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San José

$129+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
May 18 — May 251
Mon 5/18
Mon 5/25
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 April 18, 2026.

This CheapOair deal was found by Cheapflights users on 4/12. 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.
Thu 5/147:33 pm
ORD
-
SJO
1 stop17h 12m
Spirit Airlines
Mon 5/181:00 pm
SJO
-
ORD
2 stops19h 54m
Spirit Airlines
Deal found 4/12$380
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:59 pm
ORD
-
SJO
2 stops26h 06m
Multiple Airlines
Fri 5/151:00 pm
SJO
-
ORD
1 stop9h 59m
Multiple Airlines
Deal found 4/13$381
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:27 pm
ORD
-
SJO
1 stop23h 06m
Multiple Airlines
Tue 5/57:00 am
SJO
-
ORD
1 stop15h 13m
Multiple Airlines
Deal found 4/12$383
This Mytrip deal was found by Cheapflights users on 4/12. 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.
Mon 5/115:05 am
ORD
-
SJO
1 stop7h 40m
Spirit Airlines
Sun 5/171:00 pm
SJO
-
ORD
1 stop18h 22m
Spirit Airlines
Deal found 4/12$387
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:11 pm
ORD
-
SJO
1 stop16h 08m
Frontier
Thu 6/119:35 am
SJO
-
ORD
1 stop12h 44m
Frontier
Deal found 4/13$388
This Volaris deal was found by Cheapflights users on 4/12. 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 Volaris 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 6/94:15 pm
SJO
-
ORD
1 stop18h 54m
Multiple Airlines
Deal found 4/12$392
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:05 am
ORD
-
SJO
1 stop7h 40m
Multiple Airlines
Sun 5/171:00 pm
SJO
-
ORD
2 stops17h 55m
Multiple Airlines
Deal found 4/12$393
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:27 pm
ORD
-
SJO
1 stop23h 06m
Multiple Airlines
Mon 5/41:00 pm
SJO
-
ORD
2 stops17h 55m
Multiple Airlines
Deal found 4/12$394
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/49:20 am
ORD
-
SJO
3 stops27h 10m
Multiple Airlines
Mon 5/111:00 pm
SJO
-
ORD
1 stop9h 15m
Multiple Airlines
Deal found 4/12$397
This Volaris deal was found by Cheapflights users on 4/13. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/132:35 am
ORD
-
SJO
1 stop22h 24m
Multiple Airlines
Sun 4/194:18 pm
SJO
-
ORD
1 stop18h 51m
Multiple Airlines
Deal found 4/13$398
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:27 pm
ORD
-
SJO
1 stop23h 06m
Multiple Airlines
Sun 5/312:38 pm
SJO
-
ORD
2 stops28h 36m
Multiple Airlines
Deal found 4/12$399
This CheapOair deal was found by Cheapflights users on 4/12. 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.
Mon 5/185:05 am
ORD
-
SJO
1 stop7h 40m
Spirit Airlines
Fri 5/221:00 pm
SJO
-
ORD
1 stop18h 22m
Spirit Airlines
Deal found 4/12$400

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 April 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$380
(CheapOair)

One-way from

$129
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$642
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. 16% potential increase in price ($129 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 18, 2026.
Use the filters below to find and compare flights from Wisconsin to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 6/11

3:21 pm-9:06 am

1 stop18h 45m

San José Juan Santamaria Intl

Mon 6/15

6:19 pm-4:00 am

1 stop8h 41m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 6/15

3:21 pm-8:21 am

1 stop18h 00m

San José Juan Santamaria Intl

Fri 6/19

6:19 pm-4:00 am

1 stop8h 41m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 6/12

3:21 pm-7:12 am

1 stop16h 51m

San José Juan Santamaria Intl

Wed 6/17

10:05 am-4:00 am

1 stop16h 55m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 5/16

3:21 pm-7:09 am

1 stop16h 48m

San José Juan Santamaria Intl

Sat 5/23

5:50 am-1:15 am

1 stop18h 25m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 6/18

3:21 pm-7:12 am

1 stop16h 51m

San José Juan Santamaria Intl

Mon 6/22

5:57 pm-4:00 am

1 stop9h 03m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 4/29

8:06 am-9:46 pm

1 stop14h 40m

San José Juan Santamaria Intl

Wed 5/6

5:50 am-1:15 am

1 stop18h 25m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 5/9

3:21 pm-7:09 am

1 stop16h 48m

San José Juan Santamaria Intl

Sat 5/16

10:05 am-1:15 am

1 stop14h 10m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 6/5

3:21 pm-8:21 am

1 stop18h 00m

San José Juan Santamaria Intl

Mon 6/8

5:57 pm-4:00 am

1 stop9h 03m

$470

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Fri 5/8

5:30 am-11:52 am

1 stop7h 22m

San José Juan Santamaria Intl

Sat 5/16

2:40 pm-11:59 pm

1 stop8h 19m

$482

MinneapolisSan José

MSP - SJO

MSPSJO

Minneapolis St Paul

Wed 5/6

5:20 am-7:00 pm

2 stops14h 40m

San José Juan Santamaria Intl

Wed 5/13

9:00 am-10:30 pm

2 stops12h 30m

$537

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/12

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $179). Flying from Wisconsin to San José in July is currently the most expensive (average of $475). 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.

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, Southwest, and Delta can get you from Wisconsin to San José in just under 14h 40m. Your travel time can differ by up to 4h 05m. There are 2468 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?

    $145 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and American Airlines, with prices starting from $170 and $213, 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 $179). Flying from Wisconsin to San José in July is currently the most expensive (average of $475). 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
Alajuela
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio

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Top 4 airlines flying from Wisconsin to San José

Discover the top 4 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 April 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$252Average$684FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$378Average$641FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$426Average$707FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$475Average$708FlexibilityNo cancel feeOn-time69%

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