$159+ Cheap flights from Portland to Milwaukee (PDX - MKE)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Portland 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Portland to Milwaukee
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Cheapest flights from Portland to MilwaukeeExplore the most affordable flight options available from Portland to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
Explore the most affordable flight options available from Portland to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
This Delta deal was found by Cheapflights users on 9/19. 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 10/101:44 pm -
1 stop5h 29m
Wed 10/287:03 am -
1 stop8h 35m
Deal found 9/19![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:30 pm -
1 stop7h 06m
Sat 11/76:48 am -
2 stops8h 37m
Deal found 9/22![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 9/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:55 pm -
1 stop7h 12m
Mon 10/265:00 am -
1 stop9h 22m
Deal found 9/21![American Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 9/19. 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 10/1611:12 pm -
1 stop7h 38m
Wed 10/285:30 am -
1 stop10h 08m
Deal found 9/19![Delta logo]()
$330
This Southwest deal was found by Cheapflights users on 9/22. 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 10/1911:35 pm -
1 stop9h 30m
Fri 10/235:00 pm -
2 stops10h 25m
Deal found 9/22![Southwest logo]()
$341
This Delta deal was found by Cheapflights users on 9/18. 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 10/911:12 pm -
1 stop7h 38m
Fri 10/164:56 pm -
1 stop7h 06m
Deal found 9/18![Delta logo]()
$343
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:59 pm -
1 stop8h 06m
Tue 10/135:00 am -
1 stop6h 31m
Deal found 9/18![United Airlines logo]()
$347
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:15 am -
1 stop6h 44m
Mon 11/236:21 pm -
1 stop7h 55m
Deal found 9/18![American Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 9/19. 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 10/136:00 am -
1 stop6h 30m
Mon 10/264:56 pm -
1 stop7h 06m
Deal found 9/19![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 9/18. 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 10/2710:45 am -
2 stops9h 15m
Wed 11/44:15 pm -
1 stop9h 10m
Deal found 9/18![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 9/18. 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 11/1811:40 am -
2 stops8h 35m
Mon 11/237:40 pm -
1 stop7h 45m
Deal found 9/18![Southwest logo]()
$372
Best flights from Portland to MilwaukeeDiscover carefully curated flight deals from Portland to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
Discover carefully curated flight deals from Portland to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
This Delta deal was found by Cheapflights users on 9/19. 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 10/101:44 pm -
1 stop5h 29m
Tue 10/136:30 am -
1 stop8h 08m
Deal found 9/19![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:27 pm -
1 stop6h 32m
Tue 10/2712:03 pm -
1 stop9h 09m
Deal found 9/22![United Airlines logo]()
$317
This Alaska Airlines deal was found by Cheapflights users on 9/21. 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 10/272:30 pm -
2 stops15h 37m
Tue 11/35:04 am -
2 stops10h 33m
Deal found 9/21![Alaska Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 9/18. 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 10/1011:15 am -
2 stops10h 55m
Sat 10/175:40 am -
2 stops13h 40m
Deal found 9/18![Southwest logo]()
$433
This Delta deal was found by Cheapflights users on 9/19. 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 10/176:00 am -
1 stop6h 09m
Sat 10/2412:42 pm -
1 stop8h 27m
Deal found 9/19![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:59 pm -
1 stop8h 06m
Tue 10/135:00 am -
1 stop6h 31m
Deal found 9/18![United Airlines logo]()
$347
This Alaska Airlines deal was found by Cheapflights users on 9/20. 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 10/2811:03 am -
2 stops19h 04m
Thu 11/55:04 am -
2 stops13h 43m
Deal found 9/20![Alaska Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 9/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:34 pm -
1 stop5h 41m
Tue 11/38:00 am -
2 stops12h 09m
Deal found 9/22![United Airlines logo]()
$442
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated September 23, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/18. 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 10/911:12 pm -
1 stop7h 38m
Fri 10/164:56 pm -
1 stop7h 06m
Deal found 9/18![Delta logo]()
$343
This Delta deal was found by Cheapflights users on 9/19. 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 10/101:44 pm -
1 stop5h 29m
Mon 10/264:56 pm -
1 stop7h 06m
Deal found 9/19![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:59 pm -
1 stop8h 06m
Tue 10/135:00 am -
1 stop6h 31m
Deal found 9/18![United Airlines logo]()
$347
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:58 am -
1 stop7h 54m
Tue 10/135:47 pm -
1 stop7h 52m
Deal found 9/18![American Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 9/19. 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 10/132:20 pm -
1 stop7h 33m
Wed 10/287:03 am -
1 stop8h 35m
Deal found 9/19![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 9/19. 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 10/132:20 pm -
1 stop7h 33m
Fri 10/232:59 pm -
1 stop8h 50m
Deal found 9/19![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 9/19. 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 10/1611:12 pm -
1 stop7h 38m
Sat 10/246:30 am -
1 stop6h 04m
Deal found 9/19![Delta logo]()
$330
This Southwest deal was found by Cheapflights users on 9/22. 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 10/1911:35 pm -
1 stop9h 30m
Fri 10/235:00 pm -
2 stops10h 25m
Deal found 9/22![Southwest logo]()
$341
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:02 am -
1 stop6h 09m
Sat 10/248:30 am -
2 stops8h 35m
Deal found 9/20![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 9/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:55 pm -
1 stop7h 12m
Mon 10/265:00 am -
1 stop9h 22m
Deal found 9/21![American Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 9/18. 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 10/2710:45 am -
2 stops9h 15m
Wed 11/44:15 pm -
1 stop9h 10m
