37m
1 stop
American Airlines Logo
5:00 am - 4:28 pm
MKE
-
SJU
9h 28m
1 stop
$241American Airlines
Mon, Feb 23 - Tue, Mar 17
Frontier Logo
3:53 am - 3:44 pm
SJU
-
MKE
13h 51m
1 stop
Frontier Logo
6:35 pm - 2:03 am
MKE
-
SJU
6h 28m
1 stop
$244Frontier
Thu, Feb 12 - Mon, Feb 16
Multiple Airlines Logo
11:52 am - 9:43 am
SJU
-
MKE
23h 51m
1 stop
Multiple Airlines Logo
7:52 pm - 10:17 am
MKE
-
SJU
12h 25m
1 stop
$247Multiple Airlines
Tue, Feb 24 - Tue, Mar 17
Delta Logo
6:15 am - 12:31 pm
SJU
-
MKE
8h 16m
1 stop
Delta Logo
1:21 pm - 11:12 pm
MKE
-
SJU
8h 51m
1 stop
$256Delta
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
2:55 pm - 9:44 pm
PUJ
-
MKE
8h 49m
1 stop
United Airlines Logo
6:00 am - 4:02 pm
MKE
-
PUJ
8h 02m
1 stop
$527United Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
5:20 pm - 2:05 pm
PUJ
-
MKE
22h 45m
2 stops
United Airlines Logo
1:25 pm - 12:59 pm
MKE
-
PUJ
21h 34m
2 stops
$531United 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
$708Sun Country Air
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$91
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 30% 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 4258 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

3 hour delay. Had to change plans and was still delayed.

2.0 MediocreAnonymous, Jan 2026
SFO - SAN
Read more Southwest reviews

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

The entertainment screens were not working and there was no air condition the entire flight. Very uncomfortable.

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Safe made to destination. Late to start at GVA for icy reasons but we fought our next fly.

I just think it’s unfortunate that Airlines have completely abandoned the idea of serving any kind of decent or even real food on flights, not even on a four hour flight!? Those days are gone, I guess.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

Both flights delayed. 2nd flight over 3 hours late mechanical issues

l really enjoy very much the flight was very pleasant

left on time, reasonable boarding process arrived early luggage came out quickly

I like flying first class, and United has a nice one

Flight was delayed 45 minutes because originating flight was coming from Newark. No complimentary snacks were offered on this 5+ hour flight. No screens for the flight, but movies offered if you had already downloaded the United app (which I hadn't on my ipad). No USB ports, only a flimsy plug-in port near the bottom of the seat that was hard to see and kept coming unplugged.

We were upgraded to First Class and it was a great flight

Amazing I love American. I’ll never fly anyone else if I can help it.

I love American. I’ll never fly anyone else if I can help it.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Little warm on the plane and delayed for an hour

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

Bags took over and hour to come out. Delays due to wind caused rebooking.

Services, food products, and crew friendliness on American Airlines international flights is mediocre compared to Emirates, Qatar, and Singapore Airways. American does not do much to differentiate its product on international routes. Its menu options are similar on international flights. American Airlines flight attendants do not call elite frequent travelers by their names; American Airlines flight attendants do not seem to be motivated to go above and beyond in the service they provide. American Airlines personnel do not seem to take pride in their work.

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

Flight was cancelled with very little notice. Had to scramble to find transportation to my Mexico vacation.

Liked early boarding for disabled customers. Seat comfort could have been better, would have appreciated an empty seat between my wife and I since I suffer from arthritis, neuropathy, and spinal stenosis. Also aisle seat armrest was immobile and this made it difficult to get into and out of my seat during the flight

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

It was delayed but the landing was the smoothest in a while that I’ve had.

Second time in 3 days I walked off the plane late. This time - almost an hour.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

Everything went well. The flight was slightly delayed however we landed on time.

I've flown two Spirit flights recently - boarding for one was somewhat chaotic, with the board listing the wrong flight and causing much confusion; boarding for the other was very smooth and easy. My seat (for which I did not pay extra) was a bit narrow and without great legroom, but it was fine for a NY-Florida trip and was more than worth the low price I paid. The crew was friendly and one flight landed early and the other was only very slightly delayed. All in all a very good experience.

Had to pay for water if wanted it. Seats are close unless you get upgraded. Flight was fine. Will travel again with spirit.

Spirit sucks. Horrible employees in Medellín. Never again. I hope this company goes out of business completely.

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