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Flight Deals
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
Sun, Jan 31 - Sat, Feb 6
8:15 am - 9:48 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
11h 33m1 stop Orlando
10:53 pm - 7:16 amSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 23m1 stop Orlando
$356Frontier
Tue, Nov 24 - Thu, Dec 3
6:11 pm - 9:59 amMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
13h 48m1 stop Orlando
8:44 pm - 4:26 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
21h 42m1 stop Orlando
$370Frontier
Wed, Jan 13 - Wed, Jan 13
10:35 am - 10:22 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
9h 47m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
2:05 am - 12:05 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
12h 00m2 stops Newark Chicago O'Hare Intl
$421United Airlines
Wed, Jan 13 - Thu, Jan 14
10:35 am - 9:00 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
8h 25m1 stop Chicago O'Hare Intl
8:25 am - 3:10 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
8h 45m1 stop Chicago O'Hare Intl
$421United Airlines
Thu, Dec 3 - Mon, Dec 14
7:20 pm - 9:55 amMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
12h 35m1 stop Orlando
10:45 am - 5:20 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
8h 35m1 stop Orlando
$426Southwest
Sat, Feb 20 - Sun, Feb 28
7:20 am - 4:10 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
6h 50m1 stop Orlando
10:05 pm - 8:25 amSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
12h 20m1 stop Orlando
$426Southwest
Sat, Jan 30 - Tue, Feb 9
5:17 am - 9:11 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
13h 54m2 stops Chicago O'Hare Intl Charlotte Douglas
6:20 am - 3:04 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 44m2 stops Charlotte Douglas Chicago O'Hare Intl
$426American Airlines
Tue, Feb 2 - Tue, Feb 9
5:18 am - 11:39 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
16h 21m1 stop Chicago O'Hare Intl
3:14 pm - 11:59 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 45m2 stops Miami Washington, D.C. Reagan-National
$426American Airlines
Sun, Feb 7 - Fri, Feb 12
3:22 pm - 11:58 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
6h 36m1 stop Atlanta Hartsfield-Jackson
6:30 pm - 11:49 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 19m1 stop Atlanta Hartsfield-Jackson
$426Delta
Tue, Feb 23 - Sun, Feb 28
5:55 am - 5:20 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
9h 25m1 stop Atlanta Hartsfield-Jackson
6:15 am - 11:15 amSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
7h 00m1 stop Atlanta Hartsfield-Jackson
$426Delta
Recent one-way flight deals from Milwaukee to Puerto Rico
Mon, Nov 23
6:11 pm - 9:59 amMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
13h 48m1 stop Orlando
$152Frontier
Mon, Dec 7
6:13 pm - 10:37 amMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
14h 24m1 stop Orlando
$152Frontier
Thu, Dec 31
6:30 am - 11:44 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
15h 14m2 stops Orlando Atlanta Hartsfield-Jackson
$211Multiple Airlines
Wed, Nov 25
2:45 pm - 12:20 amMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
7h 35m1 stop Fort Lauderdale
$213Southwest
Mon, Nov 30
8:15 pm - 9:55 amMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
11h 40m1 stop Orlando
$213Southwest
Sat, Jan 23
12:35 pm - 11:59 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
9h 24m1 stop Philadelphia
$213American Airlines
Sat, Jan 23
6:07 am - 9:11 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
13h 04m2 stops Washington, D.C. Reagan-National Charlotte Douglas
$213American Airlines
Sun, Jan 17
9:20 am - 10:22 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
11h 02m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
$213United Airlines
Wed, Nov 18
9:17 am - 12:36 amMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
13h 19m2 stops Chicago O'Hare Intl Newark
$213United Airlines
Thu, Dec 17
7:30 am - 9:46 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
12h 16m1 stop Orlando
$280Multiple Airlines
Recent last minute flight deals from Milwaukee to Puerto Rico
Sat, Oct 31 - Thu, Nov 5
2:58 pm - 10:45 amMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
18h 47m2 stops Chicago O'Hare Intl Miami
4:45 pm - 11:56 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
9h 11m1 stop Charlotte Douglas
$578American Airlines
Sat, Oct 31 - Thu, Nov 5
7:19 pm - 1:39 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
17h 20m2 stops Chicago O'Hare Intl Charlotte Douglas
3:17 pm - 11:56 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 39m2 stops Miami Charlotte Douglas
$578American Airlines
Sat, Oct 31 - Thu, Nov 5
9:10 am - 8:10 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
10h 00m1 stop Orlando
9:40 pm - 9:40 amSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
14h 00m1 stop Orlando
$598Southwest
Sat, Oct 31 - Mon, Nov 2
11:15 am - 8:10 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
7h 55m1 stop Orlando
6:35 am - 5:15 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
12h 40m1 stop Baltimore/Washington
$598Southwest
Sat, Oct 31 - Sat, Nov 7
10:48 am - 9:22 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
9h 34m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
8:05 am - 5:03 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
10h 58m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
$598United Airlines
Sat, Oct 31 - Mon, Nov 2
6:05 am - 3:40 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
8h 35m2 stops Lambert-St Louis Orlando
7:30 am - 2:55 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
9h 25m1 stop Orlando
$598Southwest
Sat, Oct 31 - Sat, Nov 7
5:00 am - 3:38 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
9h 38m2 stops Chicago O'Hare Intl Miami
7:05 am - 2:22 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
9h 17m2 stops Charlotte Douglas Chicago O'Hare Intl
$658American Airlines
Thu, Nov 5 - Mon, Nov 9
8:00 am - 10:22 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
12h 22m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
2:05 am - 11:28 amSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
11h 23m2 stops Newark Chicago O'Hare Intl
$698United Airlines
Wed, Nov 4 - Mon, Nov 9
2:59 pm - 11:18 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
6h 19m1 stop Atlanta Hartsfield-Jackson
4:20 pm - 11:54 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
9h 34m1 stop Atlanta Hartsfield-Jackson
$983Delta
Thu, Nov 5 - Mon, Nov 9
7:03 am - 5:49 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl
8h 46m1 stop Atlanta Hartsfield-Jackson
1:52 pm - 9:03 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell
9h 11m1 stop Atlanta Hartsfield-Jackson
$1,178Delta
Booking Insights
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.
