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Wisconsin

$106+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
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 February 11, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/11. 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 5/710:57 am
OAK
-
ORD
1 stop10h 46m
Alaska Airlines
Thu 5/143:43 pm
ORD
-
OAK
1 stop9h 54m
Alaska Airlines
Deal found 2/11$223
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1012:35 pm
OAK
-
ORD
1 stop6h 59m
Delta
Tue 3/177:10 pm
ORD
-
OAK
1 stop6h 36m
Delta
Deal found 2/9$237
This Delta deal was found by Cheapflights users on 2/11. 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 3/185:55 am
OAK
-
ORD
2 stops8h 48m
Delta
Wed 3/257:10 pm
ORD
-
OAK
1 stop6h 36m
Delta
Deal found 2/11$242
This Delta deal was found by Cheapflights users on 2/10. 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 3/55:55 am
OAK
-
ORD
2 stops10h 06m
Delta
Mon 3/91:57 pm
ORD
-
OAK
2 stops11h 49m
Delta
Deal found 2/10$247
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:55 am
OAK
-
ORD
2 stops8h 48m
Delta
Thu 3/127:20 am
ORD
-
OAK
1 stop6h 31m
Delta
Deal found 2/9$252
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 5/113:18 pm
OAK
-
ORD
1 stop6h 25m
Alaska Airlines
Fri 5/153:43 pm
ORD
-
OAK
1 stop20h 06m
Alaska Airlines
Deal found 2/10$253
This Southwest deal was found by Cheapflights users on 2/10. 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.
Mon 3/91:50 pm
OAK
-
ORD
1 stop7h 05m
Southwest
Wed 3/114:50 pm
ORD
-
OAK
1 stop7h 10m
Southwest
Deal found 2/10$254
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:31 pm
OAK
-
ORD
1 stop18h 40m
Alaska Airlines
Tue 3/177:00 am
ORD
-
OAK
1 stop11h 37m
Alaska Airlines
Deal found 2/9$255
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:46 am
OAK
-
ORD
2 stops15h 13m
Alaska Airlines
Tue 5/123:52 pm
ORD
-
OAK
1 stop8h 31m
Alaska Airlines
Deal found 2/10$258
This Southwest deal was found by Cheapflights users on 2/10. 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.
Wed 4/86:00 am
OAK
-
ORD
1 stop10h 50m
Southwest
Tue 4/147:45 am
ORD
-
OAK
1 stop7h 45m
Southwest
Deal found 2/10$259
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:31 pm
OAK
-
ORD
1 stop16h 30m
Alaska Airlines
Sat 3/77:00 am
ORD
-
OAK
1 stop11h 37m
Alaska Airlines
Deal found 2/9$260
This Alaska Airlines deal was found by Cheapflights users on 2/11. 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.
Wed 4/2210:57 am
OAK
-
ORD
2 stops11h 02m
Alaska Airlines
Thu 4/303:52 pm
ORD
-
OAK
1 stop8h 31m
Alaska Airlines
Deal found 2/11$265

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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$223
(Alaska Airlines)

One-way from

$106
(Southwest)

Popular in

November

Cheapest in

April

Average price

$385
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. 3% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 11, 2026.
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

Sat 5/16

1:00 pm-10:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 5/19

3:43 pm-11:37 pm

1 stop9h 54m

$248

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/15

12:34 pm-9:18 pm

1 stop6h 44m

Chicago O'Hare Intl

Thu 4/16

7:12 pm-11:54 pm

1 stop6h 42m

$268

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 3/4

4:59 pm-8:38 am

2 stops13h 39m

Chicago O'Hare Intl

Mon 3/9

7:20 am-11:51 am

1 stop6h 31m

$273

OaklandChicago

OAK - ORD

OAKORD

Oakland

Tue 3/10

12:35 pm-9:34 pm

1 stop6h 59m

Chicago O'Hare Intl

Tue 3/17

1:57 pm-11:46 pm

2 stops11h 49m

$273

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Tue 3/3

12:40 pm-9:32 pm

1 stop6h 52m

Milwaukee-Mitchell

Tue 3/10

7:35 am-11:51 am

1 stop6h 16m

$277

OaklandChicago

OAK - ORD

OAKORD

Oakland

Wed 4/1

2:00 pm-10:55 pm

1 stop6h 55m

Chicago O'Hare Intl

Sat 4/4

7:20 pm-12:55 am

1 stop7h 35m

$280

OaklandMinneapolis

OAK - MSP

OAKMSP

Oakland

Tue 5/26

1:00 pm-11:59 pm

1 stop8h 59m

Minneapolis St Paul

Tue 6/2

5:00 pm-11:54 pm

1 stop8h 54m

$289

OaklandMinneapolis

OAK - MSP

OAKMSP

Oakland

Wed 5/27

7:00 am-6:03 pm

1 stop9h 03m

Minneapolis St Paul

Tue 6/2

5:00 pm-11:54 pm

1 stop8h 54m

$289

OaklandMinneapolis

OAK - MSP

OAKMSP

Oakland

Fri 5/8

5:06 pm-12:35 am

1 stop5h 29m

Minneapolis St Paul

Mon 5/11

8:19 pm-11:57 pm

1 stop5h 38m

$289

OaklandChicago

OAK - ORD

OAKORD

Oakland

Mon 3/9

1:50 pm-10:55 pm

1 stop7h 05m

Chicago O'Hare Intl

Wed 3/11

7:00 am-3:10 pm

2 stops10h 10m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

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 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 11, 2026.
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
4,280 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

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
8,181 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

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 $268, Alaska Airlines can have you in Wisconsin from Oakland, California in 6h 44m. 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 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 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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$519FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$286Average$456FlexibilityNo cancel feeOn-time63%

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