$140+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Milwaukee with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from 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 30, 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 30, 2026.
This Delta deal was found by Cheapflights users on 10/27. 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 12/71:30 pm -
1 stop6h 22m
Wed 12/167:20 am -
1 stop7h 08m
Deal found 10/27![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/91:15 pm -
1 stop5h 55m
Wed 12/169:15 am -
2 stops10h 52m
Deal found 10/27![United Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 10/27. 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 12/910:10 am -
2 stops9h 20m
Wed 12/166:20 am -
2 stops8h 50m
Deal found 10/27![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 10/29. 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 12/710:15 am -
1 stop11h 00m
Thu 12/106:20 am -
2 stops8h 50m
Deal found 10/29![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 10/27. 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 12/111:45 pm -
1 stop9h 00m
Mon 12/145:15 am -
1 stop7h 35m
Deal found 10/27![Southwest logo]()
$299
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/117:25 pm -
2 stops10h 10m
Tue 12/157:00 am -
1 stop6h 41m
Deal found 10/28![United Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 10/27. 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 12/711:17 pm -
1 stop7h 30m
Fri 12/186:24 am -
1 stop6h 15m
Deal found 10/27![Delta logo]()
$308
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/2611:10 pm -
1 stop9h 13m
Thu 12/39:15 am -
2 stops10h 52m
Deal found 10/28![United Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 10/27. 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.
Sun 12/66:00 am -
1 stop7h 02m
Tue 12/153:50 pm -
1 stop6h 34m
Deal found 10/27![Delta logo]()
$328
This Expedia deal was found by Cheapflights users on 10/27. 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.
Wed 11/259:30 pm -
1 stop16h 05m
Tue 12/14:25 pm -
1 stop6h 29m
Deal found 10/27![Alaska Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/15:00 am -
1 stop6h 24m
Sun 12/65:00 am -
2 stops10h 16m
Deal found 10/27![United Airlines logo]()
$333
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 30, 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 30, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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 11/195:05 am -
1 stop8h 37m
Wed 11/254:33 pm -
1 stop7h 21m
Deal found 10/27![Alaska Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 10/25. 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 12/910:10 am -
2 stops9h 20m
Wed 12/165:45 am -
1 stop9h 25m
Deal found 10/25![Southwest logo]()
$284
This United Airlines deal was found by Cheapflights users on 10/27. 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 12/22:26 pm -
1 stop5h 49m
Sun 12/65:00 am -
2 stops10h 16m
Deal found 10/27![United Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 10/26. 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 12/118:00 am -
1 stop9h 00m
Wed 12/166:20 am -
2 stops8h 50m
Deal found 10/26![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 10/26. 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
Sun 12/65:00 am -
1 stop9h 05m
Deal found 10/26![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 10/27. 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 1/2210:50 am -
1 stop7h 40m
Thu 1/2810:25 am -
1 stop8h 10m
Deal found 10/27![Southwest logo]()
$337
This United Airlines deal was found by Cheapflights users on 10/29. 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 2/910:45 am -
1 stop6h 11m
Wed 2/105:00 am -
1 stop8h 31m
Deal found 10/29![United Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 10/28. 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 12/1112:10 pm -
2 stops9h 00m
Mon 12/145:45 am -
2 stops9h 40m
Deal found 10/28![Southwest logo]()
$399
This Southwest deal was found by Cheapflights users on 10/28. 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 12/212:00 pm -
2 stops9h 25m
Tue 1/56:20 am -
2 stops8h 50m
Deal found 10/28![Southwest logo]()
$453
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated October 30, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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 11/177:18 am -
2 stops13h 19m
Mon 11/234:33 pm -
1 stop6h 18m
Deal found 10/27![Alaska Airlines logo]()
$384
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/175:00 am -
2 stops11h 58m
Mon 11/239:17 am -
2 stops13h 45m
Deal found 10/27![United Airlines logo]()
$451
This Orbitz deal was found by Cheapflights users on 10/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:10 pm -
1 stop23h 32m
Mon 11/234:33 pm -
1 stop8h 25m
Deal found 10/26![Alaska Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 10/26. 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 11/1810:15 am -
2 stops11h 00m
Mon 11/237:40 pm -
1 stop7h 45m
Deal found 10/26![Southwest logo]()
$284
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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 11/1910:34 am -
2 stops11h 25m
Wed 11/254:33 pm -
1 stop7h 21m
Deal found 10/27![Alaska Airlines logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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
Fri 11/274:33 pm -
1 stop8h 25m
Deal found 10/26![Alaska Airlines logo]()
$398
This Alaska Airlines deal was found by Cheapflights users on 10/25. 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 11/227:22 am -
1 stop6h 13m
Tue 12/16:00 am -
1 stop7h 24m
Deal found 10/25![Alaska Airlines logo]()
$386
This Alaska Airlines deal was found by Cheapflights users on 10/25. 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.
