$244 Find Cheap Flights from Milwaukee to Costa Rica

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 Costa Rica departing on 10/12. 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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Cheap Flights from Milwaukee to Costa Rica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
San José
San José1 stop$491
Liberia
Liberia2 stops$525
San José
San José1 stop$491
Liberia
Liberia2 stops$525

Book Cheap Milwaukee to Costa Rica 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 Costa Rica 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 Costa Rica

Mon, Oct 5 - Sat, Oct 10
Multiple Airlines Logo
8:10 pm - 3:11 pm
MKE
-
SJO
20h 01m
1 stop
Multiple Airlines Logo
7:07 am - 7:15 pm
SJO
-
MKE
11h 08m
1 stop
$491Multiple Airlines
Tue, Oct 27 - Tue, Nov 3
United Airlines Logo
6:30 am - 7:39 pm
MKE
-
SJO
14h 09m
2 stops
United Airlines Logo
2:25 pm - 10:50 pm
SJO
-
MKE
8h 25m
1 stop
$520United Airlines
Sun, Oct 11 - Fri, Oct 16
Southwest Logo
5:30 am - 12:40 pm
MKE
-
SJO
8h 10m
1 stop
Southwest Logo
9:00 am - 5:55 pm
SJO
-
MKE
7h 55m
1 stop
$522Southwest
Wed, Sep 9 - Thu, Sep 24
American Airlines Logo
5:03 am - 8:07 pm
MKE
-
SJO
16h 04m
2 stops
American Airlines Logo
2:57 pm - 11:27 am
SJO
-
MKE
19h 30m
2 stops
$525American Airlines
Sun, Dec 6 - Wed, Dec 16
American Airlines Logo
6:50 pm - 12:25 pm
MKE
-
LIR
17h 35m
2 stops
American Airlines Logo
3:28 pm - 10:13 am
LIR
-
MKE
18h 45m
2 stops
$525American Airlines
Sat, Oct 24 - Tue, Nov 3
American Airlines Logo
12:22 pm - 1:58 pm
MKE
-
SJO
26h 36m
1 stop
American Airlines Logo
1:23 pm - 11:59 pm
SJO
-
MKE
10h 36m
1 stop
$530American Airlines
Sun, Dec 6 - Wed, Dec 16
American Airlines Logo
6:12 am - 2:45 pm
MKE
-
LIR
8h 33m
1 stop
American Airlines Logo
3:10 pm - 11:03 am
LIR
-
MKE
19h 53m
1 stop
$530American Airlines
Tue, Dec 1 - Fri, Dec 11
American Airlines Logo
6:01 am - 8:55 pm
MKE
-
SJO
14h 54m
2 stops
American Airlines Logo
3:06 pm - 6:04 pm
SJO
-
MKE
26h 58m
1 stop
$534American Airlines
Wed, Sep 9 - Thu, Sep 24
American Airlines Logo
6:01 am - 8:07 pm
MKE
-
SJO
15h 06m
2 stops
American Airlines Logo
1:00 pm - 11:27 am
SJO
-
MKE
21h 27m
1 stop
$535American Airlines
Tue, Dec 1 - Fri, Dec 11
American Airlines Logo
6:48 pm - 2:02 pm
MKE
-
SJO
19h 14m
1 stop
American Airlines Logo
3:06 pm - 6:04 pm
SJO
-
MKE
26h 58m
1 stop
$538American Airlines
Booking Insights

KAYAK's insights & trends for Milwaukee to Costa Rica flights

Get data-powered insights and trends into flights from Milwaukee to Costa Rica 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 Costa Rica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Costa Rica, 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 Costa Rica is February, when tickets cost $193 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $546 and $540 respectively.

How far in advance should I book a flight from Milwaukee to Costa Rica?

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 Costa Rica, 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 Costa Rica, you should book around 2 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$244
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 2% increase in price.
Flight from Milwaukee to Liberia

FAQs - booking Costa Rica flights

  • How does KAYAK find such low prices on flights from Milwaukee to Costa Rica?

    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 Costa Rica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to Costa Rica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to Costa Rica 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 Costa Rica?

    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 Costa Rica 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 Costa Rica?

    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 Costa Rica up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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 4242 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

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.

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!

Great. Seamless. Check in agent at kiosk international was amazing and extremely helpful.

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.

Delta planes have the WORST seat comfort of any plane in history. It's the opposite of ergonomic, in every sense. They also recline minimally, are covered in a vinyl and have no feet rests. Then the disembarking process is chaotic and time consuming (because of the way they load the plane and deal with luggage). Overall, somewhat frustrating but we arrived safely :)

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 needed internet for critical matters and it never worked.

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

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 experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

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.

A much better flight than our previous. The flight attendant took care of us and regularly checked in to see if we needed anything. Brought us drinks prior to the departure and then a couple more times. Totally makes the difference in how you travel when the crew is checking on their passengers. Great job on this leg of our trip.

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.

Boarding was relatively fast and easy and the crew was attentive throughout.

Everything you need to know for your flight from Milwaukee to Costa Rica

Information on your arrival and departure airports