$165+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
May 29 — Jun 51
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 April 29, 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 April 29, 2026.
This Southwest deal was found by Cheapflights users on 4/27. 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.
Mon 5/252:00 pm
OAK
- MKE
1 stop6h 20m
Southwest
Tue 6/25:45 pm
MKE
- OAK
1 stop6h 40m
Southwest
Deal found 4/27![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:05 pm
OAK
- MKE
2 stops14h 03m
Delta
Mon 6/14:02 pm
MKE
- OAK
2 stops9h 55m
Delta
Deal found 4/29![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 4/29. 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.
Thu 5/2812:10 pm
OAK
- MKE
1 stop8h 10m
Southwest
Mon 6/17:05 pm
MKE
- OAK
1 stop7h 00m
Southwest
Deal found 4/29![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 4/26. 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 5/2912:28 pm
OAK
- MKE
1 stop7h 05m
Delta
Wed 6/35:48 pm
MKE
- OAK
2 stops8h 09m
Delta
Deal found 4/26![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 4/28. 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 5/2612:28 pm
OAK
- MKE
1 stop7h 05m
Delta
Thu 5/285:48 pm
MKE
- OAK
2 stops8h 09m
Delta
Deal found 4/28![Delta logo]()
$392
This Southwest deal was found by Cheapflights users on 4/29. 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.
Fri 5/295:15 am
OAK
- MKE
1 stop6h 20m
Southwest
Mon 6/17:05 pm
MKE
- OAK
1 stop7h 00m
Southwest
Deal found 4/29![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 4/28. 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 6/104:20 pm
OAK
- MKE
1 stop6h 35m
Southwest
Sun 6/148:15 pm
MKE
- OAK
1 stop12h 15m
Southwest
Deal found 4/28![Southwest logo]()
$403
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 April 29, 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 April 29, 2026.
This Southwest deal was found by Cheapflights users on 4/27. 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.
Mon 5/252:00 pm
OAK
- MKE
1 stop6h 20m
Southwest
Tue 6/212:30 pm
MKE
- OAK
2 stops7h 45m
Southwest
Deal found 4/27![Southwest logo]()
$347
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 5/271:01 pm
OAK
- MKE
1 stop8h 58m
Alaska Airlines
Sat 5/304:40 pm
MKE
- OAK
1 stop9h 19m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 4/27. 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.
Tue 6/303:55 pm
OAK
- MKE
1 stop6h 00m
Southwest
Mon 7/132:30 pm
MKE
- OAK
1 stop7h 25m
Southwest
Deal found 4/27![Southwest logo]()
$428
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 9/2410:05 am
OAK
- MKE
1 stop26h 02m
Alaska Airlines
Tue 9/293:03 pm
MKE
- OAK
1 stop9h 51m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$465
This Southwest deal was found by Cheapflights users on 4/28. 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 8/219:15 am
OAK
- MKE
2 stops10h 10m
Southwest
Mon 8/2410:15 am
MKE
- OAK
1 stop6h 00m
Southwest
Deal found 4/28![Southwest logo]()
$440
This Southwest deal was found by Cheapflights users on 4/28. 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 6/42:30 pm
OAK
- MKE
1 stop7h 15m
Southwest
Sun 6/78:15 pm
MKE
- OAK
1 stop6h 30m
Southwest
Deal found 4/28![Southwest logo]()
$458
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/304:45 pm
OAK
- MKE
1 stop6h 30m
Southwest
Mon 8/36:30 pm
MKE
- OAK
1 stop7h 15m
Southwest
Deal found 4/25![Southwest logo]()
$458
This Southwest deal was found by Cheapflights users on 4/24. 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.
Thu 7/234:45 pm
OAK
- MKE
1 stop6h 30m
Southwest
Sun 7/262:30 pm
MKE
- OAK
2 stops11h 25m
Southwest
Deal found 4/24![Southwest logo]()
$469
Last-minute flights from Oakland to MilwaukeeDiscover last-minute flight deals from Oakland to Milwaukee. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Milwaukee. Data last updated April 29, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 4/26. 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 5/206:00 am
OAK
- MKE
1 stop6h 00m
Southwest
Mon 5/255:15 am
MKE
- OAK
1 stop7h 05m
Southwest
Deal found 4/26![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 4/27. 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.
Mon 5/252:00 pm
OAK
- MKE
1 stop6h 20m
Southwest
Tue 6/25:45 pm
MKE
- OAK
1 stop6h 40m
Southwest
Deal found 4/27![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 4/28. 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 5/2612:28 pm
OAK
- MKE
1 stop7h 05m
Delta
Thu 5/285:48 pm
MKE
- OAK
2 stops8h 09m
Delta
Deal found 4/28![Delta logo]()
$392
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:05 pm
OAK
- MKE
2 stops14h 03m
Delta
Mon 6/14:02 pm
MKE
- OAK
2 stops9h 55m
Delta
Deal found 4/29![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 4/29. 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.
