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$120+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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Cheap flight deals from Oakland to Wisconsin

Keep the following information in mind while searching for Oakland to Wisconsin flight deals. Data was last updated November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$238
(KAYAK)

One-way from

$120
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$536
Provider with most accurate pricing for San Francisco-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Milwaukee-Mitchell flights.
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From Oakland to Wisconsin
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One-way flight from Oakland to Wisconsin
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Highest demand for flights based on searches. 16% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 12, 2025.

This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/82:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Mon 12/155:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 11/10$238
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 12/32:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Wed 12/105:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 11/10$256
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:40 amOAK - ORD
1 stop8h 15mAlaska Airlines
Mon 12/155:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 11/10$258
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.
Tue 12/912:30 pmOAK - ORD
1 stop6h 51mDelta
Sat 12/135:29 pmORD - OAK
1 stop6h 31mDelta
Deal found 11/10$259
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.
Wed 12/35:55 amOAK - ORD
2 stops9h 02mDelta
Mon 12/87:40 pmORD - OAK
1 stop6h 28mDelta
Deal found 11/9$264
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/32:31 pmOAK - MSP
1 stop7h 28mAlaska Airlines
Wed 12/107:00 amMSP - OAK
1 stop8h 32mAlaska Airlines
Deal found 11/10$269
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.
Wed 12/35:55 amOAK - ORD
2 stops9h 02mDelta
Tue 12/92:30 pmORD - OAK
2 stops11h 38mDelta
Deal found 11/9$269
This KAYAK deal was found by Cheapflights users on 11/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/52:31 pmOAK - ORD
1 stop7h 28mAlaska Airlines
Mon 12/85:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 11/12$278
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:25 amOAK - ORD
1 stop6h 05mSouthwest
Thu 12/181:00 pmORD - OAK
1 stop6h 55mSouthwest
Deal found 11/9$279
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:40 amOAK - ORD
1 stop15h 19mAlaska Airlines
Wed 12/105:51 pmORD - OAK
1 stop8h 08mAlaska Airlines
Deal found 11/9$280
This Southwest deal was found by Cheapflights users on 11/12. 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 12/69:35 amOAK - MKE
1 stop9h 45mSouthwest
Sat 12/135:15 amMKE - OAK
1 stop6h 15mSouthwest
Deal found 11/12$281
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/912:45 pmOAK - ORD
2 stops7h 50mSouthwest
Thu 12/114:25 pmORD - OAK
1 stop7h 20mSouthwest
Deal found 11/10$284

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 November 12, 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

Wed 12/3

2:31 pm-11:59 pm

1 stop7h 28m

Chicago O'Hare Intl

Tue 12/9

5:51 pm-11:59 pm

1 stop8h 08m

$258

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 12/6

6:40 am-4:55 pm

1 stop8h 15m

Chicago O'Hare Intl

Tue 12/9

5:51 pm-11:59 pm

1 stop8h 08m

$258

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 12/3

5:55 am-4:57 pm

2 stops9h 02m

Chicago O'Hare Intl

Mon 12/8

7:40 pm-12:08 am

1 stop6h 28m

$264

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 12/9

4:50 pm-8:39 am

2 stops13h 49m

Chicago O'Hare Intl

Sat 12/13

5:29 pm-10:00 pm

1 stop6h 31m

$264

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 12/9

5:55 am-4:57 pm

2 stops9h 02m

Chicago O'Hare Intl

Sun 12/14

7:20 am-11:50 am

1 stop6h 30m

$264

OaklandMinneapolis

OAK - MSP

OAKMSP

Oakland

Thu 4/30

2:50 pm-11:54 pm

1 stop7h 04m

Minneapolis St Paul

Wed 5/6

1:55 pm-7:14 pm

1 stop7h 19m

$269

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 12/3

5:55 am-4:57 pm

2 stops9h 02m

Chicago O'Hare Intl

Wed 12/10

2:30 pm-12:08 am

2 stops11h 38m

$269

OaklandChicago

OAK - ORD

OAKORD

Oakland

Fri 2/20

6:15 am-4:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Tue 2/24

7:00 am-4:37 pm

1 stop11h 37m

$270

OaklandChicago

OAK - ORD

OAKORD

Oakland

Thu 1/29

5:17 pm-5:10 pm

1 stop21h 53m

Chicago O'Hare Intl

Sun 2/1

8:00 am-4:23 pm

1 stop10h 23m

$270

OaklandChicago

OAK - ORD

OAKORD

Oakland

Sat 2/21

6:15 am-4:33 pm

1 stop8h 18m

Chicago O'Hare Intl

Tue 2/24

7:00 am-10:49 pm

1 stop17h 49m

$270

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 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 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 OAK to WI?

Find hourly flight availability from Oakland 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 12, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 45% on flights from Oakland, California to Wisconsin by exploring options for tickets in the afternoon.

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 12, 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
4,235 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
8,009 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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 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 $304, Alaska Airlines can have you in Wisconsin from Oakland, California in 5h 25m. The distance from Oakland, California to Wisconsin is about 1574 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airlines for a one-way flight from Oakland, California to Wisconsin are Alaska Airlines ($129), Southwest ($130), and Delta ($130).

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

    While some choose either Oakland - Milwaukee-Mitchell or Oakland - Minneapolis St Paul, 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 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.

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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$654FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$296Average$454FlexibilityNo cancel feeOn-time63%

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