$69 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 1/11. 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.
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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

Sat, Feb 21 - Wed, Feb 25
Frontier Logo
6:02 pm - 9:55 amMKE-SJU
13h 53m1 stop
Frontier Logo
3:55 am - 6:45 pmSJU-MKE
16h 50m1 stop
$153Frontier
Find Deal
Mon, Feb 9 - Sat, Feb 14
Frontier Logo
7:40 pm - 9:55 amMKE-SJU
12h 15m1 stop
Frontier Logo
11:05 am - 5:04 pmSJU-MKE
7h 59m1 stop
$231Frontier
Find Deal
Tue, Feb 3 - Tue, Feb 10
United Airlines Logo
10:30 am - 12:36 amMKE-SJU
12h 06m2 stops
United Airlines Logo
3:46 pm - 10:59 pmSJU-MKE
9h 13m1 stop
$235United Airlines
Find Deal
Tue, Jan 20 - Tue, Jan 20
United Airlines Logo
8:33 am - 9:26 pmMKE-SJU
10h 53m2 stops
United Airlines Logo
2:05 am - 10:46 amSJU-MKE
10h 41m1 stop
$256United Airlines
Find Deal
Fri, Feb 6 - Sat, Feb 14
Southwest Logo
4:15 pm - 12:40 amMKE-SJU
6h 25m1 stop
Southwest Logo
6:05 am - 1:50 pmSJU-MKE
9h 45m1 stop
$274Southwest
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Sun, Feb 1 - Thu, Feb 5
Delta Logo
12:17 pm - 8:57 pmMKE-SJU
6h 40m1 stop
Delta Logo
7:30 am - 2:38 pmSJU-MKE
9h 08m1 stop
$300Delta
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Sat, Jan 31 - Mon, Feb 9
Southwest Logo
12:30 pm - 9:30 pmMKE-SJU
7h 00m1 stop
Southwest Logo
5:35 am - 10:45 amSJU-MKE
7h 10m1 stop
$305Southwest
Find Deal
Tue, Mar 3 - Tue, Mar 10
Delta Logo
7:02 am - 4:51 pmMKE-SJU
7h 49m1 stop
Delta Logo
6:15 am - 4:17 pmSJU-MKE
11h 02m1 stop
$306Delta
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Tue, Feb 3 - Tue, Feb 10
American Airlines Logo
6:00 am - 6:22 pmMKE-SJU
10h 22m2 stops
American Airlines Logo
8:20 am - 11:23 pmSJU-MKE
17h 03m1 stop
$308American Airlines
Find Deal
Mon, Nov 24 - Sat, Dec 6
American Airlines Logo
6:29 am - 8:48 pmMKE-SJU
12h 19m1 stop
American Airlines Logo
8:18 am - 12:01 amSJU-MKE
17h 43m1 stop
$317American Airlines
Find Deal
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 September, when tickets cost $315 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $559 and $532 respectively.

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

The average price of all round-trip flights from Milwaukee to Puerto Rico clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Puerto Rico on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Milwaukee to Puerto Rico. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

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$69
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 20% 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.

  • What is the cheapest time of day to fly to Puerto Rico?

    The cheapest time of day to fly to Puerto Rico is generally at night, when round-trip flights cost $360 on average. Morning departures are around 13% more expensive than evening flights, on average. The most expensive time of day to fly to Puerto Rico is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $458.

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 4241 reviews
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

Plane boarded early a quickly, was mostly full. We left close to on time. And landed early.

My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.

Premium Plus is a really good idea for longer flights

7 hours delayed due to operational issues on United’s end. Basically laziness.

Short flight but an "eager to help" crew made the journey more enjoyable!

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

The person I bought the ticket for didn’t make the flight.

We were very rushed by a staff member at the gate when transferring from American Airlines to Fijian. Then the plane stayed put for ages anyhow! The plane was delayed and my bag sent to San Francisco instead of Fiji

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

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

Information on your arrival and departure airports