$135+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
May 24 — May 311
Round-trip
1 adult, Economy
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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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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 April 24, 2026.
Explore the most affordable flight options available from Portland to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2026.
This Delta deal was found by Cheapflights users on 4/20. 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.
Wed 5/203:10 pm
PDX
- MKE
1 stop5h 45m
Delta
Tue 5/265:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 4/20![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 4/22. 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.
Wed 8/1911:30 pm
PDX
- MKE
1 stop9h 30m
Southwest
Wed 8/267:10 am
MKE
- PDX
1 stop7h 15m
Southwest
Deal found 4/22![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 4/21. 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 5/1311:12 pm
PDX
- MKE
1 stop7h 37m
Delta
Mon 5/185:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 4/21![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:12 pm
PDX
- MKE
1 stop7h 37m
Delta
Tue 5/196:45 am
MKE
- PDX
1 stop7h 48m
Delta
Deal found 4/20![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 4/23. 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.
Thu 9/1012:40 am
PDX
- MKE
1 stop5h 34m
Delta
Wed 9/1612:00 pm
MKE
- PDX
1 stop5h 58m
Delta
Deal found 4/23![Delta logo]()
$324
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Sat 5/2311:30 am
PDX
- MKE
1 stop7h 34m
American Airlines
Thu 5/287:30 am
MKE
- PDX
1 stop9h 05m
American Airlines
Deal found 4/21![American Airlines logo]()
$325
This CheapOair deal was found by Cheapflights users on 4/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:48 am
PDX
- MKE
1 stop27h 46m
Frontier
Mon 4/275:05 pm
MKE
- PDX
1 stop20h 47m
Frontier
Deal found 4/20![Frontier logo]()
$326
This Southwest deal was found by Cheapflights users on 4/20. 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 5/2611:55 pm
PDX
- MKE
1 stop9h 00m
Southwest
Thu 5/284:50 pm
MKE
- PDX
2 stops10h 05m
Southwest
Deal found 4/20![Southwest logo]()
$331
This deal was found by Cheapflights users on 4/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:40 pm
PDX
- MKE
1 stop5h 53m
Delta
Mon 5/185:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 4/23![Delta logo]()
$349
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 April 24, 2026.
Discover carefully curated flight deals from Portland to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 24, 2026.
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:54 pm
PDX
- MKE
1 stop8h 25m
United Airlines
Wed 5/275:00 am
MKE
- PDX
1 stop6h 39m
United Airlines
Deal found 4/23![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 4/19. 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 5/2611:55 pm
PDX
- MKE
1 stop9h 00m
Southwest
Thu 6/47:30 pm
MKE
- PDX
1 stop7h 00m
Southwest
Deal found 4/19![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 6/1612:31 am
PDX
- MKE
1 stop6h 44m
Delta
Wed 6/246:30 am
MKE
- PDX
1 stop6h 14m
Delta
Deal found 4/21![Delta logo]()
$417
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 6/27:00 am
PDX
- MKE
1 stop9h 15m
Alaska Airlines
Wed 6/36:08 am
MKE
- PDX
2 stops12h 50m
Alaska Airlines
Deal found 4/23![Alaska Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/22:12 pm
PDX
- MKE
1 stop6h 12m
United Airlines
Wed 6/35:29 pm
MKE
- PDX
1 stop7h 01m
United Airlines
Deal found 4/22![United Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 4/22. 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.
Fri 5/2211:35 am
PDX
- MKE
1 stop8h 45m
Southwest
Wed 6/32:40 pm
MKE
- PDX
2 stops10h 30m
Southwest
Deal found 4/22![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 4/20. 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 7/205:50 am
PDX
- MKE
1 stop5h 50m
Southwest
Tue 7/286:20 pm
MKE
- PDX
1 stop6h 15m
Southwest
Deal found 4/20![Southwest logo]()
$447
This Southwest deal was found by Cheapflights users on 4/22. 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.
Wed 7/13:40 pm
PDX
- MKE
1 stop7h 15m
Southwest
Mon 7/67:30 pm
MKE
- PDX
1 stop7h 00m
Southwest
Deal found 4/22![Southwest logo]()
$447
This Southwest deal was found by Cheapflights users on 4/22. 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.
Wed 7/13:40 pm
PDX
- MKE
1 stop7h 15m
Southwest
Sun 7/55:30 am
MKE
- PDX
1 stop8h 45m
Southwest
Deal found 4/22![Southwest logo]()
$462
This Southwest deal was found by Cheapflights users on 4/21. 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 5/206:00 am
PDX
- MKE
2 stops9h 25m
Southwest
Wed 5/274:05 pm
MKE
- PDX
2 stops8h 55m
Southwest
Deal found 4/21![Southwest logo]()
$467
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated April 24, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated April 24, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 4/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:48 am
PDX
- MKE
1 stop27h 46m
Frontier
Mon 4/275:05 pm
MKE
- PDX
1 stop20h 47m
Frontier
Deal found 4/20![Frontier logo]()
$326
This deal was found by Cheapflights users on 4/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:40 pm
PDX
- MKE
1 stop5h 53m
Delta
Mon 5/185:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 4/23![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 4/19. 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.
