$100 Find Cheap Flights from Milwaukee to Puerto Rico - Compare and Save

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Price, demand and travel trends for Milwaukee to Puerto Rico flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Milwaukee to Puerto Rico cheaper or more expensive than last year?

Fares from Milwaukee to Puerto Rico are running about 7% higher than they were around this time last year, averaging $458 round-trip.

What are the cheapest fares from Milwaukee to Puerto Rico right now?

The cheapest fares from Milwaukee to Puerto Rico on KAYAK in the last week were to San Juan Luis Munoz Marin Intl (SJU) from $262 round-trip, and to Aguadilla Borinquen (BQN) from $406 round-trip.

What’s the cheapest month to fly from Milwaukee to Puerto Rico?

September is the cheapest time of year to fly, with average fares of $340. Prices are highest in December, when average flight costs increase to around $758.

When is the best time to book flights from Milwaukee to Puerto Rico?

Book your flights 13 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 19% compared to booking last-minute (within 2 weeks of departure).

Which airport in Puerto Rico is the cheapest to fly to from Milwaukee?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into Puerto Rico are:

• Aguadilla Borinquen (BQN) from $406
• San Juan Luis Munoz Marin Intl (SJU) from $462

What’s the cheapest day to fly from Milwaukee to Puerto Rico?

Sunday tends to be the cheapest day to fly from Milwaukee to Puerto Rico, while Thursday is the most expensive. Fares run about 21% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Milwaukee to Puerto Rico?

Data from the past 12 months shows it's cheapest to fly to Puerto Rico during the afternoon with average prices of $428. The morning is the most expensive time to fly, with average prices of $474.

Key details for Milwaukee to Puerto Rico flights

Low season

October

Cheapest flight

$100
Beat the crowds with an average 42% drop in travelers.
The most popular month to fly with an average 18% increase in travelers.
One-way flight from Milwaukee to San Juan Luis Munoz Marin Intl Airport

Your Milwaukee to Puerto Rico flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Milwaukee to Puerto Rico?

    Yes. Fares from Milwaukee to Puerto Rico are low right now. As a rule of thumb, a round-trip under $370 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Milwaukee to Puerto Rico?

    Over the past 12 months, round-trip fares from Milwaukee to Puerto Rico have ranged from $370 to $582.

  • What are the main airports serving Puerto Rico?

    Flights to Puerto Rico use two main airports, San Juan Luis Munoz Marin Intl (SJU) and Aguadilla Borinquen (BQN).

  • What airlines fly nonstop from Milwaukee to Puerto Rico?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Milwaukee to Puerto Rico. One-stop options include:

    • Southwest
    • Delta
    • American Airlines

  • Which cabin classes are available on flights from Milwaukee to Puerto Rico?

    On flights from Milwaukee to Puerto Rico you can only book Economy Class.

  • What are some popular landmarks in Puerto Rico?

    KAYAK travelers' favorite landmarks in Puerto Rico include:

    • Viejo San Juan
    • Condado Beach
    • Puerto Rico Convention Center
    • Ocean Park

  • 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.

Your guide to booking Milwaukee to Puerto Rico flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 13 weeks before your trip. KAYAK data shows fares in this window are around 19% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for September when flights are typically cheapest and avoid December when prices are at their highest.
  • Flying on Sunday is usually the cheapest. Flights on Thursday cost about 21% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, Aguadilla Borinquen (BQN) is the cheapest airport to fly into from Milwaukee. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in San Juan, which is the most popular destination in Puerto Rico. From there, it's easy to continue on to other popular destinations such as Carolina, Fajardo and Rio Grande.
  • 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 4222 reviews
8.6Crew
7.4Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

8.0 ExcellentDanielle, Oct 2026
Read more Southwest reviews

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

They did not fix the wifi that they knew was an issue on an earlier flight. The flight was filled with business people that were clearly frustrated not being able to work. That can’t happen on a 3 1/2 hour flight. Would rather have been delayed a bit.

The WiFi did not work three hours of productivity lost. 15 people from the firm were on the flight. Loss of revenue

Very rude stewardess; there was a senior citizen woman next to me who asked the stewardess for help getting her purse out of the overhead bin, and it was as though she asked the stewardess for $1M . . . . I was shocked how rude that stewardess was. The stewardess also refused to get the senior citizen woman a drink about half way thru the flight, telling her that we were almost landing . . . . that stewardess made my flight (and in particular the flight of the senior citizen next to me) very uncomfortable

Overall good experience...exception: very cold temp in teh cabin.

I liked how it boarded fast. I do not like how the seats are just too narrow, and I’m not a big person.

Stop asking fir people to check carry on and then bind are free. Then the wait to get your luggage is ridiculous. This particular flight came with a 45 min wait, after waiting in tarmac waiting for a gate inhaling jet exhaust. And how about those landings?! Do the pilots not know the earth is coming up under the descending plane?! This is the only airline I get sick on. Every. Time.

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.

This was a small aircraft (relatively) and we were delayed half an hour on takeoff, which is not the airlines fault.

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.

More options for your flight from Milwaukee to Puerto Rico

Complete your trip to Puerto Rico with a hotel stay or car rental