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$91+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Apr 15 — Apr 221
Wed 4/15
Wed 4/22
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 March 16, 2026.

This CheapOair deal was found by Cheapflights users on 3/12. 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 8/111:49 pm
ORD
-
SJO
1 stop11h 10m
Multiple Airlines
Tue 8/254:18 pm
SJO
-
ORD
1 stop18h 51m
Multiple Airlines
Deal found 3/12$330
This Gotogate deal was found by Cheapflights users on 3/12. 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.
Mon 6/12:53 am
ORD
-
SJO
1 stop22h 06m
Multiple Airlines
Tue 6/94:18 pm
SJO
-
ORD
1 stop18h 51m
Multiple Airlines
Deal found 3/12$340
This CheapOair deal was found by Cheapflights users on 3/13. 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 5/56:16 pm
ORD
-
SJO
2 stops42h 17m
Spirit Airlines
Fri 5/812:38 pm
SJO
-
ORD
2 stops27h 49m
Spirit Airlines
Deal found 3/13$342
This Flightnetwork deal was found by Cheapflights users on 3/12. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:30 pm
ORD
-
SJO
1 stop15h 49m
Multiple Airlines
Thu 6/114:18 pm
SJO
-
ORD
1 stop18h 51m
Multiple Airlines
Deal found 3/12$345
This CheapOair deal was found by Cheapflights users on 3/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:16 pm
ORD
-
SJO
2 stops18h 17m
Spirit Airlines
Sun 5/1012:38 pm
SJO
-
ORD
2 stops27h 33m
Spirit Airlines
Deal found 3/14$348
This Mytrip deal was found by Cheapflights users on 3/12. 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.
Thu 4/161:49 pm
ORD
-
SJO
1 stop11h 10m
Multiple Airlines
Thu 4/304:18 pm
SJO
-
ORD
1 stop18h 51m
Multiple Airlines
Deal found 3/12$351
This CheapOair deal was found by Cheapflights users on 3/13. 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.
Wed 4/81:40 am
ORD
-
SJO
2 stops12h 06m
Multiple Airlines
Thu 4/164:18 pm
SJO
-
ORD
1 stop18h 51m
Multiple Airlines
Deal found 3/13$352
This American Airlines deal was found by Cheapflights users on 3/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/284:51 pm
MSN
-
SJO
2 stops19h 16m
American Airlines
Tue 5/52:22 pm
SJO
-
MSN
2 stops18h 26m
American Airlines
Deal found 3/14$357
This American Airlines deal was found by Cheapflights users on 3/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:31 pm
ATW
-
SJO
2 stops19h 51m
American Airlines
Thu 5/711:35 pm
SJO
-
ATW
2 stops21h 19m
American Airlines
Deal found 3/15$359
This American Airlines deal was found by Cheapflights users on 3/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:41 pm
MKE
-
SJO
2 stops17h 26m
American Airlines
Tue 4/212:08 pm
SJO
-
MKE
2 stops19h 35m
American Airlines
Deal found 3/16$359
This American Airlines deal was found by Cheapflights users on 3/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:08 pm
MSN
-
SJO
1 stop19h 17m
American Airlines
Tue 5/1212:35 pm
SJO
-
MSN
1 stop9h 21m
American Airlines
Deal found 3/15$362
This CheapOair deal was found by Cheapflights users on 3/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:16 pm
ORD
-
SJO
2 stops42h 17m
Spirit Airlines
Fri 5/812:38 pm
SJO
-
ORD
2 stops27h 49m
Spirit Airlines
Deal found 3/11$362

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 March 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$330
(CheapOair)

One-way from

$91
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$707
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 ($114 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 16, 2026.
Use the filters below to find and compare flights from Wisconsin to Costa Rica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AppletonSan José

ATW - SJO

ATWSJO

Appleton Intl

Sun 5/3

6:31 pm-11:07 am

2 stops17h 36m

San José Juan Santamaria Intl

Thu 5/7

12:10 pm-10:14 am

2 stops21h 04m

$359

AppletonSan José

ATW - SJO

ATWSJO

Appleton Intl

Tue 4/28

7:06 am-11:25 am

1 stop29h 19m

San José Juan Santamaria Intl

Tue 5/5

2:22 pm-1:00 pm

2 stops21h 38m

$366

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Wed 4/29

6:45 am-7:07 pm

2 stops13h 22m

San José Juan Santamaria Intl

Sat 5/9

12:31 pm-11:55 pm

1 stop10h 24m

$389

AppletonSan José

ATW - SJO

ATWSJO

Appleton Intl

Fri 5/1

6:31 pm-11:30 am

2 stops17h 59m

San José Juan Santamaria Intl

Fri 5/8

2:22 pm-10:14 am

2 stops18h 52m

$389

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Thu 4/30

8:55 pm-12:21 pm

2 stops16h 26m

San José Juan Santamaria Intl

Sat 5/9

1:00 pm-10:58 pm

1 stop8h 58m

$414

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 5/2

9:18 am-9:36 pm

2 stops13h 18m

San José Juan Santamaria Intl

Sat 5/9

6:30 am-11:55 pm

2 stops16h 25m

$419

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 5/26

3:21 pm-7:12 am

1 stop16h 51m

San José Juan Santamaria Intl

Sun 5/31

6:19 pm-2:06 pm

1 stop18h 47m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 4/17

3:05 pm-9:05 am

1 stop19h 00m

San José Juan Santamaria Intl

Tue 4/21

10:04 am-1:13 am

1 stop14h 09m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 4/22

8:06 am-7:00 pm

1 stop11h 54m

San José Juan Santamaria Intl

Mon 4/27

6:19 pm-1:50 pm

1 stop18h 31m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 5/1

3:21 pm-9:06 am

1 stop18h 45m

San José Juan Santamaria Intl

Wed 5/6

2:50 pm-1:15 am

1 stop9h 25m

$470

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/13

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $483). 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 American Airlines, United Airlines, and Copa Airlines fly from Wisconsin to Costa Rica in about 16h 26m. The time it takes to get you to your destination can typically vary by up to 1h 10m. Airlines will cover a distance of 2309 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 United Airlines, which is currently one of the cheapest options available, starting at $145. Delta flights start at $170 while deals on American Airlines start at $213 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 $194). Flying from Wisconsin to Costa Rica in July is currently the most expensive (average of $483). 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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George Bush Intcntl to Guatemala City flights
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Miami to San José flights

Top 4 airlines flying from Wisconsin to Costa Rica

Discover the top 4 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 March 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$206Average$630FlexibilityNo cancel feeOn-time69%
DeltaCheapest$221Average$749FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$378Average$659FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$426Average$707FlexibilityNo cancel feeOn-time63%

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