$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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MKE
May 8 — May 151
Round-trip
1 adult, Economy
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Find cheap flights from Oakland to Milwaukee with Cheapflights
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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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Last-minute
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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 8, 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 8, 2026.
This CheapOair deal was found by Cheapflights users on 4/4. 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.
Sat 4/256:20 am
OAK
- MKE
1 stop29h 53m
Alaska Airlines
Tue 4/287:00 am
MKE
- OAK
1 stop8h 15m
Alaska Airlines
Deal found 4/4![Alaska Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 4/3. 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 4/296:00 am
OAK
- MKE
1 stop6h 00m
Southwest
Thu 4/302:25 pm
MKE
- OAK
1 stop7h 15m
Southwest
Deal found 4/3![Southwest logo]()
$342
This CheapOair deal was found by Cheapflights users on 4/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:20 am
OAK
- MKE
1 stop15h 38m
Alaska Airlines
Sat 5/27:00 am
MKE
- OAK
1 stop8h 15m
Alaska Airlines
Deal found 4/3![Alaska Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 4/7. 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 5/1312:28 pm
OAK
- MKE
2 stops8h 27m
Delta
Sat 5/166:45 am
MKE
- OAK
1 stop7h 03m
Delta
Deal found 4/7![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 4/7. 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 5/712:10 pm
OAK
- MKE
1 stop8h 10m
Southwest
Thu 5/147:05 pm
MKE
- OAK
1 stop7h 00m
Southwest
Deal found 4/7![Southwest logo]()
$355
This Southwest deal was found by Cheapflights users on 4/4. 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 4/302:00 pm
OAK
- MKE
1 stop6h 20m
Southwest
Sat 5/21:05 pm
MKE
- OAK
1 stop6h 20m
Southwest
Deal found 4/4![Southwest logo]()
$364
This CheapOair deal was found by Cheapflights users on 4/7. 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.
Tue 5/52:09 pm
OAK
- MKE
1 stop22h 04m
Alaska Airlines
Tue 5/127:00 am
MKE
- OAK
2 stops17h 23m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$371
This CheapOair deal was found by Cheapflights users on 4/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:20 am
OAK
- MKE
1 stop15h 38m
Alaska Airlines
Tue 5/127:00 am
MKE
- OAK
2 stops17h 23m
Alaska Airlines
Deal found 4/8![Alaska Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 4/7. 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 8/258:00 am
OAK
- MKE
1 stop6h 40m
Southwest
Thu 8/2710:15 am
MKE
- OAK
1 stop6h 00m
Southwest
Deal found 4/7![Southwest logo]()
$379
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 8, 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 8, 2026.
This Southwest deal was found by Cheapflights users on 4/4. 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 5/25:00 am
OAK
- MKE
1 stop7h 00m
Southwest
Mon 5/412:50 pm
MKE
- OAK
2 stops9h 15m
Southwest
Deal found 4/4![Southwest logo]()
$347
This CheapOair deal was found by Cheapflights users on 4/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:20 am
OAK
- MKE
1 stop15h 38m
Alaska Airlines
Sat 5/27:00 am
MKE
- OAK
2 stops13h 15m
Alaska Airlines
Deal found 4/3![Alaska Airlines logo]()
$398
This Southwest deal was found by Cheapflights users on 4/3. 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 4/296:10 am
OAK
- MKE
2 stops9h 15m
Southwest
Thu 4/307:05 pm
MKE
- OAK
1 stop7h 00m
Southwest
Deal found 4/3![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 4/7. 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 8/255:30 am
OAK
- MKE
1 stop9h 10m
Southwest
Thu 8/276:00 am
MKE
- OAK
2 stops8h 55m
Southwest
Deal found 4/7![Southwest logo]()
$389
This Alaska Airlines deal was found by Cheapflights users on 4/3. 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.
