$118 Find Cheap Flights from Milwaukee to Puerto Rico

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Puerto Rico departing on 8/19. 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 Milwaukee to Puerto Rico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Aguadilla
Aguadilla2 stops$359
Culebra
Culebra2 stops$1,558
Aguadilla
Aguadilla2 stops$359
Culebra
Culebra2 stops$1,558

Book Cheap Milwaukee to Puerto Rico Plane Tickets

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

Tue, Aug 25 - Tue, Sep 1
United Airlines Logo
5:00 am - 2:44 pm
MKE
-
SJU
8h 44m
1 stop
United Airlines Logo
7:00 am - 5:09 pm
SJU
-
MKE
11h 09m
1 stop
$226United Airlines
Sat, Sep 5 - Wed, Sep 9
Southwest Logo
9:05 am - 6:05 pm
MKE
-
SJU
8h 00m
1 stop
Southwest Logo
1:45 pm - 9:05 pm
SJU
-
MKE
8h 20m
1 stop
$276Southwest
Wed, Sep 2 - Sat, Sep 5
American Airlines Logo
6:28 am - 11:59 pm
MKE
-
SJU
16h 31m
1 stop
American Airlines Logo
12:55 am - 7:44 am
SJU
-
MKE
7h 49m
1 stop
$281American Airlines
Fri, Sep 18 - Fri, Oct 2
United Airlines Logo
6:00 am - 2:44 pm
MKE
-
SJU
7h 44m
1 stop
United Airlines Logo
3:56 pm - 10:59 pm
SJU
-
MKE
8h 03m
1 stop
$293United Airlines
Tue, Sep 15 - Thu, Oct 1
American Airlines Logo
5:11 pm - 2:50 pm
MKE
-
SJU
20h 39m
2 stops
American Airlines Logo
2:58 pm - 12:48 pm
SJU
-
MKE
22h 50m
2 stops
$296American Airlines
Wed, Sep 16 - Wed, Sep 30
American Airlines Logo
6:01 am - 8:47 pm
MKE
-
SJU
13h 46m
2 stops
American Airlines Logo
6:27 am - 4:41 pm
SJU
-
MKE
11h 14m
2 stops
$301American Airlines
Fri, Oct 23 - Wed, Oct 28
United Airlines Logo
6:15 am - 2:44 pm
MKE
-
SJU
7h 29m
1 stop
United Airlines Logo
1:05 am - 9:46 am
SJU
-
MKE
9h 41m
1 stop
$305United Airlines
Wed, Sep 16 - Sat, Sep 19
United Airlines Logo
6:00 am - 8:38 pm
MKE
-
SJU
13h 38m
2 stops
United Airlines Logo
1:00 am - 10:00 am
SJU
-
MKE
10h 00m
2 stops
$316United Airlines
Tue, Sep 1 - Wed, Sep 2
Southwest Logo
10:50 am - 7:00 pm
MKE
-
SJU
7h 10m
1 stop
Southwest Logo
6:00 am - 12:00 pm
SJU
-
MKE
7h 00m
1 stop
$321Southwest
Tue, Sep 15 - Fri, Oct 2
Delta Logo
7:05 am - 4:31 pm
MKE
-
SJU
8h 26m
1 stop
Delta Logo
5:41 pm - 11:52 pm
SJU
-
MKE
7h 11m
1 stop
$326Delta
Booking Insights

KAYAK's insights & trends for Milwaukee to Puerto Rico flights

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

What is the cheapest month to fly from Milwaukee to Puerto Rico?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Puerto Rico, 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 from Milwaukee to Puerto Rico is January, when tickets cost $90 (return) on average. On the other hand, the most expensive months are June and April, when the average cost of round-trip tickets is $326 and $211 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Milwaukee to Puerto Rico, 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 on the flight from Milwaukee to Puerto Rico, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$118
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Milwaukee to San Juan

FAQs - booking Puerto Rico flights

  • Do I need a visa or passport to visit Puerto Rico?

    U.S. citizens can visit Puerto Rico without a visa or passport since it's a U.S. territory. A valid government-issued photo ID, like a driver's license or military ID, is sufficient for entry. International visitors should verify their specific entry requirements based on their nationality prior to travel.

  • Which Puerto Rico airport should I fly into?

    San Juan's Luis Muñoz Marín Airport is Puerto Rico's primary hub, offering major airlines and international connections. Ponce's Mercedita Airport provides convenient access to southern regions. Aguadilla's Borinquen Airport (BQN) serves the northwest, known for its ease of access and proximity to popular beach destinations.

  • Are there any nonstop flights from Milwaukee to Puerto Rico?

    While there are no direct flights on this route, numerous options offer just one layover. For flights to San Juan, American Airlines connects through Miami International Airport (MIA) or Charlotte Douglas International Airport (CLT). Delta routes typically include layovers in Hartsfield–Jackson Atlanta International Airport (ATL) or John F. Kennedy International Airport (JFK), and United flights often stop in Chicago O'Hare International Airport (ORD). For flights to Aguadilla or Ponce, Frontier Airlines operates these routes and first connects through Orlando International Airport (MCO).

