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$97+ Cheap flights from San Jose, CA (SJC) 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MKE
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
1 adult, Economy
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Find flight deals from San Jose to Wisconsin

Cheapest flights from San Jose to Wisconsin
Explore the most affordable flight options available from San Jose to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 10, 2025.

This Alaska Airlines deal was found by Cheapflights users on 11/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:35 pmSJC - ORD
1 stop9h 15mAlaska Airlines
Tue 12/163:05 pmORD - SJC
1 stop22h 53mAlaska Airlines
Deal found 11/8$248
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/128:08 pmSJC - ORD
1 stop7h 57mMultiple Airlines
Tue 12/169:14 pmORD - SJC
2 stops43h 18mMultiple Airlines
Deal found 11/9$250
This Cheapflightsfares deal was found by Cheapflights users on 11/8. 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 12/810:28 amSJC - ORD
1 stop7h 26mAlaska Airlines
Tue 12/98:55 amORD - SJC
1 stop7h 37mAlaska Airlines
Deal found 11/8$256
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/58:08 pmSJC - ORD
2 stops22h 01mMultiple Airlines
Sun 12/76:50 amORD - SJC
1 stop9h 42mMultiple Airlines
Deal found 11/9$274
This Cheapflightsfares deal was found by Cheapflights users on 11/10. 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 12/33:09 pmSJC - ORD
1 stop6h 41mAlaska Airlines
Wed 12/108:55 amORD - SJC
1 stop7h 37mAlaska Airlines
Deal found 11/10$276
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/812:35 pmSJC - ORD
1 stop9h 15mAlaska Airlines
Thu 12/118:55 amORD - SJC
1 stop10h 13mAlaska Airlines
Deal found 11/8$280
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/123:09 pmSJC - ORD
1 stop21h 00mAlaska Airlines
Sun 12/148:59 pmORD - SJC
1 stop14h 52mAlaska Airlines
Deal found 11/8$288
This Delta deal was found by Cheapflights users on 11/10. 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.
Thu 12/46:35 amSJC - MSN
1 stop7h 46mDelta
Wed 12/1011:44 amMSN - SJC
1 stop10h 57mDelta
Deal found 11/10$289
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/23:49 pmSJC - ORD
1 stop30h 10mAlaska Airlines
Fri 12/58:55 amORD - SJC
1 stop7h 37mAlaska Airlines
Deal found 11/8$290
This Delta deal was found by Cheapflights users on 11/9. 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 12/157:15 amSJC - ORD
1 stop8h 00mDelta
Thu 1/16:00 amORD - SJC
1 stop7h 46mDelta
Deal found 11/9$293
This Alaska Airlines deal was found by Cheapflights users on 11/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/99:49 amSJC - ORD
2 stops10h 41mAlaska Airlines
Mon 12/158:55 amORD - SJC
1 stop7h 37mAlaska Airlines
Deal found 11/8$296
This Delta deal was found by Cheapflights users on 11/10. 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.
Thu 12/46:59 pmSJC - MSN
2 stops12h 01mDelta
Sat 12/66:00 amMSN - SJC
2 stops14h 57mDelta
Deal found 11/10$299

Cheap flight deals from San Jose to Wisconsin

Keep the following information in mind while searching for San Jose to Wisconsin flight deals. Data was last updated November 10, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$248
(Alaska Airlines)

One-way from

$97
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$512
Provider with most accurate pricing for San Jose-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Jose-Milwaukee-Mitchell flights.
Search Deals
From San Jose to Wisconsin
Search Deals
One-way flight from San Jose to Wisconsin
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose 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 November 10, 2025.
Use the filters below to find and compare flights from San Jose to Wisconsin that are best for you.

Fly from

San Jose

Fly to

Wisconsin

Route

Depart

Return

Price

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 2/17

12:45 pm-2:58 pm

1 stop24h 13m

Chicago O'Hare Intl

Mon 2/23

8:20 am-2:16 pm

1 stop7h 56m

$248

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sun 1/11

8:04 pm-2:29 pm

1 stop16h 25m

Chicago O'Hare Intl

Sat 1/17

9:00 am-6:45 pm

1 stop11h 45m

$248

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 12/15

3:09 pm-11:50 pm

1 stop6h 41m

Chicago O'Hare Intl

Tue 12/16

8:55 am-5:37 pm

1 stop10h 42m

$258

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sun 12/14

12:35 pm-11:50 pm

1 stop9h 15m

Chicago O'Hare Intl

Tue 12/16

8:55 am-6:42 pm

1 stop11h 47m

$258

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 12/11

12:35 pm-11:50 pm

1 stop9h 15m

Chicago O'Hare Intl

Mon 12/15

8:55 am-2:32 pm

1 stop7h 37m

$258

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 1/29

12:46 pm-11:37 pm

1 stop8h 51m

Chicago O'Hare Intl

Sun 2/1

3:49 pm-12:09 pm

1 stop22h 20m

$280

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 3/6

12:45 pm-11:59 pm

1 stop9h 14m

Chicago O'Hare Intl

Sun 3/8

3:07 pm-9:47 am

1 stop20h 40m

$280

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 2/12

11:42 am-11:55 pm

1 stop10h 13m

Chicago O'Hare Intl

Wed 2/18

2:20 pm-10:07 pm

1 stop9h 47m

$283

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 2/20

11:42 am-11:55 pm

1 stop10h 13m

Chicago O'Hare Intl

Mon 2/23

7:40 am-4:54 pm

2 stops11h 14m

$288

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 1/14

11:40 am-11:53 pm

1 stop10h 13m

Chicago O'Hare Intl

Wed 1/21

7:30 am-4:10 pm

2 stops10h 40m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

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

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

What is the cheapest month to book a flight from San Jose, California to Wisconsin?

Currently, October is the cheapest month in which you can book a flight from San Jose, California to Wisconsin (average of $140). Flying from San Jose, California to Wisconsin in December is currently the most expensive (average of $297). 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 SJC to WI?

Find hourly flight availability from San Jose 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 November 10, 2025.

It’s optimal to fly from San Jose, California to Wisconsin in the afternoon. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight in the morning.

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 November 10, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from San Jose to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,235 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
7.9
Good
8,007 reviews
Southwest
8.0
Very good
4,235 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
9,012 reviews
Southwest
8.0
Very good
4,235 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
11,045 reviews
Southwest
8.0
Very good
4,235 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from San Jose 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 Jose to Wisconsin?

    San Jose (SJC), located 2.9 mi from the city center, is the airport you fly out of when you book flights from San Jose to Wisconsin.

  • How long is the flight from San Jose, California to Wisconsin?

    Departing from San Jose, California to Wisconsin will take you 7h 19m. San Jose, California and Wisconsin are separated by a distance of 1572 mi. This flight may include one or multiple stops.

  • What are the most popular routes from San Jose, California to Wisconsin?

    Most travelers choose San Jose - Chicago O'Hare Intl, San Jose - Minneapolis St Paul or San Jose - Milwaukee-Mitchell when deciding on the best route from San Jose, California to Wisconsin.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from San Jose 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 Jose, California to Wisconsin?

    Currently, October is the cheapest month in which you can book a flight from San Jose, California to Wisconsin (average of $140). Flying from San Jose, California to Wisconsin in December is currently the most expensive (average of $297). 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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Top 4 airlines flying from San Jose to Wisconsin

Discover the top 4 airlines that operate flights from San Jose 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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$202Average$507FlexibilityNo cancel feeOn-time69%
DeltaCheapest$256Average$410FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$459FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$294Average$465FlexibilityNo cancel feeOn-time63%

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