$159+ Cheap flights from Portland to Milwaukee (PDX - 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Sep 23 — Sep 301
Round-trip
1 adult, Economy
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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
Cheapest
Best
Last-minute
One-way
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 August 24, 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 August 24, 2026.
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Wed 9/911:08 pm -
1 stop6h 53m
Tue 9/155:03 am -
1 stop7h 52m
Deal found 8/19![American Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Tue 9/2912:45 pm -
2 stops8h 14m
Tue 10/135:00 am -
1 stop6h 31m
Deal found 8/20![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:58 am -
1 stop7h 54m
Thu 11/57:40 am -
1 stop6h 53m
Deal found 8/20![American Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 8/23. 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 10/2611:35 pm -
1 stop9h 30m
Wed 10/288:20 am -
2 stops10h 25m
Deal found 8/23![Southwest logo]()
$328
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:15 am -
1 stop6h 39m
Sat 12/512:15 pm -
1 stop7h 33m
Deal found 8/20![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/1112:01 pm -
1 stop7h 47m
Wed 9/165:43 pm -
1 stop7h 40m
Deal found 8/19![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 8/19. 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 10/911:12 pm -
1 stop7h 38m
Sat 10/173:20 pm -
1 stop6h 42m
Deal found 8/19![Delta logo]()
$332
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Sat 10/2412:45 pm -
2 stops8h 14m
Thu 10/292:17 pm -
1 stop6h 55m
Deal found 8/22![United Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Fri 10/232:27 pm -
1 stop6h 32m
Tue 10/276:47 am -
2 stops8h 35m
Deal found 8/20![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 8/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:15 am -
2 stops10h 30m
Thu 11/54:50 pm -
1 stop9h 05m
Deal found 8/19![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 8/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:50 am -
1 stop10h 00m
Fri 10/210:25 am -
2 stops14h 40m
Deal found 8/19![Southwest logo]()
$348
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 August 24, 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 August 24, 2026.
This Delta deal was found by Cheapflights users on 8/19. 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.
Wed 10/282:20 pm -
1 stop7h 33m
Thu 11/55:30 am -
1 stop10h 08m
Deal found 8/19![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Fri 10/211:30 pm -
1 stop8h 37m
Mon 10/55:00 am -
1 stop6h 31m
Deal found 8/23![United Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 8/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/72:15 pm -
1 stop7h 40m
Mon 10/127:35 pm -
1 stop6h 55m
Deal found 8/19![Southwest logo]()
$358
This Alaska Airlines deal was found by Cheapflights users on 8/21. 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.
Wed 10/289:31 am -
2 stops11h 11m
Thu 11/54:31 pm -
1 stop7h 24m
Deal found 8/21![Alaska Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 8/23. 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 10/1310:45 am -
2 stops9h 10m
Tue 10/204:00 pm -
2 stops8h 10m
Deal found 8/23![Southwest logo]()
$392
This United Airlines deal was found by Cheapflights users on 8/22. 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 12/22:34 pm -
1 stop6h 11m
Sun 12/65:00 am -
2 stops10h 15m
Deal found 8/22![United Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 8/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/305:50 am -
1 stop8h 50m
Sun 10/47:50 pm -
1 stop7h 10m
Deal found 8/20![Southwest logo]()
$402
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Wed 10/289:00 am -
2 stops11h 15m
Thu 11/53:33 pm -
1 stop8h 54m
Deal found 8/19![United Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 8/23. 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 9/911:02 pm -
1 stop8h 58m
Tue 9/152:20 pm -
2 stops10h 25m
Deal found 8/23![United Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 8/23. 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 2/98:45 am -
2 stops10h 09m
Wed 2/105:00 am -
1 stop7h 17m
Deal found 8/23![United Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 8/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:56 am -
1 stop10h 41m
Tue 9/158:39 am -
2 stops11h 30m
Deal found 8/21![United Airlines logo]()
$422
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated August 24, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated August 24, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Wed 9/911:08 pm -
1 stop6h 53m
Tue 9/155:03 am -
1 stop7h 52m
Deal found 8/19![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/1112:01 pm -
1 stop7h 47m
Wed 9/165:43 pm -
1 stop7h 40m
Deal found 8/19![American Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/172:27 pm -
1 stop6h 09m
Thu 9/243:52 pm -
1 stop8h 31m
Deal found 8/19![United Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Tue 9/222:27 pm -
1 stop6h 09m
Sat 9/268:30 am -
2 stops8h 35m
Deal found 8/20![United Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 8/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:50 am -
1 stop8h 50m
Tue 9/294:25 pm -
2 stops7h 50m
Deal found 8/20![Southwest logo]()
$363
This Delta deal was found by Cheapflights users on 8/20. 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.
