$154+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Jul 29 — Aug 51
Round-trip
1 adult, Economy
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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 29, 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 29, 2026.
This American Airlines deal was found by Cheapflights users on 6/29. 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 8/2011:34 pm
PDX
- MKE
1 stop6h 15m
American Airlines
Mon 8/246:48 pm
MKE
- PDX
1 stop7h 11m
American Airlines
Deal found 6/29![American Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 6/25. 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 8/2012:20 pm
PDX
- MKE
1 stop7h 05m
Southwest
Mon 8/244:35 pm
MKE
- PDX
1 stop8h 30m
Southwest
Deal found 6/25![Southwest logo]()
$308
This American Airlines deal was found by Cheapflights users on 6/27. 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.
Sat 8/155:18 am
PDX
- MKE
1 stop9h 42m
American Airlines
Sat 8/225:00 am
MKE
- PDX
1 stop8h 34m
American Airlines
Deal found 6/27![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Tue 7/2811:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Tue 8/46:40 pm
MKE
- PDX
1 stop8h 15m
American Airlines
Deal found 6/28![American Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 6/25. 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 10/15:00 am
PDX
- MKE
1 stop6h 30m
Southwest
Tue 10/66:20 am
MKE
- PDX
2 stops10h 25m
Southwest
Deal found 6/25![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:25 am
PDX
- MKE
1 stop6h 53m
Delta
Sat 9/2611:00 am
MKE
- PDX
1 stop8h 31m
Delta
Deal found 6/25![Delta logo]()
$317
This American Airlines deal was found by Cheapflights users on 6/28. 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 8/1211:34 pm
PDX
- MKE
1 stop6h 15m
American Airlines
Thu 8/206:48 pm
MKE
- PDX
1 stop7h 11m
American Airlines
Deal found 6/28![American Airlines logo]()
$320
This American Airlines deal was found by Cheapflights users on 6/27. 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.
Wed 9/2312:01 pm
PDX
- MKE
1 stop7h 47m
American Airlines
Wed 9/305:43 pm
MKE
- PDX
1 stop7h 40m
American Airlines
Deal found 6/27![American Airlines logo]()
$321
This United Airlines deal was found by Cheapflights users on 6/24. 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 9/234:07 pm
PDX
- MKE
1 stop5h 52m
United Airlines
Sat 9/262:20 pm
MKE
- PDX
2 stops8h 50m
United Airlines
Deal found 6/24![United Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 6/27. 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 8/512:35 am
PDX
- MKE
1 stop6h 05m
Delta
Tue 8/1112:18 pm
MKE
- PDX
1 stop7h 16m
Delta
Deal found 6/27![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 6/24. 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 8/265:50 am
PDX
- MKE
1 stop12h 15m
Southwest
Sat 8/2911:40 am
MKE
- PDX
2 stops11h 25m
Southwest
Deal found 6/24![Southwest logo]()
$328
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 29, 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 29, 2026.
