Wisconsin

$73+ 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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MKE
Mar 11 — Mar 181
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Cheap 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 February 9, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:57 pm
SJC
-
ORD
1 stop8h 34m
Multiple Airlines
Wed 5/138:53 pm
ORD
-
SJC
1 stop23h 09m
Multiple Airlines
Deal found 2/8$255
This Alaska Airlines deal was found by Cheapflights users on 2/5. 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 5/1210:21 am
SJC
-
ORD
1 stop6h 42m
Alaska Airlines
Mon 5/187:59 pm
ORD
-
SJC
1 stop18h 08m
Alaska Airlines
Deal found 2/5$260
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:57 pm
SJC
-
ORD
1 stop8h 34m
Multiple Airlines
Mon 5/117:43 am
ORD
-
SJC
2 stops12h 19m
Multiple Airlines
Deal found 2/8$261
This Expedia deal was found by Cheapflights users on 2/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:57 pm
SJC
-
ORD
1 stop9h 50m
Multiple Airlines
Mon 5/183:43 pm
ORD
-
SJC
1 stop9h 54m
Multiple Airlines
Deal found 2/8$262
This Orbitz deal was found by Cheapflights users on 2/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/82:21 pm
SJC
-
ORD
1 stop20h 52m
Alaska Airlines
Tue 5/193:43 pm
ORD
-
SJC
1 stop9h 54m
Alaska Airlines
Deal found 2/9$263
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 3/256:15 am
SJC
-
ORD
1 stop15h 44m
Hawaiian Airlines
Wed 4/18:20 am
ORD
-
SJC
1 stop7h 38m
Hawaiian Airlines
Deal found 2/7$269
This Alaska Airlines deal was found by Cheapflights users on 2/5. 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 5/129:38 am
SJC
-
ORD
2 stops19h 02m
Alaska Airlines
Tue 5/193:43 pm
ORD
-
SJC
1 stop9h 54m
Alaska Airlines
Deal found 2/5$270
This Expedia deal was found by Cheapflights users on 2/5. 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.
Sun 3/87:02 pm
SJC
-
ORD
1 stop7h 47m
Multiple Airlines
Thu 3/127:40 am
ORD
-
SJC
1 stop8h 36m
Multiple Airlines
Deal found 2/5$271
This Alaska Airlines deal was found by Cheapflights users on 2/7. 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 5/147:00 am
SJC
-
ORD
1 stop9h 46m
Alaska Airlines
Tue 5/193:43 pm
ORD
-
SJC
1 stop9h 54m
Alaska Airlines
Deal found 2/7$273
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:57 pm
SJC
-
MSP
2 stops17h 57m
Multiple Airlines
Sun 4/268:54 pm
MSP
-
SJC
1 stop24h 31m
Multiple Airlines
Deal found 2/8$274
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 3/98:20 pm
SJC
-
ORD
1 stop7h 48m
Frontier
Fri 3/135:01 am
ORD
-
SJC
2 stops15h 46m
Frontier
Deal found 2/6$276
This CheapOair deal was found by Cheapflights users on 2/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:00 am
SJC
-
ORD
1 stop14h 41m
Alaska Airlines
Mon 5/187:59 pm
ORD
-
SJC
1 stop18h 08m
Alaska Airlines
Deal found 2/8$277

Find 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 February 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$255
(Kiwi.com)

One-way from

$73
(Trip.com)

Popular in

February

Cheapest in

September

Average price

$714
Provider with most accurate pricing for San Jose-Milwaukee-Mitchell flight deals.
Provider most trusted by Cheapflights users for San Jose-Milwaukee-Mitchell flights.
From San Jose to Wisconsin
One-way flight from San Jose to Wisconsin
Highest demand for flights based on searches. 23% potential increase in price ($142 potential increase over avg. RT price).
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 9, 2026.
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

Wed 5/6

10:21 am-7:03 pm

1 stop6h 42m

Chicago O'Hare Intl

Mon 5/11

7:59 pm-12:03 pm

1 stop18h 04m

$263

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 5/6

10:21 am-7:03 pm

1 stop6h 42m

Chicago O'Hare Intl

Tue 5/12

3:52 pm-12:07 pm

1 stop22h 15m

$273

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 4/16

6:30 am-12:56 pm

Nonstop4h 26m

Chicago O'Hare Intl

Tue 4/28

7:41 pm-10:36 pm

Nonstop4h 55m

$290

San JoseAppleton

SJC - ATW

SJCATW

San Jose

Wed 3/18

7:00 am-9:15 pm

2 stops12h 15m

Appleton Intl

Mon 3/23

4:24 pm-11:58 pm

2 stops9h 34m

$290

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 3/12

10:55 pm-5:14 am

Nonstop4h 19m

Chicago O'Hare Intl

Tue 3/24

7:59 pm-10:59 pm

Nonstop5h 00m

$290

San JoseChicago

SJC - ORD

SJCORD

San Jose

Fri 3/6

7:10 pm-2:11 pm

1 stop17h 01m

Chicago O'Hare Intl

Wed 3/11

3:07 pm-10:56 pm

1 stop9h 49m

$293

San JoseMinneapolis

SJC - MSP

SJCMSP

San Jose

Thu 4/16

6:15 am-11:59 pm

1 stop15h 44m

Minneapolis St Paul

Tue 4/21

5:12 pm-9:30 am

1 stop18h 18m

$300

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 4/22

6:30 am-12:56 pm

Nonstop4h 26m

Chicago O'Hare Intl

Fri 4/24

7:41 pm-10:36 pm

Nonstop4h 55m

$303

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 3/5

2:36 pm-11:56 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 3/9

3:54 pm-10:59 pm

1 stop9h 05m

$303

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 3/2

7:40 am-11:56 pm

2 stops14h 16m

Chicago O'Hare Intl

Thu 3/5

3:07 pm-10:56 pm

1 stop9h 49m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

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 January is currently the most expensive (average of $268). 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.

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 February 9, 2026.
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.

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 4h 26m. San Jose, California and Wisconsin are separated by a distance of 1824 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from San Jose, California to Wisconsin one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $125. Southwest flights start at $133 while deals on American Airlines start at $178 one-way.

  • What are the most popular routes 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 January is currently the most expensive (average of $268). 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

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Alternative routes for San Jose to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.

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 February 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$202Average$452FlexibilityNo cancel feeOn-time69%
DeltaCheapest$256Average$409FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$428FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$288Average$463FlexibilityNo cancel feeOn-time71%

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