$113 Find Cheap Flights from Caribbean to Milwaukee - Compare and Save

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 10/27. 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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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, Aug 27 - Mon, Aug 31
Delta Logo
5:49 pm - 11:53 pm
SJU
-
MKE
7h 04m
1 stop
Delta Logo
5:34 am - 1:42 pm
MKE
-
SJU
7h 08m
1 stop
$226Delta
Thu, Aug 27 - Mon, Aug 31
Delta Logo
2:59 pm - 8:53 pm
SJU
-
MKE
6h 54m
1 stop
Delta Logo
7:03 am - 4:38 pm
MKE
-
SJU
8h 35m
1 stop
$326Delta
Thu, Jul 23 - Wed, Jul 29
American Airlines Logo
2:25 pm - 11:44 pm
SJU
-
MKE
10h 19m
1 stop
American Airlines Logo
6:00 am - 6:24 pm
MKE
-
SJU
11h 24m
2 stops
$331American Airlines
Tue, Oct 6 - Tue, Oct 20
American Airlines Logo
12:59 pm - 8:27 pm
SJU
-
MKE
8h 28m
1 stop
American Airlines Logo
8:10 am - 10:22 pm
MKE
-
SJU
13h 12m
2 stops
$333American Airlines
Sat, Aug 1 - Tue, Aug 11
Southwest Logo
8:15 pm - 8:55 am
SJU
-
MKE
13h 40m
1 stop
Southwest Logo
10:50 am - 7:00 pm
MKE
-
SJU
7h 10m
1 stop
$345Southwest
Thu, Aug 6 - Sun, Aug 9
Southwest Logo
6:30 am - 4:20 pm
SJU
-
MKE
10h 50m
1 stop
Southwest Logo
7:00 pm - 9:10 am
MKE
-
SJU
13h 10m
1 stop
$363Southwest
Tue, Jul 28 - Mon, Aug 24
JetBlue Logo
2:53 pm - 8:45 am
STT
-
MKE
18h 52m
2 stops
JetBlue Logo
9:36 am - 1:03 pm
MKE
-
STT
26h 27m
1 stop
$595JetBlue
Tue, Jul 28 - Wed, Aug 26
JetBlue Logo
2:53 pm - 8:45 am
STT
-
MKE
18h 52m
2 stops
JetBlue Logo
9:36 am - 2:55 pm
MKE
-
STT
28h 19m
2 stops
$600JetBlue
Wed, Aug 5 - Wed, Aug 26
United Airlines Logo
4:12 pm - 12:48 pm
MBJ
-
MKE
20h 36m
2 stops
United Airlines Logo
6:15 am - 11:43 am
MKE
-
MBJ
29h 28m
2 stops
$612United Airlines
Sat, Aug 1 - Mon, Aug 31
United Airlines Logo
2:40 pm - 7:00 am
MBJ
-
MKE
16h 20m
2 stops
United Airlines Logo
5:17 pm - 11:43 am
MKE
-
MBJ
42h 26m
2 stops
$624United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$113
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 6% 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 4 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.
7.9
SouthwestOverall score based on 4249 reviews
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

8.0 ExcellentAnonymous, Jul 2026
PHL - BNA
Read more Southwest reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

Slow boarding, limited food and drink portions. Bad delays and turbulence

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

Everything about this flight was good except for the very end when I reached my destination. Everyone from the tune to the wheelchair escorts were great with the case were great but I miss you with people at the check in this at the very end. I need help from the chicken desk because I forgot my pillow on the plane The female worker at the chicken desk said that they found my pillow and she was going to retrieve it for me. She left a 30 minutes without any update and her so she saw me walking back and forth waiting for her and they didn't even bother calling her or radioing her for any updates. They were busy because they were behind schedule and they were overwhelmed but thanks because at least glanced me and try to give me an update just a quick radio check or phone call. I don't care about the pillow but if you tell me to wait, I waited for at least half an hour before I said something and I just left because they wouldn't bother talking to me so I could, so everything's going in the review. I took pictures of the two men that were left working at the check-in counter. The totally ignored me despite the signals I've been giving them. I don't see any offers in the kayak review to add pictures or screenshots so I'm going to post another review I don't know their name but I'm pretty sure Delta will find other names when they see the review. Google with pictures. There was another guy at the chicken counter bring an orange workers vest who finally left after telling me that the girl that was retrieving my pillow is working the gates now. That would have been if they just told me that's what happened. But I had no update. Make me wait for nothing. Thank you Delta airlines!

