$111 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 9/16. 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.
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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

Wed, Sep 30 - Mon, Oct 5
JetBlue Logo
10:30 am - 4:20 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
6h 50m1 stop Orlando
JetBlue Logo
8:05 pm - 9:10 amMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
12h 05m1 stop Orlando
$222JetBlue
Thu, Sep 17 - Tue, Sep 22
American Airlines Logo
2:22 pm - 9:10 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 48m1 stop Philadelphia
American Airlines Logo
8:14 pm - 1:57 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
16h 43m2 stops Chicago O'Hare Intl Miami
$238American Airlines
Fri, Oct 16 - Mon, Oct 19
American Airlines Logo
3:51 pm - 11:57 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
9h 06m1 stop Charlotte Douglas
American Airlines Logo
6:27 pm - 12:09 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
16h 42m1 stop Charlotte Douglas
$238American Airlines
Sat, Sep 12 - Thu, Sep 24
Frontier Logo
2:57 am - 9:22 amSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 25m1 stop Orlando
Frontier Logo
10:10 am - 5:43 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
6h 33m1 stop Orlando
$248Frontier
Fri, Sep 18 - Sun, Sep 20
Southwest Logo
6:30 am - 4:20 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 50m1 stop Orlando
Southwest Logo
11:50 am - 11:55 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
11h 05m1 stop Baltimore/Washington
$292Southwest
Wed, Sep 30 - Wed, Oct 14
Southwest Logo
8:20 am - 4:20 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
9h 00m1 stop Orlando
Southwest Logo
3:00 pm - 11:45 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
7h 45m1 stop Orlando
$292Southwest
Sat, Sep 19 - Tue, Sep 22
United Airlines Logo
1:00 am - 10:00 amSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 00m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
6:00 am - 2:44 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
7h 44m1 stop Chicago O'Hare Intl
$346United Airlines
Fri, Oct 2 - Mon, Oct 5
United Airlines Logo
3:56 pm - 10:59 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
8h 03m1 stop Chicago O'Hare Intl
United Airlines Logo
5:00 am - 2:44 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
8h 44m1 stop Chicago O'Hare Intl
$346United Airlines
Sat, Oct 17 - Sun, Oct 25
Delta Logo
2:26 pm - 8:57 pmMBJ  Montego Bay Sangster Intl-MKE Milwaukee-Mitchell
6h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 1:00 pmMKE  Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl
6h 00m1 stop Atlanta Hartsfield-Jackson
$442Delta
Thu, Sep 24 - Tue, Sep 29
Delta Logo
2:52 pm - 8:54 pmSTT  Saint Thomas Island Cyril E King-MKE Milwaukee-Mitchell
7h 02m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 1:42 pmMKE  Milwaukee-Mitchell-STT Saint Thomas Island Cyril E King
7h 12m1 stop Atlanta Hartsfield-Jackson
$560Delta
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Good to know

Low season

January

Cheapest flight

$111
Best time to beat the crowds with an average 6% drop 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.
8.0
SouthwestOverall score based on 4218 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

Flight left on time and was early landing. Seats not comfortable and not enough space…

4.0 OkayLeo, Aug 2026
Read more Southwest reviews

Flight left on time and was early landing. Seats not comfortable and not enough space…

Flight left on time. Seat spacing is way too small…

It would have been better if the flight was on time

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

Flight time kept changing and so did the gate. It was very frustrating

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

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!

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

wifi too slow or would not connect and entertainment kept on freezing

Cancelled my flight. Left me in airport for 12 hours. Rude gate attendants. Worst delta experience I’ve had. I hope they have a focus group and return to thinking about customer service.

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.

Very kind Lufthansa agent somehow gave us all no charge extra business class seats and helped us get home rested and happy.

The lounge was not accessible because it was located before the passport control, and backtracking was impossible.

Flight was great. Almost miss my connecting flight due to late departure from Haneda. Had to run all through airport in Chicago to make the flight. Experience was great for 1st time flyers using ANA Airlines.

the seat has a problem. the back had a hole.

The back to back mechanical delays from Denver to San Diego and then on my return flight from Denver to Great Falls it added extra time both ways

Really old place. Not as clean as it should be, tray tables needed better cleaning. The items, trays and some other items need to b6 engineered. Anything task you or crew may do is incredibly load, seriously engineer for quiet smooth, easy. Just opening and closing the tray table is actually dangerous and can easily injure a finger. I'm sure it happens as it happened to me! First time I used United and likely will be the last!

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. .

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

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.

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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