$88 Find Cheap Flights from Puerto Rico 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 5/2. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Milwaukee

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Milwaukee, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Milwaukee, as well as popular online travel agencies
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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

Wed, Apr 29 - Tue, May 5
Frontier Logo
3:21 am - 11:26 am
SJU
-
MKE
9h 05m
1 stop
Frontier Logo
9:56 am - 2:08 am
MKE
-
SJU
15h 12m
1 stop
$211Frontier
Wed, May 6 - Thu, May 14
Frontier Logo
3:13 am - 9:01 am
SJU
-
MKE
6h 48m
1 stop
Frontier Logo
9:46 am - 1:15 pm
MKE
-
SJU
26h 29m
1 stop
$246Frontier
Mon, Apr 13 - Thu, Apr 16
Frontier Logo
6:00 am - 3:47 pm
SJU
-
MKE
10h 47m
1 stop
Frontier Logo
12:21 pm - 2:01 am
MKE
-
SJU
12h 40m
1 stop
$264Frontier
Sun, May 3 - Thu, May 7
Frontier Logo
3:21 am - 11:26 am
SJU
-
MKE
9h 05m
1 stop
Frontier Logo
9:46 am - 2:08 am
MKE
-
SJU
15h 22m
1 stop
$282Frontier
Fri, Apr 10 - Mon, Apr 13
Frontier Logo
3:16 am - 12:52 pm
SJU
-
MKE
10h 36m
1 stop
Frontier Logo
4:32 pm - 12:52 am
MKE
-
SJU
7h 20m
1 stop
$306Frontier
Fri, May 1 - Tue, May 5
Multiple Airlines Logo
10:55 pm - 4:20 pm
SJU
-
MKE
18h 25m
1 stop
Multiple Airlines Logo
9:56 am - 2:08 am
MKE
-
SJU
15h 12m
1 stop
$308Multiple Airlines
Fri, Sep 4 - Sat, Sep 5
United Airlines Logo
10:48 am - 11:19 pm
CPX
-
MKE
13h 31m
2 stops
United Airlines Logo
8:30 am - 5:21 pm
MKE
-
CPX
31h 51m
2 stops
$1,191United Airlines
Fri, Sep 4 - Sat, Sep 5
United Airlines Logo
10:48 am - 1:58 pm
CPX
-
MKE
28h 10m
2 stops
United Airlines Logo
7:00 pm - 5:21 pm
MKE
-
CPX
21h 21m
2 stops
$1,201United Airlines
Fri, Sep 4 - Sat, Sep 5
United Airlines Logo
10:48 am - 11:19 pm
CPX
-
MKE
13h 31m
2 stops
United Airlines Logo
6:00 am - 5:21 pm
MKE
-
CPX
10h 21m
2 stops
$1,910United Airlines
Fri, Sep 4 - Sat, Sep 5
United Airlines Logo
10:48 am - 11:19 pm
CPX
-
MKE
13h 31m
2 stops
United Airlines Logo
5:05 am - 5:21 pm
MKE
-
CPX
11h 16m
2 stops
$1,919United 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 flight to Milwaukee?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Milwaukee was found on the route from San Juan, at $211 return. The most popular connection is from Newark to Milwaukee and KAYAK users have found round-trip deals for as low as $140 in the last 3 days.

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 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 January, where tickets cost $253 on average for return flights. On the other hand, the most expensive months are March and June, where the average cost of tickets from Puerto Rico is $486 and $470 respectively. For one-way flights, the best month to travel is January with an average price of $253.

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 21% 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$88
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from San Juan to Milwaukee

FAQs - booking Milwaukee flights

  • What is the cheapest flight to Milwaukee?

    In the last 3 days, the cheapest flight deal to Milwaukee was found on the route from San Juan, at $211 return. The most popular connection is from Newark to Milwaukee and KAYAK users have found round-trip deals for as low as $140 in the last 3 days.

  • 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 734 direct flights from within Puerto Rico to Milwaukee. The most common day for departures is Friday, with 15% 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.
8.0
SouthwestOverall score based on 4338 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

6.0 GoodKenley, Apr 2026
AUS - LAS
Read more Southwest reviews

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I am very please with the service received from Southwest. Although there was a refuel stop in Fl before we got the Baltimore. The service and kindness of the staff was excellent.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Boarding was again a "free for all". We were boarding group 4, and almost the entire plane was able to board before us. It's a shame that someone who follows the rules, gets the short end of the stick. Not fair.

Food and drink service was very low quality. The flight attendants in business class must have been short some staff. Service was sluggish and not much English was spoken

Flight left on time, arrived early, pleasant staff provided water, coffee, etc. access to bathrooms was reasonable and were well maintained. blankets were available, lots of entertainment options. LUGGAGE SERVICE WAS GREAT. I got my one checked bag quickly and was able to make a bus connection for a 2 hour bus ride saving me from waiting another 1.5 hours.

The boarding process was straightforward. One pertinent observation regarding all boarding procedures is that if an individual requires assistance or possesses a special status and is part of preboarding, it is advisable to limit the number of passengers who can preboard with them, rather than the entire, sometimes large, companion groups. The seats are uncomfortable, and the entertainment options are significantly inferior compared to other airlines. During the snack service, I requested an additional bag of snacks, but my request was denied. Initially, the flight attendant agreed to my request.becoming a strange accurate moment. The flight duration was four hours.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

Food was awful. TV didn’t work for long haul flight and my husband needed credit. Staff was nice and did their best but overall conditions were very uncomfortable.

It was perfect! I've never flown with United before, but I definitely will in the future

I had a cancelled flight because of technical issues going to my destination, and a delayed flight coming home. All told it wasn’t a total bust.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

Buying ticket from kayak instant booking was a huge mistake, never to be repeated again! The Kayak didn’t book the tickets directly, it handed it off to a third party Underpricer, that booked a code shared American Airlines flight operated by Cathay Pacific!! When managing the booking American Airlines would recognize the itinerary but wouldn’t let me do anything stating, the flight is operated by Cathay Pacific so go to their website. Cathay Pacific would recognize the itinerary, neither by reservation ID or ticket number…asking to reach out to the third party Underpricer….calling Underpricer resulted in no help like seat requests, mileage number or upgrade request, 15hr layover accommodation voucher guidance…so net in net avoid booking through three layers of intermediaries

I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight

A chaotic and uncomfortable experience from start to finish. The boarding process was a disaster; despite group numbers, it was a free-for-all that the staff failed to manage (especially after group 5). Once on board, the "entertainment" was non-existent. There are no seatback screens, and the mobile app selection is incredibly thin. The hardware is severely dated. My seat had zero cushioning left—it felt like sitting on a hard board for the entire flight—and the legroom was cramped. To make matters worse, the bathroom was repulsive, with toilet paper, soiled paper towels and liquid/pee all over the floor. When I did interact with the crew, they provided the absolute bare minimum and made me feel like an inconvenience for asking for anything. Avoid this flight if you can.

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

there are no options s for snack besides cookies would ve nice to have a salty option n

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

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