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$131+ Cheap flights from Oakland, CA (OAK) 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Oakland to Wisconsin

Cheapest flights from Oakland to Wisconsin
Explore the most affordable flight options available from Oakland to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This Southwest deal was found by Cheapflights users on 12/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:25 amOAK - MSP
1 stop6h 10mSouthwest
Mon 1/56:05 amMSP - OAK
1 stop10h 30mSouthwest
Deal found 12/26$544
This Southwest deal was found by Cheapflights users on 12/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/277:15 amOAK - MSP
1 stop7h 30mSouthwest
Sat 1/35:20 amMSP - OAK
2 stops9h 25mSouthwest
Deal found 12/26$569
This Southwest deal was found by Cheapflights users on 12/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:25 amOAK - MSP
1 stop6h 10mSouthwest
Fri 1/26:30 amMSP - OAK
1 stop13h 00mSouthwest
Deal found 12/25$579
This Alaska Airlines deal was found by Cheapflights users on 12/26. 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 12/308:32 pmOAK - ORD
1 stop14h 37mAlaska Airlines
Wed 1/73:35 pmORD - OAK
1 stop21h 28mAlaska Airlines
Deal found 12/26$582
This Delta deal was found by Cheapflights users on 12/26. 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.
Fri 12/2612:34 pmOAK - ORD
1 stop7h 02mDelta
Wed 1/77:20 amORD - OAK
1 stop6h 37mDelta
Deal found 12/26$583
This Southwest deal was found by Cheapflights users on 12/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/285:40 amOAK - MSP
1 stop6h 15mSouthwest
Fri 1/25:00 amMSP - OAK
1 stop7h 35mSouthwest
Deal found 12/27$609
This Delta deal was found by Cheapflights users on 12/27. 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.
Tue 12/3012:34 pmOAK - ORD
1 stop7h 02mDelta
Mon 1/53:59 pmORD - OAK
2 stops8h 54mDelta
Deal found 12/27$639
This Delta deal was found by Cheapflights users on 12/26. 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.
Sat 12/2712:34 pmOAK - ORD
1 stop7h 02mDelta
Fri 1/27:05 pmORD - OAK
1 stop6h 53mDelta
Deal found 12/26$689
This Delta deal was found by Cheapflights users on 12/26. 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.
Tue 12/3012:34 pmOAK - ORD
1 stop7h 02mDelta
Fri 1/25:30 amORD - OAK
2 stops12h 34mDelta
Deal found 12/26$694
This Delta deal was found by Cheapflights users on 12/27. 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.
Sun 12/285:53 amOAK - ORD
2 stops13h 21mDelta
Tue 12/301:35 pmORD - OAK
2 stops12h 23mDelta
Deal found 12/27$699
This Alaska Airlines deal was found by Cheapflights users on 12/26. 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 12/263:01 pmOAK - ORD
1 stop6h 58mAlaska Airlines
Mon 1/56:00 amORD - OAK
1 stop10h 07mAlaska Airlines
Deal found 12/26$702
This Delta deal was found by Cheapflights users on 12/26. 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.
Tue 12/305:53 amOAK - ORD
2 stops9h 54mDelta
Wed 1/71:55 pmORD - OAK
2 stops10h 58mDelta
Deal found 12/26$713

Find flight deals from Oakland to Wisconsin

Keep the following information in mind while searching for Oakland to Wisconsin flight deals. Data was last updated December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$252
(Delta)

One-way from

$131
(Alaska Airlines)

Popular in

December

Cheapest in

April

Average price

$510
Provider with most accurate pricing for San Francisco-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Milwaukee-Mitchell flights.
Search Deals
From Oakland to Wisconsin
Search Deals
One-way flight from Oakland to Wisconsin
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($42 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 December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland 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 28, 2025.
Use the filters below to find and compare flights from Oakland to Wisconsin that are best for you.

Fly from

Oakland

Fly to

Wisconsin

Route

Depart

Return

Price

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 4/27

7:19 pm-2:41 pm

1 stop17h 22m

Chicago O'Hare Intl

Wed 4/29

3:52 pm-9:53 am

1 stop20h 01m

$262

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 2/24

6:15 am-4:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 2/25

3:54 pm-10:49 pm

1 stop8h 55m

$267

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 2/3

12:33 pm-9:52 pm

1 stop7h 19m

Chicago O'Hare Intl

Fri 2/6

2:20 pm-11:53 pm

2 stops11h 33m

$280

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 2/2

8:10 am-2:38 pm

1 stop28h 28m

Chicago O'Hare Intl

Mon 2/9

8:00 am-8:40 pm

1 stop14h 40m

$283

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sun 1/25

8:10 am-11:50 pm

1 stop13h 40m

Chicago O'Hare Intl

Sun 2/1

6:06 pm-8:40 pm

1 stop28h 34m

$283

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 2/4

8:10 am-2:38 pm

1 stop28h 28m

Chicago O'Hare Intl

Sun 2/8

8:00 am-8:40 pm

1 stop14h 40m

$283

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 2/19

6:15 am-4:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Mon 2/23

3:54 pm-10:52 pm

1 stop8h 58m

$283

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 2/13

6:15 am-11:56 pm

1 stop15h 41m

Chicago O'Hare Intl

Tue 2/17

3:54 pm-4:37 pm

1 stop26h 43m

$283

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 1/26

4:54 pm-11:53 pm

2 stops28h 59m

Chicago O'Hare Intl

Tue 2/3

1:58 pm-11:53 pm

2 stops11h 55m

$285

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 2/3

11:43 am-11:50 pm

1 stop10h 07m

Chicago O'Hare Intl

Fri 2/6

6:06 pm-10:28 am

1 stop18h 22m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 59 results
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Best time to book a flight from Oakland to Wisconsin

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

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

Currently, October is the cheapest month in which you can book a flight from Oakland, California to Wisconsin (average of $140). Flying from Oakland, California to Wisconsin in February is currently the most expensive (average of $277). 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 December 28, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta from Oakland to Wisconsin to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

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.
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

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.
Delta
7.9
Good
8,018 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

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 Oakland 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 Oakland to Wisconsin?

    Oakland (OAK) is the airport you will fly out of if you book a flight from Oakland to Wisconsin. It is only a 7.0 mi journey to Oakland (OAK) from Oakland’s city center.

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

    For as low as $280, Alaska Airlines can have you in Wisconsin from Oakland, California in 7h 19m. The distance from Oakland, California to Wisconsin is about 1830 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    While some choose either Oakland - Minneapolis St Paul or Oakland - Milwaukee-Mitchell, Oakland - Chicago O'Hare Intl is the most popular route from Oakland, California to Wisconsin.

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

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

  • How can I find direct flights from Oakland to Wisconsin?

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Oakland, California to Wisconsin (average of $140). Flying from Oakland, California to Wisconsin in February is currently the most expensive (average of $277). 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 Oakland to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Oakland to Wisconsin

Discover the top 2 airlines that operate flights from Oakland 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$529FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$296Average$448FlexibilityNo cancel feeOn-time63%

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