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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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
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 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$285
(KAYAK)

One-way from

$90
(Spirit)

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 21, 2025.

This Mytrip deal was found by Cheapflights users on 11/19. 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.
Sat 12/65:00 amORD - SJO
1 stop7h 25mMultiple Airlines
Sat 12/138:07 amSJO - ORD
2 stops14h 04mMultiple Airlines
Deal found 11/19$287
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/116:15 amORD - SJO
2 stops29h 27mMultiple Airlines
Mon 12/151:31 pmSJO - ORD
1 stop21h 37mMultiple Airlines
Deal found 11/18$290
This KAYAK deal was found by Cheapflights users on 11/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:26 pmORD - SJO
1 stop20h 59mSpirit Airlines
Mon 12/151:31 pmSJO - ORD
1 stop21h 37mSpirit Airlines
Deal found 11/19$291
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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.
Wed 12/35:00 amORD - SJO
1 stop7h 15mSpirit Airlines
Wed 12/101:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/19$292
This Mytrip deal was found by Cheapflights users on 11/19. 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 12/138:07 amSJO - ORD
2 stops14h 04mMultiple Airlines
Deal found 11/19$294
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Wed 12/103:26 pmORD - SJO
2 stops23h 54mMultiple Airlines
Tue 12/161:31 pmSJO - ORD
1 stop10h 38mMultiple Airlines
Deal found 11/19$295
This Gotogate deal was found by Cheapflights users on 11/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:11 amORD - SJO
1 stop7h 41mMultiple Airlines
Wed 12/101:31 pmSJO - ORD
1 stop10h 38mMultiple Airlines
Deal found 11/21$296
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Wed 12/103:26 pmORD - SJO
2 stops23h 54mMultiple Airlines
Wed 12/1712:39 pmSJO - ORD
2 stops22h 35mMultiple Airlines
Deal found 11/19$301
This Gurufare deal was found by Cheapflights users on 11/20. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:11 amORD - SJO
1 stop7h 41mFrontier
Sat 12/133:07 pmSJO - ORD
1 stop17h 09mFrontier
Deal found 11/20$303
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/1111:29 amMSP - SJO
2 stops24h 56mMultiple Airlines
Wed 12/171:31 pmSJO - MSP
1 stop25h 35mMultiple Airlines
Deal found 11/18$389
This Avianca deal was found by Cheapflights users on 11/20. 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.
Sat 12/612:15 pmMSP - SJO
1 stop15h 35mMultiple Airlines
Sat 12/135:10 pmSJO - MSP
1 stop17h 37mMultiple Airlines
Deal found 11/20$393
This FlightHub deal was found by Cheapflights users on 11/21. 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.
Sun 12/149:12 amMSP - LIR
Nonstop5h 43mSun Country Air
Mon 12/293:55 pmLIR - MSP
Nonstop5h 36mSun Country Air
Deal found 11/21$395

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 21, 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

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Wed 2/4

6:56 pm-12:22 pm

2 stops17h 26m

San José Juan Santamaria Intl

Tue 2/10

12:33 pm-5:04 pm

1 stop28h 31m

$313

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

$384

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 3/3

7:34 am-4:47 pm

1 stop9h 13m

San José Juan Santamaria Intl

Mon 3/9

4:09 am-1:31 pm

1 stop8h 22m

$384

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/19

2:22 pm-9:52 pm

1 stop7h 30m

San José Juan Santamaria Intl

Mon 2/23

11:01 am-12:04 am

1 stop13h 03m

$384

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 1/22

2:13 pm-8:21 am

1 stop18h 08m

San José Juan Santamaria Intl

Tue 1/27

4:09 am-12:46 pm

1 stop8h 37m

$387

AppletonSan José

ATW - SJO

ATWSJO

Appleton Intl

Sat 1/31

5:04 pm-10:30 pm

1 stop29h 26m

San José Juan Santamaria Intl

Sun 2/8

2:54 pm-10:55 am

2 stops20h 01m

$392

MinneapolisLiberia

MSP - LIR

MSPLIR

Minneapolis St Paul

Sun 2/15

9:12 am-3:05 pm

Nonstop5h 53m

Liberia

Sun 3/8

2:54 pm-9:36 pm

Nonstop5h 42m

$395

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Wed 1/28

2:55 pm-10:15 pm

1 stop7h 20m

San José Juan Santamaria Intl

Thu 2/5

2:31 pm-11:46 pm

1 stop9h 15m

$398

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 4/20

3:13 pm-7:06 am

1 stop16h 53m

San José Juan Santamaria Intl

Sun 4/26

11:01 am-1:24 am

1 stop13h 23m

$398

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 3/21

3:22 pm-8:20 am

1 stop17h 58m

San José Juan Santamaria Intl

Wed 3/25

4:09 am-1:31 pm

1 stop8h 22m

$398

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 21, 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 Spirit Airlines, American Airlines, and Sun Country Air fly from Wisconsin to Costa Rica in about 5h 53m. The time it takes to get you to your destination can typically vary by up to 23h 33m. Airlines will cover a distance of 2411 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 $110. American Airlines flights start at $160 while deals on Frontier start at $167 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

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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 November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$273Average$762FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$279Average$454FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$415Average$661FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$426Average$682FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$505Average$729FlexibilityNo cancel feeOn-time69%

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