$163 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 6/18. 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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Flight Deals

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

Mon, Oct 26 - Mon, Nov 2
Frontier Logo
9:03 am - 7:15 pm
SJU
-
MKE
11h 12m
1 stop
Frontier Logo
8:03 pm - 2:16 pm
MKE
-
SJU
16h 13m
1 stop
$321Frontier
Wed, Aug 5 - Fri, Aug 14
Delta Logo
2:11 pm - 8:18 pm
SJU
-
MKE
7h 07m
1 stop
Delta Logo
7:03 am - 4:37 pm
MKE
-
SJU
8h 34m
1 stop
$326Delta
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
1:38 pm - 11:57 pm
SJU
-
MKE
11h 19m
2 stops
American Airlines Logo
6:16 am - 10:24 pm
MKE
-
SJU
15h 08m
1 stop
$336American Airlines
Sat, Sep 26 - Wed, Sep 30
American Airlines Logo
2:25 pm - 9:26 pm
SJU
-
MKE
8h 01m
1 stop
American Airlines Logo
6:05 am - 6:10 pm
MKE
-
SJU
11h 05m
2 stops
$338American Airlines
Tue, Aug 4 - Fri, Sep 4
American Airlines Logo
7:00 am - 11:08 pm
SJU
-
MKE
17h 08m
1 stop
American Airlines Logo
6:16 am - 10:24 pm
MKE
-
SJU
15h 08m
1 stop
$340American Airlines
Tue, Aug 25 - Fri, Sep 4
American Airlines Logo
1:38 pm - 11:50 pm
SJU
-
MKE
11h 12m
2 stops
American Airlines Logo
6:16 am - 10:24 pm
MKE
-
SJU
15h 08m
1 stop
$341American Airlines
Tue, Aug 4 - Fri, Sep 4
American Airlines Logo
7:00 am - 5:17 pm
SJU
-
MKE
11h 17m
1 stop
American Airlines Logo
6:16 am - 10:24 pm
MKE
-
SJU
15h 08m
1 stop
$342American Airlines
Tue, Aug 4 - Fri, Sep 4
American Airlines Logo
7:00 am - 11:08 pm
SJU
-
MKE
17h 08m
1 stop
American Airlines Logo
6:16 am - 10:24 pm
MKE
-
SJU
15h 08m
1 stop
$343American Airlines
Sat, Sep 26 - Wed, Sep 30
American Airlines Logo
2:25 pm - 9:26 pm
SJU
-
MKE
8h 01m
1 stop
American Airlines Logo
6:22 am - 6:10 pm
MKE
-
SJU
10h 48m
2 stops
$348American Airlines
Tue, Aug 25 - Wed, Aug 26
United Airlines Logo
10:48 am - 10:39 pm
CPX
-
MKE
12h 51m
2 stops
United Airlines Logo
5:00 am - 5:21 pm
MKE
-
CPX
11h 21m
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 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 $321 return. The most popular connection is from Boston to Milwaukee and KAYAK users have found round-trip deals for as low as $187 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 $454 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 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 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 $321 return. The most popular connection is from Boston to Milwaukee and KAYAK users have found round-trip deals for as low as $187 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 2,042 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 4287 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

2.0 MediocreAnonymous, May 2026
MCO - MDW
Read more Southwest reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Was revoked with Jet Blue due to delay from Kenya Air

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

Much better than I expected. I had an economy ticket so I was really happy the flight was so comfy and the service so generous. Passengers were all polite too.

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

It took so long to do a baggage drop and it was bad enough. I had to go to the extreme end of the terminal because it’s a USA flight and go all the way back to the center indigo to security.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

Horrible, absolutely horrible. The airline overbooked the flight, did NOT assign seats and boarding was a hot mess with lots of confused passengers. There was no "large plane" gate for us, the 500+ passengers were squeezed in a small hold room area, and multiple busses had to shuttle us to the other side of the airfield, where boarding of the plane, that was parked on the ramp, took place in rain. The old plane had a broken seat, that the technicians tried to fix - with no success - resulting in a 50min delay. The flight attendant with heart shaped earnings with German flag was screaming on the passengers without a reason, was extremely rude and entitled the entire flight. The food was junk. I hope I don't have to fly United ever again.

Late plane. Only one crew on the ground so we b had to wait for Denver flight to come in, board, and depart. At 78 yrs of age I was not pleased trying to get my connection. What really made me angry was the notification you sent me to hurry up or I would miss my connection. Why tell me to hurry up when you got me in late. It was not a good way of treating customers.

No complaints other than luggage carousel was incorrectly guiding passengers to the wrong carousel on the screen.

We were a little disappointed to not be able to complete check in online without uploading pics of passports. Also we have KTN's and they weren't on our boarding passes when we got to security. Had to trek back to counter to have them fix.

Excellent service in Polaris class IAD to ZRH. Arrived rested and well fed after the overnight flight.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

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