$119+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Mar 13 — Mar 201
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
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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 February 11, 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 February 11, 2026.
This Delta deal was found by Cheapflights users on 2/9. 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 3/312:40 am
PDX
- MKE
1 stop7h 41m
Delta
Sat 3/73:53 pm
MKE
- PDX
1 stop6h 37m
Delta
Deal found 2/9![Delta logo]()
$268
This United Airlines deal was found by Cheapflights users on 2/9. 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 3/1010:54 pm
PDX
- MKE
1 stop9h 14m
United Airlines
Sat 3/144:10 pm
MKE
- PDX
1 stop7h 00m
United Airlines
Deal found 2/9![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/1711:59 pm
PDX
- MKE
1 stop5h 50m
American Airlines
Fri 3/204:47 pm
MKE
- PDX
1 stop9h 28m
American Airlines
Deal found 2/9![American Airlines logo]()
$292
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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 3/259:30 pm
PDX
- MKE
1 stop14h 44m
Alaska Airlines
Wed 4/13:10 pm
MKE
- PDX
1 stop8h 28m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 2/9. 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 4/181:55 pm
PDX
- MKE
1 stop6h 51m
Delta
Mon 4/205:48 pm
MKE
- PDX
2 stops25h 22m
Delta
Deal found 2/9![Delta logo]()
$300
This Delta deal was found by Cheapflights users on 2/9. 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 4/186:15 am
PDX
- MKE
1 stop8h 39m
Delta
Sun 4/193:53 pm
MKE
- PDX
1 stop6h 12m
Delta
Deal found 2/9![Delta logo]()
$302
This Delta deal was found by Cheapflights users on 2/10. 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 3/46:00 am
PDX
- MKE
1 stop6h 17m
Delta
Mon 3/94:48 pm
MKE
- PDX
1 stop7h 05m
Delta
Deal found 2/10![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 2/10. 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 3/1610:54 pm
PDX
- MKE
1 stop9h 24m
United Airlines
Wed 3/184:10 pm
MKE
- PDX
1 stop8h 50m
United Airlines
Deal found 2/10![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 2/10. 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 3/312:40 am
PDX
- MKE
1 stop7h 41m
Delta
Sun 3/86:59 pm
MKE
- PDX
2 stops15h 34m
Delta
Deal found 2/10![Delta logo]()
$320
This Delta deal was found by Cheapflights users on 2/9. 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 3/2612:30 am
PDX
- MKE
1 stop6h 09m
Delta
Tue 3/314:48 pm
MKE
- PDX
1 stop7h 05m
Delta
Deal found 2/9![Delta logo]()
$323
This United Airlines deal was found by Cheapflights users on 2/8. 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 3/35:05 am
PDX
- MKE
1 stop7h 52m
United Airlines
Wed 3/44:10 pm
MKE
- PDX
1 stop9h 04m
United Airlines
Deal found 2/8![United Airlines logo]()
$327
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 February 11, 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 February 11, 2026.
