$153+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Jul 15 — Jul 221
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Milwaukee
Cheapest
Best
Last-minute
One-way
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 15, 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 15, 2026.
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:40 am
PDX
- MKE
1 stop5h 34m
Delta
Tue 9/1512:48 pm
MKE
- PDX
1 stop10h 57m
Delta
Deal found 6/11![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 6/14. 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 9/226:35 am
PDX
- MKE
2 stops8h 05m
Southwest
Tue 9/225:40 pm
MKE
- PDX
1 stop6h 35m
Southwest
Deal found 6/14![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 6/12. 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 9/510:55 pm
PDX
- MKE
1 stop8h 21m
Delta
Wed 9/306:50 am
MKE
- PDX
1 stop7h 57m
Delta
Deal found 6/12![Delta logo]()
$323
This American Airlines deal was found by Cheapflights users on 6/13. 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 9/1012:01 pm
PDX
- MKE
1 stop7h 47m
American Airlines
Tue 9/155:43 pm
MKE
- PDX
1 stop7h 40m
American Airlines
Deal found 6/13![American Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 6/12. 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 9/27:05 am
PDX
- MKE
2 stops9h 25m
Southwest
Wed 9/303:40 pm
MKE
- PDX
1 stop9h 30m
Southwest
Deal found 6/12![Southwest logo]()
$328
This Delta deal was found by Cheapflights users on 6/14. 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 6/301:15 pm
PDX
- MKE
1 stop6h 31m
Delta
Sat 7/412:56 pm
MKE
- PDX
1 stop10h 49m
Delta
Deal found 6/14![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 6/12. 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 9/911:35 am
PDX
- MKE
2 stops7h 50m
Southwest
Tue 9/155:00 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 6/12![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 6/12. 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 9/51:15 pm
PDX
- MKE
1 stop6h 26m
Delta
Mon 9/286:50 am
MKE
- PDX
1 stop5h 49m
Delta
Deal found 6/12![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 6/12. 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
Sat 8/1512:47 pm
MKE
- PDX
1 stop10h 57m
Delta
Deal found 6/12![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 6/12. 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
Wed 9/233:40 pm
MKE
- PDX
1 stop9h 30m
Southwest
Deal found 6/12![Southwest logo]()
$338
This United Airlines deal was found by Cheapflights users on 6/12. 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 8/195:00 am
PDX
- MKE
1 stop6h 29m
United Airlines
Sat 8/298:30 am
MKE
- PDX
2 stops8h 35m
United Airlines
Deal found 6/12![United Airlines logo]()
$342
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 15, 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 15, 2026.
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 9/25:00 am
PDX
- MKE
1 stop6h 29m
United Airlines
Sun 9/610:35 am
MKE
- PDX
1 stop6h 28m
United Airlines
Deal found 6/11![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 6/12. 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 8/2410:55 pm
PDX
- MKE
1 stop8h 21m
Delta
Sat 8/2910:24 am
MKE
- PDX
1 stop10h 31m
Delta
Deal found 6/12![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:35 am
PDX
- MKE
2 stops8h 05m
Southwest
Sun 9/67:00 am
MKE
- PDX
1 stop8h 15m
Southwest
Deal found 6/11![Southwest logo]()
$345
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1311:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Thu 7/166:55 pm
MKE
- PDX
1 stop7h 55m
American Airlines
Deal found 6/10![American Airlines logo]()
$477
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 9/95:00 am
PDX
- MKE
1 stop6h 34m
United Airlines
Sun 9/205:00 am
MKE
- PDX
1 stop8h 28m
United Airlines
Deal found 6/11![United Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 6/15. 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 9/411:50 am
PDX
- MKE
1 stop7h 32m
Delta
Sun 9/67:30 am
MKE
- PDX
1 stop6h 40m
Delta
Deal found 6/15![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 6/14. 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 8/1210:35 am
PDX
- MKE
2 stops8h 50m
Southwest
Mon 8/174:50 pm
MKE
- PDX
2 stops7h 55m
Southwest
Deal found 6/14![Southwest logo]()
$409
This United Airlines deal was found by Cheapflights users on 6/13. 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
Mon 9/142:40 pm
MKE
- PDX
1 stop8h 25m
United Airlines
Deal found 6/13![United Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 6/14. 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 7/711:30 pm
PDX
- MKE
1 stop9h 25m
Southwest
Thu 7/95:15 am
MKE
- PDX
2 stops8h 20m
Southwest
Deal found 6/14![Southwest logo]()
$438
This United Airlines deal was found by Cheapflights users on 6/12. 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 9/1011:02 pm
PDX
- MKE
1 stop8h 58m
United Airlines
Tue 9/155:00 am
MKE
- PDX
2 stops11h 47m
United Airlines
Deal found 6/12![United Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 6/12. 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 7/810:25 am
PDX
- MKE
2 stops9h 40m
Southwest
Wed 7/155:00 am
MKE
- PDX
2 stops9h 00m
Southwest
Deal found 6/12![Southwest logo]()
$448
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated June 15, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/14. 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 6/301:15 pm
PDX
- MKE
1 stop6h 31m
Delta
Sat 7/412:56 pm
MKE
- PDX
1 stop10h 49m
Delta
Deal found 6/14![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 6/14. 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 6/301:15 pm
PDX
- MKE
1 stop8h 20m
Southwest
Sat 7/410:15 am
MKE
- PDX
2 stops8h 45m
Southwest
Deal found 6/14![Southwest logo]()
$356
This American Airlines deal was found by Cheapflights users on 6/12. 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 55m
American Airlines
Deal found 6/12![American Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 6/14. 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
Wed 7/156:55 pm
MKE
- PDX
1 stop7h 55m
American Airlines
