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$191+ 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Find 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 November 26, 2025.

This Southwest deal was found by Cheapflights users on 11/23. 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 12/141:15 pmOAK - MKE
1 stop8h 55mSouthwest
Thu 12/256:20 amMKE - OAK
1 stop6h 55mSouthwest
Deal found 11/23$408
This Alaska Airlines deal was found by Cheapflights users on 11/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/102:31 pmOAK - MKE
1 stop22h 24mAlaska Airlines
Sun 12/143:51 pmMKE - OAK
1 stop10h 08mAlaska Airlines
Deal found 11/25$423
This Southwest deal was found by Cheapflights users on 11/24. 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 12/155:25 amOAK - MKE
1 stop7h 20mSouthwest
Mon 12/295:10 amMKE - OAK
1 stop8h 25mSouthwest
Deal found 11/24$488
This Delta deal was found by Cheapflights users on 11/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/104:50 pmOAK - MKE
2 stops14h 38mDelta
Sun 12/147:20 amMKE - OAK
1 stop6h 30mDelta
Deal found 11/25$513
This Southwest deal was found by Cheapflights users on 11/24. 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 12/228:45 amOAK - MKE
1 stop8h 20mSouthwest
Tue 12/307:10 pmMKE - OAK
1 stop6h 35mSouthwest
Deal found 11/24$519
This Alaska Airlines deal was found by Cheapflights users on 11/24. 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 12/112:31 pmOAK - MKE
1 stop22h 24mAlaska Airlines
Sun 12/143:51 pmMKE - OAK
1 stop10h 08mAlaska Airlines
Deal found 11/24$556
This Delta deal was found by Cheapflights users on 11/24. 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 12/1212:30 pmOAK - MKE
1 stop7h 16mDelta
Sun 12/147:20 amMKE - OAK
1 stop6h 30mDelta
Deal found 11/24$557

Cheap 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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$289
(Delta)

One-way from

$191
(Alaska Airlines)

Popular in

December

Cheapest in

August

Average price

$612
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. 27% potential increase in price ($180 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 26, 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

Wed 1/21

12:33 pm-9:15 pm

1 stop6h 42m

Milwaukee-Mitchell

Fri 1/23

7:45 am-11:52 am

1 stop6h 07m

$289

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Mon 1/12

4:54 pm-9:15 am

2 stops14h 21m

Milwaukee-Mitchell

Wed 1/14

3:59 pm-10:53 pm

2 stops8h 54m

$299

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Fri 2/6

5:17 pm-6:26 pm

2 stops23h 09m

Milwaukee-Mitchell

Mon 2/9

3:53 pm-11:03 am

1 stop21h 10m

$406

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Thu 1/8

8:10 am-2:57 pm

1 stop28h 47m

Milwaukee-Mitchell

Thu 1/15

3:53 pm-4:23 pm

1 stop26h 30m

$433

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sun 12/14

7:25 am-6:20 pm

2 stops8h 55m

Milwaukee-Mitchell

Thu 12/25

6:20 am-3:20 pm

2 stops11h 00m

$448

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Thu 12/18

6:10 am-11:59 pm

1 stop15h 49m

$196

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sat 12/13

12:30 pm-9:46 pm

1 stop7h 16m

$279

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sun 12/14

4:00 pm-12:50 am

1 stop6h 50m

$279

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Fri 12/12

12:30 pm-9:46 pm

1 stop7h 16m

$279

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sat 12/20

2:15 pm-12:05 am

2 stops7h 50m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 11 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 November.
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 $110). Flying from Oakland, California to Milwaukee in March is currently the most expensive (average of $194). 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 November 26, 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 November 26, 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
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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 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 6h 42m. Delta provides one of the quickest options available for as low as $289. Oakland, California and Milwaukee are separated by a distance of 1829 mi.

  • 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 36% below the average price you’ll pay for this route.

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

    $196 is the cheapest one-way deal found within the past few days, from Alaska Airlines. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $279 and $279, respectively.

  • 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 $110). Flying from Oakland, California to Milwaukee in March is currently the most expensive (average of $194). 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$296Average$448FlexibilityNo cancel feeOn-time63%

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