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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 20 — Feb 271
Fri 2/20
Fri 2/27
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 21, 2026.

This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:20 pm
MKE
-
SJO
1 stop9h 42m
Delta
Fri 3/67:00 am
SJO
-
MKE
1 stop16h 47m
Delta
Deal found 1/19$323
This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1212:11 pm
MKE
-
SJO
1 stop10h 04m
Delta
Thu 4/231:25 pm
SJO
-
MKE
1 stop9h 00m
Delta
Deal found 1/19$334
This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:05 am
MKE
-
SJO
1 stop14h 57m
Delta
Thu 3/57:00 am
SJO
-
MKE
1 stop16h 47m
Delta
Deal found 1/19$348
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:01 am
ORD
-
SJO
1 stop14h 32m
American Airlines
Mon 3/96:00 am
SJO
-
ORD
Nonstop5h 24m
American Airlines
Deal found 1/21$348
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:30 pm
ORD
-
SJO
Nonstop5h 00m
American Airlines
Sun 2/87:09 am
SJO
-
ORD
Nonstop5h 29m
American Airlines
Deal found 1/21$349
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
Tue 2/241:31 pm
SJO
-
ORD
1 stop10h 16m
Spirit Airlines
Deal found 1/19$350
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/27:39 am
ORD
-
SJO
Nonstop5h 17m
United Airlines
Mon 2/92:05 pm
SJO
-
ORD
Nonstop5h 30m
United Airlines
Deal found 1/20$351
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/153:40 pm
ORD
-
SJO
2 stops20h 00m
Multiple Airlines
Wed 2/181:31 pm
SJO
-
ORD
1 stop10h 16m
Multiple Airlines
Deal found 1/21$352
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/68:16 pm
ORD
-
SJO
1 stop16h 06m
Spirit Airlines
Fri 3/1312:24 pm
SJO
-
ORD
1 stop9h 53m
Spirit Airlines
Deal found 1/20$353
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:39 am
ORD
-
SJO
Nonstop5h 17m
United Airlines
Thu 2/2612:35 pm
SJO
-
ORD
1 stop11h 51m
United Airlines
Deal found 1/20$354
This Avianca Connect deal was found by Cheapflights users on 1/19. 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 Avianca Connect is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:23 pm
ORD
-
SJO
1 stop21h 07m
Multiple Airlines
Fri 3/137:45 am
SJO
-
ORD
1 stop23h 40m
Multiple Airlines
Deal found 1/19$355
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/285:53 pm
ORD
-
SJO
2 stops22h 17m
Multiple Airlines
Mon 2/91:30 pm
SJO
-
ORD
1 stop21h 52m
Multiple Airlines
Deal found 1/20$356

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 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$334
(Delta)

One-way from

$92
(Sun Country Air)

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 ($110 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($28 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 21, 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

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Wed 2/25

5:23 am-10:02 pm

1 stop16h 39m

San José Juan Santamaria Intl

Fri 3/6

7:00 am-11:47 pm

1 stop16h 47m

$323

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Tue 2/24

10:10 am-10:02 pm

1 stop11h 52m

San José Juan Santamaria Intl

Fri 3/6

7:00 am-11:47 pm

1 stop16h 47m

$323

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 2/21

8:53 am-8:39 pm

1 stop11h 46m

San José Juan Santamaria Intl

Thu 2/26

2:05 pm-7:35 pm

Nonstop5h 30m

$348

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/2

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Mon 2/9

2:05 pm-7:35 pm

Nonstop5h 30m

$351

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 2/1

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Mon 2/9

2:05 pm-7:35 pm

Nonstop5h 30m

$351

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 4/15

6:34 pm-3:05 pm

1 stop21h 31m

San José Juan Santamaria Intl

Tue 4/21

7:45 am-6:15 pm

1 stop9h 30m

$357

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 3/7

2:22 pm-8:20 am

1 stop17h 58m

San José Juan Santamaria Intl

Sun 3/15

5:51 pm-1:31 pm

1 stop18h 40m

$357

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 3/6

2:22 pm-9:46 pm

1 stop7h 24m

San José Juan Santamaria Intl

Sun 3/15

5:51 pm-1:31 pm

1 stop18h 40m

$357

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/3

7:34 am-7:02 pm

1 stop11h 28m

San José Juan Santamaria Intl

Sun 2/8

10:08 am-12:04 am

1 stop13h 56m

$359

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/2

2:22 pm-7:06 am

1 stop16h 44m

San José Juan Santamaria Intl

Mon 2/9

8:11 am-12:04 am

1 stop15h 53m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 $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 Delta, United Airlines, and Copa Airlines fly from Wisconsin to Costa Rica in about 11h 46m. The time it takes to get you to your destination can typically vary by up to 6h 12m. 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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LaGuardia to San Salvador flights
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Los Angeles to Liberia flights
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LaGuardia to Liberia 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 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$252Average$748FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$296Average$593FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$397Average$680FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$417Average$636FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$475Average$638FlexibilityNo cancel feeOn-time69%

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