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San José

$90+ Cheap flights from Wisconsin to San José (SJO)

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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Wisconsin to San José

Cheapest flights from Wisconsin to San José
Explore the most affordable flight options available from Wisconsin to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Gurufare deal was found by Cheapflights users on 12/22. 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.
Wed 12/316:05 amORD - SJO
1 stop7h 37mFrontier
Wed 1/73:10 pmSJO - ORD
1 stop20h 25mFrontier
Deal found 12/22$413
This United Airlines deal was found by Cheapflights users on 12/22. 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.
Wed 12/247:39 amORD - SJO
Nonstop5h 17mUnited Airlines
Mon 12/292:05 pmSJO - ORD
Nonstop5h 30mUnited Airlines
Deal found 12/22$462
This Gurufare deal was found by Cheapflights users on 12/22. 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.
Wed 12/316:05 amORD - SJO
1 stop7h 37mFrontier
Fri 1/92:58 pmSJO - ORD
1 stop20h 37mFrontier
Deal found 12/22$463
This American Airlines deal was found by Cheapflights users on 12/22. 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 12/238:30 pmORD - SJO
1 stop15h 59mAmerican Airlines
Sun 12/287:00 amSJO - ORD
Nonstop5h 29mAmerican Airlines
Deal found 12/22$471
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:39 amORD - SJO
Nonstop5h 17mUnited Airlines
Mon 12/298:45 amSJO - ORD
1 stop10h 00mUnited Airlines
Deal found 12/21$472
This United Airlines deal was found by Cheapflights users on 12/22. 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.
Tue 12/2312:45 pmORD - SJO
1 stop9h 15mUnited Airlines
Sun 12/282:20 pmSJO - ORD
1 stop8h 17mUnited Airlines
Deal found 12/22$476
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/319:09 pmORD - SJO
2 stops26h 06mMultiple Airlines
Wed 1/73:10 pmSJO - ORD
1 stop20h 25mMultiple Airlines
Deal found 12/21$479
This American Airlines deal was found by Cheapflights users on 12/22. 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 12/236:52 pmORD - SJO
1 stop19h 37mAmerican Airlines
Sat 12/273:17 pmSJO - ORD
1 stop18h 27mAmerican Airlines
Deal found 12/22$485
This American Airlines deal was found by Cheapflights users on 12/23. 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.
Wed 12/313:10 pmORD - SJO
Nonstop5h 04mAmerican Airlines
Thu 1/86:00 amSJO - ORD
1 stop10h 20mAmerican Airlines
Deal found 12/23$497
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:25 amMKE - SJO
1 stop14h 30mDelta
Thu 1/152:31 pmSJO - MKE
1 stop8h 57mDelta
Deal found 12/21$529
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2211:00 amATW - SJO
2 stops10h 55mDelta
Wed 1/142:31 pmSJO - ATW
2 stops19h 52mDelta
Deal found 12/21$534
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Tue 12/237:45 amMKE - SJO
2 stops15h 00mAmerican Airlines
Thu 1/156:38 amSJO - MKE
1 stop15h 21mAmerican Airlines
Deal found 12/21$534

Find flight deals from Wisconsin to San José

Keep the following information in mind while searching for Wisconsin to San José flight deals. Data was last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$338
(FlightHub)

One-way from

$90
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$928
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 San José Juan Santamaria Intl
Search Deals
One-way flight from Wisconsin to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($121 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to San José 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 December 23, 2025.
Use the filters below to find and compare flights from Wisconsin to San José that are best for you.

