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Wisconsin

$123+ Cheap flights from San José (SJO) to Wisconsin

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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from San José to Wisconsin

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

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:45 amSJO - ORD
1 stop7h 30mAvianca
Thu 1/84:10 pmORD - SJO
1 stop7h 30mAvianca
Deal found 12/22$325
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:31 pmSJO - ORD
1 stop25h 31mMultiple Airlines
Thu 1/812:48 pmORD - SJO
2 stops22h 49mMultiple Airlines
Deal found 12/22$331
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:52 pmSJO - ORD
1 stop27h 41mFrontier
Mon 1/56:00 amORD - SJO
1 stop7h 42mFrontier
Deal found 12/22$333
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:50 pmSJO - ORD
1 stop19h 00mAvianca
Thu 1/224:10 pmORD - SJO
1 stop7h 30mAvianca
Deal found 12/21$342
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:45 amSJO - ORD
1 stop7h 30mMultiple Airlines
Fri 1/210:12 amORD - SJO
1 stop23h 09mMultiple Airlines
Deal found 12/22$348
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:31 pmSJO - ORD
1 stop10h 59mSpirit Airlines
Thu 1/85:15 amORD - SJO
1 stop7h 07mSpirit Airlines
Deal found 12/22$361
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:45 amSJO - ORD
1 stop7h 30mAvianca
Wed 12/312:35 pmORD - SJO
1 stop8h 40mAvianca
Deal found 12/21$379
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/234:15 pmSJO - ORD
1 stop21h 00mAvianca
Tue 12/304:10 pmORD - SJO
1 stop7h 30mAvianca
Deal found 12/21$380
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:31 pmSJO - ORD
1 stop10h 59mMultiple Airlines
Wed 12/316:05 amORD - SJO
1 stop7h 37mMultiple Airlines
Deal found 12/21$387
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:42 pmSJO - ORD
2 stops28h 39mMultiple Airlines
Mon 1/51:44 pmORD - SJO
2 stops48h 04mMultiple Airlines
Deal found 12/22$393
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/287:58 amSJO - MKE
2 stops25h 55mMultiple Airlines
Thu 1/87:30 pmMKE - SJO
2 stops40h 44mMultiple Airlines
Deal found 12/22$499
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/287:58 amSJO - MSP
1 stop15h 03mMultiple Airlines
Sun 1/116:24 amMSP - SJO
1 stop8h 56mMultiple Airlines
Deal found 12/21$502

Find flight deals from San José to Wisconsin

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$266
(KAYAK)

One-way from

$123
(Cheapflightsfares)

Popular in

February

Cheapest in

January

Average price

$528
Provider with most accurate pricing for San José Juan Santamaria Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Milwaukee-Mitchell flights.
Search Deals
From San José Juan Santamaria Intl to Wisconsin
Search Deals
One-way flight from San José Juan Santamaria Intl to Wisconsin
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 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 San José to Wisconsin 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 San José to Wisconsin that are best for you.

