$119 Find Cheap Flights from Caribbean to Milwaukee - Compare and Save

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Cheap Flights from Caribbean to Milwaukee

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Milwaukee

Thu, Jan 21 - Mon, Jan 25
American Airlines Logo
3:44 pm - 8:23 amSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
18h 39m1 stop Chicago O'Hare Intl
American Airlines Logo
9:46 am - 11:37 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
11h 51m1 stop Chicago O'Hare Intl
$238American Airlines
Fri, Oct 23 - Fri, Nov 6
American Airlines Logo
7:30 am - 9:54 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
15h 24m1 stop Philadelphia
American Airlines Logo
6:31 pm - 1:03 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
16h 32m1 stop Charlotte Douglas
$243American Airlines
Thu, Nov 19 - Sun, Nov 22
Frontier Logo
3:55 am - 5:26 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
15h 31m1 stop Orlando
Frontier Logo
6:11 pm - 11:18 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
27h 07m1 stop Orlando
$268Frontier
Wed, Sep 16 - Thu, Sep 24
Frontier Logo
2:57 am - 9:08 amSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 11m1 stop Orlando
Frontier Logo
10:10 am - 5:43 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
6h 33m1 stop Orlando
$365Frontier
Tue, Sep 29 - Sat, Oct 3
Southwest Logo
11:50 am - 8:35 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
9h 45m2 stops Orlando Nashville Intl
Southwest Logo
2:55 pm - 11:50 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
7h 55m1 stop Orlando
$366Southwest
Tue, Sep 29 - Sat, Oct 3
Southwest Logo
6:00 am - 12:00 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 00m1 stop Baltimore/Washington
Southwest Logo
2:55 pm - 11:50 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
7h 55m1 stop Orlando
$366Southwest
Sat, Dec 19 - Sat, Jan 2
United Airlines Logo
3:45 pm - 1:56 pmMBJ  Montego Bay Sangster Intl-MKE Milwaukee-Mitchell
23h 11m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
United Airlines Logo
7:00 pm - 2:39 pmMKE  Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl
18h 39m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$373United Airlines
Sat, Dec 19 - Sat, Jan 2
United Airlines Logo
2:54 pm - 1:56 pmMBJ  Montego Bay Sangster Intl-MKE Milwaukee-Mitchell
24h 02m1 stop Chicago O'Hare Intl
United Airlines Logo
7:00 pm - 2:39 pmMKE  Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl
18h 39m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$373United Airlines
Mon, Sep 28 - Sat, Oct 3
Delta Logo
5:59 pm - 11:48 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
6h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:55 pm - 10:19 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
6h 24m1 stop Atlanta Hartsfield-Jackson
$550Delta
Thu, Sep 24 - Wed, Sep 30
Delta Logo
7:00 am - 5:31 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
11h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:44 pm - 10:19 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
8h 35m1 stop Atlanta Hartsfield-Jackson
$570Delta
Useful Info

Good to know

Low season

January

Cheapest flight

$119
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 14% lower on average.
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 4195 reviews
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

Delayed and once landed waited very long for the luggage

6.0 GoodIngeborg, Sep 2026
Read more Southwest reviews

Delayed and once landed waited very long for the luggage

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

The Southwest airline was ok. A big thank you to Kayak team (David), who worked with me on Sunday afternoon to rebook my travel from Burbank, CA, to CVG. My original flight on Sunday was delayed, so I had to cancel Sunday flight and rebook my travel to Monday. Could not have done it without help from David from Kayak team. Ante Soda GE Aerospace

Very poor service with connecting flight. I missed the connection because of a delayed flight and significant delay in getting my bags in order to make the connection. The ground staff where unhelpful and rude!

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

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…

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!

All good except the dining. Both meals were the worst I’ve ever encountered on any previous flight.

Both legs on the way were smaller planes, each had a mechanical issue causing a delay

All was fine. Small plane so no food or entertainment.

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.

Boarding, time to take off, in flight offerings, and staff were all great. I recommend using UA for this short flight.

Good experience. Staff was friendly and helpful. Flight was slightly delayed due to airport construction, but they still arrived on time.

This is the worst airline I’ve ever been on in my life and I’ve been probably on 75% of them. I said 15 years ago I would never go on United again. I was an idiot. I booked a flight with them from Las Vegas to San Francisco and of course they screwed that up and cost me a day flying all over the world trying to get to Thailand. My luggage was gone for 35 hours all because they couldn’t make their route on time

This was an auto-rebook due to being delayed from an earlier UA connecting flight. The boarding was fine, but they sat me in a middle seat when my original booking was a window seat. Overall, the flight was fine as it still got me to my final destination.

The flight out of Fresno boarded 1.5 hour past scheduled and made me miss my connecting flight from SFO to SEA.

Really delayed, no effort to support customers other than “sometimes we run late.”

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. .

Our gate was changed several times, and the gate agents were just as in the dark as all of us in knowing when our plane would arrive at PHL.

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

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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