Fri 9/2510:57 pm -
1 stop8h 09m
Wed 9/305:30 am -
1 stop9h 30m
Deal found 8/20![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 8/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:50 am -
1 stop10h 00m
Fri 10/210:25 am -
2 stops14h 40m
Deal found 8/19![Southwest logo]()
$348
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Tue 9/2912:45 pm -
2 stops8h 14m
Tue 10/135:00 am -
1 stop6h 31m
Deal found 8/20![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 8/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:35 am -
2 stops8h 05m
Tue 10/67:30 am -
2 stops11h 55m
Deal found 8/19![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 8/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:35 am -
2 stops8h 05m
Tue 10/67:30 am -
2 stops11h 55m
Deal found 8/19![Southwest logo]()
$362
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 August 24, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:10 pm -
1 stop7h 38m
Deal found 8/22![Delta logo]()
$159
This United Airlines deal was found by Cheapflights users on 8/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:50 am -
2 stops9h 46m
Deal found 8/21![United Airlines logo]()
$164
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/2511:08 pm -
1 stop6h 53m
Deal found 8/19![American Airlines logo]()
$174
This Southwest deal was found by Cheapflights users on 8/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:35 am -
2 stops8h 05m
Deal found 8/19![Southwest logo]()
$205
This United Airlines deal was found by Cheapflights users on 8/22. 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 9/1510:50 am -
2 stops9h 46m
Deal found 8/22![United Airlines logo]()
$206
This Southwest deal was found by Cheapflights users on 8/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:00 am -
2 stops13h 35m
Deal found 8/20![Southwest logo]()
$211
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Mon 9/147:15 pm -
2 stops12h 45m
Deal found 8/19![United Airlines logo]()
$214
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/257:29 pm -
2 stops12h 38m
Deal found 8/19![United Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 8/20. 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.
Sat 9/2612:25 am -
1 stop6h 53m
Deal found 8/20![Delta logo]()
$244
This Alaska Airlines deal was found by Cheapflights users on 8/22. 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.
Thu 9/247:55 am -
2 stops11h 59m
Deal found 8/22![Alaska Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Sun 9/1311:08 pm -
1 stop17h 13m
Deal found 8/19![American Airlines logo]()
$268
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 August 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (American Airlines) |
One-way from | $159 (Delta) |
Popular in | June |
Cheapest in | January |
Average price | $463 |
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 August 24, 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
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 10/28
2:20 pm-11:53 pm
1 stop7h 33m
Milwaukee-Mitchell
Thu 11/5
5:30 am-1:38 pm
1 stop10h 08m
$317
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Fri 10/2
11:30 pm-10:07 am
1 stop8h 37m
Milwaukee-Mitchell
Mon 10/5
5:00 am-9:31 am
1 stop6h 31m
$332
Quickest round-trip
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 10/7
2:15 pm-11:55 pm
1 stop7h 40m
Milwaukee-Mitchell
Mon 10/12
7:35 pm-12:30 am
1 stop6h 55m
$358
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Tue 10/13
10:45 am-9:55 pm
2 stops9h 10m
Milwaukee-Mitchell
Tue 10/20
4:00 pm-10:10 pm
2 stops8h 10m
$392
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 9/30
5:50 am-4:40 pm
1 stop8h 50m
Milwaukee-Mitchell
Sun 10/4
7:50 pm-1:00 am
1 stop7h 10m
$402
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 12/2
2:34 pm-10:45 pm
1 stop6h 11m
Milwaukee-Mitchell
Sun 12/6
5:00 am-1:15 pm
2 stops10h 15m
$407
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 10/28
9:31 am-10:42 pm
2 stops11h 11m
Milwaukee-Mitchell
Thu 11/5
4:31 pm-9:55 pm
1 stop7h 24m
$422
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 10/28
9:00 am-10:15 pm
2 stops11h 15m
Milwaukee-Mitchell
Thu 11/5
3:33 pm-10:27 pm
1 stop8h 54m
$422
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 9/9
11:02 pm-10:00 am
1 stop8h 58m
Milwaukee-Mitchell
Tue 9/15
2:20 pm-10:45 pm
2 stops10h 25m
$422
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Tue 2/9
8:45 am-8:54 pm
2 stops10h 09m
Milwaukee-Mitchell
Wed 2/10
5:00 am-10:17 am
1 stop7h 17m
$422
Showing 1-10 of 20 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 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 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 $340 and $557 in September.The cheapest round-trip price found within the last 5 days was $317 on American Airlines (Sep 9-Sep 15).
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 24, 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.
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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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Book flights to Milwaukee if you plan to visit one of these locationsSheboygan
Port Washington
New Berlin
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Wauwatosa
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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 August 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$478 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$272 | Average$436 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$278 | Average$454 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$435 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$324 | Average$534 | FlexibilityNo cancel fee | On-time63% |