We had a great experience with Delta. They helped us from the start at the kiosk all the way to our final destination, including help reassigning and upgrading our seats free of charge at the gates, escorts with the wheelchair for my brother and even getting our luggage at baggage claim for us. I also had special help because I forgot my pillow on the plane. The wheelchair escort contacted for associates at the check-in desk all the way back to the plane and retrieved my pillow for me.

I am a Diamond Medallion Delta traveller and this was a disappointing flight. They allowed half the flight to preboard before Delta One and Diamond Medallion. Once on the plane in my Delta Premium Select seat we were not given any welcome or greeting. Throughout the flight the flight attendant also did not make us feel any sort of special service or attention and even rushed us when she did bring us a snack to pick in the dark not even offering a light to look at what it was -- she was overall not helpful and not accommodating. for the extra cost of the seat it was honestly not a special experience this flight. heads up that even the warm cookies are now packaged. I ate nothing. There really was nothing that was special, stood out or exceptional. Luckily I mostly slept. But I was disappointed and question if I may try a different flight next time I go to Tokyo. The last few Delta flights have been less than great. which makes me very sad.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Wifi did not work and they only served water, coffee, or tea.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Had assistance at airport getting from arrivals gate to departure gate; I couldn't have managed without that extra help. Thank you Delta.

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

The Manila airport was under renovation so there was no business class lounge. The double security check was disorganized and the flight attendants were grouchy.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

The flight was delayed an hour and a half while you tried to fix the plane so I missed my connecting flight in Chicago. In Chicago, it took an hour to get the luggage. Then the conveyor belt was broken where I have to transfer my flight from an international flight to the continuing flight so I had to carry a large suitcase through the airport. The elevators were broken in the airport. I paid people to carry the luggage for me up the escalators in two different areas. The person who helped me get the new flight was outstanding. The temperature in the airport in Chicago was horrible. We were all sweating. It was the day from hell. That was after two hours in a security line in Athens. I have TSA pre-checked and global entry and I still waited. Two hours in a security line. Something has got to be done to stream line this service. After I’ve been through all of that in Athens, why do I have to go through it again in Chicago. It was the worst travel experience I have had in a long time. Your bathrooms have gotten so small that you can hardly get your butt on the toilet. You’ve taken the airspace out of the inside of the top of the toilet. It really makes for a miserable experience. Also on a 4 1/2 hour flight from Chicago to Los Angeles. The only thing we’re given is a bag of pretzels. REALLY!!

Flight attendants on United are the worst in the business. Can’t be bothered to provide even basic levels of service and are as rude as anyone can get. This flight was not an exception to that rule.

The staff was incredible, very attentive, polite, made you feel like the center of the universe. They even all wrote me a happy birthday card. Truly just an amazing crew, cannot stress it enough.

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

there are no options s for snack besides cookies would ve nice to have a salty option n

Never ontime and always delays. Long waits for customer service and often app doesn’t work

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

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We loved the steward on the plane. He made the night enjoyable

Very poor delay in dfw was really bad n long

I didn't like that my paid for seat was changed 2 hours before my flight.

The gate changed over 6 times in the 4 hours before this flight having us walking all over and back again. The agent told me that the American app and the airport monitors are not reliable and I should Google the flight number for accurate flight information! Shocking tip but the gate still kept changing anyway and then the flight was delayed an hour because of another maintenance issue. Not a great experience.

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