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San José

$120+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Aug 23 — Aug 301
Sun 8/23
Sun 8/30
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 July 24, 2026.

This Volaris deal was found by Cheapflights users on 7/23. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/61:49 pm
ORD
-
SJO
1 stop11h 10m
Multiple Airlines
Sun 9/134:15 pm
SJO
-
ORD
1 stop18h 54m
Multiple Airlines
Deal found 7/23$487
This Volaris deal was found by Cheapflights users on 7/23. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:53 am
ORD
-
SJO
1 stop22h 06m
Multiple Airlines
Sun 10/254:15 pm
SJO
-
ORD
1 stop18h 54m
Multiple Airlines
Deal found 7/23$488
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sun 8/1612:44 am
ORD
-
SJO
2 stops22h 04m
Multiple Airlines
Thu 8/271:20 pm
SJO
-
ORD
1 stop24h 30m
Multiple Airlines
Deal found 7/20$489
This Copa Airlines deal was found by Cheapflights users on 7/21. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/313:21 pm
ORD
-
SJO
1 stop16h 49m
Copa Airlines
Mon 9/78:45 am
SJO
-
ORD
1 stop15h 17m
Copa Airlines
Deal found 7/21$490
This Copa Airlines deal was found by Cheapflights users on 7/22. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:21 pm
ORD
-
SJO
1 stop20h 37m
Copa Airlines
Tue 9/15:55 pm
SJO
-
ORD
1 stop19h 04m
Copa Airlines
Deal found 7/22$492
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Thu 8/277:44 pm
ORD
-
SJO
1 stop20h 27m
Multiple Airlines
Tue 9/17:00 am
SJO
-
ORD
1 stop27h 00m
Multiple Airlines
Deal found 7/19$495
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Thu 8/131:30 am
ORD
-
SJO
1 stop24h 50m
Multiple Airlines
Mon 8/317:00 am
SJO
-
ORD
1 stop27h 00m
Multiple Airlines
Deal found 7/20$496
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sat 9/57:44 pm
ORD
-
SJO
1 stop20h 27m
Multiple Airlines
Thu 9/101:15 pm
SJO
-
ORD
1 stop23h 04m
Multiple Airlines
Deal found 7/20$499
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 10/74:20 pm
ORD
-
SJO
1 stop20h 55m
Multiple Airlines
Thu 10/221:33 pm
SJO
-
ORD
2 stops20h 27m
Multiple Airlines
Deal found 7/19$500
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:45 am
ORD
-
SJO
2 stops49h 10m
Multiple Airlines
Mon 10/197:07 am
SJO
-
ORD
1 stop15h 48m
Multiple Airlines
Deal found 7/22$502
This Mytrip deal was found by Cheapflights users on 7/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:49 pm
ORD
-
SJO
1 stop11h 10m
Multiple Airlines
Sat 8/297:00 am
SJO
-
ORD
2 stops20h 41m
Multiple Airlines
Deal found 7/20$504
This American Airlines deal was found by Cheapflights users on 7/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:00 am
MKE
-
SJO
1 stop7h 52m
American Airlines
Wed 9/21:03 pm
SJO
-
MKE
1 stop8h 54m
American Airlines
Deal found 7/20$510

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 July 24, 2026.

Most accurate provider

Ovago
3 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$487
(Volaris)

One-way from

$120
(Viva)

Popular in

December

Cheapest in

May

Average price

$681
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. 6% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 24, 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

Wed 9/23

3:20 pm-8:19 am

1 stop17h 59m

San José Juan Santamaria Intl

Sun 9/27

5:55 pm-1:59 pm

1 stop19h 04m

$490

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 8/31

3:21 pm-7:10 am

1 stop16h 49m

San José Juan Santamaria Intl

Mon 9/7

8:45 am-1:02 am

1 stop15h 17m

$490

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 8/26

8:02 am-8:19 am

1 stop25h 17m

San José Juan Santamaria Intl

Mon 8/31

4:08 am-1:02 am

1 stop19h 54m

$490

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Sat 10/3

3:20 pm-9:04 am

1 stop18h 44m

San José Juan Santamaria Intl

Sat 10/10

10:03 am-1:59 pm

1 stop26h 56m

$501

MinneapolisSan José

MSP - SJO

MSPSJO

Minneapolis St Paul

Tue 10/20

8:05 am-7:40 pm

2 stops12h 35m

San José Juan Santamaria Intl

Tue 10/27

9:00 am-10:05 pm

2 stops12h 05m

$516

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Mon 10/19

3:20 pm-7:10 am

1 stop16h 50m

San José Juan Santamaria Intl

Mon 10/26

12:05 pm-1:05 am

1 stop12h 00m

$516

ChicagoSan José

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 9/2

8:01 am-9:04 am

1 stop26h 03m

San José Juan Santamaria Intl

Sun 9/6

4:08 am-1:59 pm

1 stop8h 51m

$540

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Sun 11/8

5:10 am-1:15 pm

1 stop8h 05m

San José Juan Santamaria Intl

Fri 11/13

1:20 pm-11:45 pm

1 stop10h 25m

$545

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Wed 9/9

5:30 am-11:54 am

1 stop7h 24m

San José Juan Santamaria Intl

Thu 9/24

1:19 pm-11:48 pm

1 stop9h 29m

$560

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Tue 8/25

10:00 am-6:40 pm

2 stops9h 40m

San José Juan Santamaria Intl

Wed 9/2

9:00 am-8:55 pm

2 stops10h 55m

$567

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/19

Showing 1-10 of 59 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, September is the cheapest month in which you can book a flight from Wisconsin to San José (average of $539). Flying from Wisconsin to San José in December is currently the most expensive (average of $852). 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?

Airfare is below average for this route at the moment.
Wisconsin to San José flights typically cost between $608 and $756 in August.
The cheapest round-trip price found within the last 5 days was $510 on American Airlines (Aug 25-Sep 2).

How far ahead should I book a flight from Wisconsin to San José?

Booking 31 days in advance of your planned departure date is, on average, the best time to get cheap flights from Wisconsin to San José. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 7h 24m. Your travel time can differ by up to 10h 35m. 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 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, September is the cheapest month in which you can book a flight from Wisconsin to San José (average of $539). Flying from Wisconsin to San José in December is currently the most expensive (average of $852). 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
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 July 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$378Average$657FlexibilityNo cancel feeOn-time71%
DeltaCheapest$385Average$744FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$426Average$707FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$505Average$710FlexibilityNo cancel feeOn-time69%

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