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$131+ Cheap flights from Oakland, CA to Milwaukee (OAK - MKE)

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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Oakland to Milwaukee

Cheapest flights from Oakland to Milwaukee
Explore the most affordable flight options available from Oakland to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Delta deal was found by Cheapflights users on 12/15. 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 12/2412:34 pmOAK - MKE
1 stop7h 14mDelta
Thu 12/257:15 amMKE - OAK
1 stop6h 39mDelta
Deal found 12/15$684
This Southwest deal was found by Cheapflights users on 12/15. 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 12/236:35 amOAK - MKE
1 stop6h 10mSouthwest
Thu 12/255:05 amMKE - OAK
1 stop6h 45mSouthwest
Deal found 12/15$698
This Southwest deal was found by Cheapflights users on 12/16. 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.
Fri 12/195:35 amOAK - MKE
1 stop8h 00mSouthwest
Wed 12/245:05 amMKE - OAK
1 stop6h 45mSouthwest
Deal found 12/16$788
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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 12/316:10 amOAK - MKE
1 stop29h 59mAlaska Airlines
Sun 1/47:00 amMKE - OAK
1 stop28h 06mAlaska Airlines
Deal found 12/16$842
This Delta deal was found by Cheapflights users on 12/15. 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 12/225:53 amOAK - MKE
2 stops8h 50mDelta
Thu 12/257:15 amMKE - OAK
1 stop6h 39mDelta
Deal found 12/15$894
This Alaska Airlines deal was found by Cheapflights users on 12/15. 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 12/193:01 pmOAK - MKE
1 stop6h 58mAlaska Airlines
Sun 12/213:05 pmMKE - OAK
1 stop10h 54mAlaska Airlines
Deal found 12/15$988

Find flight deals from Oakland to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$313
(Southwest)

One-way from

$131
(Alaska Airlines)

Popular in

December

Cheapest in

August

Average price

$666
Provider with most accurate pricing for Oakland-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Milwaukee-Mitchell flights.
Search Deals
From Oakland to Milwaukee-Mitchell
Search Deals
One-way flight from Oakland to Milwaukee-Mitchell
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($127 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 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 Milwaukee 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 18, 2025.
Use the filters below to find and compare flights from Oakland to Milwaukee that are best for you.

Fly from

Oakland

Fly to

Milwaukee

Route

Depart

Return

Price

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Fri 1/23

5:25 am-4:10 pm

1 stop8h 45m

Milwaukee-Mitchell

Sat 1/24

5:05 am-10:00 am

1 stop6h 55m

$313

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Tue 1/6

2:45 pm-10:50 pm

1 stop6h 05m

Milwaukee-Mitchell

Thu 1/8

5:10 am-10:30 am

1 stop7h 20m

$330

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Fri 2/6

8:03 pm-3:07 pm

2 stops41h 04m

Milwaukee-Mitchell

Mon 2/9

3:53 pm-4:23 pm

1 stop26h 30m

$417

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Wed 3/25

6:00 am-3:30 pm

2 stops7h 30m

Milwaukee-Mitchell

Sun 3/29

3:25 pm-10:45 pm

1 stop9h 20m

$466

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sat 2/14

6:15 am-8:24 pm

2 stops12h 09m

Milwaukee-Mitchell

Tue 2/17

12:14 pm-10:49 pm

2 stops12h 35m

$491

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sat 2/7

8:10 am-3:07 pm

1 stop28h 57m

$131

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Tue 2/3

12:33 pm-9:15 pm

1 stop6h 42m

$139

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Thu 2/5

12:33 pm-9:15 pm

1 stop6h 42m

$151

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Wed 2/4

12:33 pm-9:15 pm

1 stop6h 42m

$151

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sat 1/31

5:15 am-1:10 pm

1 stop5h 55m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 16 results
1
2

Compare providers for flights from Oakland to Milwaukee

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oakland to Milwaukee in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Oakland, California-Milwaukee flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Oakland, California-Milwaukee flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Oakland, California-Milwaukee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Milwaukee flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oakland, California-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Oakland to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee 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 Milwaukee

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

Currently, December is the cheapest month in which you can book a flight from Oakland, California to Milwaukee (average of $107). Flying from Oakland, California to Milwaukee in November is currently the most expensive (average of $210). 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 MKE?

Find hourly flight availability from Oakland to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 41% on flights from Oakland, California to Milwaukee by exploring options for tickets in the evening.

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. 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 Milwaukee. Reviews last updated December 18, 2025.
Get a feel of what it's like to fly with Southwest from Oakland to Milwaukee by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

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 Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    A quick flight from Oakland, California to Milwaukee can take about 8h 45m. Southwest provides one of the quickest options available for as low as $313. Oakland, California and Milwaukee are separated by a distance of 1829 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Oakland, California to Milwaukee round-trip?

    Cheapflights users have booked flights from Oakland, California to Milwaukee round-trip from $296. Southwest is currently priced 34% below the average price you’ll pay for this route.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to Milwaukee 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 Milwaukee?

    Currently, December is the cheapest month in which you can book a flight from Oakland, California to Milwaukee (average of $107). Flying from Oakland, California to Milwaukee in November is currently the most expensive (average of $210). 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

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
New Berlin
Oak Creek
Wauwatosa

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Top airline flying from Oakland to Milwaukee

Discover the top airline that operate flights from Oakland to Milwaukee. 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$296Average$447FlexibilityNo cancel feeOn-time63%

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