$109+ Cheap flights from Portland to Milwaukee (PDX - MKE)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Jul 1 — Jul 81
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
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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 June 1, 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 June 1, 2026.
This American Airlines deal was found by Cheapflights users on 5/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am
PDX
- MKE
1 stop8h 53m
American Airlines
Tue 9/155:43 pm
MKE
- PDX
1 stop7h 40m
American Airlines
Deal found 5/30![American Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 5/31. 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 8/2510:55 pm
PDX
- MKE
1 stop8h 21m
Delta
Sat 8/296:40 am
MKE
- PDX
1 stop8h 58m
Delta
Deal found 5/31![Delta logo]()
$249
This Delta deal was found by Cheapflights users on 5/31. 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 8/2411:20 pm
PDX
- MKE
1 stop7h 35m
Delta
Sat 8/2912:47 pm
MKE
- PDX
1 stop8h 02m
Delta
Deal found 5/31![Delta logo]()
$281
This American Airlines deal was found by Cheapflights users on 5/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/611:34 pm
PDX
- MKE
1 stop6h 10m
American Airlines
Tue 8/116:48 pm
MKE
- PDX
1 stop7h 11m
American Airlines
Deal found 5/29![American Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 5/29. 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.
Tue 8/255:50 am
PDX
- MKE
1 stop12h 15m
Southwest
Tue 9/16:40 am
MKE
- PDX
1 stop7h 55m
Southwest
Deal found 5/29![Southwest logo]()
$312
This American Airlines deal was found by Cheapflights users on 5/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Wed 7/156:55 pm
MKE
- PDX
1 stop7h 10m
American Airlines
Deal found 5/28![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/611:34 pm
PDX
- MKE
1 stop6h 10m
American Airlines
Sat 8/156:48 pm
MKE
- PDX
1 stop7h 11m
American Airlines
Deal found 5/30![American Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 5/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:25 pm
PDX
- MKE
1 stop5h 57m
Delta
Wed 9/166:50 am
MKE
- PDX
1 stop7h 57m
Delta
Deal found 5/29![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 5/28. 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 10/219:45 pm
PDX
- MKE
1 stop9h 37m
Delta
Sat 10/313:15 pm
MKE
- PDX
1 stop6h 28m
Delta
Deal found 5/28![Delta logo]()
$327
This American Airlines deal was found by Cheapflights users on 5/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Tue 7/146:01 am
MKE
- PDX
1 stop6h 35m
American Airlines
Deal found 5/29![American Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 5/28. 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.
Wed 9/96:35 am
PDX
- MKE
2 stops8h 05m
Southwest
Thu 9/104:20 pm
MKE
- PDX
1 stop8h 45m
Southwest
Deal found 5/28![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 5/27. 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.
Thu 8/2011:20 pm
PDX
- MKE
1 stop7h 35m
Delta
Mon 8/2410:22 am
MKE
- PDX
1 stop10h 27m
Delta
Deal found 5/27![Delta logo]()
$337
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 June 1, 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 June 1, 2026.
This Delta deal was found by Cheapflights users on 5/27. 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.
Thu 8/2011:20 pm
PDX
- MKE
1 stop7h 35m
Delta
Mon 8/2410:22 am
MKE
- PDX
1 stop10h 27m
Delta
Deal found 5/27![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:30 pm
PDX
- MKE
1 stop8h 30m
United Airlines
Thu 10/155:00 am
MKE
- PDX
1 stop6h 34m
United Airlines
Deal found 5/31![United Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 5/29. 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.
Thu 8/209:20 am
PDX
- MKE
2 stops10h 05m
Southwest
Mon 8/246:25 am
MKE
- PDX
1 stop10h 35m
Southwest
Deal found 5/29![Southwest logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 5/31. 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 10/65:06 am
PDX
- MKE
1 stop7h 52m
Alaska Airlines
Wed 10/73:54 pm
MKE
- PDX
1 stop8h 05m
Alaska Airlines
Deal found 5/31![Alaska Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 5/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:30 am
PDX
- MKE
1 stop6h 10m
Delta
Mon 8/1010:22 am
MKE
- PDX
1 stop10h 27m
Delta
Deal found 5/29![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 5/29. 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.
