$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 8/27. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Thu, Aug 27 - Mon, Aug 31
Delta Logo
5:49 pm - 11:53 pm
SJU
-
MKE
7h 04m
1 stop
Delta Logo
7:03 am - 4:38 pm
MKE
-
SJU
8h 35m
1 stop
$326Delta
Tue, Aug 4 - Fri, Sep 4
American Airlines Logo
7:00 am - 5:17 pm
SJU
-
MKE
11h 17m
1 stop
American Airlines Logo
6:20 am - 6:34 pm
MKE
-
SJU
11h 14m
2 stops
$332American 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
6:20 am - 6:34 pm
MKE
-
SJU
11h 14m
2 stops
$333American 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 - 6:24 pm
MKE
-
SJU
11h 08m
2 stops
$334American 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
6:20 am - 10:24 pm
MKE
-
SJU
15h 04m
1 stop
$335American Airlines
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
6:30 am - 3:25 pm
SJU
-
MKE
9h 55m
2 stops
Southwest Logo
1:55 pm - 10:15 pm
MKE
-
SJU
7h 20m
1 stop
$365Southwest
Wed, Aug 5 - Fri, Aug 14
American Airlines Logo
7:00 am - 11:14 pm
SJU
-
MKE
17h 14m
1 stop
American Airlines Logo
6:20 am - 6:34 pm
MKE
-
SJU
11h 14m
2 stops
$366American Airlines
Sat, Aug 29 - Sun, Aug 30
American Airlines Logo
12:55 am - 12:47 pm
SJU
-
MKE
12h 52m
1 stop
American Airlines Logo
4:25 pm - 12:15 am
MKE
-
SJU
6h 50m
1 stop
$368American Airlines
Thu, Nov 12 - Wed, Nov 18
American Airlines Logo
3:53 pm - 11:05 pm
SJU
-
MKE
9h 12m
1 stop
American Airlines Logo
6:48 pm - 1:04 pm
MKE
-
SJU
16h 16m
1 stop
$371American Airlines
Fri, Aug 28 - Tue, Sep 1
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 7 days.

In the last 7 days, the cheapest flight deal to Milwaukee was found on the route from San Juan, at $326 return. The most popular connection is from Boston to Milwaukee and KAYAK users have found round-trip deals for as low as $182 in the last 7 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 $456 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 32% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from San Juan to Milwaukee

FAQs - booking Milwaukee flights

  • What is the cheapest flight to Milwaukee?

    In the last 7 days, the cheapest flight deal to Milwaukee was found on the route from San Juan, at $326 return. The most popular connection is from Boston to Milwaukee and KAYAK users have found round-trip deals for as low as $182 in the last 7 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 1,712 direct flights from within Puerto Rico to Milwaukee. The most common day for departures is Sunday, with 17% 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 4264 reviews
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

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.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Flight was delayed. Then eventually cancelled. The female staff that was announcing overhead was unprofessional. She was telling everyone that the company is not going to give any money for taxi, hotel etc. then eventually the flight was cancelled.

My service light was on 15 minutes before I had to get up and find a glass of ice. And I was in business class. The meals were not for either my wife and I. She did not eat the entire 10 hour flight and I managed a bowl of soup. I was expecting much more from business with what we paid.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

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

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

Uncomfortable plastic seats even in premium economy. No free wifi. Even paid wifi was spotty to nonexistent. Bad food. Much worse than economy on foreign carriers like Qantas.

How can you rate a flight when it is canceled after you leave the gate & 3 hours into sitting there or in remote area of airport after mechanical problems

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Broken tray table. Erratic service. Premium economy is more economy than premium- other airlines treat PE much better. No lounge access.

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

MY FAMILY'S LUGGAGE WAS LOST FROM ROME TO BARI. I WAS THE ONLY ONE THAT RECEIVED MY LUGGAGE FROM ROME TO BARI. AFTER DEPLANING IN BARI, WE WASTED A LOT OF TIME AT BAG CLAIMS LOST AND FOUND REPORTING THE CLAIM AND PLEADING FOR THE BAGS TO BE DELIVERED THE NEXT DAY. WE WERE TOLD THAT IT TAKES 3 DAYS MINIMUM TO DELIVER. MY DAUGHTER AND MY GIRLFRIEND NEEDED THEIR PERSONAL THINGS AND WE WERE STAYING 3 HOURS AWAY FROM THE BARI AIRPORT. WE HAD TO DRIVE 3 HOURS TO THE AIRPORT TO COLLECT OUR LOST LUGGAGE THE NEXT DAY. WE ARE NOT HAPPY WITH THE EXPERIENCE

We had a delay, but thankfully I made it to my connection. Overall it went smooth

The flight had a delay but I made it to my connection. Flight was smooth overall

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Pewaukee
Oak Creek
Mequon
New Berlin
Port Washington

Everything you need to know for your flight to Milwaukee

Information on the airport you'll fly into in Milwaukee