$134+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
Sep 12 — Sep 191
Round-trip
1 adult, Economy
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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
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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
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Cheapest flights from Oakland to MilwaukeeExplore 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 August 13, 2026.
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 August 13, 2026.
This Southwest deal was found by Cheapflights users on 8/9. 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 9/1110:00 am -
1 stop8h 35m
Mon 9/146:25 pm -
1 stop7h 45m
Deal found 8/9![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 8/11. 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 9/29:30 am -
1 stop8h 35m
Sat 9/55:00 pm -
1 stop8h 10m
Deal found 8/11![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 8/11. 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 10/133:50 pm -
1 stop6h 05m
Tue 10/275:55 am -
1 stop8h 10m
Deal found 8/11![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 8/10. 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 9/911:40 am -
1 stop6h 30m
Mon 9/146:25 pm -
1 stop7h 45m
Deal found 8/10![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 8/10. 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 11/121:25 pm -
2 stops7h 55m
Mon 11/165:45 am -
2 stops9h 25m
Deal found 8/10![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 8/12. 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 9/1110:00 am -
1 stop8h 35m
Fri 9/186:20 pm -
1 stop6h 30m
Deal found 8/12![Southwest logo]()
$334
Best flights from Oakland to MilwaukeeDiscover carefully curated flight deals from Oakland to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
Discover carefully curated flight deals from Oakland to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
This Southwest deal was found by Cheapflights users on 8/11. 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 9/29:30 am -
1 stop8h 35m
Sat 9/55:00 pm -
1 stop8h 10m
Deal found 8/11![Southwest logo]()
$308
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 10/287:02 am -
1 stop7h 17m
Thu 10/295:17 pm -
1 stop7h 38m
Deal found 8/12![Alaska Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 8/11. 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 10/133:50 pm -
1 stop6h 05m
Tue 10/276:10 am -
2 stops7h 55m
Deal found 8/11![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 8/8. 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 9/119:10 am -
2 stops9h 25m
Sun 9/135:25 am -
2 stops8h 20m
Deal found 8/8![Southwest logo]()
$415
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 9/245:10 pm -
2 stops26h 44m
Tue 9/295:03 am -
2 stops15h 52m
Deal found 8/12![Alaska Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 8/9. 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 9/256:15 am -
1 stop8h 45m
Thu 10/225:00 pm -
1 stop9h 10m
Deal found 8/9![Southwest logo]()
$487
Last-minute flights from Oakland to MilwaukeeDiscover last-minute flight deals from Oakland to Milwaukee. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Milwaukee. Data last updated August 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/11. 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 9/29:30 am -
1 stop8h 35m
Sat 9/55:00 pm -
1 stop8h 10m
Deal found 8/11![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 8/10. 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 9/911:40 am -
1 stop6h 30m
Mon 9/146:25 pm -
1 stop7h 45m
Deal found 8/10![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 8/10. 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 9/96:00 am -
2 stops10h 18m
Tue 9/153:59 pm -
2 stops10h 00m
Deal found 8/10![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 8/9. 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 9/1110:00 am -
1 stop8h 35m
Mon 9/146:25 pm -
1 stop7h 45m
Deal found 8/9![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 8/12. 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 9/1110:00 am -
1 stop8h 35m
Fri 9/186:20 pm -
1 stop6h 30m
Deal found 8/12![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 8/10. 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 9/256:10 am -
1 stop12h 55m
Thu 10/225:00 pm -
1 stop9h 10m
Deal found 8/10![Southwest logo]()
$362
One-way flights from Oakland to MilwaukeeSearch for one-way flight options from Oakland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
Search for one-way flight options from Oakland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This Southwest deal was found by Cheapflights users on 8/11. 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 9/1110:00 am -
1 stop8h 35m
Deal found 8/11![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 8/12. 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 11/210:20 am -
1 stop6h 40m
Deal found 8/12![Southwest logo]()
$156
This Delta deal was found by Cheapflights users on 8/12. 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 11/25:02 pm -
2 stops14h 09m
Deal found 8/12![Delta logo]()
$161
This Southwest deal was found by Cheapflights users on 8/11. 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 9/11:35 pm -
1 stop5h 50m
Deal found 8/11![Southwest logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:39 pm -
2 stops44h 36m
Deal found 8/8![Frontier logo]()
$240
This Southwest deal was found by Cheapflights users on 8/9. 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.