Prices
Airlines
More
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 $356 round-trip, and to Aguadilla Borinquen (BQN) from $426 round-trip.
What’s the cheapest month to fly from Milwaukee to Puerto Rico?
These monthly figures are based on KAYAK fares from the past 12 months, with extreme outliers removed so each month's typical price is accurate.
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) (avg. price $406)
• San Juan Luis Munoz Marin Intl (SJU) (avg. price $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 are the cheapest airlines to fly with from Milwaukee to Puerto Rico?
Fares reflect aggregated pricing data and may not include every trip type.
Looking at KAYAK data from the last 12 months, the cheapest airlines to fly with from Milwaukee to Puerto Rico are:
• Frontier (avg. price $345)
• Delta (avg. price $424)
• American Airlines (avg. price $458)
• Southwest (avg. price $471)
• JetBlue (avg. price $475)
What's the most popular airline to fly with from Milwaukee to Puerto Rico?
Drawing on KAYAK data from the past three months, the most popular airlines to fly with from Milwaukee to Puerto Rico are:
• Southwest
• American Airlines
• Delta
• Frontier
• United Airlines
What are the most popular flight destinations in Puerto Rico?
San Juan and Aguadilla are the most popular flight destinations in Puerto Rico, based on KAYAK data. San Juan is the clear favorite, making up 98% of that interest.
How many one-stop flights are there from Milwaukee to Puerto Rico across the week?
There are typically 16 one-stop flights a day from Milwaukee to Puerto Rico (109 a week), with the most operating on Saturday.
Key details for Milwaukee to Puerto Rico flights
Low season | October |
|---|---|
High season | February |
Cheapest flight | $152 |
Your Milwaukee to Puerto Rico flight questions, answered
Find helpful answers about this route, including flight times, airports, airlines and booking tips.
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.Reviews of the top 5 airlines serving from Milwaukee to Puerto Rico
7.9
SouthwestOverall score based on 4217 reviews
8.6Crew
7.4Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews
On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.
8.0 ExcellentJohn, Oct 2026
On time departure and arrival. Had to be the oldest plane in the SWA fleet but it got me where I needed to be.
Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.
I got a bit sick on the flight, and was so grateful when the male flight attendant explained to me they keep the back row open for cases like mine. He took such great care of me! I was incredibly grateful.
Friendly crew. Snacks were carb-heavy. Flight was quite delaye
The service was fine, about the same as you get on most lower end airlines. I dont understand the perks of flying them much anymore for the cost.
the flight was significantly delayed. Not much was done by the airline to compensate passengers
the flight itself was totally fine. The crew were great and very helpful. The flight was delayed, however, over an hour without a lot of information as to why.
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.
I need to note that this flight experience was generally fine but the boarding situation was absolutely a mess and there wasn’t any actual priority boarding. I rated the experience poorly because I’m am genuinely so frustrated with the crew on United taking the baggage space in first class. This flight it didn’t happen, but the last few flights (when I ironically don’t get an opportunity to provide feedback) have been spoiled because upon entering the first class cabin as one of the first few seated passengers, the overhead bins are full and ‘crew’’ tags are on the bags of those taking space. I don’t intend to infer some sort of a class or caste system but it’s absolutely ridiculous that the crew takes the overhead storage above and beyond their most loyal and lucrative customers. They should not even have economy space IMO. And I’ve gotten grief when I’ve noted to the crew the ridiculousness of the notion that the crew (who are the last off the plane) should have priority over flyers who pay. I hope you find a way to convey this message to United because it’s happening with increasing frequency and I intend to find a way to expose the specific crew members who are doing this on a flight by flight basis. (And I have a day job)
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
Information on your arrival and departure airports
Cabin class types available on flights to Puerto Rico
Cabin classes available on flights to Puerto Rico. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from other airports in Milwaukee to Puerto Rico
Flights from all airports in Milwaukee to Puerto Rico. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.