This United Airlines deal was found by Cheapflights users on 6/24. 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 8/1111:02 pm
PDX
- MKE
1 stop6h 05m
United Airlines
Sat 8/155:00 am
MKE
- PDX
1 stop6h 29m
United Airlines
Deal found 6/24![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 6/24. 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 10/75:40 am
PDX
- MKE
1 stop7h 50m
Southwest
Thu 10/155:10 am
MKE
- PDX
2 stops10h 45m
Southwest
Deal found 6/24![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:35 am
PDX
- MKE
1 stop5h 59m
Delta
Wed 9/1612:13 pm
MKE
- PDX
1 stop7h 18m
Delta
Deal found 6/25![Delta logo]()
$397
This United Airlines deal was found by Cheapflights users on 6/24. 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 9/235:00 am
PDX
- MKE
1 stop6h 34m
United Airlines
Sat 9/265:00 am
MKE
- PDX
1 stop6h 31m
United Airlines
Deal found 6/24![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 6/24. 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 11/125:00 am
PDX
- MKE
1 stop6h 15m
Southwest
Tue 11/1712:45 pm
MKE
- PDX
2 stops10h 45m
Southwest
Deal found 6/24![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 6/27. 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 11/1011:40 am
PDX
- MKE
2 stops8h 25m
Southwest
Sat 11/148:55 am
MKE
- PDX
2 stops9h 45m
Southwest
Deal found 6/27![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 6/24. 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 8/267:05 am
PDX
- MKE
2 stops9h 25m
Southwest
Sat 8/291:00 pm
MKE
- PDX
2 stops10h 20m
Southwest
Deal found 6/24![Southwest logo]()
$378
This United Airlines deal was found by Cheapflights users on 6/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:02 pm
PDX
- MKE
1 stop8h 58m
United Airlines
Tue 9/1512:05 pm
MKE
- PDX
2 stops12h 40m
United Airlines
Deal found 6/25![United Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 6/28. 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 8/136:25 am
PDX
- MKE
2 stops9h 20m
Southwest
Tue 8/185:00 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 6/28![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 6/28. 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 10/12:35 pm
PDX
- MKE
1 stop6h 20m
Southwest
Sun 10/45:20 am
MKE
- PDX
2 stops9h 40m
Southwest
Deal found 6/28![Southwest logo]()
$412
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated June 29, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated June 29, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/24. 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 7/1310:40 pm
PDX
- MKE
1 stop6h 20m
United Airlines
Wed 7/155:00 am
MKE
- PDX
1 stop6h 34m
United Airlines
Deal found 6/24![United Airlines logo]()
$453
This American Airlines deal was found by Cheapflights users on 6/27. 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.
Sat 7/1811:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Tue 7/216:55 pm
MKE
- PDX
1 stop7h 55m
American Airlines
Deal found 6/27![American Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 6/24. 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 7/2111:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Sat 7/257:00 pm
MKE
- PDX
1 stop7h 50m
American Airlines
Deal found 6/24![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 6/24. 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 7/2111:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Fri 7/241:25 pm
MKE
- PDX
1 stop9h 15m
American Airlines
Deal found 6/24![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Sat 7/2511:43 pm
PDX
- MKE
1 stop9h 34m
American Airlines
Sat 8/16:40 pm
MKE
- PDX
1 stop8h 15m
American Airlines
Deal found 6/28![American Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 6/28. 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.
Sat 7/255:00 am
PDX
- MKE
2 stops10h 45m
Southwest
Sat 8/16:25 pm
MKE
- PDX
1 stop7h 05m
Southwest
Deal found 6/28![Southwest logo]()
$432
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Tue 7/2811:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Tue 8/46:40 pm
MKE
- PDX
1 stop8h 15m
American Airlines
Deal found 6/28![American Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 6/24. 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 7/285:35 am
PDX
- MKE
2 stops9h 40m
Southwest
Sat 8/16:55 pm
MKE
- PDX
1 stop7h 00m
Southwest
Deal found 6/24![Southwest logo]()
$402
This American Airlines deal was found by Cheapflights users on 6/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3011:54 am
PDX
- MKE
1 stop9h 40m
American Airlines
Wed 8/56:48 pm
MKE
- PDX
1 stop7h 11m
American Airlines
Deal found 6/26![American Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 6/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3011:59 pm
PDX
- MKE
1 stop8h 06m
United Airlines
Thu 8/65:00 am
MKE
- PDX
1 stop6h 34m
United Airlines
Deal found 6/26![United Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Thu 7/3011:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Thu 8/66:48 pm
MKE
- PDX
1 stop7h 11m
American Airlines
Deal found 6/28![American Airlines logo]()
$438
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 29, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated June 29, 2026.
