$118 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 11/18. 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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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

Tue, Feb 3 - Tue, Feb 10
United Airlines Logo
10:30 am - 12:36 amMKE-SJU
12h 06m2 stops
United Airlines Logo
7:45 am - 2:55 pmSJU-MKE
9h 10m1 stop
$235United Airlines
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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
$243Frontier
Find Deal
Tue, Feb 3 - Tue, Feb 10
United Airlines Logo
10:30 am - 10:22 pmMKE-SJU
9h 52m2 stops
United Airlines Logo
2:15 pm - 10:56 pmSJU-MKE
10h 41m2 stops
$252United Airlines
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Sat, Jan 24 - Fri, Jan 30
Southwest Logo
2:05 pm - 11:00 pmMKE-SJU
6h 55m1 stop
Southwest Logo
5:40 am - 11:05 amSJU-MKE
7h 25m1 stop
$274Southwest
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Thu, Dec 4 - Wed, Dec 10
Delta Logo
11:41 am - 11:20 pmMKE-SJU
9h 39m1 stop
Delta Logo
3:32 pm - 11:54 pmSJU-MKE
10h 22m1 stop
$305Delta
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Tue, Feb 3 - Tue, Feb 10
American Airlines Logo
6:13 am - 6:22 pmMKE-SJU
10h 09m2 stops
American Airlines Logo
6:00 am - 6:26 pmSJU-MKE
14h 26m1 stop
$308American Airlines
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Wed, Nov 12 - Sat, Nov 15
Southwest Logo
11:30 am - 9:30 pmMKE-SJU
8h 00m1 stop
Southwest Logo
8:20 am - 6:55 pmSJU-MKE
12h 35m1 stop
$313Southwest
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Sun, Jan 4 - Fri, Jan 23
Spirit Airlines Logo
11:35 am - 11:57 pmMKE-SJU
10h 22m1 stop
Spirit Airlines Logo
6:00 am - 11:29 amSJU-MKE
7h 29m1 stop
$335Spirit Airlines
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Sun, Mar 1 - Wed, Mar 11
Delta Logo
12:20 pm - 11:49 pmMKE-SJU
9h 29m1 stop
Delta Logo
6:15 am - 1:47 pmSJU-MKE
8h 32m1 stop
$358Delta
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Sat, Nov 15 - Tue, Nov 18
American Airlines Logo
5:00 am - 3:54 pmMKE-SJU
8h 54m2 stops
American Airlines Logo
2:47 pm - 11:42 pmSJU-MKE
10h 55m2 stops
$360American 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 $584 and $531 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$118
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 19% 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 4237 reviews
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

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

10.0 ExcellentStacy, Oct 2025SMF - DEN
Read more Southwest reviews

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.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

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

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Same as last comment. Food sucks. Quality. Not surprising most people have no clue about nourishment Clearly

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

Friendly and professional flight crew. Aside from departure delay after boarding, easy flight and smooth landing.

Great smooth flight. Had a seating change, but that was an improvement. Thanks United Airways Crew.

The flight attendants were great, I joked with one I can’t remember her name, a blond, really sweet. I thought it was run well very professional. This was great i survived Spirit, I know for which I speak.

My husband and I recently had an unfortunate experience with Lufthansa. At the Philadelphia International airport, the ground staff refused to board us because we didn’t have a current visa stamped on our passports for Frankfurt. We completely understand that this was our mistake. we should have double-checked the visa requirements before our trip. However, the issue that upset us most was how the situation was handled by the staff. They told us they would mark it as “boarding denied due to visa issue”, but instead they recorded it as “no show”. Because of that incorrect entry, our return flight was automatically cancelled as well, which caused additional stress and expense. Mistakes can happen, but we expected more transparency and accuracy from a reputed airline like Lufthansa. It would have made a big difference if the staff had been more careful and considerate in documenting the situation correctly.

Flight was good but there are way to many announcements for credit cards etc.

The only thing to like was that we eventually got to our destination

Delayed delayed delayed and no offer for food or vouchers

Disliked having to wait a little longer to disembark from the plan when we landed in London

Typically flights with AA are good. The staff are pleasant, welcoming, and efficient.

A couple ladies from the crew were so rude and nasty. Thought they were mad at having to be there especially if you asked a question. This will make me think twice next time if I book a flight with you.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

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.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

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