$211 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 5/11. 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.
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$275
Liberia
Liberia2 stops$547
San José
San José1 stop$275
Liberia
Liberia2 stops$547

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

Sun, May 24 - Mon, Jun 8
Frontier Logo
8:46 am - 8:19 am
MKE
-
SJO
24h 33m
1 stop
Frontier Logo
9:35 am - 7:58 am
SJO
-
MKE
21h 23m
1 stop
$275Frontier
Sun, May 24 - Mon, Jun 8
Frontier Logo
8:46 am - 8:19 am
MKE
-
SJO
24h 33m
1 stop
Frontier Logo
9:35 am - 7:58 am
SJO
-
MKE
21h 23m
1 stop
$319Frontier
Mon, May 18 - Fri, May 22
American Airlines Logo
6:42 pm - 11:07 am
MKE
-
SJO
17h 25m
2 stops
American Airlines Logo
6:00 am - 11:47 pm
SJO
-
MKE
16h 47m
2 stops
$347American Airlines
Sat, May 9 - Fri, Jun 5
American Airlines Logo
7:08 am - 9:36 pm
MKE
-
SJO
15h 28m
1 stop
American Airlines Logo
11:59 pm - 11:21 am
SJO
-
MKE
10h 22m
1 stop
$360American Airlines
Fri, May 1 - Fri, May 8
American Airlines Logo
6:41 pm - 11:07 am
MKE
-
SJO
17h 26m
2 stops
American Airlines Logo
11:35 pm - 3:56 pm
SJO
-
MKE
15h 21m
2 stops
$365American Airlines
Sun, Jul 19 - Sat, Jul 25
Frontier Logo
8:43 am - 8:20 am
MKE
-
SJO
24h 37m
1 stop
Frontier Logo
9:35 am - 7:58 am
SJO
-
MKE
21h 23m
1 stop
$404Frontier
Mon, May 4 - Sat, May 9
LATAM Airlines Logo
5:30 am - 11:56 am
MKE
-
SJO
7h 26m
1 stop
LATAM Airlines Logo
2:40 pm - 9:08 am
SJO
-
MKE
17h 28m
1 stop
$430LATAM Airlines
Sun, May 3 - Wed, May 6
Delta Logo
6:50 pm - 11:56 am
MKE
-
SJO
18h 06m
1 stop
Delta Logo
1:21 pm - 11:58 pm
SJO
-
MKE
9h 37m
1 stop
$466Delta
Tue, Aug 18 - Tue, Aug 25
United Airlines Logo
5:56 pm - 12:10 pm
MKE
-
LIR
19h 14m
1 stop
United Airlines Logo
1:20 pm - 11:19 pm
LIR
-
MKE
8h 59m
1 stop
$681United Airlines
Tue, Jun 2 - Tue, Jun 9
United Airlines Logo
8:00 am - 2:25 pm
MKE
-
LIR
7h 25m
1 stop
United Airlines Logo
1:20 pm - 10:45 pm
LIR
-
MKE
8h 25m
1 stop
$683United 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 September, when tickets cost $525 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $939 and $724 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$211
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly with an average 9% increase in price.
Flight from Milwaukee to San José

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.
8.0
SouthwestOverall score based on 4329 reviews
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
Airline reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

2.0 MediocreStuart, Mar 2026
HOU - STL
Read more Southwest reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

We purchase first class seats for the first time for multiples of standard economy ticket. There was no access to the club lounge and no priority boarding. The meal and the service once on the plane were superior and the seat was nicer, but not worth the price difference. I will be happy to seat in economy and spend the difference on more travel.

The business class seat is exceptional. I wish the food is more palatable.

Wonderful in-seat entertainment with seatback screens and huge selection of quality movies. The ability to bluetooth connect headphones was amazing.

the entire flight felt off. The crew seemed uninterested and disengaged. The food service was really bad - overcooked, bland, weird food service. They actually woke us up to serve chicken wraps in the middle of the night, after dinner and before breakfast. Made no sense. Ultimately, I was glad they did though, because the breakfast had been held for so long it was inedible. Eggs, potatoes, sausage - all disgusting. We were asked to "honor" the lavatories for premium customers and stay in our own cabin: this was also strange. So people in economy didn't pay enough to use the closest toilet to them??? It's a toilet. All in all, not the experience I have come to expect from United Airlines. The return flight from Paris to SFO was better, btw.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Overall, the flight was good. Lounge access should be with all business class tickets.

They promise free wi-fi prior to boarding and then once on board you are informed you have to purchase wifi even after being a mileagePlus member.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Awful. No counter attendants. No dinner offered due to delays.

Plane was super cold. No entertainment unless you were with mileage program Getting off the plane was super slow

Flight was on-time, boarding was flawless and the crew was friendly.

The staff are very, very professional. It's what flying should feel like.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

For an international flight the seats were smaller than most flight I have been on in economy. I don’t know the size of the seats or perhaps it was the size of the seat dividers that made the seats feel smaller and little amount of space to even turn your body if you needed to

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

Tv screens and movie selection v good. Friendly staff. They were really worried about max capacity and room for carryons. That is never fun but i had no problem finding space when I boarded.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

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

Information on your arrival and departure airports