
Book Cheap Milwaukee to Puerto Rico Plane Tickets
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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?
The cheapest month for flights from Milwaukee to Puerto Rico is September, when tickets cost $376 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $770 and $537 respectively.
How far in advance should I book a flight from Milwaukee to Puerto Rico?
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 15 weeks before departure.
Which airlines fly non-stop between Milwaukee and Puerto Rico?
There are 2 airlines that fly nonstop from Milwaukee to Puerto Rico. They are American Airlines and United Airlines. The cheapest airline for this route is United Airlines, with the best round-trip deal found costing $235 and arriving in San Juan Luis Munoz Marin Intl Airport (SJU). On average, American Airlines offers the best prices for nonstop flights between Milwaukee and Puerto Rico.
Which airlines provide the cheapest flights from Milwaukee to Puerto Rico?
In the past 5 days, the cheapest round-trip tickets from Milwaukee to Puerto Rico were found on Southwest ($386) and United Airlines ($486).
Good to know
Low season | September |
|---|---|
High season | March |
Cheapest flight | $105 |
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Reviews of the top 5 airlines serving from Milwaukee to Puerto Rico
One, we were met with more than six hours of delays with no information flowing from the airline to the passenger. I had to continually refresh for updates to departure time - which changed multiple times throughout the day. Updates were never pushed to me nor was an explanation provided for the delay until this morning. Two, while they claim that "due to the short flight" no beverage service would be provided. Our flight was mostly empty. I'd think given the massive inconvenience, SW could have shared a Diet Coke and some peanuts. And BTW, SW used to always make these available on this flight back in the day. Let's be honest, this is cost savings at the customer's expense.
One, we were met with more than six hours of delays with no information flowing from the airline to the passenger. I had to continually refresh for updates to departure time - which changed multiple times throughout the day. Updates were never pushed to me nor was an explanation provided for the delay until this morning. Two, while they claim that "due to the short flight" no beverage service would be provided. Our flight was mostly empty. I'd think given the massive inconvenience, SW could have shared a Diet Coke and some peanuts. And BTW, SW used to always make these available on this flight back in the day. Let's be honest, this is cost savings at the customer's expense.
Despite paying for an ‘upgraded’ seat in row 1, I had to put my luggage in the middle of the plane. Snacks were bleh and seat was small and uncomfortable and I am not large. Attendants were fine but not super helpful. Plane just seemed outdated.
It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.
Delayed for no reason at all originally. Then they said it was due to weather conditions. Communication between kayak and Southwest was terrible because both displayed different delays and departure times for HOURS throughout the day. The plane then had technical issues which delayed us from taking off even longer. Didn’t actually take off until 11:45pm when the original departure time was 7:35pm. I didn’t get home until 1:30am the next day. I was exhausted and pissed off. I am not confident if I’ll fly southwest in the future or use kayak to book.
A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack
I like the staff members they were super nice and helpful very sweet people :)
Unfortunately, I left my headphone's case in the bag of the front seat. I was seating on 9C. Hopefully the found it and I can get it back. I have not been able to get in contact with Southwest. Other than that, everything went fine.
Flight time kept changing and so did the gate. It was very frustrating
it was great. the crew is exceptional. the flight was on time.
We were headed for Florida and anxious to get there. Everything was absolutely the best. This is our first time with Southwest and it’s now our go to airline. Best ever.
The wait in the tunnel to enter the plane was too long. The counter personnel, specially ''Israel'' was really not welcoming considering Delta Standards. Other than this everything was good overall.
The flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.
The Delta assistsed services were awesome for my aunt. So very helpful.
Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning
Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!
Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.
A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.
Pretty standard flight. Delta has a good selection of movies.
The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.
Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.
On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.
Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.
The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.
My flight was completely full. Making me very stressful with people walking around all the time. I believe airlines can do better for entertain people during the flight.
The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.
It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!
At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables
All good except paid for wifi that did not work
Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.
The United website was easy to use and had all the information I needed. I needed to change my flight and it was accomplished easily on line. I was also easily able to upgrade and for a reasonable price. Boarding went smoothly and the flight was in time. The service was good in board but the crew did not seem happy at all. Limited availability of meals - not much choice for purchase and in business class they ran out of one of the meal choices by row 4. .
My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.
The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.
The flight could have actually taken place. Canceled flight and no option to rebook that day.
Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.
I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.
Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.
There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh
The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.
Our flight was changed from Madison to DC to Madison to Charlotte.
We were told we had no flights before our flight was continually delayed then cancelled.
During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.
First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.
The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides
Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck
I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.
It was a no frills flight. Would have liked to be able to charge my device
The flight left over two hours late. They charged me $180 to bring a carry on. There was an error with the spelling of my name and Frontair agent lied that I would need to pay $200 for her to fix the spelling, and pressured me that if I don't do it quick I would lose the flight. I called back and another agent said it costs $75 to fix. All in all, this company is a complete scam.
I took my first and last flight with FRONTIER. The seats are not able to be reclined so it’s not a very comfortable experience when you take a flight of 3 hours or longer. You must pay for your luggage either carry on or check in, so taking all this in consideration at the end what you think you’re saving your paying in services that should be included. Not a beverage in sight. . You’re seriously better off getting on a proper airline such as Delta, AA, United, etc.
Frontier notifying me earlier of flight delay of over 2 hours.
Both flights were delayed. The sizing of bags is crazy. I know it is advertised as a no frills cheaper option but it does feel like you are being extorted for money the whole way-- $20 dollars to talk to a gate agent? Charging for soda a pretzels? I don't think I will be flying Frontier again if I can help it. That said, all the staff were wonderful.