Fly from

San José

Fly to

Wisconsin

Route

Depart

Return

Price

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 2/6

12:33 pm-11:22 am

2 stops22h 49m

Chicago O'Hare Intl

Sat 2/14

9:00 am-11:40 am

2 stops26h 40m

$277

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Mon 1/12

7:45 am-8:18 am

1 stop24h 33m

Chicago O'Hare Intl

Wed 1/28

9:23 am-3:30 pm

1 stop30h 07m

$281

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Wed 2/11

12:33 pm-11:47 pm

2 stops11h 14m

Chicago O'Hare Intl

Wed 2/18

5:15 am-12:22 pm

1 stop7h 07m

$301

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Sat 1/17

3:12 pm-12:08 pm

1 stop20h 56m

Chicago O'Hare Intl

Thu 1/22

8:43 pm-12:22 pm

1 stop15h 39m

$315

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 2/6

12:33 pm-11:47 pm

2 stops11h 14m

Chicago O'Hare Intl

Sun 2/15

9:00 am-11:40 am

2 stops26h 40m

$316

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/29

12:33 pm-11:47 am

3 stops23h 14m

Chicago O'Hare Intl

Tue 2/3

10:07 am-3:20 pm

3 stops29h 13m

$327

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Fri 1/30

2:05 pm-7:35 pm

Nonstop5h 30m

Chicago O'Hare Intl

Mon 2/2

7:39 am-12:56 pm

Nonstop5h 17m

$340

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/15

2:05 pm-7:35 pm

Nonstop5h 30m

Chicago O'Hare Intl

Mon 1/26

7:35 am-8:39 pm

1 stop13h 04m

$340

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/15

2:05 pm-7:35 pm

Nonstop5h 30m

Chicago O'Hare Intl

Sun 1/25

7:35 am-8:39 pm

1 stop13h 04m

$340

San JoséChicago

SJO - ORD

SJOORD

San José Juan Santamaria Intl

Thu 1/29

2:05 pm-7:35 pm

Nonstop5h 30m

Chicago O'Hare Intl

Tue 2/3

7:50 pm-1:15 pm

1 stop17h 25m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 50 results
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Best time to book a flight from San José to Wisconsin

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

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

Currently, January is the cheapest month in which you can book a flight from San José to Wisconsin (average of $262). Flying from San José to Wisconsin in October is currently the most expensive (average of $505). 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 SJO to WI?

Find hourly flight availability from San José to Wisconsin. 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.

Unlike in the morning, when flights are generally more expensive, you can save up to 17% on flights from San José to Wisconsin by exploring options for tickets at noon.

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

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated December 23, 2025.
Read through reviews of airlines operating flights from San José to Wisconsin, such as United Airlines and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,105 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,105 reviews
United Airlines
7.4
Good
9,105 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
American Airlines
7.2
Good
11,054 reviews
United Airlines
7.4
Good
9,105 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

Related info for your journey

Find useful and relevant information for your journey from San José to Wisconsin. 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 from for flights from San José to Wisconsin?

    Located just 8.8 mi from the city center, San José Juan Santamaria Intl (SJO) is the airport most travelers will use when flying to Wisconsin from San José.

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

    A quick flight from San José to Wisconsin can take about 11h 30m. Spirit Airlines provides one of the quickest options available for as low as $485. Airlines will cover a distance of 2286 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airlines for a one-way flight from San José to Wisconsin are Spirit Airlines ($193), American Airlines ($218), and United Airlines ($248).

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

    The most popular route from San José to Wisconsin is San José Juan Santamaria Intl - Chicago O'Hare Intl. You may also consider San José Juan Santamaria Intl - Minneapolis St Paul or San José Juan Santamaria Intl - Milwaukee-Mitchell.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from San José to Wisconsin (average of $262). Flying from San José to Wisconsin in October is currently the most expensive (average of $505). 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.

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Alternative routes for San José to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
San José to John F Kennedy Intl flights
San José to Orlando flights
San José to Newark flights
San José to Miami flights
San José to Fort Lauderdale flights
San José to Los Angeles flights
San José to LaGuardia flights
San José to Las Vegas flights
San José to Hobby flights
San José to George Bush Intcntl flights
San José to Denver flights
San José to Atlanta flights
San José to O'Hare Intl flights
San José to Dulles Intl flights
San José to San Francisco flights
San José to Dallas/Fort Worth flights
San José to Boston flights
San José to Baltimore flights
San José to Seattle flights
San José to Reagan-National flights
San José to Midway flights
San José to Ontario flights
San José to Raleigh flights
San José to Salt Lake City flights
Liberia to Newark flights
San José to Burbank flights
San José to Charlotte flights
San José to Tampa flights
San José to Austin flights
San José to New Orleans flights
Liberia to John F Kennedy Intl flights
Liberia to Los Angeles flights
San José to Nashville flights
Liberia to Atlanta flights
San José to Sky Harbor Intl flights
San José to Love Field flights
San José to Portland flights
San José to Philadelphia flights
San José to Honolulu flights
San José to San Antonio flights
Liberia to Miami flights
San José to Minneapolis flights
San José to Hartford flights
San José to Kansas City flights
San José to Oakland flights
San José to West Palm Beach flights
San José to San Diego flights
Liberia to LaGuardia flights
San José to Anchorage flights

Top 2 airlines flying from San José to Wisconsin

Discover the top 2 airlines that operate flights from San José to Wisconsin. 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
American AirlinesCheapest$399Average$757FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$458Average$537FlexibilityNo cancel feeOn-time69%

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