Costa Rica

$124+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Mar 14 — Mar 211
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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 February 12, 2026.

This CheapOair deal was found by Cheapflights users on 2/11. 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.
Sat 3/78:16 pm
ORD
-
SJO
1 stop15h 06m
Spirit Airlines
Sun 3/1511:38 am
SJO
-
ORD
1 stop28h 18m
Spirit Airlines
Deal found 2/11$316
This CheapOair deal was found by Cheapflights users on 2/11. 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.
Wed 2/258:16 pm
ORD
-
SJO
1 stop16h 06m
Spirit Airlines
Wed 3/412:35 pm
SJO
-
ORD
2 stops11h 12m
Spirit Airlines
Deal found 2/11$317
This FlightHub deal was found by Cheapflights users on 2/10. 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.
Wed 3/44:43 pm
ORD
-
SJO
2 stops18h 57m
Spirit Airlines
Mon 3/911:35 am
SJO
-
ORD
2 stops11h 12m
Spirit Airlines
Deal found 2/10$318
This CheapOair deal was found by Cheapflights users on 2/10. 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 3/115:15 am
ORD
-
SJO
1 stop7h 07m
Spirit Airlines
Wed 3/1812:19 pm
SJO
-
ORD
2 stops30h 44m
Spirit Airlines
Deal found 2/10$319
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sat 2/289:18 am
ORD
-
SJO
3 stops14h 12m
Multiple Airlines
Wed 3/1112:31 pm
SJO
-
ORD
1 stop7h 42m
Multiple Airlines
Deal found 2/9$320
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 5/61:27 pm
ORD
-
SJO
1 stop22h 55m
Multiple Airlines
Fri 5/1512:31 pm
SJO
-
ORD
1 stop9h 26m
Multiple Airlines
Deal found 2/9$321
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:05 am
ORD
-
SJO
1 stop7h 10m
Spirit Airlines
Wed 5/1312:20 pm
SJO
-
ORD
1 stop10h 54m
Spirit Airlines
Deal found 2/11$322
This Copa Airlines deal was found by Cheapflights users on 2/9. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/12:22 pm
ORD
-
SJO
3 stops26h 24m
Copa Airlines
Sun 3/88:48 am
SJO
-
ORD
1 stop15h 16m
Copa Airlines
Deal found 2/9$323
This Travelocity deal was found by Cheapflights users on 2/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:05 am
ORD
-
SJO
1 stop8h 10m
Multiple Airlines
Thu 2/261:31 pm
SJO
-
ORD
1 stop10h 16m
Multiple Airlines
Deal found 2/10$324
This Mytrip deal was found by Cheapflights users on 2/9. 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 2/218:59 am
ORD
-
SJO
2 stops26h 41m
Spirit Airlines
Thu 2/261:31 pm
SJO
-
ORD
1 stop7h 42m
Spirit Airlines
Deal found 2/9$325
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sat 2/289:18 am
ORD
-
SJO
3 stops14h 12m
Multiple Airlines
Sat 3/71:31 pm
SJO
-
ORD
1 stop7h 42m
Multiple Airlines
Deal found 2/9$326
This CheapOair deal was found by Cheapflights users on 2/10. 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 2/278:16 pm
ORD
-
SJO
1 stop16h 06m
Spirit Airlines
Mon 3/21:31 pm
SJO
-
ORD
2 stops28h 15m
Spirit Airlines
Deal found 2/10$327

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 February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$316
(CheapOair)

One-way from

$124
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$591
Provider with most accurate pricing for Milwaukee-Mitchell-San José Juan Santamaria Intl flight deals.
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-San José Juan Santamaria Intl flights.
From Wisconsin to Costa Rica
One-way flight from Wisconsin to Costa Rica
Highest demand for flights based on searches. 16% potential increase in price ($127 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($29 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 12, 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

Thu 4/23

3:21 pm-4:48 pm

3 stops26h 27m

San José Juan Santamaria Intl

Tue 4/28

4:09 am-1:58 pm

1 stop8h 49m

$319

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 3/5

2:22 pm-4:46 pm

3 stops26h 24m

San José Juan Santamaria Intl

Thu 3/12

11:01 am-1:04 am

1 stop13h 03m

$319

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/23

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Thu 2/26

2:05 pm-7:35 pm

Nonstop5h 30m

$329

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 3/15

3:22 pm-7:05 am

1 stop16h 43m

San José Juan Santamaria Intl

Thu 3/19

8:48 am-1:04 am

1 stop15h 16m

$336

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 3/8

5:30 am-9:15 pm

1 stop16h 45m

San José Juan Santamaria Intl

Wed 3/18

7:00 am-9:10 am

2 stops25h 10m

$353

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 3/3

6:30 am-10:02 pm

2 stops15h 32m

San José Juan Santamaria Intl

Wed 3/18

7:00 am-8:17 pm

2 stops12h 17m

$353

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 3/6

5:25 am-10:02 pm

1 stop16h 37m

San José Juan Santamaria Intl

Wed 3/18

7:00 am-8:17 pm

2 stops12h 17m

$364

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 3/3

6:30 am-10:02 pm

2 stops15h 32m

San José Juan Santamaria Intl

Wed 3/11

7:00 am-8:17 pm

2 stops12h 17m

$369

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/23

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Fri 2/27

2:05 pm-7:35 pm

Nonstop5h 30m

$373

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/24

8:53 am-8:39 pm

1 stop11h 46m

San José Juan Santamaria Intl

Fri 2/27

2:05 pm-7:35 pm

Nonstop5h 30m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

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 Copa 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 21h 10m. 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.

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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$221Average$750FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$393Average$668FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$417Average$636FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$475Average$623FlexibilityNo cancel feeOn-time69%

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