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$90+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/9. 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 12/105:18 pmORD - SJO
Nonstop5h 10mAmerican Airlines
Mon 12/156:00 amSJO - ORD
Nonstop5h 31mAmerican Airlines
Deal found 12/9$343
This Copa Airlines deal was found by Cheapflights users on 12/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:07 pmORD - SJO
1 stop17h 03mCopa Airlines
Thu 12/188:10 amSJO - ORD
1 stop15h 55mCopa Airlines
Deal found 12/10$346
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/1110:35 amORD - SJO
1 stop10h 04mUnited Airlines
Thu 12/182:05 pmSJO - ORD
Nonstop5h 30mUnited Airlines
Deal found 12/10$348
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/115:18 pmORD - SJO
Nonstop5h 10mAmerican Airlines
Thu 12/187:00 amSJO - ORD
Nonstop5h 29mAmerican Airlines
Deal found 12/10$350
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:30 amORD - SJO
1 stop16h 50mDelta
Sat 12/202:21 pmSJO - ORD
1 stop9h 41mDelta
Deal found 12/11$358
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:30 amORD - SJO
1 stop16h 50mDelta
Sun 12/217:00 amSJO - ORD
2 stops13h 36mDelta
Deal found 12/11$362
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/101:45 pmORD - SJO
1 stop24h 17mAmerican Airlines
Sun 12/146:00 amSJO - ORD
Nonstop5h 31mAmerican Airlines
Deal found 12/10$366
This Delta deal was found by Cheapflights users on 12/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:45 amORD - SJO
2 stops15h 35mDelta
Thu 12/187:00 amSJO - ORD
2 stops13h 35mDelta
Deal found 12/10$372
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/1112:45 pmORD - SJO
1 stop7h 54mUnited Airlines
Mon 2/22:05 pmSJO - ORD
Nonstop5h 30mUnited Airlines
Deal found 12/10$374
This FlightHub deal was found by Cheapflights users on 12/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Mon 2/21:30 pmSJO - ORD
1 stop10h 16mSpirit Airlines
Deal found 12/10$384
This United Airlines deal was found by Cheapflights users on 12/10. 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 12/177:35 amORD - LIR
1 stop11h 02mUnited Airlines
Wed 12/2412:30 pmLIR - ORD
Nonstop5h 19mUnited Airlines
Deal found 12/10$463
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/175:00 amORD - LIR
2 stops9h 20mAmerican Airlines
Wed 12/242:37 pmLIR - ORD
Nonstop5h 25mAmerican Airlines
Deal found 12/10$467

Find 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$334
(Kiwi.com)

One-way from

$90
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$928
Provider with most accurate pricing for Milwaukee-Mitchell-San José Juan Santamaria Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-San José Juan Santamaria Intl flights.
Search Deals
From Wisconsin to Costa Rica
Search Deals
One-way flight from Wisconsin to Costa Rica
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($120 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 12, 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

Sun 1/18

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Thu 1/22

2:05 pm-7:35 pm

Nonstop5h 30m

$343

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 1/26

10:52 am-7:53 pm

1 stop9h 01m

San José Juan Santamaria Intl

Fri 1/30

2:05 pm-7:35 pm

Nonstop5h 30m

$348

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

Thu 2/26

4:09 am-12:31 pm

1 stop8h 22m

$361

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 1/29

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Thu 2/5

2:05 pm-7:35 pm

Nonstop5h 30m

$369

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/12

5:25 am-10:02 pm

1 stop16h 37m

San José Juan Santamaria Intl

Tue 2/17

7:00 am-7:19 pm

1 stop12h 19m

$384

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/9

6:50 am-10:15 pm

2 stops15h 25m

San José Juan Santamaria Intl

Sun 2/15

7:00 am-11:57 pm

1 stop16h 57m

$388

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 5/2

7:36 am-11:55 am

Nonstop5h 19m

San José Juan Santamaria Intl

Sat 5/9

1:00 pm-7:35 pm

Nonstop5h 35m

$395

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Wed 1/21

6:00 am-10:30 pm

1 stop16h 30m

San José Juan Santamaria Intl

Wed 1/28

7:09 am-6:44 pm

1 stop11h 35m

$398

AppletonSan José

ATW - SJO

ATWSJO

Appleton Intl

Sun 2/1

11:25 am-10:30 pm

1 stop11h 05m

San José Juan Santamaria Intl

Thu 2/5

7:09 am-5:51 pm

1 stop10h 42m

$398

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 4/17

3:21 pm-7:11 am

1 stop16h 50m

San José Juan Santamaria Intl

Sun 4/26

5:56 pm-1:58 pm

1 stop19h 02m

$398

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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.

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 December 12, 2025.

It’s optimal to fly from Wisconsin to Costa Rica in the afternoon. By choosing this option you can save up to 60% 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 United Airlines, Copa Airlines, and Delta fly from Wisconsin to Costa Rica in about 5h 17m. The time it takes to get you to your destination can typically vary by up to 11h 27m. Airlines will cover a distance of 2220 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$273Average$776FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$292Average$472FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$415Average$672FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$426Average$682FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$505Average$721FlexibilityNo cancel feeOn-time69%

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