$288 Find Cheap Flights from Milwaukee to Costa Rica - Compare and Save

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Cheap Flights from Milwaukee to Costa Rica

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
San José
San José1 stop$558
Liberia
Liberia2 stops$572
San José
San José1 stop$558
Liberia
Liberia2 stops$572
Booking Insights

Price, demand and travel trends for Milwaukee to Costa Rica 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 Costa Rica cheaper or more expensive than last year?

Fares from Milwaukee to Costa Rica are running about 5% higher than they were around this time last year, averaging $694 round-trip.

What are the cheapest fares from Milwaukee to Costa Rica right now?

The cheapest fares from Milwaukee to Costa Rica on KAYAK in the last week were to San José Juan Santamaria Intl (SJO) from $439 round-trip, and to Liberia (LIR) from $572 round-trip.

What’s the cheapest month to fly from Milwaukee to Costa Rica?

January is the cheapest time of year to fly, with average fares of $636. Prices are highest in August, when average flight costs increase to around $825.

When is the best time to book flights from Milwaukee to Costa Rica?

Book your flights 16 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 42% compared to booking last-minute (within 2 weeks of departure).

Which airport in Costa Rica is the cheapest to fly to from Milwaukee?

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

• San José Juan Santamaria Intl (SJO) from $698
• Liberia (LIR) from $730

What’s the cheapest day to fly from Milwaukee to Costa Rica?

Tuesday tends to be the cheapest day to fly from Milwaukee to Costa Rica, while Saturday is the most expensive. Fares run about 31% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Milwaukee to Costa Rica?

Data from the past 12 months shows it's cheapest to fly to Costa Rica during the afternoon with average prices of $626. The evening is the most expensive time to fly, with average prices of $760.

Key details for Milwaukee to Costa Rica flights

Low season

October

Cheapest flight

$288
Beat the crowds with an average 91% drop in travelers.
The most popular month to fly with an average 50% increase in travelers.
One-way flight from Milwaukee to San José

Your Milwaukee to Costa Rica 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 Costa Rica?

    Yes. Fares from Milwaukee to Costa Rica are low right now. As a rule of thumb, a round-trip under $600 (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 Costa Rica?

    Over the past 12 months, round-trip fares from Milwaukee to Costa Rica have ranged from $600 to $859.

  • What are the main airports serving Costa Rica?

    Flights to Costa Rica use two main airports, San José Juan Santamaria Intl (SJO) and Liberia (LIR).

  • What airlines fly nonstop from Milwaukee to Costa Rica?

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

    • Delta
    • Southwest
    • American Airlines

  • Which cabin classes are available on flights from Milwaukee to Costa Rica?

    On flights from Milwaukee to Costa Rica you can book Economy Class or First Class.

  • What are some popular landmarks in Costa Rica?

    KAYAK travelers' favorite landmarks in Costa Rica include:

    • Parque Metropolitano La Sabana
    • Estadio Nacional de Costa Rica
    • Museo de Oro
    • Morazan Park

Your guide to booking Milwaukee to Costa Rica 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 16 weeks before your trip. KAYAK data shows fares in this window are around 42% 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 January when flights are typically cheapest and avoid August when prices are at their highest.
  • Flying on Tuesday is usually the cheapest. Flights on Saturday cost about 31% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, San José Juan Santamaria Intl (SJO) 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 José, which is the most popular destination in Costa Rica. From there, it's easy to continue on to other popular destinations such as La Fortuna, Tamarindo and Manuel Antonio.

Reviews of the top 4 airlines serving from Milwaukee to Costa Rica

 
Need help choosing which airline to fly with from Milwaukee to Costa Rica? 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 4214 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

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

6.0 GoodRobert, Oct 2026
Read more Southwest reviews

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.

I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

One, we were met with more than six hours of delays with no information flowing from the airline to the passenger. I had to continually refresh for updates to departure time - which changed multiple times throughout the day. Updates were never pushed to me nor was an explanation provided for the delay until this morning. Two, while they claim that "due to the short flight" no beverage service would be provided. Our flight was mostly empty. I'd think given the massive inconvenience, SW could have shared a Diet Coke and some peanuts. And BTW, SW used to always make these available on this flight back in the day. Let's be honest, this is cost savings at the customer's expense.

Despite paying for an ‘upgraded’ seat in row 1, I had to put my luggage in the middle of the plane. Snacks were bleh and seat was small and uncomfortable and I am not large. Attendants were fine but not super helpful. Plane just seemed outdated.

It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.

Flight time kept changing and so did the gate. It was very frustrating

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 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

Easiest airport experience ever in my life at MSP with Delta check-in and flight attendant gave us a bottle of champagne in celebration of our 10-year wedding anniversary, so overall amazing!

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.

Entertainment was great. Seats were good. They did not have my pre-ordered hot food product available but did comp me something cold in place of the item.

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 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.

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.

I had very little time to change planes originally in Denver after my flight from Omaha. I had an hour and a half layover in Denver originally and my flight leaving Omaha was delayed an hour because they had to change a tire, which I can understand. When I reached Denver my other flight was late, fortunately, but I still had only 10 minutes to run about a mile through the airport to get to my flight. Again, fortunately, I am a healthy 71-year-old and was able to accomplish this feat. However, the stress was more than necessary to bear.

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.

More options for your flight from Milwaukee to Costa Rica

Complete your trip to Costa Rica with a hotel stay or car rental