Costa Rica

$271+ Cheap flights from Milwaukee (MKE) to Costa Rica

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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Jul 23 — Jul 301
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Cheap flight deals from Milwaukee to Costa Rica

Cheapest flights from Milwaukee to Costa Rica
Explore the most affordable flight options available from Milwaukee to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 23, 2026.

This American Airlines deal was found by Cheapflights users on 6/18. 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.
Wed 9/95:03 am
MKE
-
SJO
2 stops16h 04m
American Airlines
Thu 9/242:57 pm
SJO
-
MKE
2 stops19h 30m
American Airlines
Deal found 6/18$515
This United Airlines deal was found by Cheapflights users on 6/21. 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 10/276:30 am
MKE
-
SJO
2 stops14h 09m
United Airlines
Tue 11/32:25 pm
SJO
-
MKE
1 stop8h 25m
United Airlines
Deal found 6/21$520
This Southwest deal was found by Cheapflights users on 6/22. 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.
Sun 10/115:30 am
MKE
-
SJO
1 stop8h 10m
Southwest
Fri 10/169:00 am
SJO
-
MKE
1 stop7h 55m
Southwest
Deal found 6/22$522
This American Airlines deal was found by Cheapflights users on 6/19. 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 10/275:50 pm
MKE
-
SJO
1 stop21h 08m
American Airlines
Tue 11/31:23 pm
SJO
-
MKE
1 stop10h 36m
American Airlines
Deal found 6/19$530
This American Airlines deal was found by Cheapflights users on 6/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:01 am
MKE
-
SJO
2 stops14h 54m
American Airlines
Fri 12/113:06 pm
SJO
-
MKE
1 stop26h 58m
American Airlines
Deal found 6/22$534
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Mon 8/176:28 am
MKE
-
SJO
1 stop6h 58m
American Airlines
Mon 8/311:29 pm
SJO
-
MKE
1 stop8h 30m
American Airlines
Deal found 6/21$555
This Southwest deal was found by Cheapflights users on 6/22. 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.
Mon 8/315:35 am
MKE
-
SJO
1 stop8h 10m
Southwest
Sat 9/59:30 am
SJO
-
MKE
1 stop8h 50m
Southwest
Deal found 6/22$557
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Sat 8/155:50 pm
MKE
-
SJO
2 stops19h 13m
American Airlines
Sat 8/291:29 pm
SJO
-
MKE
2 stops19h 22m
American Airlines
Deal found 6/21$560
This Southwest deal was found by Cheapflights users on 6/22. 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.
Tue 9/110:00 am
MKE
-
SJO
2 stops9h 40m
Southwest
Sun 9/69:00 am
SJO
-
MKE
2 stops11h 20m
Southwest
Deal found 6/22$562
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Thu 8/276:00 pm
MKE
-
LIR
2 stops18h 29m
American Airlines
Thu 9/32:15 pm
LIR
-
MKE
2 stops19h 42m
American Airlines
Deal found 6/18$611
This American Airlines deal was found by Cheapflights users on 6/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am
MKE
-
LIR
1 stop7h 47m
American Airlines
Sat 10/32:47 pm
LIR
-
MKE
2 stops19h 20m
American Airlines
Deal found 6/22$641
This United Airlines deal was found by Cheapflights users on 6/22. 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.
Mon 11/26:18 pm
MKE
-
LIR
2 stops18h 52m
United Airlines
Thu 11/512:50 pm
LIR
-
MKE
2 stops21h 11m
United Airlines
Deal found 6/22$645

Find flight deals from Milwaukee to Costa Rica

Keep the following information in mind while searching for Milwaukee to Costa Rica flight deals. Data was last updated June 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$510
(American Airlines)

One-way from

$271
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$729
Provider with most accurate pricing for Milwaukee-Mitchell-San José Juan Santamaria Intl flight deals.
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-San José Juan Santamaria Intl flights.
From Milwaukee-Mitchell to Costa Rica
One-way flight from Milwaukee-Mitchell to Costa Rica
Highest demand for flights based on searches. 7% potential increase in price ($52 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Average for round-trip flights in June 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee to Costa Rica 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 June 23, 2026.
Use the filters below to find and compare flights from Milwaukee to Costa Rica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Tue 11/10