Tue 4/286:20 am
OAK
- MKE
2 stops13h 40m
Alaska Airlines
Wed 4/297:00 am
MKE
- OAK
1 stop8h 15m
Alaska Airlines
Deal found 4/3![Alaska Airlines logo]()
$463
This Southwest deal was found by Cheapflights users on 4/4. 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 4/3012:50 pm
OAK
- MKE
2 stops7h 40m
Southwest
Sun 5/36:10 am
MKE
- OAK
1 stop8h 25m
Southwest
Deal found 4/4![Southwest logo]()
$402
This Southwest deal was found by Cheapflights users on 4/3. 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.
Tue 7/72:35 pm
OAK
- MKE
1 stop5h 40m
Southwest
Tue 8/47:10 am
MKE
- OAK
2 stops9h 35m
Southwest
Deal found 4/3![Southwest logo]()
$444
This Southwest deal was found by Cheapflights users on 4/6. 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 8/149:15 am
OAK
- MKE
2 stops9h 45m
Southwest
Mon 8/175:45 am
MKE
- OAK
2 stops10h 50m
Southwest
Deal found 4/6![Southwest logo]()
$450
This Southwest deal was found by Cheapflights users on 4/3. 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 10/19:40 am
OAK
- MKE
2 stops11h 10m
Southwest
Sun 10/47:40 pm
MKE
- OAK
1 stop12h 55m
Southwest
Deal found 4/3![Southwest logo]()
$455
This Southwest deal was found by Cheapflights users on 4/7. 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 6/2712:30 pm
OAK
- MKE
2 stops9h 10m
Southwest
Sun 7/58:15 pm
MKE
- OAK
1 stop12h 15m
Southwest
Deal found 4/7![Southwest logo]()
$469
Last-minute flights from Oakland to MilwaukeeDiscover last-minute flight deals from Oakland to Milwaukee. Data last updated April 8, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Milwaukee. Data last updated April 8, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 4/4. 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.
Sat 4/256:20 am
OAK
- MKE
1 stop29h 53m
Alaska Airlines
Tue 4/287:00 am
MKE
- OAK
1 stop8h 15m
Alaska Airlines
Deal found 4/4![Alaska Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 4/3. 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 4/296:00 am
OAK
- MKE
1 stop6h 00m
Southwest
Thu 4/302:25 pm
MKE
- OAK
1 stop7h 15m
Southwest
Deal found 4/3![Southwest logo]()
$342
This CheapOair deal was found by Cheapflights users on 4/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:20 am
OAK
- MKE
1 stop15h 38m
Alaska Airlines
Sat 5/27:00 am
MKE
- OAK
1 stop8h 15m
Alaska Airlines
Deal found 4/3![Alaska Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 4/4. 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 4/302:00 pm
OAK
- MKE
1 stop6h 20m
Southwest
Sat 5/21:05 pm
MKE
- OAK
1 stop6h 20m
Southwest
Deal found 4/4![Southwest logo]()
$364
This CheapOair deal was found by Cheapflights users on 4/7. 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.
Tue 5/52:09 pm
OAK
- MKE
1 stop22h 04m
Alaska Airlines
Tue 5/127:00 am
MKE
- OAK
2 stops17h 23m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$371
This Southwest deal was found by Cheapflights users on 4/7. 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 5/712:10 pm
OAK
- MKE
1 stop8h 10m
Southwest
Thu 5/147:05 pm
MKE
- OAK
1 stop7h 00m
Southwest
Deal found 4/7![Southwest logo]()
$355
This CheapOair deal was found by Cheapflights users on 4/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:20 am
OAK
- MKE
1 stop15h 38m
Alaska Airlines
Tue 5/127:00 am
MKE
- OAK
2 stops17h 23m
Alaska Airlines
Deal found 4/8![Alaska Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 4/7. 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 5/1312:28 pm
OAK
- MKE
2 stops8h 27m
Delta
Sat 5/166:45 am
MKE
- OAK
1 stop7h 03m
Delta
Deal found 4/7![Delta logo]()
$354
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 8, 2026.
Search for one-way flight options from Oakland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated April 8, 2026.