Tue 7/143:40 pm
PDX
- MKE
1 stop7h 15m
Southwest
Tue 7/215:00 am
MKE
- PDX
2 stops9h 00m
Southwest
Deal found 5/29![Southwest logo]()
$379
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Mon 10/192:27 pm
PDX
- MKE
1 stop6h 32m
United Airlines
Fri 10/232:35 pm
MKE
- PDX
1 stop8h 30m
United Airlines
Deal found 5/28![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 5/31. 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 10/910:55 pm
PDX
- MKE
1 stop7h 50m
Delta
Wed 10/145:50 pm
MKE
- PDX
1 stop7h 57m
Delta
Deal found 5/31![Delta logo]()
$403
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Wed 9/97:15 pm
PDX
- MKE
2 stops12h 45m
United Airlines
Tue 9/152:20 pm
MKE
- PDX
2 stops10h 25m
United Airlines
Deal found 5/28![United Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 5/28. 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.
Wed 9/237:05 am
PDX
- MKE
2 stops9h 25m
Southwest
Sun 9/275:45 am
MKE
- PDX
2 stops10h 20m
Southwest
Deal found 5/28![Southwest logo]()
$452
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated June 1, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated June 1, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/28. 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.
Mon 6/2912:33 am
PDX
- MKE
1 stop6h 42m
Delta
Mon 7/64:49 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 5/28![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 5/28. 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.
Mon 6/2912:33 am
PDX
- MKE
1 stop6h 42m
Delta
Sun 7/56:20 am
MKE
- PDX
1 stop6h 20m
Delta
Deal found 5/28![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 6/1. 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 6/303:40 pm
PDX
- MKE
1 stop7h 15m
Southwest
Tue 7/76:55 pm
MKE
- PDX
1 stop7h 00m
Southwest
Deal found 6/1![Southwest logo]()
$329
This American Airlines deal was found by Cheapflights users on 5/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3010:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Tue 7/76:55 pm
MKE
- PDX
1 stop7h 09m
American Airlines
Deal found 5/27![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 6/1. 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 6/3010:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Sun 7/55:02 am
MKE
- PDX
1 stop7h 34m
American Airlines
Deal found 6/1![American Airlines logo]()
$418
This United Airlines deal was found by Cheapflights users on 6/1. 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 6/3010:40 pm
PDX
- MKE
1 stop6h 20m
United Airlines
Wed 7/85:00 am
MKE
- PDX
1 stop6h 34m
United Airlines
Deal found 6/1![United Airlines logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 6/1. 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 6/3010:59 pm
PDX
- MKE
1 stop6h 43m
Alaska Airlines
Wed 7/81:15 pm
MKE
- PDX
2 stops13h 07m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$434
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 June 1, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated June 1, 2026.
This American Airlines deal was found by Cheapflights users on 5/31. 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 9/16:27 am
PDX
- MKE
1 stop8h 33m
American Airlines
Deal found 5/31![American Airlines logo]()
$109
This Delta deal was found by Cheapflights users on 6/1. 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 9/2312:20 am
PDX
- MKE
1 stop6h 58m
Delta
Deal found 6/1![Delta logo]()
$141
This American Airlines deal was found by Cheapflights users on 5/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/110:59 pm
PDX
- MKE
1 stop7h 03m
American Airlines
Deal found 5/28![American Airlines logo]()
$159
This American Airlines deal was found by Cheapflights users on 5/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:08 pm
PDX
- MKE
1 stop6h 53m
American Airlines
Deal found 5/30![American Airlines logo]()
$164
This United Airlines deal was found by Cheapflights users on 5/29. 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.
