$143+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Nov 20 — Nov 271
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 October 21, 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 October 21, 2026.
This Southwest deal was found by Cheapflights users on 10/20. 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 12/31:05 pm -
1 stop8h 10m
Sun 12/65:30 am -
1 stop9h 15m
Deal found 10/20![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:00 pm -
1 stop13h 05m
Sat 11/145:05 am -
1 stop7h 50m
Deal found 10/21![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:00 pm -
1 stop13h 05m
Wed 11/185:45 am -
2 stops9h 40m
Deal found 10/21![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 10/21. 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 12/101:05 pm -
1 stop8h 10m
Wed 12/165:45 am -
1 stop6h 55m
Deal found 10/21![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 10/19. 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 12/910:15 am -
2 stops11h 00m
Mon 12/145:45 am -
2 stops9h 40m
Deal found 10/19![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:35 am -
1 stop7h 37m
Sat 11/146:30 am -
1 stop6h 14m
Deal found 10/21![Delta logo]()
$323
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/112:34 pm -
1 stop5h 41m
Wed 12/1610:38 am -
2 stops9h 45m
Deal found 10/21![United Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 10/19. 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 12/126:55 am -
2 stops7h 15m
Mon 12/145:45 am -
2 stops9h 40m
Deal found 10/19![Southwest logo]()
$335
This American Airlines deal was found by Cheapflights users on 10/19. 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 12/16:00 am -
1 stop9h 41m
Sat 12/57:40 am -
1 stop6h 57m
Deal found 10/19![American Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:00 pm -
1 stop13h 05m
Fri 11/207:40 pm -
1 stop7h 45m
Deal found 10/21![Southwest logo]()
$356
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 October 21, 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 October 21, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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 12/311:40 am -
2 stops7h 50m
Mon 12/75:45 am -
1 stop6h 55m
Deal found 10/19![Southwest logo]()
$290
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Tue 11/1011:30 pm -
1 stop8h 43m
Tue 12/153:59 pm -
1 stop7h 16m
Deal found 10/21![United Airlines logo]()
$323
This Alaska Airlines deal was found by Cheapflights users on 10/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:22 am -
1 stop7h 13m
Mon 11/234:33 pm -
1 stop6h 18m
Deal found 10/19![Alaska Airlines logo]()
$507
This Southwest deal was found by Cheapflights users on 10/21. 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.
Tue 1/196:05 am -
2 stops10h 05m
Wed 2/36:15 am -
2 stops8h 50m
Deal found 10/21![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:00 pm -
1 stop13h 05m
Fri 11/207:40 pm -
1 stop7h 45m
Deal found 10/21![Southwest logo]()
$356
This Alaska Airlines deal was found by Cheapflights users on 10/18. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:30 am -
1 stop8h 05m
Sun 11/226:00 am -
1 stop9h 29m
Deal found 10/18![Alaska Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 10/16. 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 11/127:26 pm -
2 stops11h 09m
Sun 11/156:47 am -
1 stop7h 00m
Deal found 10/16![United Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 10/18. 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 11/182:10 pm -
1 stop6h 35m
Tue 11/245:20 pm -
1 stop8h 50m
Deal found 10/18![Southwest logo]()
$507
This Southwest deal was found by Cheapflights users on 10/17. 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 12/118:25 am -
1 stop7h 05m
Mon 12/145:15 am -
1 stop7h 35m
Deal found 10/17![Southwest logo]()
$507
This Southwest deal was found by Cheapflights users on 10/17. 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 11/1611:40 am -
2 stops8h 35m
Mon 11/233:55 pm -
2 stops11h 30m
Deal found 10/17![Southwest logo]()
$517
This Southwest deal was found by Cheapflights users on 10/19. 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 12/236:20 am -
1 stop12h 40m
Mon 12/288:00 pm -
1 stop7h 15m
Deal found 10/19![Southwest logo]()
$542
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated October 21, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated October 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/21. 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.