Sat 10/105:05 am -
1 stop7h 05m
Deal found 8/9![Southwest logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:13 pm -
2 stops29h 02m
Deal found 8/9![Frontier logo]()
$268
This Delta deal was found by Cheapflights users on 8/11. 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 9/912:39 pm -
1 stop6h 32m
Deal found 8/11![Delta logo]()
$270
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 August 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $290 (Southwest) |
One-way from | $134 (Southwest) |
Popular in | January |
Cheapest in | April |
Average price | $441 |
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 August 13, 2026.
Use the filters below to find and compare flights from Oakland to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandMilwaukee
OAK Oakland - MKE Milwaukee-Mitchell
OAKMKE
Oakland
Wed 9/2
9:30 am-8:05 pm
1 stop8h 35m
Milwaukee-Mitchell
Sat 9/5
5:00 pm-11:10 pm
1 stop8h 10m
$308
Quickest round-trip
OaklandMilwaukee
OAK Oakland - MKE Milwaukee-Mitchell
OAKMKE
Oakland
Tue 10/13
3:50 pm-11:55 pm
1 stop6h 05m
Milwaukee-Mitchell
Tue 10/27
6:10 am-12:05 pm
2 stops7h 55m
$316
OaklandMilwaukee
OAK Oakland - MKE Milwaukee-Mitchell
OAKMKE
Oakland
Wed 10/28
7:02 am-4:19 pm
1 stop7h 17m
Milwaukee-Mitchell
Thu 10/29
5:17 pm-10:55 pm
1 stop7h 38m
$397
OaklandMilwaukee
OAK Oakland - MKE Milwaukee-Mitchell
OAKMKE
Oakland
Fri 9/11
9:10 am-8:35 pm
2 stops9h 25m
Milwaukee-Mitchell
Sun 9/13
5:25 am-11:45 am
2 stops8h 20m
$415
OaklandMilwaukee
OAK Oakland - MKE Milwaukee-Mitchell
OAKMKE
Oakland
Fri 9/25
6:15 am-5:00 pm
1 stop8h 45m
Milwaukee-Mitchell
Thu 10/22
5:00 pm-12:10 am
1 stop9h 10m
$487
OaklandMilwaukee
OAK Oakland - MKE Milwaukee-Mitchell
OAKMKE
Oakland
Thu 9/24
5:10 pm-9:54 pm
2 stops26h 44m
Milwaukee-Mitchell
Tue 9/29
5:03 am-6:55 pm
2 stops15h 52m
$488
Cheapest one-way
OaklandMilwaukee
OAK Oakland - MKE Milwaukee-Mitchell
OAKMKE
Oakland
Fri 9/11
10:00 am-8:35 pm
1 stop8h 35m
$134
OaklandMilwaukee
OAK Oakland - MKE Milwaukee-Mitchell
OAKMKE
Oakland
Wed 11/4
5:30 am-2:55 pm
1 stop7h 25m
$156
OaklandMilwaukee
OAK Oakland - MKE Milwaukee-Mitchell
OAKMKE
Oakland
Mon 11/2
10:20 am-7:00 pm
1 stop6h 40m
$156
Quickest one-way
OaklandMilwaukee
OAK Oakland - MKE Milwaukee-Mitchell
OAKMKE
Oakland
Tue 9/1
1:35 pm-9:25 pm
1 stop5h 50m
$174
Showing 1-10 of 15 resultsSorted by cheapest first
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
OAK-MKE
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, April is the cheapest month in which you can book a flight from Oakland, California to Milwaukee (average of $397). Flying from Oakland, California to Milwaukee in January is currently the most expensive (average of $809). 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.
How much does it cost to fly round-trip from Oakland, California to Milwaukee?
Airfare is below average for this route at the moment.
Oakland, California to Milwaukee flights typically cost between $403 and $464 in September.The cheapest round-trip price found within the last 5 days was $290 on Southwest (Sep 11-Sep 14).
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 August 13, 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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.
Traveling to a place near Milwaukee?
Book flights to Milwaukee if you plan to visit one of these locationsSheboygan
Port Washington
New Berlin
Oak Creek
Wauwatosa
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Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
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Other flights to Milwaukee
Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 13, 2026.
Oakland and Milwaukee flights
Browse other Oakland and Milwaukee flight options. Last updated on August 13, 2026.
Other flights from Oakland
Browse through other flights departing from Oakland. Flights are based on user searches made on Cheapflights and were last updated on August 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 August 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$325 | Average$527 | FlexibilityNo cancel fee | On-time63% |