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$92+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This CheapOair deal was found by Cheapflights users on 1/28. 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 2/218:59 am
ORD
-
SJO
2 stops26h 41m
Spirit Airlines
Sat 2/281:31 pm
SJO
-
ORD
2 stops18h 23m
Spirit Airlines
Deal found 1/28$335
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Mon 2/25:30 pm
ORD
-
SJO
Nonstop5h 00m
American Airlines
Wed 2/117:09 am
SJO
-
ORD
Nonstop5h 29m
American Airlines
Deal found 1/28$336
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 5/25:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
Wed 5/612:31 pm
SJO
-
ORD
1 stop10h 10m
Spirit Airlines
Deal found 1/28$337
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/237:34 am
ORD
-
SJO
1 stop9h 14m
Copa Airlines
Sun 3/14:09 am
SJO
-
ORD
1 stop8h 22m
Copa Airlines
Deal found 1/28$338
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Mon 2/97:39 am
ORD
-
SJO
Nonstop5h 17m
United Airlines
Wed 2/112:20 pm
SJO
-
ORD
1 stop17h 27m
United Airlines
Deal found 1/28$339
This CheapOair deal was found by Cheapflights users on 1/28. 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.
Sun 2/155:15 am
ORD
-
SJO
2 stops30h 25m
Spirit Airlines
Mon 3/212:35 pm
SJO
-
ORD
1 stop29h 11m
Spirit Airlines
Deal found 1/28$340
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/212:05 pm
ORD
-
SJO
2 stops35h 25m
Multiple Airlines
Sat 2/71:30 pm
SJO
-
ORD
1 stop10h 17m
Multiple Airlines
Deal found 1/28$341
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 4/255:32 pm
ORD
-
SJO
1 stop18h 50m
Spirit Airlines
Fri 5/112:31 pm
SJO
-
ORD
1 stop10h 10m
Spirit Airlines
Deal found 1/28$342
This Delta deal was found by Cheapflights users on 1/28. 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.
Mon 2/237:41 pm
ORD
-
SJO
2 stops26h 21m
Delta
Wed 3/47:00 am
SJO
-
ORD
1 stop16h 56m
Delta
Deal found 1/28$343
This United Airlines deal was found by Cheapflights users on 1/27. 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 2/267:39 am
ORD
-
SJO
Nonstop5h 17m
United Airlines
Thu 3/512:35 pm
SJO
-
ORD
1 stop10h 33m
United Airlines
Deal found 1/27$344
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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.
Sun 2/225:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
Sat 2/281:31 pm
SJO
-
ORD
1 stop7h 42m
Spirit Airlines
Deal found 1/26$345
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 3/248:41 pm
ORD
-
SJO
1 stop15h 38m
Spirit Airlines
Thu 4/212:24 pm
SJO
-
ORD
1 stop9h 53m
Spirit Airlines
Deal found 1/27$346

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$335
(CheapOair)

One-way from

$92
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$583
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. 14% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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 5/3

5:15 am-11:22 am

1 stop7h 07m

San José Juan Santamaria Intl

Sat 5/16

12:31 pm-11:41 pm

1 stop10h 10m

$337

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/9

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Wed 2/11

2:20 pm-7:47 am

1 stop17h 27m

$339

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 3/5

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Tue 3/10

7:45 am-9:38 pm

1 stop12h 53m

$344

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/26

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Thu 3/5

12:35 pm-11:08 pm

1 stop10h 33m

$344

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 3/6

5:58 pm-3:20 pm

2 stops21h 22m

San José Juan Santamaria Intl

Sat 3/14

11:38 am-9:10 am

2 stops20h 32m

$348

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 2/25

5:15 am-12:22 pm

1 stop7h 07m

San José Juan Santamaria Intl

Sun 3/1

7:45 am-10:51 am

2 stops51h 06m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 5/6

6:34 pm-3:05 pm

1 stop21h 31m

San José Juan Santamaria Intl

Sun 5/10

7:45 am-6:15 pm

1 stop9h 30m

$362

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 4/22

6:34 pm-3:05 pm

1 stop21h 31m

San José Juan Santamaria Intl

Sun 4/26

7:45 am-6:15 pm

1 stop9h 30m

$364

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 4/23

3:21 pm-7:11 am

1 stop16h 50m

San José Juan Santamaria Intl

Sun 4/26

5:46 am-1:13 am

1 stop18h 27m

$372

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 4/6

3:21 pm-7:11 am

1 stop16h 50m

San José Juan Santamaria Intl

Sun 4/12

5:56 pm-1:58 pm

1 stop19h 02m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 $194). 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.

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, United 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 9h 55m. 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 $194). 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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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$252Average$761FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$296Average$587FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$397Average$678FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$417Average$644FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$475Average$624FlexibilityNo cancel feeOn-time69%

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