HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Milwaukee

$140+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Milwaukee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 4, 2025.

This Southwest deal was found by Cheapflights users on 12/3. 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 12/177:50 amOAK - MKE
1 stop5h 35mSouthwest
Sat 12/205:50 amMKE - OAK
1 stop8h 45mSouthwest
Deal found 12/3$404
This Southwest deal was found by Cheapflights users on 12/3. 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.
Thu 12/259:00 amOAK - MKE
1 stop6h 30mSouthwest
Mon 1/510:55 amMKE - OAK
2 stops10h 20mSouthwest
Deal found 12/3$433
This Southwest deal was found by Cheapflights users on 12/3. 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 12/242:55 pmOAK - MKE
1 stop5h 45mSouthwest
Tue 12/305:10 amMKE - OAK
1 stop8h 25mSouthwest
Deal found 12/3$528
This Alaska Airlines deal was found by Cheapflights users on 12/3. 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 12/189:35 amOAK - MKE
2 stops12h 24mAlaska Airlines
Mon 12/223:05 pmMKE - OAK
1 stop10h 54mAlaska Airlines
Deal found 12/3$705
This Alaska Airlines deal was found by Cheapflights users on 12/2. 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 12/176:40 amOAK - MKE
1 stop29h 29mAlaska Airlines
Sun 12/213:05 pmMKE - OAK
1 stop20h 01mAlaska Airlines
Deal found 12/2$842
This Delta deal was found by Cheapflights users on 12/3. 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 12/185:55 amOAK - MKE
2 stops10h 56mDelta
Mon 12/224:04 pmMKE - OAK
2 stops9h 54mDelta
Deal found 12/3$869

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 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$257
(Alaska Airlines)

One-way from

$140
(Southwest)

Popular in

December

Cheapest in

August

Average price

$696
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 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 4, 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

Thu 2/5

8:10 am-2:57 pm

1 stop28h 47m

Milwaukee-Mitchell

Mon 2/9

3:53 pm-11:03 am

1 stop21h 10m

$257

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sun 1/18

12:10 pm-10:50 pm

1 stop8h 40m

Milwaukee-Mitchell

Sat 1/24

6:05 am-12:20 pm

1 stop8h 15m

$284

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Fri 2/6

12:33 pm-9:15 pm

1 stop6h 42m

Milwaukee-Mitchell

Mon 2/9

3:59 pm-11:53 pm

2 stops9h 54m

$361

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

$362

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Wed 12/17

7:50 am-3:25 pm

1 stop5h 35m

Milwaukee-Mitchell

Sat 12/20

5:50 am-12:35 pm

1 stop8h 45m

$404

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Thu 12/25

9:00 am-5:30 pm

1 stop6h 30m

Milwaukee-Mitchell

Mon 1/5

10:55 am-7:15 pm

2 stops10h 20m

$433

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Thu 12/25

9:00 am-5:30 pm

1 stop6h 30m

$200

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sat 12/27

6:00 am-4:55 pm

1 stop8h 55m

$250

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Thu 12/18

3:01 pm-11:59 pm

1 stop6h 58m

$278

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Mon 12/22

7:25 am-7:50 pm

2 stops10h 25m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 13 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
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*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 December 4, 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 4, 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
4,250 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

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 6h 42m. Alaska Airlines provides one of the quickest options available for as low as $361. 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 36% 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 $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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oakland to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Ontario to O'Hare Intl flights
Los Angeles to Minneapolis flights
San Francisco to Minneapolis flights
Santa Ana to O'Hare Intl flights
San Diego to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
San Jose to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Ontario to Minneapolis flights
San Diego to Minneapolis flights
Burbank to O'Hare Intl flights
Santa Ana to Minneapolis flights
San Jose to Minneapolis flights
Oakland to O'Hare Intl flights
Los Angeles to Milwaukee flights
Sacramento to Minneapolis flights
Las Vegas to Minneapolis flights
Oakland to Minneapolis flights
Fresno to O'Hare Intl flights
Reno to O'Hare Intl flights
Los Angeles to Madison flights
Long Beach to O'Hare Intl flights
Las Vegas to Milwaukee flights
Los Angeles to Green Bay flights
San Francisco to Milwaukee flights
Palm Springs to O'Hare Intl flights
Ontario to Milwaukee flights
Ontario to Madison flights
Monterey to O'Hare Intl flights
San Francisco to Madison flights
San Diego to Milwaukee flights
Burbank to Minneapolis flights
Santa Barbara to O'Hare Intl flights
Santa Ana to Madison flights
Palm Springs to Minneapolis flights
Reno to Minneapolis flights
San Diego to Madison flights
Burbank to Madison flights
Santa Barbara to Minneapolis flights
Fresno to Minneapolis flights
Long Beach to Minneapolis flights
Los Angeles to Appleton flights
Bakersfield to O'Hare Intl flights
Santa Ana to Milwaukee flights
Las Vegas to Madison flights
San Jose to Milwaukee flights
Palm Springs to Madison flights

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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$296Average$445FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.