$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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Aug 24 — Aug 311
Round-trip
1 adult, Economy
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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 July 25, 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 July 25, 2026.
This Delta deal was found by Cheapflights users on 7/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:25 am
PDX
- MKE
1 stop6h 53m
Delta
Wed 9/233:59 pm
MKE
- PDX
1 stop6h 17m
Delta
Deal found 7/23![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:30 pm
PDX
- MKE
2 stops10h 30m
Southwest
Mon 9/214:20 pm
MKE
- PDX
1 stop8h 45m
Southwest
Deal found 7/21![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 7/22. 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.
Tue 9/812:25 am
PDX
- MKE
1 stop6h 53m
Delta
Mon 9/144:57 pm
MKE
- PDX
1 stop7h 02m
Delta
Deal found 7/22![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 7/23. 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 8/2411:30 pm
PDX
- MKE
1 stop9h 35m
Southwest
Thu 8/276:00 am
MKE
- PDX
2 stops11h 40m
Southwest
Deal found 7/23![Southwest logo]()
$328
This United Airlines deal was found by Cheapflights users on 7/22. 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 8/192:27 pm
PDX
- MKE
1 stop6h 09m
United Airlines
Sat 9/511:18 am
MKE
- PDX
2 stops8h 32m
United Airlines
Deal found 7/22![United Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:35 am
PDX
- MKE
2 stops8h 05m
Southwest
Thu 9/244:20 pm
MKE
- PDX
1 stop8h 45m
Southwest
Deal found 7/21![Southwest logo]()
$332
This United Airlines deal was found by Cheapflights users on 7/19. 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 8/1211:02 pm
PDX
- MKE
1 stop6h 05m
United Airlines
Tue 8/185:00 am
MKE
- PDX
1 stop6h 29m
United Airlines
Deal found 7/19![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 7/23. 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.
Fri 9/115:00 am
PDX
- MKE
2 stops13h 35m
Southwest
Tue 9/154:25 pm
MKE
- PDX
2 stops7h 50m
Southwest
Deal found 7/23![Southwest logo]()
$338
This American Airlines deal was found by Cheapflights users on 7/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:12 pm
PDX
- MKE
1 stop7h 30m
American Airlines
Thu 11/56:19 pm
MKE
- PDX
1 stop7h 40m
American Airlines
Deal found 7/22![American Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 7/20. 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 9/146:25 am
PDX
- MKE
1 stop9h 50m
Southwest
Thu 9/176:20 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 7/20![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:00 am
PDX
- MKE
2 stops13h 30m
Southwest
Mon 9/76:25 am
MKE
- PDX
1 stop10h 35m
Southwest
Deal found 7/21![Southwest logo]()
$343
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 July 25, 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 July 25, 2026.
This Southwest deal was found by Cheapflights users on 7/24. 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.
