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$119+ Cheap flights from Wisconsin 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from Wisconsin to Costa Rica

Keep the following information in mind while searching for Wisconsin to Costa Rica flight deals. Data was last updated January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$275
(Kiwi.com)

One-way from

$119
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$583
Provider with most accurate pricing for Milwaukee-Mitchell-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-San José Juan Santamaria Intl flights.
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From Wisconsin to Costa Rica
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One-way flight from Wisconsin to Costa Rica
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Highest demand for flights based on searches. 14% potential increase in price ($110 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Wisconsin to Costa Rica

Cheapest flights from Wisconsin to Costa Rica
Explore the most affordable flight options available from Wisconsin to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Mon 2/27:01 pmMKE - SJO
1 stop16h 36mMultiple Airlines
Wed 2/412:33 pmSJO - MKE
1 stop29h 43mMultiple Airlines
Deal found 1/7$275
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Mon 2/27:01 pmMKE - SJO
1 stop16h 36mMultiple Airlines
Fri 2/612:33 pmSJO - MKE
1 stop21h 44mMultiple Airlines
Deal found 1/7$288
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Mon 2/97:01 pmMKE - SJO
1 stop16h 36mMultiple Airlines
Thu 2/1912:35 pmSJO - MKE
1 stop21h 08mMultiple Airlines
Deal found 1/6$289
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Tue 2/36:53 pmMKE - SJO
1 stop16h 44mMultiple Airlines
Fri 2/61:30 pmSJO - MKE
2 stops20h 47mMultiple Airlines
Deal found 1/7$312
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Mon 2/97:01 pmMKE - SJO
1 stop16h 36mMultiple Airlines
Wed 2/1812:35 pmSJO - MKE
1 stop19h 05mMultiple Airlines
Deal found 1/6$313
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Tue 2/36:53 pmMKE - SJO
1 stop16h 44mMultiple Airlines
Sun 2/812:33 pmSJO - MKE
2 stops21h 25mMultiple Airlines
Deal found 1/7$323
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Tue 2/36:53 pmMKE - SJO
1 stop16h 44mMultiple Airlines
Mon 2/912:33 pmSJO - MKE
1 stop27h 14mMultiple Airlines
Deal found 1/7$326
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Mon 2/97:01 pmMKE - SJO
1 stop16h 36mMultiple Airlines
Tue 2/1712:35 pmSJO - MKE
1 stop27h 09mMultiple Airlines
Deal found 1/6$327
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Mon 2/1611:01 amMSP - SJO
1 stop24h 39mMultiple Airlines
Wed 2/2512:35 pmSJO - MSP
1 stop30h 57mMultiple Airlines
Deal found 1/7$331
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Mon 2/27:01 pmMKE - SJO
1 stop16h 36mMultiple Airlines
Sun 2/812:33 pmSJO - MKE
2 stops21h 25mMultiple Airlines
Deal found 1/7$336
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Mon 2/27:01 pmMKE - SJO
1 stop16h 36mMultiple Airlines
Tue 2/1012:33 pmSJO - MKE
1 stop27h 11mMultiple Airlines
Deal found 1/7$339
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Tue 2/179:30 amMSP - SJO
2 stops26h 10mMultiple Airlines
Wed 2/2512:35 pmSJO - MSP
1 stop30h 57mMultiple Airlines
Deal found 1/7$341

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 January 8, 2026.
Use the filters below to find and compare flights from Wisconsin to Costa Rica that are best for you.

Fly from

Wisconsin

Fly to

Costa Rica

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/16

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Sun 2/22

6:08 pm-12:31 pm

1 stop18h 23m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 2/14

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Wed 2/18

2:54 pm-12:04 am

1 stop9h 10m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 2/4

7:34 am-6:56 pm

1 stop11h 22m

San José Juan Santamaria Intl

Mon 2/9

11:01 am-12:04 am

1 stop13h 03m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 2/6

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Sun 2/8

8:11 am-12:04 am

1 stop15h 53m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/2

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Sun 2/8

4:09 am-12:31 pm

1 stop8h 22m

$347

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/17

7:34 am-9:52 pm

1 stop14h 18m

San José Juan Santamaria Intl

Sun 2/22

6:08 pm-12:31 pm

1 stop18h 23m

$347

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Sun 2/1

5:30 am-10:15 pm

1 stop16h 45m

San José Juan Santamaria Intl

Wed 2/4

2:31 pm-11:46 pm

1 stop9h 15m

$353

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Sun 2/1

5:30 am-10:15 pm

1 stop16h 45m

San José Juan Santamaria Intl

Fri 2/6

7:00 am-2:36 pm

1 stop7h 36m

$353

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/20

5:30 am-1:00 pm

1 stop7h 30m

San José Juan Santamaria Intl

Tue 1/27

7:00 am-4:55 pm

1 stop9h 55m

$359

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/20

5:30 am-1:00 pm

1 stop7h 30m

San José Juan Santamaria Intl

Fri 1/30

2:31 pm-1:08 pm

2 stops22h 37m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to Costa Rica

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

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

Currently, August is the cheapest month in which you can book a flight from Wisconsin to Costa Rica (average of $184). Flying from Wisconsin to Costa Rica in July is currently the most expensive (average of $485). 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.

Related info for your journey

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

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

    Airlines like Copa Airlines, Delta, and American Airlines fly from Wisconsin to Costa Rica in about 7h 30m. The time it takes to get you to your destination can typically vary by up to 10h 29m. Airlines will cover a distance of 2309 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 Wisconsin to Costa Rica that include hotel bookings?

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Wisconsin to Costa Rica (average of $184). Flying from Wisconsin to Costa Rica in July is currently the most expensive (average of $485). 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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Alternative routes for Wisconsin to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Wisconsin to Costa Rica

Discover the top 5 airlines that operate flights from Wisconsin 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$273Average$765FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$296Average$587FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$397Average$675FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$417Average$582FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$505Average$644FlexibilityNo cancel feeOn-time69%

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