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$82+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$251
(Kiwi.com)

One-way from

$82
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$552
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. 2% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Mytrip deal was found by Cheapflights users on 9/16. 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.
Fri 10/36:44 pmORD - SJO
2 stops16h 43mSpirit Airlines
Wed 10/812:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/16$252
This Mytrip deal was found by Cheapflights users on 9/14. 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.
Tue 9/305:05 amORD - SJO
1 stop7h 09mSpirit Airlines
Sat 10/411:37 amSJO - ORD
2 stops22h 13mSpirit Airlines
Deal found 9/14$253
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Thu 12/48:41 amORD - SJO
1 stop15h 40mSpirit Airlines
Wed 12/101:19 pmSJO - ORD
1 stop7h 41mSpirit Airlines
Deal found 9/16$254
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 11/65:05 amORD - SJO
1 stop7h 09mMultiple Airlines
Fri 11/72:20 amSJO - ORD
1 stop12h 50mMultiple Airlines
Deal found 9/14$255
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/195:05 amORD - SJO
1 stop7h 25mSpirit Airlines
Wed 10/2212:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/15$256
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Sat 10/117:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Sat 10/1812:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/16$257
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/215:05 amORD - SJO
1 stop7h 25mSpirit Airlines
Wed 10/2212:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/15$258
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/205:05 amORD - SJO
1 stop7h 25mSpirit Airlines
Wed 10/2212:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/15$259
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/217:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Sat 10/2512:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/15$260
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 11/115:59 pmORD - SJO
1 stop18h 15mSpirit Airlines
Wed 11/191:19 pmSJO - ORD
1 stop7h 41mSpirit Airlines
Deal found 9/15$261
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/205:05 amORD - SJO
1 stop7h 25mSpirit Airlines
Sat 10/2512:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/15$262
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Thu 10/97:43 pmORD - SJO
1 stop16h 47mSpirit Airlines
Tue 10/1412:35 pmSJO - ORD
1 stop10h 10mSpirit Airlines
Deal found 9/15$263

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 September 17, 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

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Mon 10/27

6:59 pm-11:40 am

2 stops17h 41m

Liberia

Wed 10/29

1:05 pm-11:58 pm

1 stop9h 53m

$300

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sun 10/26

5:20 am-12:00 pm

1 stop7h 40m

Liberia

Wed 10/29

1:05 pm-11:58 pm

1 stop9h 53m

$300

ChicagoLiberia

ORD - LIR

ORDLIR

Chicago O'Hare Intl

Sun 10/26

10:30 am-12:00 pm

2 stops26h 30m

Liberia

Thu 10/30

1:05 pm-12:40 pm

2 stops22h 35m

$300

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 10/8

7:59 am-4:34 pm

1 stop9h 35m

San José Juan Santamaria Intl

Mon 10/13

5:55 pm-1:41 pm

1 stop18h 46m

$328

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 11/6

2:07 pm-8:19 am

1 stop18h 12m

San José Juan Santamaria Intl

Mon 11/10

4:08 am-12:46 pm

1 stop8h 38m

$332

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 11/11

6:56 am-4:40 pm

1 stop9h 44m

San José Juan Santamaria Intl

Tue 11/18

4:08 am-12:46 pm

1 stop8h 38m

$332

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 11/1

3:07 pm-7:33 am

1 stop17h 26m

San José Juan Santamaria Intl

Wed 11/5

4:08 am-12:46 pm

1 stop8h 38m

$332

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 11/18

6:56 am-6:55 pm

1 stop11h 59m

San José Juan Santamaria Intl

Mon 11/24

11:00 am-12:05 am

1 stop13h 05m

$332

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 11/3

2:07 pm-7:33 am

1 stop17h 26m

San José Juan Santamaria Intl

Sun 11/9

4:08 am-12:46 pm

1 stop8h 38m

$332

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 11/13

2:07 pm-8:19 am

1 stop18h 12m

San José Juan Santamaria Intl

Mon 11/17

4:08 am-12:46 pm

1 stop8h 38m

$332

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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, September is the cheapest month in which you can book a flight from Wisconsin to Costa Rica (average of $398). Flying from Wisconsin to Costa Rica in March is currently the most expensive (average of $554). 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 September 17, 2025.

When flying from Wisconsin to Costa Rica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 Delta, Copa Airlines, and United Airlines fly from Wisconsin to Costa Rica in about 5h 04m. The time it takes to get you to your destination can typically vary by up to 12h 37m. Airlines will cover a distance of 2172 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 $93. Southwest flights start at $159 while deals on Air Canada start at $178 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, September is the cheapest month in which you can book a flight from Wisconsin to Costa Rica (average of $398). Flying from Wisconsin to Costa Rica in March is currently the most expensive (average of $554). 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.
John F Kennedy Intl to San José flights
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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$273Average$754FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$279Average$472FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$415Average$662FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$417Average$683FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$475Average$806FlexibilityNo cancel feeOn-time69%

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