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$242+ Cheap flights from Costa Rica to Milwaukee (MKE)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
May 25 — Jun 11
Mon 5/25
Mon 6/1
1 adult, Economy
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Cheap flight deals from Costa Rica to Milwaukee

Cheapest flights from Costa Rica to Milwaukee
Explore the most affordable flight options available from Costa Rica to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2026.

This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:55 am
SJO
-
MKE
1 stop8h 13m
United Airlines
Sun 9/206:00 am
MKE
-
SJO
2 stops31h 21m
United Airlines
Deal found 4/23$457
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:30 am
SJO
-
MKE
1 stop8h 35m
United Airlines
Mon 6/155:56 pm
MKE
-
SJO
1 stop17h 15m
United Airlines
Deal found 4/23$489
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:13 am
SJO
-
MKE
1 stop10h 32m
United Airlines
Wed 5/278:00 am
MKE
-
SJO
1 stop15h 39m
United Airlines
Deal found 4/22$498
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/161:00 pm
SJO
-
MKE
1 stop8h 33m
United Airlines
Sat 5/3010:46 am
MKE
-
SJO
1 stop24h 25m
United Airlines
Deal found 4/24$520
This KAYAK deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/228:45 am
SJO
-
MKE
2 stops13h 54m
Multiple Airlines
Mon 1/48:45 pm
MKE
-
SJO
2 stops23h 54m
Multiple Airlines
Deal found 4/23$521
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:07 am
SJO
-
MKE
1 stop23h 54m
Multiple Airlines
Sun 6/78:46 am
MKE
-
SJO
1 stop24h 33m
Multiple Airlines
Deal found 4/22$523
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:00 am
SJO
-
MKE
1 stop25h 01m
Multiple Airlines
Wed 5/1312:09 pm
MKE
-
SJO
2 stops28h 09m
Multiple Airlines
Deal found 4/23$524
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:25 pm
SJO
-
MKE
2 stops23h 49m
United Airlines
Wed 5/278:35 am
MKE
-
SJO
2 stops12h 02m
United Airlines
Deal found 4/22$527
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:30 am
SJO
-
MKE
1 stop8h 35m
United Airlines
Sat 6/67:00 pm
MKE
-
SJO
2 stops17h 38m
United Airlines
Deal found 4/24$534
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:30 am
SJO
-
MKE
2 stops14h 27m
American Airlines
Sun 5/245:00 am
MKE
-
SJO
2 stops8h 59m
American Airlines
Deal found 4/20$540
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:00 am
SJO
-
MKE
1 stop10h 45m
Southwest
Thu 9/245:35 am
MKE
-
SJO
1 stop8h 10m
Southwest
Deal found 4/22$544

Find flight deals from Costa Rica to Milwaukee

Keep the following information in mind while searching for Costa Rica to Milwaukee flight deals. Data was last updated April 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$457
(United Airlines)

One-way from

$242
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$525
Provider with most accurate pricing for San José Juan Santamaria Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Milwaukee-Mitchell flights.
Search Deals
From Costa Rica to Milwaukee-Mitchell
Search Deals
One-way flight from Costa Rica to Milwaukee-Mitchell
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Costa Rica to Milwaukee that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 25, 2026.
Use the filters below to find and compare flights from Costa Rica to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 9/15

1:25 pm-11:35 am

2 stops21h 10m

Milwaukee-Mitchell

Sun 9/20

12:10 pm-7:37 pm

2 stops32h 27m

$457

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 6/2

11:13 am-10:45 pm

1 stop10h 32m

Milwaukee-Mitchell

Tue 6/9

5:56 pm-10:11 am

1 stop17h 15m

$489

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sat 5/23

6:40 am-9:15 pm

1 stop13h 35m

Milwaukee-Mitchell

Wed 5/27

8:00 am-10:39 pm

1 stop15h 39m

$498

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 8/25

9:00 am-8:30 pm

2 stops10h 30m

Milwaukee-Mitchell

Fri 9/4

8:00 am-6:40 pm

2 stops11h 40m

$550
Quickest round-trip

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 8/3

8:45 am-9:45 pm

1 stop12h 00m

Milwaukee-Mitchell

Mon 8/17

5:45 am-12:45 pm

2 stops8h 00m

$550

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 8/3

12:30 am-10:45 pm

1 stop21h 15m

Milwaukee-Mitchell

Mon 8/31

5:56 pm-12:21 pm

1 stop19h 25m

$570
Cheapest one-way
Quickest one-way

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 6/8

12:30 am-10:05 am

1 stop8h 35m

$263

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 8/25

9:00 am-9:05 pm

1 stop11h 05m

$264

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 5/14

1:25 pm-2:50 pm

1 stop24h 25m

$293

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 5/15

7:55 am-10:38 am

1 stop25h 43m

$293

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

Best time to book a flight from Costa Rica to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Costa Rica with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Costa Rica to Milwaukee?

Currently, May is the cheapest month in which you can book a flight from Costa Rica to Milwaukee (average of $256). Flying from Costa Rica to Milwaukee in October is currently the most expensive (average of $520). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated April 25, 2026.
Read through reviews of airlines operating flights from Costa Rica to Milwaukee, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,650 reviews

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,650 reviews
United Airlines
7.4
Good
9,650 reviews

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
American Airlines
7.1
Good
11,672 reviews
United Airlines
7.4
Good
9,650 reviews

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

Related info for your journey

Find useful and relevant information for your journey from Costa Rica to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Milwaukee from Costa Rica?

    Most people fly into Milwaukee-Mitchell (MKE) if they book a flight to Milwaukee from Costa Rica. Milwaukee-Mitchell is conveniently located just 6.4 mi from Milwaukee’s city center.

  • How long is the flight from Costa Rica to Milwaukee?

    Departing from Costa Rica to Milwaukee will take you 21h 10m. The distance between Costa Rica and Milwaukee is about 2286 mi.

  • Can I find deals for flights from Costa Rica to Milwaukee that include hotel bookings?

    Yes. In addition to deals on Costa Rica to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Costa Rica to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Costa Rica to Milwaukee.

  • Can I find deals for business class flights from Costa Rica to Milwaukee?

    Yes. Cheapflights offers flight deals from Costa Rica to Milwaukee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Costa Rica to Milwaukee?

    Currently, May is the cheapest month in which you can book a flight from Costa Rica to Milwaukee (average of $256). Flying from Costa Rica to Milwaukee in October is currently the most expensive (average of $520). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Port Washington
New Berlin
Oak Creek
Wauwatosa

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Costa Rica to Milwaukee

Discover the top 2 airlines that operate flights from Costa Rica to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$399Average$554FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$458Average$537FlexibilityNo cancel feeOn-time69%

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