Tue 11/1010:15 am -
2 stops11h 00m
Tue 12/1512:45 pm -
2 stops10h 45m
Deal found 10/21![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:35 am -
1 stop7h 37m
Sat 11/146:30 am -
1 stop6h 14m
Deal found 10/21![Delta logo]()
$323
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/112:34 pm -
1 stop5h 41m
Wed 12/1610:38 am -
2 stops9h 45m
Deal found 10/21![United Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:00 pm -
1 stop13h 05m
Sat 11/145:05 am -
1 stop7h 50m
Deal found 10/21![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:00 pm -
1 stop13h 05m
Wed 11/185:45 am -
2 stops9h 40m
Deal found 10/21![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:00 pm -
1 stop13h 05m
Fri 11/207:40 pm -
1 stop7h 45m
Deal found 10/21![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 10/21. 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 11/127:00 pm -
1 stop13h 05m
Fri 11/136:10 pm -
2 stops9h 15m
Deal found 10/21![Southwest logo]()
$385
This Expedia deal was found by Cheapflights users on 10/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:08 am -
2 stops10h 54m
Mon 11/234:33 pm -
1 stop8h 25m
Deal found 10/21![Alaska Airlines logo]()
$378
This Alaska Airlines deal was found by Cheapflights users on 10/21. 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 11/186:08 am -
1 stop7h 34m
Mon 11/234:33 pm -
1 stop7h 21m
Deal found 10/21![Alaska Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:35 am -
1 stop7h 37m
Sun 11/226:30 am -
1 stop6h 14m
Deal found 10/21![Delta logo]()
$382
This Alaska Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 11/206:22 am -
1 stop7h 13m
Mon 11/234:33 pm -
1 stop8h 25m
Deal found 10/21![Alaska Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 10/19. 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.
Fri 11/208:00 am -
1 stop9h 00m
Mon 11/237:40 pm -
1 stop7h 45m
Deal found 10/19![Southwest logo]()
$370
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 October 21, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
This Southwest deal was found by Cheapflights users on 10/20. 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 12/1611:25 am -
1 stop9h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$143
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop7h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$162
This American Airlines deal was found by Cheapflights users on 10/16. 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.
Mon 11/2311:11 pm -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![American Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 10/16. 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 11/2411:20 pm -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Delta logo]()
$182
This United Airlines deal was found by Cheapflights users on 10/19. 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 11/265:00 am -
2 stops15h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$185
This Delta deal was found by Cheapflights users on 10/19. 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 11/276:00 am -
1 stop8h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$208
This Alaska Airlines deal was found by Cheapflights users on 10/16. 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 12/178:21 am -
1 stop13h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Alaska Airlines logo]()
$215
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/127:26 pm -
2 stops12h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 10/18. 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.
Sun 12/61:45 pm -
1 stop9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Southwest logo]()
$231
This Sun Country Air deal was found by Cheapflights users on 10/17. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:26 pm -
1 stop21h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Sun Country Air logo]()
$249
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 October 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $285 (Southwest) |
One-way from | $143 (Southwest) |
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 7,457,451 searches. Data last updated October 21, 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
Mon 11/23
12:35 am-10:12 am
1 stop7h 37m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$162
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 11/26
11:10 pm-10:23 am
1 stop9h 13m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$162
Quickest round-trip
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 11/12
6:00 am-3:19 pm
1 stop7h 19m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$162
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 12/24
11:52 pm-10:03 am
1 stop8h 11m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$162
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 11/25
11:20 pm-8:50 am
1 stop7h 30m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$162
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 12/23
2:02 pm-12:03 am
1 stop8h 01m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$215
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Sun 12/6
1:45 pm-12:45 am
1 stop9h 00m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$231
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 12/17
6:26 pm-5:26 pm
1 stop21h 00m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$249
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Sun 12/20
1:52 pm-11:59 pm
1 stop8h 07m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$254
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 12/3
11:40 am-9:30 pm
2 stops7h 50m
Milwaukee-Mitchell
Mon 12/7
5:45 am-10:40 am
1 stop6h 55m
$290
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 October.
| 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 $443 and $642 in December.The cheapest round-trip price found within the last 5 days was $285 on Southwest (Dec 3-Dec 6).
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 October 21, 2026.
Read through reviews of airlines operating flights from Portland to Milwaukee, such as Alaska Airlines,Southwest, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
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 locationsPort Washington
Sheboygan
New Berlin
Oak Creek
Wauwatosa
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Other flights to Milwaukee
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Portland and Milwaukee flights
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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 October 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$483 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$291 | Average$467 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$307 | Average$601 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$307 | Average$476 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$339 | Average$556 | FlexibilityNo cancel fee | On-time63% |