Deal found 9/18![Southwest logo]()
$371
One-way flights from Portland to MilwaukeeSearch for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This United Airlines deal was found by Cheapflights users on 9/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:33 pm -
1 stop10h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![United Airlines logo]()
$159
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:00 am -
2 stops11h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![United Airlines logo]()
$164
This Delta deal was found by Cheapflights users on 9/18. 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 10/911:12 pm -
1 stop7h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$172
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:00 am -
2 stops10h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![United Airlines logo]()
$194
This KAYAK deal was found by Cheapflights users on 9/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:52 am -
1 stop10h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 9/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:45 pm -
2 stops8h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![United Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 9/22. 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.
Sun 10/1111:49 am -
2 stops43h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$207
This American Airlines deal was found by Cheapflights users on 9/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:19 am -
1 stop9h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![American Airlines logo]()
$208
This Delta deal was found by Cheapflights users on 9/20. 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 10/2011:00 pm -
1 stop8h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Delta logo]()
$210
This Southwest deal was found by Cheapflights users on 9/18. 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 10/2711:15 am -
2 stops8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Southwest logo]()
$213
This Alaska Airlines deal was found by Cheapflights users on 9/22. 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 10/208:09 am -
2 stops11h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Alaska Airlines logo]()
$214
Find flight deals from Portland to Milwaukee
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) 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 September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (Delta) |
One-way from | $159 (United Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $459 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland 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 7,457,451 searches. Data last updated September 23, 2026.
Use the filters below to find and compare flights from Portland to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Mon 10/26
10:55 pm-8:07 am
1 stop7h 12m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Tue 10/27
6:00 am-4:31 pm
1 stop8h 31m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Tue 10/20
10:33 pm-10:48 am
1 stop10h 15m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Sat 10/31
5:00 am-5:02 pm
2 stops10h 02m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$164
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 10/14
12:45 pm-10:59 pm
2 stops8h 14m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$202
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Tue 10/27
11:15 am-9:50 pm
2 stops8h 35m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$213
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Sat 10/24
7:09 am-9:54 pm
2 stops12h 45m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$214
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 12/24
11:59 pm-10:03 am
1 stop8h 04m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$219
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Sat 10/17
8:25 am-10:59 pm
2 stops12h 34m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$224
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Sat 10/10
1:44 pm-9:13 pm
1 stop5h 29m
Milwaukee-Mitchell
Tue 10/13
6:30 am-12:38 pm
1 stop8h 08m
$317
Showing 1-10 of 17 resultsSorted by cheapest first
Compare providers for flights from Portland 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 Portland to Milwaukee in September.
| 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 Portland-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Milwaukee flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-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 Portland-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 Portland to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Portland with our price prediction graph.
PDX-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 Portland to Milwaukee
How far ahead should I book a flight from Portland to Milwaukee?
Booking 55 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Milwaukee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Portland to Milwaukee?
Currently, January is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $324). Flying from Portland to Milwaukee in June is currently the most expensive (average of $576). 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 Portland to Milwaukee?
Airfare is below average for this route at the moment.
Portland to Milwaukee flights typically cost between $388 and $622 in October.The cheapest round-trip price found within the last 5 days was $317 on Delta (Oct 10-Oct 26).
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 September 23, 2026.
Read through reviews of airlines operating flights from Portland to Milwaukee, such as Southwest,Alaska Airlines, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Portland to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Top 5 airlines flying from Portland to Milwaukee
Discover the top 5 airlines that operate flights from Portland 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 7,457,451 searches. Data last updated September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$489 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$291 | Average$441 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$298 | Average$459 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$324 | Average$547 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$339 | Average$536 | FlexibilityNo cancel fee | On-time63% |