Deal found 6/14![American Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 6/13. 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 7/711:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Tue 7/146:01 am
MKE
- PDX
1 stop6h 35m
American Airlines
Deal found 6/13![American Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 6/12. 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 7/712:33 am
PDX
- MKE
1 stop6h 25m
Delta
Sat 7/182:59 pm
MKE
- PDX
1 stop8h 45m
Delta
Deal found 6/12![Delta logo]()
$418
This Southwest deal was found by Cheapflights users on 6/12. 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 7/81:15 pm
PDX
- MKE
1 stop8h 25m
Southwest
Wed 7/1511:30 am
MKE
- PDX
2 stops9h 30m
Southwest
Deal found 6/12![Southwest logo]()
$402
This American Airlines deal was found by Cheapflights users on 6/13. 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 7/1411:41 pm
PDX
- MKE
1 stop9h 36m
American Airlines
Mon 7/206:55 pm
MKE
- PDX
1 stop7h 55m
American Airlines
Deal found 6/13![American Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 6/14. 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 7/1410:40 am
PDX
- MKE
2 stops9h 40m
Southwest
Tue 7/217:05 pm
MKE
- PDX
1 stop7h 05m
Southwest
Deal found 6/14![Southwest logo]()
$404
This Southwest deal was found by Cheapflights users on 6/15. 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 7/149:20 pm
PDX
- MKE
1 stop12h 30m
Southwest
Sat 7/185:45 am
MKE
- PDX
2 stops10h 40m
Southwest
Deal found 6/15![Southwest logo]()
$425
This American Airlines deal was found by Cheapflights users on 6/12. 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 7/1511:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Wed 7/226:55 pm
MKE
- PDX
1 stop7h 55m
American Airlines
Deal found 6/12![American Airlines logo]()
$317
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 15, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
This United Airlines deal was found by Cheapflights users on 6/11. 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 8/2511:02 pm
PDX
- MKE
1 stop8h 58m
United Airlines
Deal found 6/11![United Airlines logo]()
$153
This Delta deal was found by Cheapflights users on 6/12. 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 7/712:33 am
PDX
- MKE
1 stop6h 25m
Delta
Deal found 6/12![Delta logo]()
$159
This Southwest deal was found by Cheapflights users on 6/12. 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 7/711:30 pm
PDX
- MKE
1 stop9h 25m
Southwest
Deal found 6/12![Southwest logo]()
$164
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/31:45 pm
PDX
- MKE
1 stop6h 36m
American Airlines
Deal found 6/11![American Airlines logo]()
$165
This Delta deal was found by Cheapflights users on 6/12. 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 8/1311:20 pm
PDX
- MKE
1 stop7h 35m
Delta
Deal found 6/12![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:10 am
PDX
- MKE
2 stops9h 10m
Southwest
Deal found 6/11![Southwest logo]()
$170
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:55 pm
PDX
- MKE
1 stop8h 21m
Delta
Deal found 6/11![Delta logo]()
$185
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/711:30 pm
PDX
- MKE
2 stops10h 30m
Southwest
Deal found 6/11![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:15 pm
PDX
- MKE
2 stops8h 10m
Southwest
Deal found 6/11![Southwest logo]()
$192
This Alaska Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:59 pm
PDX
- MKE
1 stop8h 00m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$200
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 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (Delta) |
One-way from | $153 (United Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $572 |
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 15, 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
Wed 9/2
5:00 am-1:29 pm
1 stop6h 29m
Milwaukee-Mitchell
Sun 9/6
10:35 am-3:03 pm
1 stop6h 28m
$317
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Mon 8/24
10:55 pm-9:16 am
1 stop8h 21m
Milwaukee-Mitchell
Sat 8/29
10:24 am-6:55 pm
1 stop10h 31m
$337
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/2
6:35 am-4:40 pm
2 stops8h 05m
Milwaukee-Mitchell
Sun 9/6
7:00 am-1:15 pm
1 stop8h 15m
$345
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/9
5:00 am-1:34 pm
1 stop6h 34m
Milwaukee-Mitchell
Sun 9/20
5:00 am-11:28 am
1 stop8h 28m
$391
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 9/4
11:50 am-9:22 pm
1 stop7h 32m
Milwaukee-Mitchell
Sun 9/6
7:30 am-12:10 pm
1 stop6h 40m
$403
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 8/12
10:35 am-9:25 pm
2 stops8h 50m
Milwaukee-Mitchell
Mon 8/17
4:50 pm-10:45 pm
2 stops7h 55m
$409
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/9
7:15 pm-10:00 am
2 stops12h 45m
Milwaukee-Mitchell
Mon 9/14
2:40 pm-9:05 pm
1 stop8h 25m
$432
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Thu 9/10
11:02 pm-10:00 am
1 stop8h 58m
Milwaukee-Mitchell
Tue 9/15
5:00 am-2:47 pm
2 stops11h 47m
$432
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 7/7
11:30 pm-10:55 am
1 stop9h 25m
Milwaukee-Mitchell
Thu 7/9
5:15 am-11:35 am
2 stops8h 20m
$438
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 7/8
10:25 am-10:05 pm
2 stops9h 40m
Milwaukee-Mitchell
Wed 7/15
5:00 am-12:00 pm
2 stops9h 00m
$448
Showing 1-10 of 23 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 $572). 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 15, 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
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Milwaukee flight routes
Other flight options
Other flights from Portland
Popular flights
Alternative routes for Portland to Milwaukee
See prices for flight routes from nearby airports that may be better suited for you.
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
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 15, 2026.
Portland and Milwaukee flights
Browse other Portland and Milwaukee flight options. Last updated on June 15, 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 15, 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 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$424 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$489 | 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$535 | FlexibilityNo cancel fee | On-time63% |