$98 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 4/17. 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

Fri, Apr 17 - Mon, Apr 20
Frontier Logo
7:15 am - 1:52 pm
SJU
-
MKE
7h 37m
1 stop
Frontier Logo
2:47 pm - 11:29 pm
MKE
-
SJU
7h 42m
1 stop
$186Frontier
Wed, Apr 29 - Tue, May 5
Frontier Logo
3:21 am - 11:26 am
SJU
-
MKE
9h 05m
1 stop
Frontier Logo
8:46 am - 10:43 pm
MKE
-
SJU
12h 57m
1 stop
$196Frontier
Fri, Apr 10 - Fri, Apr 17
Frontier Logo
4:40 pm - 3:20 pm
SJU
-
MKE
23h 40m
1 stop
Frontier Logo
7:34 pm - 10:48 pm
MKE
-
SJU
26h 14m
1 stop
$216Frontier
Fri, May 1 - Mon, May 4
Southwest Logo
6:50 am - 7:10 pm
SJU
-
MKE
13h 20m
1 stop
Southwest Logo
3:30 pm - 11:40 pm
MKE
-
SJU
7h 10m
1 stop
$276Southwest
Fri, May 1 - Mon, May 4
American Airlines Logo
7:25 am - 5:51 pm
SJU
-
MKE
11h 26m
1 stop
American Airlines Logo
12:00 pm - 8:51 pm
MKE
-
SJU
7h 51m
1 stop
$282American Airlines
Wed, Apr 15 - Wed, Apr 29
American Airlines Logo
6:00 am - 9:41 pm
SJU
-
MKE
16h 41m
1 stop
American Airlines Logo
6:00 am - 10:05 pm
MKE
-
SJU
15h 05m
1 stop
$286American Airlines
Wed, Apr 15 - Wed, Apr 29
American Airlines Logo
6:00 am - 9:41 pm
SJU
-
MKE
16h 41m
1 stop
American Airlines Logo
6:00 am - 10:05 pm
MKE
-
SJU
15h 05m
1 stop
$287American Airlines
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
7:15 am - 1:52 pm
SJU
-
MKE
7h 37m
1 stop
Frontier Logo
12:21 pm - 2:01 am
MKE
-
SJU
12h 40m
1 stop
$294Frontier
Fri, May 1 - Mon, May 4
Southwest Logo
6:50 am - 7:10 pm
SJU
-
MKE
13h 20m
1 stop
Southwest Logo
8:00 am - 8:00 pm
MKE
-
SJU
11h 00m
2 stops
$301Southwest
Mon, May 25 - Fri, May 29
United Airlines Logo
10:30 am - 5:04 pm
CPX
-
MKE
31h 34m
2 stops
United Airlines Logo
8:45 pm - 5:21 pm
MKE
-
CPX
19h 36m
2 stops
$1,583United 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 $186 return. The most popular connection is from Newark to Milwaukee and KAYAK users have found round-trip deals for as low as $160 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 June and July, where the average cost of tickets from Puerto Rico is $486 and $485 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$98
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 27% 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 $186 return. The most popular connection is from Newark to Milwaukee and KAYAK users have found round-trip deals for as low as $160 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 1,125 direct flights from within Puerto Rico to Milwaukee. The most common day for departures is Sunday, 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 5 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 4331 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

10.0 ExcellentGwen, Mar 2026
DAL - BNA
Read more Southwest reviews

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The cabin temperature was nice and cool. The wifi was not working.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

As previously noted, this flight was great: departure was timely, the crew was friendly and attentive, and wifi connectivity was seamless. In particular, I appreciated that the flight attendant just told me to stow the laptop right before takeoff/landing, and trusted me to do so (which I did!).

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

2000 USD for a 10 hour flight on the worst seats I've ever flown in.

I will never fly ANA again. They lost one of my large pieces of checked luggage, the heaviest one with the most valuable items in it, and they said they will not send me an email unless they can't find it, even though the paper they gave me to track the status of my lost luggage requires a code from an email they are supposed to send me so I can do baggage tracing. They claim to be an international airline, but they also insist on calling a Japanese telephone number to confirm where to send the lost baggage if they find it. It is impossible to find an actual contact email address for customer support on their website, and their AI chatbot is unhelpful, directing you to a webpage that says it is for contact information but does not have any actual email addresses or phone numbers listed on it. My seat in economy did not recline at all, even though I was not sitting in an exit row nor the very back row. I had to sit in the fully upright position for over ten hours of international travel. Awful experience overall.

I could not get the wifi to work. But like the screen on the seats.

My flight was canceled a few hours before boarding. I was rebooked on Copa airlines and missed an important meeting .

The head flight attendant made the trip excellent. He was very accommodating.

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

Offered to check carry on to final destination. This is the most absurd thing in the world. I'm carrying on because I need what is in the carry-on. I'm okay with picking up at next stop but then I will be on much larger plane that can accommodate it. Also, if there is ever a change to your flight. Go to the airport and have the people there fix your ticket. Don't do it over the phone or online with United they screwed us up and ended up with flights for our last leg that took off before our first leg.

The economy seats on the 777 was not as cramped as I had feared, but the food was terrible.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Delays with no explanation. It could have been handled better.

Ceiling fell down and had to have maintenance come and duct tape it up. No WiFi on the flight.

A first class seat should fit a fat person, and this doesn't. The trays in the armrest are less functional than an ordinary tray in the back of the seat.

The flight attendant was friendly and efficient. The temperature was kept nice and cool. The plane was nice, but filthy. There were visible spills on my tray table. The gate agent was somewhat rude with her announcements and in speaking with other customers.

I appreciate that I finally got the seat I paid extra for this time. Thank you

I would have liked vegetarian and gluten free options for evening dinner time flight. I would have like a pillow on the international overnight flight . The veg wrap and oaten desert on the international flight was good

The experience at checkin for my American Airlines flight from Sacramento to LAX was very good including the assistance I received in getting my bags checked in and boarding passes printed. Was pleasantly surprised the my bags were checked through all the way to my destination at Clark International Airport in Angeles, Philippines.

Very poor food. Took more than 90 minutes for baggage to arrive at DFW

British Airways is an excellent airline. Comfort, food and airline personnel.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

The flight was a big joke very uncomfortable I had a horrible experience and I will never fly with them again everything about the flight was bogus and I’m not happy with it at all this experience makes me not want to fly ever again

Pricing, boarding time communication, over priced baggage and overall service is lacking, seating unconfortable

Flight attendant was all so sweet and pilot got us to our destination safely and on time

we boarded the plane and then sat for OVER AN HOUR on it, first waiting for fuel and then the crew timed out. the flight kept getting delayed longer and longer, a 9:30pm flight is still on the ground at 1:15am.

The airplane rattled near the left wing as if several screws were loose. Then after we landed in Fort Lauderdale, we had to sit and wait on the runway for quite some time. It was very scary and TOTALLY unacceptable!

Smooth flight staff very friendly and we arrived 15 mins earlier

I was in the airport when I'll check the status of my flight and it was canceled and without any reason. The worst of the worst ...

I never had an opportunity to experience them! They cancelled my flight TWICE!!!

Return flight was canceled. Needed to reschedule with another airline the next day. Cost an an additional $84. At another airport 45 miles further away

Spent seven hours in the airport with spirit pushing he flight time back two hours every two hours only to then have it canceled without explanation. The employees said, “They’ve been doing this for the last five days.” Would have been great if they told us to expect that when we arrived.

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