This Southwest deal was found by Cheapflights users on 4/7. 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 6/304:20 pm
OAK
- MKE
1 stop6h 35m
Southwest
Deal found 4/7![Southwest logo]()
$165
This Southwest deal was found by Cheapflights users on 4/3. 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 4/295:45 am
OAK
- MKE
2 stops9h 30m
Southwest
Deal found 4/3![Southwest logo]()
$170
This CheapOair deal was found by Cheapflights users on 4/4. 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.
Wed 6/31:01 pm
OAK
- MKE
1 stop8h 58m
Alaska Airlines
Deal found 4/4![Alaska Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 4/6. 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 5/183:30 pm
OAK
- MKE
2 stops7h 25m
Southwest
Deal found 4/6![Southwest logo]()
$179
This CheapOair deal was found by Cheapflights users on 4/5. 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.
Sat 5/167:00 am
OAK
- MKE
1 stop14h 59m
Alaska Airlines
Deal found 4/5![Alaska Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 4/4. 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 4/3012:50 pm
OAK
- MKE
2 stops7h 40m
Southwest
Deal found 4/4![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 4/7. 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 8/2510:15 am
OAK
- MKE
2 stops9h 10m
Southwest
Deal found 4/7![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 4/5. 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 5/712:28 pm
OAK
- MKE
1 stop7h 05m
Delta
Deal found 4/5![Delta logo]()
$210
This Southwest deal was found by Cheapflights users on 4/7. 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.
Sun 5/32:25 pm
OAK
- MKE
1 stop6h 35m
Southwest
Deal found 4/7![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 4/6. 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 6/166:00 am
OAK
- MKE
2 stops11h 43m
Delta
Deal found 4/6![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 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (CheapOair) |
One-way from | $165 (Southwest) |
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 8, 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
Sat 5/2
5:00 am-2:00 pm
1 stop7h 00m
Milwaukee-Mitchell
Mon 5/4
12:50 pm-8:05 pm
2 stops9h 15m
$347
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Wed 4/29
6:10 am-5:25 pm
2 stops9h 15m
Milwaukee-Mitchell
Thu 4/30
7:05 pm-12:05 am
1 stop7h 00m
$347
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Tue 8/25
5:30 am-4:40 pm
1 stop9h 10m
Milwaukee-Mitchell
Thu 8/27
6:00 am-12:55 pm
2 stops8h 55m
$389
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Thu 4/30
6:20 am-11:58 pm
1 stop15h 38m
Milwaukee-Mitchell
Sat 5/2
7:00 am-6:15 pm
2 stops13h 15m
$398
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Thu 4/30
12:50 pm-10:30 pm
2 stops7h 40m
Milwaukee-Mitchell
Sun 5/3
6:10 am-12:35 pm
1 stop8h 25m
$402
Quickest round-trip
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Tue 7/7
2:35 pm-10:15 pm
1 stop5h 40m
Milwaukee-Mitchell
Tue 8/4
7:10 am-2:45 pm
2 stops9h 35m
$444
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Fri 8/14
9:15 am-9:00 pm
2 stops9h 45m
Milwaukee-Mitchell
Mon 8/17
5:45 am-2:35 pm
2 stops10h 50m
$450
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Thu 10/1
9:40 am-10:50 pm
2 stops11h 10m
Milwaukee-Mitchell
Sun 10/4
7:40 pm-6:35 am
1 stop12h 55m
$455
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Tue 4/28
6:20 am-10:00 pm
2 stops13h 40m
Milwaukee-Mitchell
Wed 4/29
7:00 am-1:15 pm
1 stop8h 15m
$463
OaklandMilwaukee
OAK - MKE
OAKMKE
Oakland
Sat 6/27
12:30 pm-11:40 pm
2 stops9h 10m
Milwaukee-Mitchell
Sun 7/5
8:15 pm-6:30 am
1 stop12h 15m
$469
Showing 1-10 of 20 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, 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.
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 8, 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
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
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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Alternative routes for Oakland to Milwaukee
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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 April 8, 2026.
Oakland and Milwaukee flights
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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 April 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$296 | Average$517 | FlexibilityNo cancel fee | On-time63% |