This Delta deal was found by Cheapflights users on 2/9. 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 3/312:40 am
PDX
- MKE
1 stop7h 41m
Delta
Sat 3/73:53 pm
MKE
- PDX
1 stop6h 37m
Delta
Deal found 2/9![Delta logo]()
$268
This United Airlines deal was found by Cheapflights users on 2/9. 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 3/1010:54 pm
PDX
- MKE
1 stop9h 14m
United Airlines
Sat 3/144:10 pm
MKE
- PDX
1 stop7h 00m
United Airlines
Deal found 2/9![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/1711:59 pm
PDX
- MKE
1 stop5h 50m
American Airlines
Fri 3/204:47 pm
MKE
- PDX
1 stop9h 28m
American Airlines
Deal found 2/9![American Airlines logo]()
$292
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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 3/259:30 pm
PDX
- MKE
1 stop14h 44m
Alaska Airlines
Wed 4/13:10 pm
MKE
- PDX
1 stop8h 28m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 2/9. 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 4/186:15 am
PDX
- MKE
1 stop8h 39m
Delta
Sun 4/193:53 pm
MKE
- PDX
1 stop6h 12m
Delta
Deal found 2/9![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 2/10. 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 3/1610:54 pm
PDX
- MKE
1 stop9h 24m
United Airlines
Wed 3/184:10 pm
MKE
- PDX
1 stop8h 50m
United Airlines
Deal found 2/10![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 2/9. 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 4/181:55 pm
PDX
- MKE
1 stop6h 51m
Delta
Mon 4/203:53 pm
MKE
- PDX
1 stop6h 12m
Delta
Deal found 2/9![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 2/7. 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 3/31:18 pm
PDX
- MKE
1 stop5h 48m
United Airlines
Wed 3/46:00 am
MKE
- PDX
1 stop7h 55m
United Airlines
Deal found 2/7![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 2/9. 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 3/2612:30 am
PDX
- MKE
1 stop6h 09m
Delta
Tue 3/314:48 pm
MKE
- PDX
1 stop7h 05m
Delta
Deal found 2/9![Delta logo]()
$323
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated February 11, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/9. 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 3/312:40 am
PDX
- MKE
1 stop7h 41m
Delta
Sat 3/73:53 pm
MKE
- PDX
1 stop6h 37m
Delta
Deal found 2/9![Delta logo]()
$268
This Delta deal was found by Cheapflights users on 2/10. 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 3/312:40 am
PDX
- MKE
1 stop7h 41m
Delta
Sun 3/86:59 pm
MKE
- PDX
2 stops15h 34m
Delta
Deal found 2/10![Delta logo]()
$320
This United Airlines deal was found by Cheapflights users on 2/8. 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 3/35:05 am
PDX
- MKE
1 stop7h 52m
United Airlines
Wed 3/44:10 pm
MKE
- PDX
1 stop9h 04m
United Airlines
Deal found 2/8![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 2/10. 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 3/46:00 am
PDX
- MKE
1 stop6h 17m
Delta
Mon 3/94:48 pm
MKE
- PDX
1 stop7h 05m
Delta
Deal found 2/10![Delta logo]()
$307
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
PDX
- MKE
1 stop6h 51m
Alaska Airlines
Mon 3/93:47 pm
MKE
- PDX
1 stop8h 54m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 2/9. 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 3/1010:54 pm
PDX
- MKE
1 stop9h 14m
United Airlines
Sat 3/144:10 pm
MKE
- PDX
1 stop7h 00m
United Airlines
Deal found 2/9![United Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 2/10. 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 3/1610:54 pm
PDX
- MKE
1 stop9h 24m
United Airlines
Wed 3/184:10 pm
MKE
- PDX
1 stop8h 50m
United Airlines
Deal found 2/10![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/1711:59 pm
PDX
- MKE
1 stop5h 50m
American Airlines
Fri 3/204:47 pm
MKE
- PDX
1 stop9h 28m
American Airlines
Deal found 2/9![American Airlines logo]()
$292
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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 3/259:30 pm
PDX
- MKE
1 stop14h 44m
Alaska Airlines
Wed 4/13:10 pm
MKE
- PDX
1 stop8h 28m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 2/9. 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 3/2612:30 am
PDX
- MKE
1 stop6h 09m
Delta
Tue 3/314:48 pm
MKE
- PDX
1 stop7h 05m
Delta
Deal found 2/9![Delta logo]()
$323
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 February 11, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/1010:35 pm
PDX
- MKE
1 stop10h 17m
American Airlines
Deal found 2/9![American Airlines logo]()
$119
This United Airlines deal was found by Cheapflights users on 2/9. 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 3/48:30 am
PDX
- MKE
2 stops11h 58m
United Airlines
Deal found 2/9![United Airlines logo]()
$124
