$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, Oct 1 - Mon, Oct 5
Delta Logo
2:59 pm - 9:49 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 4:49 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
10h 19m1 stop Atlanta Hartsfield-Jackson
$238Delta
Fri, Oct 23 - Sun, Oct 25
American Airlines Logo
12:41 pm - 9:54 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 13m2 stops Charlotte Douglas Chicago O'Hare Intl
American Airlines Logo
6:27 pm - 11:31 amMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
16h 04m2 stops Charlotte Douglas Miami
$238American Airlines
Fri, Oct 23 - Sun, Oct 25
American Airlines Logo
12:41 pm - 9:52 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 11m1 stop Charlotte Douglas
American Airlines Logo
6:10 am - 10:57 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
15h 47m1 stop Philadelphia
$238American Airlines
Wed, Oct 14 - Tue, Oct 20
Frontier Logo
3:00 am - 9:20 amSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 20m1 stop Orlando
Frontier Logo
10:15 am - 1:53 amMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
14h 38m1 stop Orlando
$268Frontier
Sat, Sep 26 - Sun, Oct 4
Frontier Logo
7:00 am - 9:22 amSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
27h 22m1 stop Orlando
Frontier Logo
10:10 am - 9:35 amMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
22h 25m1 stop Orlando
$268Frontier
Sat, Oct 10 - Wed, Oct 14
Southwest Logo
3:05 pm - 9:30 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 25m1 stop Baltimore/Washington
Southwest Logo
3:00 pm - 11:50 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
7h 50m1 stop Orlando
$278Southwest
Fri, Sep 25 - Fri, Oct 2
Southwest Logo
2:35 pm - 8:50 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 15m1 stop Orlando
Southwest Logo
8:05 pm - 9:40 amMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
12h 35m1 stop Orlando
$300Southwest
Tue, Sep 22 - Sat, Sep 26
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
10:42 am - 11:50 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
12h 08m2 stops Chicago O'Hare Intl Newark
$366United Airlines
Sat, Sep 26 - Mon, Sep 28
Delta Logo
2:30 pm - 8:05 pmSJU  San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
6h 35m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:30 am - 4:49 pmMKE  Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
10h 19m1 stop Atlanta Hartsfield-Jackson
$366Delta
Thu, Oct 22 - Fri, Dec 11
United Airlines Logo
12:52 pm - 7:07 amMBJ  Montego Bay Sangster Intl-MKE Milwaukee-Mitchell
18h 15m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
2:36 pm - 4:19 pmMKE  Milwaukee-Mitchell-MBJ Montego Bay Sangster Intl
24h 43m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
$372United 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 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 4191 reviews
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

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

10.0 ExcellentAnte, Aug 2026
Read more Southwest reviews

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…

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. :(

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!

The temperature on the flight was unbearably hot and they were unable to serve waters and did t make any adjustments. This impacted us both when leaving, we pushed away from the gate but didn’t taxi for takeoff for awhile then arrived ‘early’ yet were stuck in the plane for longer than we should have been.

Terrible - the flight was delayed taking off after boarding. Then the flight circled lga before landing. Significant delay

I booked a round trip with Delta, and each of the four segments was sold off to three other airlines. All four were late or cancelled, so I had to troubleshoot with three different airlines, NOT Delta. In fact, even though I had paid money to Delta, they could not help or troubleshoot anything. Not nice.

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.

I missed the flight due to maintenance issues. This is the second flight I’ve missed in four days because United allows such little time between layovers. Very disappointing

My return flight to Honolulu (UA 1170) was on a 777-200. I’d forgotten the weird seating arrangement in first-class (2-2-2); I was in 1B, so I faced the passenger in 1C. Unfortunately, there was a problem with the flight computer, so we left LA an hour late (6:05pm). The meal I chose was Korean BBQ Glazed short rib. It was served with a nice salad and fried rice. This meal was better than breakfast on the outgoing leg. All in all, a decent flying experience. Ratings: 777: 3.75, food: 3.5, service: 5 (out of 5).

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

We couldn’t take the direct flight back home in Florida because the flight in Palermo was delayed flor long time and keep us inside the cabin without moving the plane. The plane from Munich to Orlando was still there when we arrived to the gate but they said it was late for us to board the plane. We rushed the most to get there. It was a bad experience and got back exhausted and with pain in all muy body. We are seniors 72 and for us was very bad

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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