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$177+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$289
(Delta)

One-way from

$177
(Alaska Airlines)

Popular in

December

Cheapest in

August

Average price

$652
Provider with most accurate pricing for Oakland-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Oakland-Milwaukee-Mitchell flights.
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From Oakland to Milwaukee-Mitchell
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One-way flight from Oakland to Milwaukee-Mitchell
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Highest demand for flights based on searches. 22% potential increase in price ($130 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 15, 2026.

This Delta deal was found by Cheapflights users on 1/15. 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 2/1112:33 pm
OAK
-
MKE
1 stop6h 42m
Delta
Sun 2/157:30 am
MKE
-
OAK
1 stop6h 25m
Delta
Deal found 1/15$289
This Delta deal was found by Cheapflights users on 1/14. 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 3/24:59 pm
OAK
-
MKE
2 stops14h 10m
Delta
Tue 3/103:59 pm
MKE
-
OAK
2 stops9h 47m
Delta
Deal found 1/14$300
This Delta deal was found by Cheapflights users on 1/15. 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.
Tue 2/1012:33 pm
OAK
-
MKE
1 stop6h 42m
Delta
Sun 2/157:30 am
MKE
-
OAK
1 stop6h 25m
Delta
Deal found 1/15$301
This Southwest deal was found by Cheapflights users on 1/15. 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.
Thu 4/912:10 pm
OAK
-
MKE
1 stop8h 10m
Southwest
Mon 4/136:20 pm
MKE
-
OAK
1 stop7h 35m
Southwest
Deal found 1/15$330
This Southwest deal was found by Cheapflights users on 1/13. 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 4/95:25 am
OAK
-
MKE
1 stop6h 25m
Southwest
Sun 4/128:15 pm
MKE
-
OAK
1 stop6h 30m
Southwest
Deal found 1/13$340
This Southwest deal was found by Cheapflights users on 1/13. 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 4/2312:50 pm
OAK
-
MKE
2 stops7h 40m
Southwest
Wed 4/295:45 pm
MKE
-
OAK
1 stop6h 40m
Southwest
Deal found 1/13$347
This Expedia deal was found by Cheapflights users on 1/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:20 pm
OAK
-
MKE
1 stop8h 39m
Alaska Airlines
Wed 7/16:24 am
MKE
-
OAK
1 stop8h 00m
Alaska Airlines
Deal found 1/15$350
This Alaska Airlines deal was found by Cheapflights users on 1/14. 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.
Sat 5/301:00 pm
OAK
-
MKE
1 stop8h 57m
Alaska Airlines
Thu 6/44:42 pm
MKE
-
OAK
2 stops27h 41m
Alaska Airlines
Deal found 1/14$357
This Southwest deal was found by Cheapflights users on 1/14. 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 4/175:25 am
OAK
-
MKE
1 stop6h 25m
Southwest
Mon 4/206:20 pm
MKE
-
OAK
1 stop7h 35m
Southwest
Deal found 1/14$359

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 January 15, 2026.
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

Sat 3/14

12:35 pm-9:25 pm

1 stop6h 50m

Milwaukee-Mitchell

Mon 3/16

4:48 pm-11:46 pm

2 stops8h 58m

$294

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Wed 2/11

5:55 am-6:14 pm

2 stops10h 19m

Milwaukee-Mitchell

Sun 2/15

7:30 am-11:55 am

1 stop6h 25m

$294

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Mon 3/2

4:59 pm-9:09 am

2 stops14h 10m

Milwaukee-Mitchell

Tue 3/10

3:59 pm-11:46 pm

2 stops9h 47m

$300

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sat 5/30

1:00 pm-11:57 pm

1 stop8h 57m

Milwaukee-Mitchell

Thu 6/4

4:42 pm-11:54 pm

1 stop9h 12m

$301

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Thu 4/9

12:10 pm-10:20 pm

1 stop8h 10m

Milwaukee-Mitchell

Mon 4/13

6:20 pm-11:55 pm

1 stop7h 35m

$330

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Thu 4/9

5:25 am-1:50 pm

1 stop6h 25m

Milwaukee-Mitchell

Sun 4/12

8:15 pm-12:45 am

1 stop6h 30m

$340

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Thu 4/23

12:50 pm-10:30 pm

2 stops7h 40m

Milwaukee-Mitchell

Wed 4/29

5:45 pm-10:25 pm

1 stop6h 40m

$347

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Fri 4/17

5:25 am-1:50 pm

1 stop6h 25m

Milwaukee-Mitchell

Mon 4/20

6:20 pm-11:55 pm

1 stop7h 35m

$359

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Sat 2/7

8:10 am-3:07 pm

1 stop28h 57m

$177

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

Fri 3/6

5:55 am-6:16 pm

2 stops10h 21m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 15 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 January.
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, October is the cheapest month in which you can book a flight from Oakland, California to Milwaukee (average of $125). Flying from Oakland, California to Milwaukee in December is currently the most expensive (average of $233). 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 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 January 15, 2026.
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
4,258 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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
8.0
Very good
4,258 reviews
Southwest
8.0
Very good
4,258 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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 6h 50m. Delta provides one of the quickest options available for as low as $294. 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, October is the cheapest month in which you can book a flight from Oakland, California to Milwaukee (average of $125). Flying from Oakland, California to Milwaukee in December is currently the most expensive (average of $233). 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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Alternative routes for Oakland to Milwaukee

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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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$296Average$447FlexibilityNo cancel feeOn-time63%

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