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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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
févr. 28 — mars 71
sam. 2/28
sam. 3/7
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 janvier 29, 2026.

This Southwest deal was found by Cheapflights users on 1/27. 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.
mer. 2/252:50 pm
OAK
-
MKE
1 stop5h 55m
Southwest
jeu. 2/267:30 pm
MKE
-
OAK
1 stop6h 40m
Southwest
Deal found 1/27$289
This CheapOair deal was found by Cheapflights users on 1/27. 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.
mer. 5/137:00 am
OAK
-
MKE
1 stop6h 46m
Alaska Airlines
sam. 5/164:42 pm
MKE
-
OAK
1 stop9h 12m
Alaska Airlines
Deal found 1/27$301
This Southwest deal was found by Cheapflights users on 1/27. 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.
mar. 2/2412:30 pm
OAK
-
MKE
1 stop8h 15m
Southwest
sam. 2/282:20 pm
MKE
-
OAK
1 stop9h 25m
Southwest
Deal found 1/27$317
This Southwest deal was found by Cheapflights users on 1/29. 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.
mar. 3/312:10 pm
OAK
-
MKE
1 stop8h 40m
Southwest
dim. 3/85:40 pm
MKE
-
OAK
1 stop8h 00m
Southwest
Deal found 1/29$336
This Delta deal was found by Cheapflights users on 1/27. 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.
lun. 3/94:49 pm
OAK
-
MKE
2 stops14h 15m
Delta
ven. 3/133:59 pm
MKE
-
OAK
2 stops9h 47m
Delta
Deal found 1/27$341
This CheapOair deal was found by Cheapflights users on 1/27. 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.
lun. 6/17:59 pm
OAK
-
MKE
1 stop17h 47m
Alaska Airlines
ven. 6/54:42 pm
MKE
-
OAK
1 stop9h 12m
Alaska Airlines
Deal found 1/27$350

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 janvier 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$289
(Southwest)

One-way from

$131
(CheapOair)

Popular in

December

Cheapest in

August

Average price

$652
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 ($131 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 janvier 29, 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

mer. 2/25

2:50 pm-10:45 pm

1 stop5h 55m

Milwaukee-Mitchell

jeu. 2/26

7:30 pm-12:10 am

1 stop6h 40m

$289

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

mar. 2/24

12:30 pm-10:45 pm

1 stop8h 15m

Milwaukee-Mitchell

sam. 2/28

2:20 pm-9:45 pm

1 stop9h 25m

$317

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

mar. 3/3

12:10 pm-10:50 pm

1 stop8h 40m

Milwaukee-Mitchell

dim. 3/8

5:40 pm-11:40 pm

1 stop8h 00m

$336

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

mer. 3/18

1:45 pm-9:35 pm

1 stop5h 50m

Milwaukee-Mitchell

dim. 3/22

5:40 pm-11:40 pm

1 stop8h 00m

$359

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

mar. 3/24

6:00 am-2:30 pm

1 stop6h 30m

Milwaukee-Mitchell

lun. 3/30

7:30 pm-12:10 am

1 stop6h 40m

$359

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

mer. 5/13

12:25 pm-11:10 pm

2 stops8h 45m

Milwaukee-Mitchell

sam. 5/16

5:30 am-12:25 pm

2 stops8h 55m

$367

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

jeu. 4/30

6:20 am-11:58 pm

1 stop15h 38m

Milwaukee-Mitchell

dim. 5/3

7:00 am-9:13 am

1 stop28h 13m

$382

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

mar. 5/19

7:59 pm-11:57 pm

1 stop25h 58m

Milwaukee-Mitchell

mar. 5/26

4:42 pm-6:23 pm

2 stops27h 41m

$382

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

mar. 2/24

12:40 pm-9:32 pm

1 stop6h 52m

$139

OaklandMilwaukee

OAK - MKE

OAKMKE

Oakland

mar. 3/3

6:15 am-2:00 pm

1 stop5h 45m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 19 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 Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Milwaukee flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 janvier 29, 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
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

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 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 5h 55m. Southwest 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 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 janvier 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$296Average$442FlexibilityNo cancel feeOn-time63%

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