Thu 5/2812:10 pm
OAK
- MKE
1 stop8h 10m
Southwest
Mon 6/17:05 pm
MKE
- OAK
1 stop7h 00m
Southwest
Deal found 4/29![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 4/26. 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 5/2912:28 pm
OAK
- MKE
1 stop7h 05m
Delta
Wed 6/35:48 pm
MKE
- OAK
2 stops8h 09m
Delta
Deal found 4/26![Delta logo]()
$389
This Southwest deal was found by Cheapflights users on 4/29. 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.
Fri 5/295:15 am
OAK
- MKE
1 stop6h 20m
Southwest
Mon 6/17:05 pm
MKE
- OAK
1 stop7h 00m
Southwest
Deal found 4/29![Southwest logo]()
$397
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 April 29, 2026.
Search for one-way flight options from Oakland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This Delta deal was found by Cheapflights users on 4/26. 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 6/912:33 pm
OAK
- MKE
1 stop7h 13m
Delta
Deal found 4/26![Delta logo]()
$165
This Delta deal was found by Cheapflights users on 4/26. 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.
Sat 5/2312:28 pm
OAK
- MKE
1 stop7h 05m
Delta
Deal found 4/26![Delta logo]()
$178
This Delta deal was found by Cheapflights users on 4/24. 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.
Sat 5/306:00 am
OAK
- MKE
2 stops11h 47m
Delta
Deal found 4/24![Delta logo]()
$183
This Southwest deal was found by Cheapflights users on 4/28. 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 5/2812:10 pm
OAK
- MKE
1 stop8h 10m
Southwest
Deal found 4/28![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 4/26. 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 7/14:20 pm
OAK
- MKE
1 stop6h 35m
Southwest
Deal found 4/26![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1010:30 am
OAK
- MKE
2 stops12h 25m
Southwest
Deal found 4/25![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 4/25. 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.
Mon 6/16:00 am
OAK
- MKE
2 stops8h 06m
Delta
Deal found 4/25![Delta logo]()
$215
This Delta deal was found by Cheapflights users on 4/27. 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.
Fri 5/2912:28 pm
OAK
- MKE
1 stop7h 05m
Delta
Deal found 4/27![Delta logo]()
$220
This Delta deal was found by Cheapflights users on 4/28. 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 8/205:55 am
OAK
- MKE
2 stops8h 47m
Delta
Deal found 4/28![Delta logo]()
$225
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 April 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $342 (Southwest) |
One-way from | $165 (Delta) |
Popular in | January |
Cheapest in | August |
Average price | $402 |
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 April 29, 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 - MKE
OAKMKE
Oakland
Mon 5/25
2:00 pm-10:20 pm
1 stop6h 20m
Milwaukee-Mitchell
Tue 6/2
12:30 pm-6:15 pm
2 stops7h 45m
$347
Quickest round-trip
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Tue 6/30
3:55 pm-11:55 pm
1 stop6h 00m
Milwaukee-Mitchell
Mon 7/13
2:30 pm-7:55 pm
1 stop7h 25m
$428
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Wed 5/27
1:01 pm-11:59 pm
1 stop8h 58m
Milwaukee-Mitchell
Sat 5/30
4:40 pm-11:59 pm
1 stop9h 19m
$439
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Fri 8/21
9:15 am-9:25 pm
2 stops10h 10m
Milwaukee-Mitchell
Mon 8/24
10:15 am-2:15 pm
1 stop6h 00m
$440
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Thu 6/4
2:30 pm-11:45 pm
1 stop7h 15m
Milwaukee-Mitchell
Sun 6/7
8:15 pm-12:45 am
1 stop6h 30m
$458
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Thu 7/30
4:45 pm-1:15 am
1 stop6h 30m
Milwaukee-Mitchell
Mon 8/3
6:30 pm-11:45 pm
1 stop7h 15m
$458
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Thu 9/24
10:05 am-2:07 pm
1 stop26h 02m
Milwaukee-Mitchell
Tue 9/29
3:03 pm-10:54 pm
1 stop9h 51m
$465
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Thu 7/23
4:45 pm-1:15 am
1 stop6h 30m
Milwaukee-Mitchell
Sun 7/26
2:30 pm-11:55 pm
2 stops11h 25m
$469
Cheapest one-way
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Mon 6/1
6:00 am-4:06 pm
2 stops8h 06m
$183
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Sat 5/23
12:28 pm-9:33 pm
1 stop7h 05m
$199
Showing 1-10 of 19 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 April.
| 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, August is the cheapest month in which you can book a flight from Oakland, California to Milwaukee (average of $334). 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?
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 April 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.
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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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Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 29, 2026.
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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 April 29, 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 April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$296 | Average$517 | FlexibilityNo cancel fee | On-time63% |