This CheapOair deal was found by Cheapflights users on 2/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:04 pm
PDX
- MKE
1 stop28h 47m
Frontier
Deal found 2/8![Frontier logo]()
$131
This United Airlines deal was found by Cheapflights users on 2/11. 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 3/1010:54 pm
PDX
- MKE
1 stop9h 14m
United Airlines
Deal found 2/11![United Airlines logo]()
$139
This Delta deal was found by Cheapflights users on 2/10. 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 5/56:00 am
PDX
- MKE
1 stop7h 03m
Delta
Deal found 2/10![Delta logo]()
$144
This United Airlines deal was found by Cheapflights users on 2/8. 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 5/55:30 am
PDX
- MKE
3 stops14h 18m
United Airlines
Deal found 2/8![United Airlines logo]()
$174
This United Airlines deal was found by Cheapflights users on 2/10. 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 4/1611:59 pm
PDX
- MKE
1 stop8h 01m
United Airlines
Deal found 2/10![United Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 2/7. 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 4/276:00 am
PDX
- MKE
2 stops14h 20m
Southwest
Deal found 2/7![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 2/10. 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 4/166:00 am
PDX
- MKE
2 stops14h 20m
Southwest
Deal found 2/10![Southwest logo]()
$190
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 February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $268 (Delta) |
One-way from | $119 (American Airlines) |
Popular in | February |
Cheapest in | January |
Average price | $650 |
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 February 11, 2026.
Use the filters below to find and compare flights from Portland to Milwaukee that are best for you.
Fly from
Portland
Fly to
Milwaukee
Route
Depart
Return
Price
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 3/3
12:40 am-10:21 am
1 stop7h 41m
Milwaukee-Mitchell
Sat 3/7
3:53 pm-8:30 pm
1 stop6h 37m
$268
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 3/10
10:54 pm-10:08 am
1 stop9h 14m
Milwaukee-Mitchell
Sat 3/14
4:10 pm-9:10 pm
1 stop7h 00m
$269
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 3/17
11:59 pm-7:49 am
1 stop5h 50m
Milwaukee-Mitchell
Fri 3/20
4:47 pm-12:15 am
1 stop9h 28m
$292
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 3/25
9:30 pm-2:14 pm
1 stop14h 44m
Milwaukee-Mitchell
Wed 4/1
3:10 pm-9:38 pm
1 stop8h 28m
$297
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Sat 4/18
6:15 am-4:54 pm
1 stop8h 39m
Milwaukee-Mitchell
Sun 4/19
3:53 pm-8:05 pm
1 stop6h 12m
$302
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Sat 4/18
1:55 pm-10:46 pm
1 stop6h 51m
Milwaukee-Mitchell
Mon 4/20
3:53 pm-8:05 pm
1 stop6h 12m
$302
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Mon 3/16
10:54 pm-10:18 am
1 stop9h 24m
Milwaukee-Mitchell
Wed 3/18
4:10 pm-11:00 pm
1 stop8h 50m
$317
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Thu 3/26
12:30 am-8:39 am
1 stop6h 09m
Milwaukee-Mitchell
Tue 3/31
4:48 pm-9:53 pm
1 stop7h 05m
$323
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 3/3
1:18 pm-9:06 pm
1 stop5h 48m
Milwaukee-Mitchell
Wed 3/4
6:00 am-11:55 am
1 stop7h 55m
$327
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 3/10
2:05 pm-11:18 pm
1 stop7h 13m
$119
Showing 1-10 of 19 results
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 February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- 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?
Use this chart to determine the optimal time to book a round-trip flight from Portland to Milwaukee. Price data was last updated on February 6, 2026.
Booking 35 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, August is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $88). Flying from Portland to Milwaukee in July is currently the most expensive (average of $238). 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.
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 February 11, 2026.
Read through reviews of airlines operating flights from Portland to Milwaukee, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Entertainment
7.0
Comfort
7.8
Crew
8.5
Food
7.1
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
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
New Berlin
Oak Creek
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 2,558,603 searches. Data last updated February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$421 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$402 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$307 | Average$479 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$324 | Average$403 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$339 | Average$521 | FlexibilityNo cancel fee | On-time63% |