$138 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 7/21. 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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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

Thu, Jun 25 - Mon, Jun 29
Frontier Logo
8:53 am - 1:16 pm
MKE
-
SJU
27h 23m
1 stop
Frontier Logo
6:00 am - 7:58 am
SJU
-
MKE
26h 58m
1 stop
$321Frontier
Sat, Oct 17 - Wed, Oct 28
Delta Logo
5:45 am - 4:33 pm
MKE
-
SJU
9h 48m
1 stop
Delta Logo
7:30 am - 3:04 pm
SJU
-
MKE
8h 34m
1 stop
$326Delta
Wed, Aug 12 - Tue, Aug 18
American Airlines Logo
6:16 am - 6:24 pm
MKE
-
SJU
11h 08m
2 stops
American Airlines Logo
6:51 am - 11:23 pm
SJU
-
MKE
17h 32m
1 stop
$331American Airlines
Tue, Aug 18 - Sat, Aug 22
American Airlines Logo
11:29 am - 11:07 pm
MKE
-
SJU
10h 38m
1 stop
American Airlines Logo
6:00 am - 5:00 pm
SJU
-
MKE
12h 00m
2 stops
$333American Airlines
Thu, Jun 25 - Wed, Jul 15
Frontier Logo
8:53 am - 1:16 pm
MKE
-
SJU
27h 23m
1 stop
Frontier Logo
4:05 pm - 7:58 am
SJU
-
MKE
16h 53m
1 stop
$340Frontier
Sat, Sep 5 - Wed, Sep 9
American Airlines Logo
5:00 am - 10:52 pm
MKE
-
SJU
16h 52m
1 stop
American Airlines Logo
6:30 am - 9:54 pm
SJU
-
MKE
16h 24m
2 stops
$351American Airlines
Thu, Jul 16 - Mon, Jul 20
Frontier Logo
8:43 am - 2:11 am
MKE
-
SJU
16h 28m
1 stop
Frontier Logo
4:05 pm - 7:58 am
SJU
-
MKE
16h 53m
1 stop
$361Frontier
Wed, Jul 29 - Wed, Aug 5
Southwest Logo
9:25 am - 11:45 pm
MKE
-
SJU
13h 20m
1 stop
Southwest Logo
5:15 am - 10:55 am
SJU
-
MKE
6h 40m
1 stop
$365Southwest
Mon, Aug 17 - Fri, Aug 21
American Airlines Logo
8:20 am - 11:07 pm
MKE
-
SJU
13h 47m
1 stop
American Airlines Logo
1:38 pm - 10:59 pm
SJU
-
MKE
10h 21m
2 stops
$366American Airlines
Sun, Jul 5 - Fri, Jul 10
Frontier Logo
8:43 am - 2:11 am
MKE
-
SJU
16h 28m
1 stop
Frontier Logo
3:06 am - 7:58 am
SJU
-
MKE
29h 52m
1 stop
$367Frontier
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 February, when the average cost of round-trip tickets is $344 and $168 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 seasonJuly
Cheapest flight$138
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 2% 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.
8.0
SouthwestOverall score based on 4298 reviews
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

I'm glad it wasn't only 75% full because I could get a good seat

8.0 ExcellentBobby, May 2026
BNA - GSP
Read more Southwest reviews

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

I didn’t have a seat assignment and my seat was very dirty on the flight from Frankfurt to Budapest.

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Cree was organized and pleasant. Plane had good seating but as it’s a shuttle toilets hadn’t been thoroughly cleaned (eg. bins too full)

I liked that my son and I were reseated next to each other (we had different bookings). I liked that it was a directg flight and mostly on time. I liked that you provided pillows and blankets. Flight attendants were generally courteous. The messaging through wifi did not work well. The food was not good. Seats are very narrow and I felt slightly claustraphobic in the window seat.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

Flight was delayed an no one cares, or try to help passengers to get the conexión.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

The small flights with Valet Luggage has a poor service

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

The crew was very attentive through out the flight. Seats were comfortable, nice flight bag with pillow and blanket. Food was okay, since it was a overnight flight seemed to go by fast.

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.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

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

Information on your arrival and departure airports