Wed 12/1611:40 am
PDX
- MKE
2 stops8h 25m
Southwest
Wed 1/65:45 am
MKE
- PDX
1 stop6h 45m
Southwest
Deal found 7/24![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 7/20. 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 10/137:02 am
PDX
- MKE
1 stop6h 09m
United Airlines
Sat 10/172:20 pm
MKE
- PDX
2 stops8h 50m
United Airlines
Deal found 7/20![United Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 7/20. 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 10/131:38 pm
PDX
- MKE
1 stop6h 02m
Delta
Fri 10/1612:44 pm
MKE
- PDX
1 stop9h 01m
Delta
Deal found 7/20![Delta logo]()
$407
This Alaska Airlines deal was found by Cheapflights users on 7/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:13 am
PDX
- MKE
2 stops10h 41m
Alaska Airlines
Wed 9/163:03 pm
MKE
- PDX
1 stop6h 47m
Alaska Airlines
Deal found 7/23![Alaska Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 7/20. 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 9/1411:30 pm
PDX
- MKE
2 stops10h 30m
Southwest
Thu 9/176:00 am
MKE
- PDX
2 stops11h 40m
Southwest
Deal found 7/20![Southwest logo]()
$378
This United Airlines deal was found by Cheapflights users on 7/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/88:46 am
PDX
- MKE
1 stop6h 27m
United Airlines
Sat 1/164:00 pm
MKE
- PDX
1 stop9h 18m
United Airlines
Deal found 7/24![United Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 7/24. 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 12/175:00 am
PDX
- MKE
1 stop6h 15m
Southwest
Thu 12/3112:45 pm
MKE
- PDX
1 stop7h 20m
Southwest
Deal found 7/24![Southwest logo]()
$402
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Wed 9/2311:02 pm
PDX
- MKE
1 stop9h 05m
United Airlines
Sat 9/265:00 am
MKE
- PDX
1 stop8h 33m
United Airlines
Deal found 7/21![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:05 am
PDX
- MKE
2 stops9h 35m
Southwest
Mon 9/76:25 am
MKE
- PDX
1 stop10h 35m
Southwest
Deal found 7/21![Southwest logo]()
$407
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Wed 9/911:02 pm
PDX
- MKE
1 stop8h 58m
United Airlines
Tue 9/1512:05 pm
MKE
- PDX
2 stops12h 40m
United Airlines
Deal found 7/21![United Airlines logo]()
$422
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated July 25, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated July 25, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 7/19. 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 8/1211:02 pm
PDX
- MKE
1 stop6h 05m
United Airlines
Tue 8/185:00 am
MKE
- PDX
1 stop6h 29m
United Airlines
Deal found 7/19![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 7/19. 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 8/1211:35 am
PDX
- MKE
2 stops7h 50m
Southwest
Tue 8/185:20 pm
MKE
- PDX
1 stop7h 00m
Southwest
Deal found 7/19![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 7/23. 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.
Sat 8/159:00 am
PDX
- MKE
2 stops10h 00m
Southwest
Sat 8/295:30 am
MKE
- PDX
1 stop9h 20m
Southwest
Deal found 7/23![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 7/19. 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 8/1811:35 am
PDX
- MKE
2 stops7h 50m
Southwest
Wed 8/2611:40 am
MKE
- PDX
1 stop8h 10m
Southwest
Deal found 7/19![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 7/22. 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 8/192:27 pm
PDX
- MKE
1 stop6h 09m
United Airlines
Sat 9/511:18 am
MKE
- PDX
2 stops8h 32m
United Airlines
Deal found 7/22![United Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2010:45 pm
PDX
- MKE
1 stop11h 10m
Southwest
Mon 8/244:20 pm
MKE
- PDX
2 stops9h 20m
Southwest
Deal found 7/21![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 7/23. 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 8/2411:30 pm
PDX
- MKE
1 stop9h 35m
Southwest
Thu 8/276:00 am
MKE
- PDX
2 stops11h 40m
Southwest
Deal found 7/23![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:00 am
PDX
- MKE
1 stop7h 00m
Southwest
Wed 9/95:00 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 7/21![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:00 am
PDX
- MKE
2 stops13h 30m
Southwest
Mon 9/76:25 am
MKE
- PDX
1 stop10h 35m
Southwest
Deal found 7/21![Southwest logo]()
$343
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 July 25, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated July 25, 2026.
This American Airlines deal was found by Cheapflights users on 7/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:08 pm
PDX
- MKE
1 stop6h 53m
American Airlines
Deal found 7/22![American Airlines logo]()
$159
This United Airlines deal was found by Cheapflights users on 7/23. 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.
Sat 9/2610:43 am
PDX
- MKE
2 stops8h 42m
United Airlines
Deal found 7/23![United Airlines logo]()
$164
This Delta deal was found by Cheapflights users on 7/20. 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 8/1412:35 am
PDX
- MKE
1 stop7h 45m
Delta
Deal found 7/20![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 7/20. 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 8/256:35 am
PDX
- MKE
2 stops8h 05m
Southwest
Deal found 7/20![Southwest logo]()
$174
This American Airlines deal was found by Cheapflights users on 7/21. 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 8/1311:34 pm
PDX
- MKE
1 stop6h 15m
American Airlines
Deal found 7/21![American Airlines logo]()
$182
This American Airlines deal was found by Cheapflights users on 7/20. 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.