This Delta deal was found by Cheapflights users on 6/28. 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 9/2312:25 am
PDX
- MKE
1 stop6h 53m
Delta
Deal found 6/28![Delta logo]()
$154
This United Airlines deal was found by Cheapflights users on 6/24. 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 8/2211:02 pm
PDX
- MKE
1 stop6h 05m
United Airlines
Deal found 6/24![United Airlines logo]()
$159
This American Airlines deal was found by Cheapflights users on 6/25. 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 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 6/25![American Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 6/25. 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 8/209:20 am
PDX
- MKE
2 stops10h 05m
Southwest
Deal found 6/25![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 6/28. 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 8/197:05 am
PDX
- MKE
2 stops9h 25m
Southwest
Deal found 6/28![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 6/24. 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 8/226:50 am
PDX
- MKE
2 stops9h 35m
Southwest
Deal found 6/24![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 6/26. 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 8/276:25 am
PDX
- MKE
2 stops9h 20m
Southwest
Deal found 6/26![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 6/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2612:33 am
PDX
- MKE
1 stop6h 25m
Delta
Deal found 6/25![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2311:15 am
PDX
- MKE
2 stops8h 40m
Southwest
Deal found 6/24![Southwest logo]()
$244
This CheapOair deal was found by Cheapflights users on 6/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:41 pm
PDX
- MKE
2 stops15h 26m
Alaska Airlines
Deal found 6/25![Alaska Airlines logo]()
$261
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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $307 (American Airlines) |
One-way from | $154 (Delta) |
Popular in | June |
Cheapest in | January |
Average price | $576 |
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 29, 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
Quickest round-trip
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 8/11
11:02 pm-7:07 am
1 stop6h 05m
Milwaukee-Mitchell
Sat 8/15
5:00 am-9:29 am
1 stop6h 29m
$317
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/23
5:00 am-1:34 pm
1 stop6h 34m
Milwaukee-Mitchell
Sat 9/26
5:00 am-9:31 am
1 stop6h 31m
$317
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 10/7
5:40 am-3:30 pm
1 stop7h 50m
Milwaukee-Mitchell
Thu 10/15
5:10 am-1:55 pm
2 stops10h 45m
$332
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Thu 11/12
5:00 am-1:15 pm
1 stop6h 15m
Milwaukee-Mitchell
Tue 11/17
12:45 pm-9:30 pm
2 stops10h 45m
$332
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 11/10
11:40 am-10:05 pm
2 stops8h 25m
Milwaukee-Mitchell
Sat 11/14
8:55 am-4:40 pm
2 stops9h 45m
$373
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 8/26
7:05 am-6:30 pm
2 stops9h 25m
Milwaukee-Mitchell
Sat 8/29
1:00 pm-9:20 pm
2 stops10h 20m
$378
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Thu 8/13
6:25 am-5:45 pm
2 stops9h 20m
Milwaukee-Mitchell
Tue 8/18
5:00 pm-9:55 pm
1 stop6h 55m
$383
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 9/11
11:35 am-7:34 pm
1 stop5h 59m
Milwaukee-Mitchell
Wed 9/16
12:13 pm-5:31 pm
1 stop7h 18m
$397
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Thu 10/1
2:35 pm-10:55 pm
1 stop6h 20m
Milwaukee-Mitchell
Sun 10/4
5:20 am-1:00 pm
2 stops9h 40m
$412
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/9
11:02 pm-10:00 am
1 stop8h 58m
Milwaukee-Mitchell
Tue 9/15
12:05 pm-10:45 pm
2 stops12h 40m
$422
Showing 1-10 of 19 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 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?
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 29, 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
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Crew
8.5
Boarding
8.1
Comfort
7.8
Overall
7.9
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 locationsSheboygan
Port Washington
New Berlin
Oak Creek
Wauwatosa
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Alternative routes for Portland to Milwaukee
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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.
Search flights from Portland to Milwaukee by cabin class
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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 June 29, 2026.
Portland and Milwaukee flights
Browse other Portland and Milwaukee flight options. Last updated on June 29, 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 29, 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 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$417 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$492 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$278 | Average$448 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$403 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$322 | Average$536 | FlexibilityNo cancel fee | On-time63% |