Tue 5/129:39 pm
PDX
- MKE
1 stop9h 29m
Delta
Tue 5/196:45 am
MKE
- PDX
1 stop7h 48m
Delta
Deal found 4/19![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 4/21. 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 5/1311:12 pm
PDX
- MKE
1 stop7h 37m
Delta
Mon 5/185:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 4/21![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 4/20. 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 5/159:39 pm
PDX
- MKE
1 stop9h 28m
Delta
Tue 5/196:45 am
MKE
- PDX
1 stop7h 48m
Delta
Deal found 4/20![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:12 pm
PDX
- MKE
1 stop7h 37m
Delta
Tue 5/196:45 am
MKE
- PDX
1 stop7h 48m
Delta
Deal found 4/20![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/189:39 pm
PDX
- MKE
1 stop9h 29m
Delta
Wed 5/205:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 4/22![Delta logo]()
$352
This Delta deal was found by Cheapflights users on 4/20. 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.
Wed 5/203:10 pm
PDX
- MKE
1 stop5h 45m
Delta
Tue 5/265:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 4/20![Delta logo]()
$269
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Sat 5/2311:30 am
PDX
- MKE
1 stop7h 34m
American Airlines
Thu 5/287:30 am
MKE
- PDX
1 stop9h 05m
American Airlines
Deal found 4/21![American Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 4/20. 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 5/2611:55 pm
PDX
- MKE
1 stop9h 00m
Southwest
Thu 5/284:50 pm
MKE
- PDX
2 stops10h 05m
Southwest
Deal found 4/20![Southwest logo]()
$331
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 April 24, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated April 24, 2026.
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Mon 5/1812:59 am
PDX
- MKE
1 stop8h 00m
American Airlines
Deal found 4/21![American Airlines logo]()
$135
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Mon 5/2511:40 pm
PDX
- MKE
1 stop8h 17m
United Airlines
Deal found 4/23![United Airlines logo]()
$163
This American Airlines deal was found by Cheapflights users on 4/20. 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.
Mon 6/810:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Deal found 4/20![American Airlines logo]()
$185
This United Airlines deal was found by Cheapflights users on 4/21. 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 5/197:15 am
PDX
- MKE
2 stops12h 12m
United Airlines
Deal found 4/21![United Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:20 pm
PDX
- MKE
2 stops36h 38m
Frontier
Deal found 4/20![Frontier logo]()
$203
This Southwest deal was found by Cheapflights users on 4/20. 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 5/2711:15 am
PDX
- MKE
2 stops8h 20m
Southwest
Deal found 4/20![Southwest logo]()
$214
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 5/268:11 pm
PDX
- MKE
2 stops10h 38m
Delta
Deal found 4/21![Delta logo]()
$218
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 April 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $269 (Delta) |
One-way from | $135 (American Airlines) |
Popular in | February |
Cheapest in | January |
Average price | $421 |
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 April 24, 2026.
Use the filters below to find and compare flights from Portland to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 5/20
1:54 pm-12:19 am
1 stop8h 25m
Milwaukee-Mitchell
Wed 5/27
5:00 am-9:39 am
1 stop6h 39m
$269
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 5/26
11:55 pm-10:55 am
1 stop9h 00m
Milwaukee-Mitchell
Thu 6/4
7:30 pm-12:30 am
1 stop7h 00m
$326
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 6/2
2:12 pm-10:24 pm
1 stop6h 12m
Milwaukee-Mitchell
Wed 6/3
5:29 pm-10:30 pm
1 stop7h 01m
$369
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 5/22
11:35 am-10:20 pm
1 stop8h 45m
Milwaukee-Mitchell
Wed 6/3
2:40 pm-11:10 pm
2 stops10h 30m
$379
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 6/16
12:31 am-9:15 am
1 stop6h 44m
Milwaukee-Mitchell
Wed 6/24
6:30 am-10:44 am
1 stop6h 14m
$417
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 6/2
7:00 am-6:15 pm
1 stop9h 15m
Milwaukee-Mitchell
Wed 6/3
6:08 am-4:58 pm
2 stops12h 50m
$433
Quickest round-trip
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Mon 7/20
5:50 am-1:40 pm
1 stop5h 50m
Milwaukee-Mitchell
Tue 7/28
6:20 pm-10:35 pm
1 stop6h 15m
$447
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 7/1
3:40 pm-12:55 am
1 stop7h 15m
Milwaukee-Mitchell
Mon 7/6
7:30 pm-12:30 am
1 stop7h 00m
$447
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 7/1
3:40 pm-12:55 am
1 stop7h 15m
Milwaukee-Mitchell
Sun 7/5
5:30 am-12:15 pm
1 stop8h 45m
$462
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 5/20
6:00 am-5:25 pm
2 stops9h 25m
Milwaukee-Mitchell
Wed 5/27
4:05 pm-11:00 pm
2 stops8h 55m
$467
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 April.
| 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 34 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 February is currently the most expensive (average of $570). 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?
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 April 24, 2026.
Read through reviews of airlines operating flights from Portland to Milwaukee, such as Southwest,Alaska Airlines, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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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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 April 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$434 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$405 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$298 | Average$454 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$307 | Average$406 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$322 | Average$493 | FlexibilityNo cancel fee | On-time63% |