Sat 8/155:15 am
PDX
- MKE
1 stop6h 39m
American Airlines
Deal found 7/20![American Airlines logo]()
$194
This Southwest deal was found by Cheapflights users on 7/20. 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.
Thu 8/205:45 am
PDX
- MKE
2 stops10h 00m
Southwest
Deal found 7/20![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:00 am
PDX
- MKE
2 stops13h 30m
Southwest
Deal found 7/21![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 7/22. 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.
Thu 9/179:20 am
PDX
- MKE
2 stops10h 05m
Southwest
Deal found 7/22![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 7/20. 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.
Sat 8/159:00 am
PDX
- MKE
2 stops10h 00m
Southwest
Deal found 7/20![Southwest logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Fri 8/216:17 pm
PDX
- MKE
2 stops38h 56m
Frontier
Deal found 7/22![Frontier logo]()
$228
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 July 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (Delta) |
One-way from | $159 (American Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $552 |
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 2,558,603 searches. Data last updated July 25, 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 - MKE
PDXMKE
Portland
Wed 12/16
11:40 am-10:05 pm
2 stops8h 25m
Milwaukee-Mitchell
Wed 1/6
5:45 am-10:30 am
1 stop6h 45m
$322
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 10/13
7:02 am-3:11 pm
1 stop6h 09m
Milwaukee-Mitchell
Sat 10/17
2:20 pm-9:10 pm
2 stops8h 50m
$342
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Mon 9/14
11:30 pm-12:00 pm
2 stops10h 30m
Milwaukee-Mitchell
Thu 9/17
6:00 am-3:40 pm
2 stops11h 40m
$378
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 1/8
8:46 am-5:13 pm
1 stop6h 27m
Milwaukee-Mitchell
Sat 1/16
4:00 pm-11:18 pm
1 stop9h 18m
$402
Quickest round-trip
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Thu 12/17
5:00 am-1:15 pm
1 stop6h 15m
Milwaukee-Mitchell
Thu 12/31
12:45 pm-6:05 pm
1 stop7h 20m
$402
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 10/13
1:38 pm-9:40 pm
1 stop6h 02m
Milwaukee-Mitchell
Fri 10/16
12:44 pm-7:45 pm
1 stop9h 01m
$407
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 9/4
6:05 am-5:40 pm
2 stops9h 35m
Milwaukee-Mitchell
Mon 9/7
6:25 am-3:00 pm
1 stop10h 35m
$407
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/23
11:02 pm-10:07 am
1 stop9h 05m
Milwaukee-Mitchell
Sat 9/26
5:00 am-11:33 am
1 stop8h 33m
$417
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 9/11
9:13 am-9:54 pm
2 stops10h 41m
Milwaukee-Mitchell
Wed 9/16
3:03 pm-7:50 pm
1 stop6h 47m
$422
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/9
11:02 pm-10:00 am
1 stop8h 58m
Milwaukee-Mitchell
Tue 9/15
12:05 pm-10:45 pm
2 stops12h 40m
$422
Showing 1-10 of 19 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 July.
| 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 $410 and $593 in September.The cheapest round-trip price found within the last 5 days was $317 on Delta (Sep 9-Sep 14).
Reviews of airlines servicing Milwaukee
Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated July 25, 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.
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
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.
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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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 July 25, 2026.
Portland and Milwaukee flights
Browse other Portland and Milwaukee flight options. Last updated on July 25, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on July 25, 2026.
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Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated July 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$478 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$211 | Average$437 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$278 | Average$451 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$406 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$324 | Average$536 | FlexibilityNo cancel fee | On-time63% |