$107 Find Cheap Flights from Caribbean Islands to Milwaukee

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 2/19. 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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Everything you should know

Cheapest round-trip
$202
Typical prices: $236-$324
Frontier
Thu 2/19Mon 2/23
SJU - MKE • 1 stop
Cheapest non-stop
$708
Sun Country Air
Thu 2/26Mon 3/2
PUJ - MKE • Non-stop
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Flight Deals
Useful Info
Flight Deals

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, Feb 19 - Mon, Feb 23
Frontier Logo
4:25 pm - 9:43 am
SJU
-
MKE
19h 18m
1 stop
Frontier Logo
8:11 pm - 9:54 am
MKE
-
SJU
11h 43m
1 stop
$202Frontier
Tue, Feb 24 - Sat, Feb 28
Frontier Logo
5:25 pm - 3:44 pm
SJU
-
MKE
24h 19m
1 stop
Frontier Logo
7:47 pm - 2:53 am
MKE
-
SJU
29h 06m
1 stop
$244Frontier
Tue, Feb 24 - Tue, Mar 17
Delta Logo
6:37 pm - 11:47 pm
SJU
-
MKE
7h 10m
1 stop
Delta Logo
1:21 pm - 11:15 pm
MKE
-
SJU
8h 54m
1 stop
$256Delta
Wed, Apr 15 - Wed, Apr 29
American Airlines Logo
11:59 pm - 11:00 am
SJU
-
MKE
12h 01m
1 stop
American Airlines Logo
1:10 pm - 10:05 pm
MKE
-
SJU
7h 55m
1 stop
$263American Airlines
Thu, Feb 12 - Tue, Feb 17
Frontier Logo
3:53 am - 9:43 am
SJU
-
MKE
7h 50m
1 stop
Frontier Logo
4:39 pm - 2:48 am
MKE
-
SJU
8h 09m
1 stop
$268Frontier
Thu, Feb 19 - Mon, Feb 23
Southwest Logo
8:00 am - 1:30 pm
SJU
-
MKE
7h 30m
1 stop
Southwest Logo
6:45 am - 7:20 pm
MKE
-
SJU
10h 35m
2 stops
$285Southwest
Thu, Feb 12 - Mon, Feb 16
Frontier Logo
3:53 am - 9:43 am
SJU
-
MKE
7h 50m
1 stop
Frontier Logo
7:52 pm - 9:54 am
MKE
-
SJU
12h 02m
1 stop
$292Frontier
Wed, Apr 15 - Sun, Apr 19
United Airlines Logo
1:00 am - 11:32 am
SJU
-
MKE
11h 32m
2 stops
United Airlines Logo
5:10 am - 2:44 pm
MKE
-
SJU
8h 34m
1 stop
$317United Airlines
Tue, Feb 24 - Tue, Mar 17
American Airlines Logo
8:00 am - 4:56 pm
SJU
-
MKE
10h 56m
2 stops
American Airlines Logo
3:05 pm - 5:28 am
MKE
-
SJU
13h 23m
1 stop
$319American Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
2:55 pm - 10:28 pm
PUJ
-
MKE
9h 33m
1 stop
United Airlines Logo
5:00 am - 4:02 pm
MKE
-
PUJ
9h 02m
1 stop
$471United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$107
Most popular time to fly with an average 15% 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.
7.9
DeltaOverall score based on 8123 reviews
7.9Comfort
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

10.0 ExcellentDr. Simon, Jan 2026
LAX - JFK
Read more Delta reviews

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Very convenient considering that is a non-stop flight, but the Aeromexico still has old model planes, so the entertainment was very poor and the space for carry-on luggage was very limited.

Flight taking off must have been behind, because there was no pre-departure drink for first class like normal. Also, person in front of mine’s seat got stuck in the as far back as it normally goes position for the whole flight even during landing, flight attendant unable to fix it. Gate was not empty when we arrived, but that is MSP’s fault since was overdue for push back, not Delta’s, so had to sit on tarmac for a while and international flight so then still had to go through customs. Flight crew was excellent throughout though!

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

This Japanese airline provides great service and very helpful in assisting their passengers.

Good crew. Boarding delays. Almost two hours wait for the bags in DC.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

We were upgraded to Business Class. So comfortable with great service and food options

The flight attendant use 1.5 hours to answer my call. My dirty food tray was unattended.

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