$98 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 5/2. 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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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

Sun, May 3 - Thu, May 7
Frontier Logo
3:21 am - 8:01 am
SJU
-
MKE
29h 40m
1 stop
Frontier Logo
8:46 am - 2:08 am
MKE
-
SJU
16h 22m
1 stop
$211Frontier
Wed, Apr 29 - Tue, May 5
Frontier Logo
3:21 am - 11:26 am
SJU
-
MKE
9h 05m
1 stop
Frontier Logo
8:46 am - 10:43 pm
MKE
-
SJU
12h 57m
1 stop
$221Frontier
Sun, May 3 - Thu, May 7
Frontier Logo
3:21 am - 11:26 am
SJU
-
MKE
9h 05m
1 stop
Frontier Logo
8:46 am - 2:08 am
MKE
-
SJU
16h 22m
1 stop
$222Frontier
Thu, Apr 30 - Tue, May 5
American Airlines Logo
6:00 am - 9:41 pm
SJU
-
MKE
16h 41m
1 stop
American Airlines Logo
8:11 am - 8:51 pm
MKE
-
SJU
11h 40m
2 stops
$226American Airlines
Thu, May 7 - Sun, May 10
American Airlines Logo
6:00 am - 9:41 pm
SJU
-
MKE
16h 41m
1 stop
American Airlines Logo
7:01 am - 8:51 pm
MKE
-
SJU
12h 50m
2 stops
$276American Airlines
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
8:00 am - 8:38 am
SJU
-
MKE
25h 38m
1 stop
Multiple Airlines Logo
5:15 pm - 12:05 pm
MKE
-
SJU
17h 50m
1 stop
$290Multiple Airlines
Sat, Apr 25 - Sat, May 2
United Airlines Logo
7:20 am - 4:47 pm
SJU
-
MKE
10h 27m
2 stops
United Airlines Logo
9:37 am - 8:34 pm
MKE
-
SJU
9h 57m
1 stop
$308United Airlines
Fri, May 8 - Thu, Sep 10
United Airlines Logo
2:40 pm - 5:07 pm
MBJ
-
MKE
26h 27m
2 stops
United Airlines Logo
8:45 pm - 1:30 pm
MKE
-
MBJ
40h 45m
2 stops
$311United Airlines
Wed, Jul 1 - Tue, Jul 7
Delta Logo
1:20 pm - 11:59 pm
STT
-
MKE
11h 39m
1 stop
Delta Logo
6:50 am - 3:20 pm
MKE
-
STT
7h 30m
1 stop
$512Delta
Sat, Aug 1 - Fri, Aug 7
Multiple Airlines Logo
1:40 am - 10:39 pm
POS
-
MKE
21h 59m
2 stops
Multiple Airlines Logo
5:29 pm - 1:25 am
MKE
-
POS
30h 56m
3 stops
$5,847Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$98
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 14% 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 4329 reviews
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

2.0 MediocreStuart, Mar 2026
HOU - STL
Read more Southwest reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Wonderful crew, great movie selection and good food. I prefer Airbus to Boeing, much more comfortable

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

In general, flight attendants were not very welcoming. Because of delays in departure and luggage handling, we missed our connecting flight. Offered a later flight on standby but available seats were then taken by 4 or 5 airline crew so slept at airport and got home next day. I am a frequent traveler, and this experience was the worst.

Wonderful in-seat entertainment with seatback screens and huge selection of quality movies. The ability to bluetooth connect headphones was amazing.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

we did a return flight from Paris CDG to SFO. This trip was much better than the departing flight SFO to CDG. The food was better quality, the crew was nicer, and the interior of the plane seemed cleaner.

They promise free wi-fi prior to boarding and then once on board you are informed you have to purchase wifi even after being a mileagePlus member.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Awful. No counter attendants. No dinner offered due to delays.

Horrible service no Wi-Fi connection on both leg of the flight and they are refusing to fix bad service

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Plane was super cold. No entertainment unless you were with mileage program Getting off the plane was super slow

Flight was on-time, boarding was flawless and the crew was friendly.

The staff are very, very professional. It's what flying should feel like.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

Flight was on time. Cabin attendants made no recognition of my name or being an Advantage Executive Platinum member.

Award tickets are some of the best... seats lack entertainment options.

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Every connection was late but that meant I was not running from one to the next so that was a good thing. No one wants to miss a connection

Food and entertainment see irrelevant to rate them as that’s not really an option anymore. The flight was fast and friendly. The plane was immaculately clean.

Last flight to get me home got delayed almost an hour, which was bad because I have to work in the morning.

it was great except the extra charges. for carry on ,seat choice, and wifi. these should all be included in flight charge. The extra charges are redicuolouse and because of that I will not be flying spirit again

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

We had to take a bus to the plane with a old woman and carry on bags, and at landing at the airport we have to wait one hour seating on the plane waiting for a gate. We came back from Australia Bussines class Quantas 16 hours traveling, then wait in Dallas 7 hours for connection...honestly waiting 1 hour more at the plane was the worst part.

Flight delayed twice (not Spirit fault) No food served* No entertainment * *in response to my choices in the rating. None was provided so couldn’t rate properly

Delayed over two hours. Only knew about a 30 minute delay in advance

Poor service but I guess that’s what you get for picking cheap flight. Overacted with all extra up-charge fees, so annoying.

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