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San José

$132+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap 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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$257
(Kiwi.com)

One-way from

$132
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$668
Provider with most accurate pricing for Milwaukee-Mitchell-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-San José Juan Santamaria Intl flights.
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From Wisconsin to San José Juan Santamaria Intl
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One-way flight from Wisconsin to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 7% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/103:26 pmORD - SJO
1 stop20h 59mSpirit Airlines
Wed 12/171:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/3$257
This Mytrip deal was found by Cheapflights users on 11/1. 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 12/64:49 pmORD - SJO
2 stops19h 36mSpirit Airlines
Wed 12/101:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/1$260
This Priceline deal was found by Cheapflights users on 11/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Mon 11/171:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 11/1$261
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 12/95:00 amORD - SJO
1 stop7h 25mSpirit Airlines
Sat 12/131:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/3$262
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 12/24:58 pmORD - SJO
1 stop17h 21mSpirit Airlines
Tue 12/161:31 pmSJO - ORD
1 stop10h 38mSpirit Airlines
Deal found 11/2$263
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Thu 11/278:45 amORD - SJO
1 stop27h 30mMultiple Airlines
Mon 12/81:31 pmSJO - ORD
1 stop30h 30mMultiple Airlines
Deal found 10/31$264
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Fri 11/145:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Wed 11/191:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 11/3$266
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Tue 11/112:31 pmORD - SJO
2 stops21h 08mSpirit Airlines
Wed 11/191:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 11/3$267
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 12/54:20 pmORD - SJO
1 stop21h 32mMultiple Airlines
Wed 12/101:31 pmSJO - ORD
1 stop10h 38mMultiple Airlines
Deal found 11/2$268
This Mytrip deal was found by Cheapflights users on 11/2. 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.
Sun 11/165:10 amORD - SJO
1 stop7h 15mSpirit Airlines
Wed 11/191:30 pmSJO - ORD
2 stops19h 31mSpirit Airlines
Deal found 11/2$269
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/177:34 pmORD - SJO
2 stops16h 51mSpirit Airlines
Mon 12/81:31 pmSJO - ORD
1 stop30h 30mSpirit Airlines
Deal found 11/2$270
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/157:34 pmORD - SJO
2 stops16h 51mSpirit Airlines
Wed 11/191:30 pmSJO - ORD
1 stop10h 57mSpirit Airlines
Deal found 11/3$271

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 November 3, 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 11/16

5:25 am-3:20 pm

1 stop9h 55m

San José Juan Santamaria Intl

Fri 11/21

2:20 am-3:10 pm

1 stop12h 50m

$289

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 11/28

5:23 am-10:07 pm

1 stop16h 44m

San José Juan Santamaria Intl

Fri 12/19

2:31 pm-10:43 pm

1 stop8h 12m

$342

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 11/27

6:45 am-10:07 pm

2 stops15h 22m

San José Juan Santamaria Intl

Wed 12/3

7:00 am-4:42 pm

1 stop9h 42m

$346

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 1/31

5:37 pm-10:15 pm

2 stops28h 38m

San José Juan Santamaria Intl

Tue 2/3

7:00 am-9:04 pm

2 stops14h 04m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 1/29

6:50 am-10:15 pm

2 stops15h 25m

San José Juan Santamaria Intl

Mon 2/2

7:00 am-9:04 pm

2 stops14h 04m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/30

10:35 am-10:15 pm

2 stops11h 40m

San José Juan Santamaria Intl

Fri 2/6

2:31 pm-9:40 am

2 stops19h 09m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/27

6:00 pm-10:15 pm

2 stops28h 15m

San José Juan Santamaria Intl

Sat 1/31

7:00 am-9:04 pm

2 stops14h 04m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/30

10:35 am-10:15 pm

2 stops11h 40m

San José Juan Santamaria Intl

Thu 2/5

7:00 am-6:45 pm

2 stops11h 45m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 1/30

10:35 am-10:15 pm

2 stops11h 40m

San José Juan Santamaria Intl

Wed 2/4

2:31 pm-8:42 am

1 stop18h 11m

$350

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 1/27

6:00 pm-10:15 pm

2 stops28h 15m

San José Juan Santamaria Intl

Thu 2/5

7:00 am-4:54 pm

1 stop9h 54m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 56 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 $491). 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 November 3, 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 50% 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?

    Delta, Spirit Airlines, and American Airlines can get you from Wisconsin to San José in just under 7h 19m. Your travel time can differ by up to 17h 49m. There are 2286 mi between Wisconsin and San José. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Wisconsin to San José one-way?

    $136 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $150 and $225, respectively.

  • 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 $491). 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
Heredia
Manuel Antonio
Alajuela
Monteverde
Jacó
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.
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Atlanta to Liberia flights
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Baltimore to Liberia flights
Midway to San José flights
Hobby to Liberia flights
Salt Lake City to San José flights
Raleigh to San José flights
Philadelphia to San José flights
Reagan-National to Liberia flights
George Bush Intcntl to Liberia flights
Ontario to San José flights
Dallas/Fort Worth to Liberia flights
Philadelphia to Liberia flights
Austin to San José flights
Portland to San José flights
Cleveland to San José flights
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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$273Average$769FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$279Average$454FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$426Average$682FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$486Average$643FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$505Average$800FlexibilityNo cancel feeOn-time69%

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