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$96+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$293
(KAYAK)

One-way from

$96
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$732
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. 11% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
Wed 12/313:26 pmORD - SJO
1 stop20h 59mSpirit Airlines
Thu 1/151:30 pmSJO - ORD
1 stop10h 16mSpirit Airlines
Deal found 11/23$300
This Cheapflightsfares deal was found by Cheapflights users on 11/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Wed 12/101:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/24$301
This Mytrip deal was found by Cheapflights users on 11/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/84:38 pmORD - SJO
2 stops22h 42mMultiple Airlines
Sat 12/131:31 pmSJO - ORD
1 stop10h 38mMultiple Airlines
Deal found 11/25$306
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/14:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Thu 12/111:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/24$307
This CheapOair deal was found by Cheapflights users on 11/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Tue 12/912:39 pmSJO - ORD
2 stops11h 30mSpirit Airlines
Deal found 11/24$308
This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
Wed 12/313:26 pmORD - SJO
2 stops20h 16mMultiple Airlines
Wed 1/141:30 pmSJO - ORD
1 stop31h 27mMultiple Airlines
Deal found 11/23$309
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Thu 12/111:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/24$310
This Mytrip deal was found by Cheapflights users on 11/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/84:38 pmORD - SJO
2 stops19h 04mSpirit Airlines
Sat 12/131:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/25$311
This Mytrip deal was found by Cheapflights users on 11/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:20 amORD - SJO
1 stop8h 00mMultiple Airlines
Mon 12/221:31 pmSJO - ORD
1 stop10h 59mMultiple Airlines
Deal found 11/24$315
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:36 amORD - SJO
2 stops27h 06mMultiple Airlines
Thu 12/181:31 pmSJO - ORD
1 stop10h 59mMultiple Airlines
Deal found 11/24$316
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 pmMKE - SJO
1 stop15h 27mMultiple Airlines
Fri 1/92:58 pmSJO - MKE
2 stops28h 16mMultiple Airlines
Deal found 11/24$374
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/710:34 amMKE - SJO
1 stop25h 08mMultiple Airlines
Thu 12/1812:39 pmSJO - MKE
1 stop29h 47mMultiple Airlines
Deal found 11/24$390

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 November 26, 2025.
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

Fri 2/20

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Fri 2/27

11:01 am-12:04 am

1 stop13h 03m

$345

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/5

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Sun 2/15

10:08 am-12:04 am

1 stop13h 56m

$345

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 2/18

7:34 am-6:56 pm

1 stop11h 22m

San José Juan Santamaria Intl

Tue 2/24

4:09 am-12:31 pm

1 stop8h 22m

$345

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/19

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Mon 2/23

10:08 am-12:04 am

1 stop13h 56m

$345

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 5/5

6:49 pm-1:09 pm

2 stops19h 20m

San José Juan Santamaria Intl

Wed 5/13

2:25 pm-10:32 am

2 stops19h 07m

$356

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Mon 1/12

1:16 pm-10:30 pm

1 stop9h 14m

San José Juan Santamaria Intl

Thu 1/29

8:00 am-10:40 pm

2 stops14h 40m

$356

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

Thu 2/19

4:09 am-12:31 pm

1 stop8h 22m

$360

AppletonSan José

ATW - SJO

ATWSJO

Appleton Intl

Sat 1/17

11:21 am-11:37 am

2 stops24h 16m

San José Juan Santamaria Intl

Thu 1/22

12:33 pm-9:31 pm

1 stop8h 58m

$364

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/30

7:35 am-5:01 pm

1 stop9h 26m

San José Juan Santamaria Intl

Fri 2/6

4:09 am-12:31 pm

1 stop8h 22m

$375

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Mon 1/26

6:30 am-8:39 pm

2 stops14h 09m

San José Juan Santamaria Intl

Mon 2/9

2:00 pm-11:44 pm

1 stop9h 44m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

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 $490). 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.

What is the cheapest time of day to fly from WI to CR?

Find hourly flight availability from Wisconsin to Costa Rica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 26, 2025.

It’s optimal to fly from Wisconsin to Costa Rica in the afternoon. By choosing this option you can save up to 45% on the cost of your flight, compared to a flight in the evening.

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, American Airlines, and United Airlines fly from Wisconsin to Costa Rica in about 14h 09m. The time it takes to get you to your destination can typically vary by up to 5h 11m. 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.

  • What are the cheapest airlines to fly from Wisconsin to Costa Rica one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $134. JetBlue flights start at $161 while deals on American Airlines start at $175 one-way.

  • 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 $490). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$273Average$772FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$292Average$454FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$415Average$674FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$426Average$682FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$505Average$726FlexibilityNo cancel feeOn-time69%

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