$173 Find Cheap Flights from Caribbean Islands 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 10/26. 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 Islands to Milwaukee

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands 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 Islands to Milwaukee

Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
3:47 pm - 9:47 pm
SJU
-
MKE
7h 00m
1 stop
American Airlines Logo
6:20 am - 10:24 pm
MKE
-
SJU
15h 04m
1 stop
$346American Airlines
Sun, Sep 6 - Sun, Sep 13
Delta Logo
4:59 pm - 11:53 pm
MBJ
-
MKE
6h 54m
1 stop
Delta Logo
5:30 am - 1:01 pm
MKE
-
MBJ
7h 31m
1 stop
$347Delta
Wed, Nov 4 - Wed, Feb 24
American Airlines Logo
3:50 pm - 10:37 pm
SJU
-
MKE
8h 47m
1 stop
American Airlines Logo
10:30 am - 11:27 pm
MKE
-
SJU
10h 57m
2 stops
$351American Airlines
Mon, Aug 24 - Sat, Aug 29
American Airlines Logo
12:55 am - 7:49 am
SJU
-
MKE
7h 54m
1 stop
American Airlines Logo
8:20 am - 10:54 pm
MKE
-
SJU
13h 34m
1 stop
$353American Airlines
Thu, Sep 24 - Wed, Sep 30
American Airlines Logo
4:38 pm - 8:01 am
SJU
-
MKE
16h 23m
2 stops
American Airlines Logo
2:48 pm - 9:24 am
MKE
-
SJU
17h 36m
2 stops
$358American Airlines
Tue, Sep 1 - Sat, Jan 9
Southwest Logo
5:15 am - 10:55 am
SJU
-
MKE
6h 40m
1 stop
Southwest Logo
7:10 am - 10:00 pm
MKE
-
SJU
12h 50m
1 stop
$361Southwest
Thu, Sep 3 - Tue, Sep 8
Southwest Logo
6:00 am - 3:25 pm
SJU
-
MKE
10h 25m
2 stops
Southwest Logo
7:40 am - 7:05 pm
MKE
-
SJU
10h 25m
2 stops
$374Southwest
Sat, Oct 17 - Sun, Oct 25
Delta Logo
1:32 pm - 9:02 pm
MBJ
-
MKE
7h 30m
1 stop
Delta Logo
5:40 am - 3:34 pm
MKE
-
MBJ
9h 54m
1 stop
$442Delta
Fri, Sep 4 - Tue, Sep 8
United Airlines Logo
3:35 pm - 2:33 pm
PUJ
-
MKE
23h 58m
2 stops
United Airlines Logo
6:05 am - 2:27 pm
MKE
-
PUJ
7h 22m
1 stop
$644United Airlines
Fri, Sep 4 - Tue, Sep 8
United Airlines Logo
3:35 pm - 12:38 pm
PUJ
-
MKE
22h 03m
2 stops
United Airlines Logo
10:30 am - 12:40 pm
MKE
-
PUJ
25h 10m
2 stops
$656United Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$173
Best time to beat the crowds with an average 3% 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 Islands to Milwaukee

  • How does KAYAK find such low prices on flights from Caribbean Islands 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 Islands to Milwaukee.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Milwaukee?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Milwaukee from Caribbean Islands 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 Islands 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 Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands 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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Caribbean Islands to Milwaukee

 
Need help choosing which airline to fly with from Caribbean Islands 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.
7.8
DeltaOverall score based on 8496 reviews
8.5Crew
8.1Boarding
7.8Comfort
7.2Food
7.8Entertainment
Airline reviews

Seats were not bad enough and uncomfortable good legroom in the emergency exit row we were in, but we were forbidden to hold my grandson on my lap for a little while, and the stewardess passed us saying it was against regulations which makes little or no sense when you’re 36,000 feet. The food snacks were really bad. Tasteless tasted like wallpaper, but we’re supposed to be protein bars, and the announcements were all completely incoherent because of the noise of the airplane and the lowness and crackly nature of the PA system.. this was disgraceful. No one in our party could understand a word of what the captain or the flight attendant were saying —not a word! The landing was a little hairy in a pretty stiff crosswind -we bounced before the plane stabilized on the runway

6.0 GoodJeremy, Jul 2026
LAX - OGG
Read more Delta reviews

Seats were not bad enough and uncomfortable good legroom in the emergency exit row we were in, but we were forbidden to hold my grandson on my lap for a little while, and the stewardess passed us saying it was against regulations which makes little or no sense when you’re 36,000 feet. The food snacks were really bad. Tasteless tasted like wallpaper, but we’re supposed to be protein bars, and the announcements were all completely incoherent because of the noise of the airplane and the lowness and crackly nature of the PA system.. this was disgraceful. No one in our party could understand a word of what the captain or the flight attendant were saying —not a word! The landing was a little hairy in a pretty stiff crosswind -we bounced before the plane stabilized on the runway

Chaotic boarding at these gates, multiple gates squeezed in at the very end of a concourse, behind a restaurant. Agents gave up on boarding by individual zones. Flight itself was uneventful, which is all we hope for any more.

Unprepared to rebook a flight of people. Uncommunicative. When I received updates in the app it was well after the announcement in the hold room. Offered a single $12 meal voucher, not enough for a sandwich at DEN, for a 17 hour delay. No one was able to explain their meal or hotel reimbursement policy for this cancellation, just handed a card to call the Help desk. My previous flight went through several delays and was finally cancelled, without explanation. The customer help desk closed while there was a long line. I then waited in line for a gate agent almost an hour while simultaneously on hold and trying to text with a remote Delta agent. Communicating with the text agent was almost impossible; they could not find any flights that got me back to my original city before the following evening. Kept offering itineraries that did not get me back to my origin airport or involved additional layovers. In 50 minutes on hold, never got through to an agent by phone. Finally spoke to one of the gate agents who was able to rebook on a red eye that had only one stop and got me back in the afternoon the next day, rather than late evening. Later by email, Delta offered 10,000 loyalty points for the inconvenience of the cancellation. The crew on the red eye flight were delightful. I don’t remember any food or entertainment on that flight.

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.

Gluten free snack options and meals that offer both gluten free and dairy free.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

The experience with United Airlines was excellent; however, the experience with Houston Intercontinental Airport (IAH) was horrible. Although our flight departed from Terminal B, we had to go through security in Terminal C and then get on a train for travel to Terminal B. Additionally, there was significant walking required to get to the boarding location.

Delayed 2 hours while stuck on the aircraft. If the luggage was properly loaded the first time we probably wouldn’t have been delayed at all

The international portion was good. Food and beverage options were good. The sustainable wooden eatery was less than desirable. Your Star Alliance partner ANA provided real silverware. I'm 6'3" & 198 lbs and felt cramped in the exit row. How can that be? Flight attendant all had a pleasant disposition which is always good.

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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