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$129+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$258
(CheapOair)

One-way from

$129
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$595
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. 8% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This CheapOair deal was found by Cheapflights users on 10/30. 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.
Tue 11/115:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Fri 11/141:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 10/30$258
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 11/185:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Mon 11/2411:24 amSJO - ORD
1 stop11h 42mSpirit Airlines
Deal found 10/30$259
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 12/115:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Mon 12/151:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 10/29$260
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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
Tue 12/161:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 10/30$263
This Mytrip deal was found by Cheapflights users on 10/30. 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 11/165:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Sat 11/2211:24 amSJO - ORD
2 stops21h 53mSpirit Airlines
Deal found 10/30$266
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/75:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Thu 12/111:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 10/29$267
This Mytrip deal was found by Cheapflights users on 10/29. 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 11/147:34 pmORD - SJO
3 stops40h 05mSpirit Airlines
Wed 11/191:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 10/29$268
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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.
Fri 11/284:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Fri 12/51:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 10/29$271
This Avianca deal was found by Cheapflights users on 10/30. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:10 amORD - SJO
2 stops11h 45mAvianca
Mon 11/105:00 amSJO - ORD
2 stops13h 10mAvianca
Deal found 10/30$272
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/810:52 amORD - SJO
2 stops24h 47mSpirit Airlines
Wed 11/1212:34 pmSJO - ORD
1 stop10h 32mSpirit Airlines
Deal found 10/30$273
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/147:34 pmORD - SJO
2 stops16h 51mSpirit Airlines
Thu 11/201:20 pmSJO - ORD
1 stop9h 53mSpirit Airlines
Deal found 10/29$274
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/131:05 pmMSP - SJO
2 stops23h 20mMultiple Airlines
Wed 11/191:30 pmSJO - MSP
1 stop25h 30mMultiple Airlines
Deal found 10/29$328

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 October 30, 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

Tue 2/3

7:35 am-12:21 am

2 stops16h 46m

San José Juan Santamaria Intl

Tue 2/10

7:22 am-9:23 pm

1 stop14h 01m

$271

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 11/25

6:56 am-7:07 pm

1 stop12h 11m

San José Juan Santamaria Intl

Tue 12/2

4:08 am-12:52 pm

1 stop8h 44m

$330

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/10

7:34 am-4:48 pm

1 stop9h 14m

San José Juan Santamaria Intl

Tue 2/17

5:51 pm-12:31 pm

1 stop18h 40m

$330

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/3

7:35 am-12:21 am

2 stops16h 46m

San José Juan Santamaria Intl

Mon 2/9

12:22 pm-9:00 pm

3 stops32h 38m

$336

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 11/14

5:23 am-1:05 pm

1 stop7h 42m

San José Juan Santamaria Intl

Sat 11/15

2:31 pm-8:41 am

1 stop18h 10m

$344

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 11/19

10:46 am-10:07 pm

2 stops11h 21m

San José Juan Santamaria Intl

Tue 11/25

7:00 am-8:29 pm

2 stops13h 29m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 12/7

6:45 am-10:20 pm

2 stops15h 35m

San José Juan Santamaria Intl

Sun 12/21

7:00 am-4:19 pm

1 stop9h 19m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/23

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Mon 3/2

4:09 am-12:31 pm

1 stop8h 22m

$357

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 2/25

2:22 pm-8:21 am

1 stop17h 59m

San José Juan Santamaria Intl

Sun 3/1

6:08 pm-12:31 pm

1 stop18h 23m

$357

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 11/18

6:56 am-4:40 pm

1 stop9h 44m

San José Juan Santamaria Intl

Sun 11/23

4:08 am-12:46 pm

1 stop8h 38m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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 April is currently the most expensive (average of $491). 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 October 30, 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, Spirit Airlines, and Delta fly from Wisconsin to Costa Rica in about 7h 42m. The time it takes to get you to your destination can typically vary by up to 9h 04m. 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.

  • 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 $129. Air Canada flights start at $193 while deals on Sun Country Air start at $199 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 April is currently the most expensive (average of $491). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$273Average$758FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$279Average$472FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$415Average$658FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$426Average$680FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$475Average$729FlexibilityNo cancel feeOn-time69%

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