2:45 pm-10:15 pm

1 stop7h 30m

San José Juan Santamaria Intl

Tue 11/17

7:00 am-3:04 pm

1 stop8h 04m

$520

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Tue 9/22

6:00 am-7:37 pm

2 stops14h 37m

San José Juan Santamaria Intl

Sat 9/26

12:44 pm-11:37 pm

1 stop9h 53m

$555

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Mon 8/31

6:15 am-7:37 pm

2 stops14h 22m

San José Juan Santamaria Intl

Sat 9/5

1:25 pm-10:39 pm

1 stop8h 14m

$555

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Mon 11/2

5:10 am-1:15 pm

1 stop8h 05m

San José Juan Santamaria Intl

Mon 11/9

9:00 am-7:15 pm

1 stop10h 15m

$563

MilwaukeeLiberia

MKE - LIR

MKELIR

Milwaukee-Mitchell

Thu 8/27

6:00 pm-11:29 am

2 stops18h 29m

Liberia

Thu 9/3

2:15 pm-10:57 am

2 stops19h 42m

$611

MilwaukeeLiberia

MKE - LIR

MKELIR

Milwaukee-Mitchell

Fri 9/18

6:47 pm-12:10 pm

2 stops18h 23m

Liberia

Fri 9/25

1:20 pm-10:45 pm

1 stop8h 25m

$611

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Tue 8/25

6:05 am-12:45 pm

1 stop7h 40m

San José Juan Santamaria Intl

Sun 8/30

9:00 am-5:55 pm

1 stop7h 55m

$612

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Sun 10/25

5:45 am-11:58 am

1 stop7h 13m

San José Juan Santamaria Intl

Thu 11/5

2:23 pm-11:49 pm

1 stop9h 26m

$624

MilwaukeeLiberia

MKE - LIR

MKELIR

Milwaukee-Mitchell

Mon 11/2

6:18 pm-1:10 pm

2 stops18h 52m

Liberia

Thu 11/5

12:50 pm-10:01 am

2 stops21h 11m

$645

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Tue 10/27

5:45 am-11:58 am

1 stop7h 13m

San José Juan Santamaria Intl

Mon 11/2

2:23 pm-11:49 pm

1 stop9h 26m

$659

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/23

Showing 1-10 of 24 resultsSorted by cheapest first
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2
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Best time to book a flight from Milwaukee to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica from Milwaukee 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 Milwaukee to Costa Rica

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

Currently, February is the cheapest month in which you can book a flight from Milwaukee to Costa Rica (average of $193). Flying from Milwaukee to Costa Rica in December is currently the most expensive (average of $546). 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.

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

The best time to book flights from Milwaukee to Costa Rica is 31 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Reviews of airlines servicing Costa Rica

Get insights into the airlines that provide service to Costa Rica. 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 Costa Rica. Reviews last updated June 23, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Milwaukee to Costa Rica. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Entertainment

7.5

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Milwaukee to Costa Rica. 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 from for flights from Milwaukee to Costa Rica?

    Milwaukee-Mitchell (MKE) is the airport you will fly out of if you book a flight from Milwaukee to Costa Rica. It is only a 6.4 mi journey to Milwaukee-Mitchell (MKE) from Milwaukee’s city center.

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

    Departing from Milwaukee to Costa Rica will take you 7h 30m. The distance from Milwaukee to Costa Rica is about 2286 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee to Costa Rica 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 Milwaukee to Costa Rica?

    Currently, February is the cheapest month in which you can book a flight from Milwaukee to Costa Rica (average of $193). Flying from Milwaukee to Costa Rica in December is currently the most expensive (average of $546). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 4 airlines flying from Milwaukee to Costa Rica

Discover the top 4 airlines that operate flights from Milwaukee to Costa Rica. 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 June 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$206Average$642FlexibilityNo cancel feeOn-time69%
DeltaCheapest$318Average$710FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$402Average$674FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$426Average$707FlexibilityNo cancel feeOn-time63%

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