Fly from

Wisconsin

Fly to

San José

Route

Depart

Return

Price

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sun 1/18

2:13 pm-8:21 am

1 stop18h 08m

San José Juan Santamaria Intl

Sun 1/25

5:50 am-12:24 am

1 stop18h 34m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/20

2:13 pm-9:52 pm

1 stop7h 39m

San José Juan Santamaria Intl

Sat 1/31

11:01 am-12:24 am

1 stop13h 23m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/20

7:35 am-8:39 pm

1 stop13h 04m

San José Juan Santamaria Intl

Tue 1/27

8:45 am-5:06 pm

1 stop8h 21m

$358

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 2/17

6:45 am-10:02 pm

1 stop15h 17m

San José Juan Santamaria Intl

Tue 2/24

2:25 pm-11:56 pm

1 stop9h 31m

$358

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 2/9

9:55 am-10:15 pm

1 stop12h 20m

San José Juan Santamaria Intl

Tue 2/17

7:00 am-4:49 pm

1 stop9h 49m

$358

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/20

6:50 am-10:15 pm

2 stops15h 25m

San José Juan Santamaria Intl

Tue 2/3

2:31 pm-11:56 pm

1 stop9h 25m

$363

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 1/19

7:39 am-12:56 pm

Nonstop5h 17m

San José Juan Santamaria Intl

Mon 1/26

2:05 pm-7:35 pm

Nonstop5h 30m

$370

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/16

7:35 am-8:39 pm

1 stop13h 04m

San José Juan Santamaria Intl

Fri 1/30

2:05 pm-7:35 pm

Nonstop5h 30m

$378

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 2/19

10:35 am-10:02 pm

2 stops11h 27m

San José Juan Santamaria Intl

Tue 2/24

2:25 pm-1:20 pm

2 stops22h 55m

$389

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 1/31

5:35 pm-10:15 pm

2 stops28h 40m

San José Juan Santamaria Intl

Wed 2/11

2:31 pm-6:59 pm

2 stops28h 28m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to San José

Have a flexible travel schedule? Discover the best time to fly to San José 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 San José

What is the cheapest month to book a flight from Wisconsin to San José?

Currently, August is the cheapest month in which you can book a flight from Wisconsin to San José (average of $184). Flying from Wisconsin to San José in April is currently the most expensive (average of $494). 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 SJO?

Find hourly flight availability from Wisconsin to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

When flying from Wisconsin to San José, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 63% versus a flight in the evening.

How much does it cost to fly round-trip from Wisconsin to San José?

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to San José from Wisconsin?

    Most people fly into San José Juan Santamaria Intl (SJO) if they book a flight to San José from Wisconsin. Juan Santamaria Intl is conveniently located just 8.8 mi from San José’s city center.

  • How long is the flight from Wisconsin to San José?

    Copa Airlines, United Airlines, and Delta can get you from Wisconsin to San José in just under 13h 04m. Your travel time can differ by up to 5h 04m. There are 2220 mi between Wisconsin and San José. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Wisconsin to San José?

    The most popular flight routes from Wisconsin to San José are Chicago O'Hare Intl - San José Juan Santamaria Intl, Minneapolis St Paul - San José Juan Santamaria Intl and Milwaukee-Mitchell - San José Juan Santamaria Intl.

  • Can I find deals for flights from Wisconsin to San José that include hotel bookings?

    Yes. In addition to deals on Wisconsin to San José flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to San José?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to San José.

  • Can I find deals for business class flights from Wisconsin to San José?

    Yes. Cheapflights offers flight deals from Wisconsin to San José 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 San José?

    Currently, August is the cheapest month in which you can book a flight from Wisconsin to San José (average of $184). Flying from Wisconsin to San José in April is currently the most expensive (average of $494). 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

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Alajuela
Monteverde
Jacó
Heredia
Dominical

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Alternative routes for Wisconsin to San José

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to San José flights
Newark to San José flights
John F Kennedy Intl to Liberia flights
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George Bush Intcntl to San José flights
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Fort Lauderdale to San José flights
Los Angeles to Liberia flights
O'Hare Intl to Liberia flights
LaGuardia to Liberia flights
Baltimore to San José flights
Boston to Liberia flights
Seattle to San José flights
Minneapolis to Liberia flights
Minneapolis to San José flights
San Francisco to Liberia flights
Dulles Intl to Liberia flights
Dallas/Fort Worth to Liberia flights
Baltimore to Liberia flights
Philadelphia to San José flights
Detroit to San José flights
Reagan-National to Liberia flights
Midway to San José flights
Seattle to Liberia flights
Atlanta to Liberia flights
Raleigh to San José flights
Portland to San José flights
Charlotte to San José flights
Ontario to San José flights
Philadelphia to Liberia flights
Sky Harbor Intl to San José flights
Hobby to Liberia flights
Tampa to San José flights
Miami to Liberia flights
Indianapolis to San José flights
San Diego to San José flights
George Bush Intcntl to Liberia flights

Top 5 airlines flying from Wisconsin to San José

Discover the top 5 airlines that operate flights from Wisconsin to San José. 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$273Average$758FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$292Average$573FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$397Average$683FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$417Average$675FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$505Average$790FlexibilityNo cancel feeOn-time69%

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