Wed 7/1511:40 pm
PDX
- MKE
1 stop8h 13m
United Airlines
Deal found 5/29![United Airlines logo]()
$165
This Delta deal was found by Cheapflights users on 5/27. 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.
Wed 8/1212:30 am
PDX
- MKE
1 stop6h 10m
Delta
Deal found 5/27![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 5/31. 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 9/16:35 am
PDX
- MKE
2 stops8h 05m
Southwest
Deal found 5/31![Southwest logo]()
$170
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/712:30 am
PDX
- MKE
1 stop7h 50m
Delta
Deal found 5/31![Delta logo]()
$180
This Southwest deal was found by Cheapflights users on 5/29. 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.
Thu 9/1011:30 pm
PDX
- MKE
2 stops10h 25m
Southwest
Deal found 5/29![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 5/27. 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.
Tue 7/1410:25 am
PDX
- MKE
2 stops9h 40m
Southwest
Deal found 5/27![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:00 am
PDX
- MKE
2 stops10h 00m
Southwest
Deal found 5/31![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:15 pm
PDX
- MKE
2 stops14h 25m
Southwest
Deal found 5/31![Southwest logo]()
$221
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 June 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (American Airlines) |
One-way from | $109 (American Airlines) |
Popular in | February |
Cheapest in | January |
Average price | $567 |
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 June 1, 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
Thu 8/20
11:20 pm-8:55 am
1 stop7h 35m
Milwaukee-Mitchell
Mon 8/24
10:22 am-6:49 pm
1 stop10h 27m
$337
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Sat 10/10
11:30 pm-10:00 am
1 stop8h 30m
Milwaukee-Mitchell
Thu 10/15
5:00 am-9:34 am
1 stop6h 34m
$358
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 8/5
12:30 am-8:40 am
1 stop6h 10m
Milwaukee-Mitchell
Mon 8/10
10:22 am-6:49 pm
1 stop10h 27m
$359
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Thu 8/20
9:20 am-9:25 pm
2 stops10h 05m
Milwaukee-Mitchell
Mon 8/24
6:25 am-3:00 pm
1 stop10h 35m
$370
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 10/6
5:06 am-2:58 pm
1 stop7h 52m
Milwaukee-Mitchell
Wed 10/7
3:54 pm-9:59 pm
1 stop8h 05m
$374
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 7/14
3:40 pm-12:55 am
1 stop7h 15m
Milwaukee-Mitchell
Tue 7/21
5:00 am-12:00 pm
2 stops9h 00m
$379
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 10/9
10:55 pm-8:45 am
1 stop7h 50m
Milwaukee-Mitchell
Wed 10/14
5:50 pm-11:47 pm
1 stop7h 57m
$403
Quickest round-trip
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Mon 10/19
2:27 pm-10:59 pm
1 stop6h 32m
Milwaukee-Mitchell
Fri 10/23
2:35 pm-9:05 pm
1 stop8h 30m
$407
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/9
7:15 pm-10:00 am
2 stops12h 45m
Milwaukee-Mitchell
Tue 9/15
2:20 pm-10:45 pm
2 stops10h 25m
$427
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/23
7:05 am-6:30 pm
2 stops9h 25m
Milwaukee-Mitchell
Sun 9/27
5:45 am-2:05 pm
2 stops10h 20m
$452
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 June.
| 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 June 1, 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.
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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
Browse thousands of different options on Cheapflights for your next trip
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Complete your trip
Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Portland to Milwaukee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 June 1, 2026.
Portland and Milwaukee flights
Browse other Portland and Milwaukee flight options. Last updated on June 1, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on June 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Portland to Milwaukee
Discover the top 5 airlines that operate flights from Portland to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$424 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$414 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$278 | Average$448 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$307 | Average$427 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$322 | Average$515 | FlexibilityNo cancel fee | On-time63% |