$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 - Sun, Jan 24
Delta Logo
6:30 pm - 11:49 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 19m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:20 pm - 9:00 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
6h 40m1 stop Atlanta Hartsfield-Jackson
$238Delta
Thu, Sep 24 - Mon, Sep 28
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
$238Delta
Thu, Sep 17 - Thu, Sep 24
American Airlines Logo
6:00 am - 7:33 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
14h 33m2 stops Miami Charlotte Douglas
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
Thu, Sep 17 - Thu, Sep 24
American Airlines Logo
6:00 am - 7:33 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
14h 33m2 stops Miami Charlotte Douglas
American Airlines Logo
5:11 pm - 11:00 amMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
16h 49m2 stops Washington, D.C. Reagan-National Miami
$238American Airlines
Wed, Sep 16 - Wed, Sep 23
Southwest Logo
11:50 am - 9:10 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 20m1 stop Orlando
Southwest Logo
6:10 am - 4:25 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
9h 15m1 stop Orlando
$238Southwest
Thu, Sep 17 - Thu, Sep 24
Southwest Logo
11:35 am - 8:50 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 15m1 stop Orlando
Southwest Logo
1:55 pm - 10:15 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
7h 20m1 stop Orlando
$238Southwest
Mon, Oct 19 - Tue, Oct 27
JetBlue Logo
8:50 pm - 8:55 amSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
13h 05m1 stop Orlando
JetBlue Logo
6:55 pm - 9:10 amMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
13h 15m1 stop Orlando
$238JetBlue
Wed, Sep 16 - Wed, Sep 23
United Airlines Logo
4:20 pm - 11:37 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
8h 17m1 stop Newark
United Airlines Logo
6:00 am - 8:38 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
13h 38m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
$258United Airlines
Sat, Sep 19 - Sun, Sep 27
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 - 9:35 amMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
22h 25m1 stop Orlando
$268Frontier
Wed, Oct 7 - Sun, Oct 11
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
$304United Airlines
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 16% 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 4204 reviews
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

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.

4.0 OkayMather, Aug 2026
Read more Southwest reviews

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…

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.

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 great because the flight was almost 5 hours so I had access to tons of movies news, etc. so it helped past the time by no other plane WestJet did not have movies so Delta was the best

Noting this only because it’s so unusual for delta: this was just an uncomfortable flight. The jet ridge was too hot and the plane wasn’t any better. By the time we got off the ground the AC was on but for such a short flight it was almost too late.

1) It was extremely hot in the cabin. All the passengers were sweating and it almost became suffocating 2) It was a 50 min flight but there was no service. How can a 50 minute flight not have any drink/snack 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.

This flight did not take place because the passenger was in the hospital. We have made so many attempts to rebook this flight and have spoken to so many United Airlines representatives and everyone is giving you a different answer. It has become beyond frustrating to the point where we now have to seek legal help. This is a family of 4 so a lot of money was spent to purchase 4 tickets to go visit their daughter/sister who is a US servicewoman in Okinawa and to be treated with such disdain and disrespect is beyond reprehensible. The main traveler was given sent a letter by United confirming a refund on the tickets and to be able to use them but every attempt to use this has been met with a negative response so much so that the client is over stressed.

First time flying business class. Very comfortable for our long flight to Europe.

Not a United thing, but late afternoon departures from Denver with thunderstorms is always prone to delays.

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Sitting in coach even in the larger leg space is extremely uncomfortable and the staff pay no attention.

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. .

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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