  • Can I bring my surfboard on the flight to Puerto Rico?

    If you're planning to explore Puerto Rico's famous West Coast surf destinations, you can bring your own board when flying with American Airlines. You can transport one bag or case containing multiple boards, but ensure you remove all fins and accessories prior to packing. Boards weighing 50 lbs. or less qualify as a standard checked bag, while heavier ones will result in extra fees.

  • How does KAYAK find such low prices on flights from Milwaukee to Puerto Rico?

    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 from Milwaukee to Puerto Rico.

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

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

  • What is the Hacker Fare option on flights from Milwaukee to Puerto Rico?

    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 from Milwaukee to Puerto Rico 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 from Milwaukee to Puerto Rico?

    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 from Milwaukee to Puerto Rico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Puerto Rico

  • Your journey will start at Milwaukee Mitchell Airport (MKE), which is located around 7 miles from downtown. It is well-connected via the Wisconsin Coach Lines, Milwaukee County Transit System, as well as the Amtrak trains.
  • In the capital city of San Juan, you’ll find there are two airports. Luis Muñoz Marín Airport (SJU) serves major airlines and international flights, while Isla Grande Airport (SIG) caters to smaller aircraft and domestic routes. Flying to other cities on the island might require you to switch to the domestic airport.
  • Some Frontier Airlines flights require self-transfers. This means that upon reaching the layover city, you must recheck your luggage and pass through security again. Ensure your connection leaves enough time to do all of this and safely make it to your next flight. Traveling with only a carry-on can streamline this process and minimize potential issues.
  • For eco-conscious travelers, Delta is a good choice. They're shifting towards a more sustainable fleet and incorporating eco-friendly aviation fuels. Additionally, Delta is enhancing sustainability by using electric ground equipment and serving meals onboard that are sustainably sourced.
  • If you’re traveling on a budget, Frontier Airlines often has the lowest fares along this route, but be aware that this is for only airfare. Any additional services, like baggage or seat selection, will be charged an extra fee. This can add up, so consider one of their bundles, which offer an easy and affordable way to customize your trip.

Reviews of the top 5 airlines serving from Milwaukee to Puerto Rico

 
Need help choosing which airline to fly with from Milwaukee to Puerto Rico? 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 4235 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

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

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

The entertainment they offer could use some games, and maybe they could add some cookies to the snack menu. And the automated messages are a bit repetitive. But it was comfortable temperature wise and the seats were comfortable. The crew is very polite and helpful

The entertainment is a bit limited, it would be better if they added some games to play besides the movies and tv shows. But the seats are comfortable and the crew is polite

This planes staff was top tier. Everything went great and had a great flight home.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

This was an overnight flight, and in the morning they did know coffee service. How you can throw passengers in a San Francisco airport at 5:40 a.m. in the morning and not giving them Coffee is a crime.

I was promised by United Airline (operated by ANA) that I will be seated together with my kids as I am the only adult flying with two minors. We did not get seats together in our 11 hours flight from LA to Tokyo. When asked at the gate, ANA representative said United Airline should have informed them that there is a parent flying with two minors. He said they can’t do anything in the system as the flight is full. He ask me to ask passengers next to me and the kids if they are willing to change seats. This is ridiculous! However, I went in the flight and asked other passages but no one willing to change seats. 11 hours and we were seating separately. I was very disappointed with this. It made things super inconvenient for me.

Our flight was delayed several Times due to mechanical issues. Although I understand this may happen at times, it was very inconvenient and we had to book a hotel for an overnight stay. We were traveling with my 3-yo grandson and waiting at the airport from noon until 6:30pm with no reassurance that our next rescheduled flight would depart, we had to decide what’s best for him. A day later, I found out that I may be able to demand compensation if my flight is delayed more than 4 hours. I will hav to read the fine print next time.

Flight cancelled instead of leaving Friday am now, maybe, leaving Sunday

The pilot had to extend the flight time from san antonio to Houston to burn off fuel. This caused a lot of unnecessary stress since we had a tight connection to Aruba. And with no other flights going to Aruba we were worried about spending a night in Houston. We had to to run to our connection because of the flight crews mistake. Not happy.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Crew were professional and kind. The flight was smooth. But... The internet, which we paid 35 dollars for, did not work for most of the flight. This made providing media for our child an uncomfortable hassle.

Overall fine. Seemed like one of the older model planes? Crew was mostly very kind, though some of the female attendants were a rather abrupt during the food service.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

The Charleston, WV airport was cute. Very good staff and small enough to feel comfortable. The plane had more leg room than bigger planes. Much more comfortable.

Another uncoordinated American experience. Always surprises me at DFW for them of all places. Have to take this flight as there are no other good time options. We knew from the start that something was wrong, but the pilot wouldn't tell us. I just watched my Kayak app grow the delay by 10 minutes as it went to 3.5 hours. They were uncoordinated with maintenance (as maintenance, when finally arriving, knew within 15 minutes the plane wasn't going. No 'sorry' or 'this is what is going on' comment. The pilot seemed unfazed / didn't care about the process we were going through.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

Everything you need to know for your flight from Milwaukee to Puerto Rico

Information on your arrival and departure airports