$215 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 4/27. 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$452
Liberia
Liberia1 stop$608
San José
San José1 stop$452
Liberia
Liberia1 stop$608

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

Wed, Apr 15 - Tue, Apr 21
American Airlines Logo
11:49 am - 9:36 pm
MKE
-
SJO
10h 47m
1 stop
American Airlines Logo
12:35 pm - 9:57 pm
SJO
-
MKE
8h 22m
1 stop
$452American Airlines
Tue, Apr 21 - Tue, May 5
American Airlines Logo
6:39 am - 7:07 pm
MKE
-
SJO
13h 28m
2 stops
American Airlines Logo
12:35 pm - 9:57 pm
SJO
-
MKE
8h 22m
1 stop
$457American Airlines
Sat, Apr 25 - Tue, Apr 28
American Airlines Logo
6:32 pm - 11:25 am
MKE
-
SJO
17h 53m
1 stop
American Airlines Logo
2:08 pm - 10:59 am
SJO
-
MKE
19h 51m
1 stop
$461American Airlines
Fri, May 1 - Fri, May 8
American Airlines Logo
6:41 pm - 11:30 am
MKE
-
SJO
17h 49m
1 stop
American Airlines Logo
11:35 pm - 5:01 pm
SJO
-
MKE
16h 26m
1 stop
$472American Airlines
Fri, May 1 - Fri, May 8
American Airlines Logo
5:06 am - 7:07 pm
MKE
-
SJO
15h 01m
2 stops
American Airlines Logo
11:35 pm - 1:23 pm
SJO
-
MKE
12h 48m
2 stops
$477American Airlines
Mon, Apr 20 - Sat, Apr 25
Multiple Airlines Logo
12:10 pm - 11:40 pm
MKE
-
SJO
12h 30m
2 stops
Multiple Airlines Logo
5:05 am - 10:59 pm
SJO
-
MKE
16h 54m
2 stops
$479Multiple Airlines
Fri, May 1 - Fri, May 8
American Airlines Logo
7:08 am - 9:36 pm
MKE
-
SJO
15h 28m
1 stop
American Airlines Logo
11:35 pm - 10:27 pm
SJO
-
MKE
21h 52m
1 stop
$481American Airlines
Sun, Apr 12 - Sun, Apr 19
American Airlines Logo
7:01 am - 9:36 pm
MKE
-
SJO
15h 35m
2 stops
American Airlines Logo
11:35 pm - 10:59 am
SJO
-
MKE
10h 24m
1 stop
$482American Airlines
Mon, Mar 23 - Tue, Mar 24
Delta Logo
5:45 am - 11:50 am
MKE
-
LIR
7h 05m
1 stop
Delta Logo
1:05 pm - 11:58 pm
LIR
-
MKE
9h 53m
1 stop
$608Delta
Fri, Apr 17 - Mon, Apr 20
Alaska Airlines Logo
3:10 pm - 5:02 pm
MKE
-
LIR
26h 52m
2 stops
Alaska Airlines Logo
6:12 pm - 11:58 pm
LIR
-
MKE
28h 46m
3 stops
$630Alaska 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 $467 (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$146
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 6% 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 4303 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Terrible because it was cancelled due to volcanic ash clouds in Guatemala while all other airlines kept flying. Had to pay for a hotel to stay overnight in Houston and try to fly next day.

Flight delayed for more than 16 hrs and no effort was spent to provide an alternate

We got delayed three hours and nobody thought to have the bathroom fixed while we were sitting waiting to board? took a full hour to have maintenance come and check it off. Had to shut the bathroom down twice so that the pilots could go to the bathroom. Everyone missed their connections.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Flight on time. Excellent service in Premium Economy. Great food served and cleaned up promptly. Unfortunately the climate control was malfunctioning and it was very cold and felt a bit like camping. Cold helps with sleep though so not complaining too much. Slept well. It asks to rate "entertainment". I do not like any IFE, don't shove a big screen in my face—I have my own phone if I want it. So this will always get low ratings.

We had turbulence ever 1/2 hr or so and the captains announcements were SOOOO LOUD

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

It was good experience this time. The flight was on time.

I very rarely fly American and my experience today reenforces that is the correct decision. While the staff were all very courteous, our flight was first thing in the morning so there was no reason to be delayed, yet appropriate maintenance checks weren’t completed prior to our flight so we were delayed multiple times. Not a great showing, American Airlines.

It's very confusing because Kayak has it as American Airlines, but it was Hawaiian Airlines, but operated by Alaska Airlines. I had to go to the airport for my boarding pass because American said I didn't have any trips.

Smooth flight. From the early boarding and all were on board before departure time and arrived early in ONT. Great crew. Thank you!!!!

Small plane, poor meal choices for first class, bad terminal and boarding experience at LAX

Lack of gluten free options in food service. I have Celiac disease and it appears you no longer offer special meals for people with dietary restrictions. I am a frequent flyer traveling into and out of Omaha airport. I have noticed over the course of several months that although our flight typically arrives ahead of schedule (awesome job AA!) - we typically sit on the runway for several minutes waiting for the ground crew to get in place. Not sure if it is a ground crew issue or a gate availability issue (due to construction at this airport). Seems to be more of a ground crew being on time issue.

Arrived early picked up my bag in a few minutes- great trip - thank you

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

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

Information on your arrival and departure airports