$163 Find Cheap Flights from Puerto Rico 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 Puerto Rico to Milwaukee

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

Thu, Aug 27 - Mon, Aug 31
Delta Logo
2:59 pm - 8:53 pm
SJU
-
MKE
6h 54m
1 stop
Delta Logo
7:03 am - 4:38 pm
MKE
-
SJU
8h 35m
1 stop
$326Delta
Thu, Jul 23 - Wed, Jul 29
American Airlines Logo
2:25 pm - 11:44 pm
SJU
-
MKE
10h 19m
1 stop
American Airlines Logo
6:00 am - 6:24 pm
MKE
-
SJU
11h 24m
2 stops
$331American Airlines
Sat, Aug 1 - Tue, Aug 11
Southwest Logo
8:15 pm - 8:55 am
SJU
-
MKE
13h 40m
1 stop
Southwest Logo
10:50 am - 7:00 pm
MKE
-
SJU
7h 10m
1 stop
$345Southwest
Thu, Aug 6 - Sun, Aug 9
Southwest Logo
6:30 am - 4:20 pm
SJU
-
MKE
10h 50m
1 stop
Southwest Logo
7:00 pm - 9:10 am
MKE
-
SJU
13h 10m
1 stop
$363Southwest
Tue, Aug 4 - Fri, Aug 14
American Airlines Logo
12:55 am - 12:47 pm
SJU
-
MKE
12h 52m
1 stop
American Airlines Logo
6:20 am - 6:33 pm
MKE
-
SJU
11h 13m
2 stops
$366American Airlines
Thu, Aug 13 - Sun, Aug 16
American Airlines Logo
12:55 am - 7:49 am
SJU
-
MKE
7h 54m
1 stop
American Airlines Logo
6:20 am - 4:57 pm
MKE
-
SJU
9h 37m
2 stops
$372American Airlines
Sat, Aug 1 - Tue, Aug 11
Southwest Logo
9:25 pm - 8:55 am
SJU
-
MKE
12h 30m
1 stop
Southwest Logo
7:40 am - 7:00 pm
MKE
-
SJU
10h 20m
2 stops
$382Southwest
Sat, Aug 15 - Sat, Aug 29
Delta Logo
7:00 am - 2:45 pm
SJU
-
MKE
8h 45m
1 stop
Delta Logo
6:00 am - 1:42 pm
MKE
-
SJU
6h 42m
1 stop
$383Delta
Thu, Aug 6 - Sun, Aug 9
Southwest Logo
6:30 am - 3:25 pm
SJU
-
MKE
9h 55m
2 stops
Southwest Logo
7:00 pm - 9:10 am
MKE
-
SJU
13h 10m
1 stop
$401Southwest
Tue, Sep 29 - Thu, Oct 1
United Airlines Logo
10:48 am - 10:45 pm
CPX
-
MKE
12h 57m
2 stops
United Airlines Logo
6:15 am - 5:21 pm
MKE
-
CPX
10h 06m
2 stops
$1,558United Airlines
Booking Insights

KAYAK's insights & trends for flights to Milwaukee

Get data-powered insights and trends for flights to Milwaukee to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly to Milwaukee?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights to Milwaukee, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Milwaukee is May, where tickets cost $98 on average for return flights. On the other hand, the most expensive months are June and March, where the average cost of tickets from Puerto Rico is $286 and $256 respectively. For one-way flights, the best month to travel is March with an average price of $90.

How far in advance should I book a flight to Milwaukee?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Milwaukee, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 4 weeks before departure, which saves you about 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$163
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from San Juan to Milwaukee

FAQs - booking Milwaukee flights

  • How far is Milwaukee-Mitchell Airport from central Milwaukee?

    The city center of Milwaukee is 6 miles from Milwaukee-Mitchell Airport.

  • What is the name of Milwaukee’s airport?

    Milwaukee is served by Milwaukee-Mitchell Airport, also commonly referred to as General Mitchell Intl or Milwaukee-Mitchell. The airport code is MKE.

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Milwaukee is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights 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 with another airline.

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

  • How many direct flights to Milwaukee are there each week?

    Each week there are around 1,858 direct flights from within Puerto Rico to Milwaukee. The most common day for departures is Sunday, with 18% of flights taking off on this day.

Top tips for finding cheap flights to Milwaukee

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Milwaukee flight deals.

Reviews of the top 4 airlines serving from Puerto Rico to Milwaukee

 
See real verified KAYAK customer reviews for airlines flying to Milwaukee. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Puerto Rico to Milwaukee. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with 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
SouthwestOverall score based on 4250 reviews
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

8.0 ExcellentAnonymous, Jul 2026
PHL - BNA
Read more Southwest reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

Slow boarding, limited food and drink portions. Bad delays and turbulence

Terrible all around. Left prior review detailing massive delay/cancellation to then rebook travel. Topping on the cake was lost luggage even after travel to ultimate destination was secured on a new plane(s).

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!

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

I like everything about Southwest. From customer service to crew and prices. I travel a lot during the year and Southwest is the best!!

The seats were really comfortable. Flight crew were friendly with passengers. Overall was a great flight.

Great crew, flight on time, luggage pick up a breeze

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.

Unfortunately I was stuck next to someone who should have purchased 2 seats instead of taking up their space and mine. I couldn’t move the entire 3+ hour flight. Very uncomfortable flight.

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.

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

The Manila airport was under renovation so there was no business class lounge. The double security check was disorganized and the flight attendants were grouchy.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Awful. There was a minor problem with a fridge and they had us 2 hours in the runway before take off. The paper work alone took them half hour. There was no attemp to make up time up while in teansit and when we arrived, they had us another half hour in the plane because of traffic. I, and a bunch of people, lost their onnection flights for 5 to 10 minutes. Not even the attemp to wait given thar all delays, but the taxing, were United's fault. Then another 45 mins to get an agent and no flight alternatives for 2 days. Im am very disapointed with this "premium carrier".

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

IT WAS A LONG TIME SINCE THE LAST TIME I TRAVELED. I THOUGHT I WAS TO BE LOST BUT EVERYONE WAS PRETTY NICE WITH ME AND MADE MY EXPERIENCE NICE. THANKS

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.

There was a delay that was unexpected. The seats were uncomfortable for the length of the flight.

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

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.

We loved the steward on the plane. He made the night enjoyable

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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