Mon 11/232:49 pm -
1 stop7h 10m
Tue 12/16:00 am -
1 stop7h 24m
Deal found 10/25![Alaska Airlines logo]()
$337
This Expedia deal was found by Cheapflights users on 10/27. 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.
Wed 11/259:30 pm -
1 stop16h 05m
Tue 12/14:25 pm -
1 stop6h 29m
Deal found 10/27![Alaska Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/2611:10 pm -
1 stop9h 13m
Thu 12/39:15 am -
2 stops10h 52m
Deal found 10/28![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 10/28. 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 11/266:15 am -
2 stops8h 25m
Thu 12/36:20 am -
2 stops8h 50m
Deal found 10/28![Southwest logo]()
$339
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 30, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Delta deal was found by Cheapflights users on 10/28. 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 11/2511:20 pm -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Delta logo]()
$140
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/268:30 am -
2 stops12h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$145
This Southwest deal was found by Cheapflights users on 10/30. 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 12/256:20 am -
1 stop5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Southwest logo]()
$159
This United Airlines deal was found by Cheapflights users on 10/30. 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 12/258:46 am -
2 stops10h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![United Airlines logo]()
$164
This Priceline deal was found by Cheapflights users on 10/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/176:05 am -
1 stop7h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Alaska Airlines logo]()
$169
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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.
Mon 11/3010:30 pm -
1 stop14h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Alaska Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Tue 11/248:54 pm -
2 stops18h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$177
This United Airlines deal was found by Cheapflights users on 10/30. 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 12/315:00 am -
2 stops10h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![United Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 10/25. 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 12/1712:10 pm -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$187
This Priceline deal was found by Cheapflights users on 10/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/224:13 pm -
1 stop5h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Alaska Airlines logo]()
$189
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/241:49 pm -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Alaska Airlines logo]()
$190
This Orbitz deal was found by Cheapflights users on 10/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:30 pm -
1 stop16h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Alaska Airlines logo]()
$195
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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (Delta) |
One-way from | $140 (Delta) |
Popular in | December |
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 30, 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 11/25
11:20 pm-8:50 am
1 stop7h 30m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$140
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 11/26
6:00 am-2:14 pm
1 stop6h 14m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$140
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 11/26
8:30 am-10:50 pm
2 stops12h 20m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$145
Quickest round-trip
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Fri 12/25
6:20 am-2:05 pm
1 stop5h 45m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Tue 12/29
11:50 pm-10:03 am
1 stop8h 13m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 12/17
6:05 am-3:29 pm
1 stop7h 24m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 12/31
11:55 am-9:21 pm
1 stop7h 26m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Mon 11/30
10:30 pm-3:27 pm
1 stop14h 57m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$174
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Tue 1/19
8:40 am-8:59 pm
2 stops10h 19m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$174
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 12/31
5:00 am-5:51 pm
2 stops10h 51m
Milwaukee-Mitchell
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$180
Showing 1-10 of 21 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 | |
| Price Accuracy2 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 $425 and $601 in December.The cheapest round-trip price found within the last 5 days was $279 on Delta (Dec 7-Dec 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 October 30, 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.
Entertainment
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Comfort
7.8
Food
7.0
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
Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 30, 2026.
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 30, 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$541 | FlexibilityNo cancel fee | On-time63% |