$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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Jul 10 — Jul 171
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Portland to MilwaukeeExplore the most affordable flight options available from Portland to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 10, 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 10, 2026.
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:00 am
PDX
- MKE
1 stop6h 34m
United Airlines
Wed 9/235:00 am
MKE
- PDX
1 stop6h 29m
United Airlines
Deal found 6/9![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:50 am
PDX
- MKE
1 stop8h 50m
Southwest
Wed 9/234:25 pm
MKE
- PDX
2 stops7h 50m
Southwest
Deal found 6/9![Southwest logo]()
$311
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.
Tue 7/2811:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Tue 8/45:02 am
MKE
- PDX
1 stop7h 34m
American Airlines
Deal found 6/10![American Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sat 7/43:58 pm
MKE
- PDX
1 stop6h 19m
Delta
Deal found 6/7![Delta logo]()
$329
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:15 am
PDX
- MKE
1 stop5h 58m
Delta
Mon 10/195:50 pm
MKE
- PDX
1 stop7h 57m
Delta
Deal found 6/10![Delta logo]()
$337
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3010:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Tue 7/76:01 am
MKE
- PDX
1 stop6h 35m
American Airlines
Deal found 6/9![American Airlines logo]()
$341
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:45 pm
PDX
- MKE
2 stops8h 14m
United Airlines
Tue 10/135:00 am
MKE
- PDX
1 stop6h 31m
United Airlines
Deal found 6/8![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:35 am
PDX
- MKE
2 stops8h 05m
Southwest
Sat 8/295:30 am
MKE
- PDX
1 stop9h 20m
Southwest
Deal found 6/8![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 6/6. 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 8/1912:30 am
PDX
- MKE
1 stop6h 10m
Delta
Mon 8/246:59 pm
MKE
- PDX
1 stop6h 26m
Delta
Deal found 6/6![Delta logo]()
$359
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:55 am
PDX
- MKE
1 stop7h 14m
Delta
Tue 10/205:50 pm
MKE
- PDX
1 stop7h 57m
Delta
Deal found 6/10![Delta logo]()
$362
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 10, 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 10, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:55 am
PDX
- MKE
1 stop7h 14m
Delta
Tue 10/205:50 pm
MKE
- PDX
1 stop7h 57m
Delta
Deal found 6/10![Delta logo]()
$305
This United 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 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 6/10![United Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 6/5. 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
Sun 8/95:45 am
MKE
- PDX
2 stops10h 20m
Southwest
Deal found 6/5![Southwest logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/305:07 am
PDX
- MKE
1 stop7h 00m
Alaska Airlines
Sat 10/33:54 pm
MKE
- PDX
1 stop8h 05m
Alaska Airlines
Deal found 6/7![Alaska Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 6/5. 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 10/2111:55 am
PDX
- MKE
1 stop7h 14m
Delta
Sat 10/316:45 am
MKE
- PDX
1 stop7h 44m
Delta
Deal found 6/5![Delta logo]()
$344
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:15 am
PDX
- MKE
1 stop5h 58m
Delta
Tue 10/205:00 pm
MKE
- PDX
1 stop6h 53m
Delta
Deal found 6/10![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:30 am
PDX
- MKE
2 stops13h 20m
Southwest
Sun 10/1812:10 pm
MKE
- PDX
1 stop8h 50m
Southwest
Deal found 6/8![Southwest logo]()
$435
This United Airlines deal was found by Cheapflights users on 6/5. 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 9/3010:58 am
PDX
- MKE
1 stop10h 39m
United Airlines
Sat 10/312:05 pm
MKE
- PDX
2 stops12h 52m
United Airlines
Deal found 6/5![United Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:27 pm
PDX
- MKE
1 stop6h 09m
United Airlines
Sun 9/205:00 am
MKE
- PDX
1 stop8h 28m
United Airlines
Deal found 6/8![United Airlines logo]()
$455
This United Airlines deal was found by Cheapflights users on 6/5. 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 10/2110:43 am
PDX
- MKE
1 stop8h 42m
United Airlines
Sat 10/3110:45 am
MKE
- PDX
2 stops8h 53m
United Airlines
Deal found 6/5![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1810:40 pm
PDX
- MKE
1 stop6h 20m
United Airlines
Sat 7/255:00 am
MKE
- PDX
1 stop6h 34m
United Airlines
Deal found 6/9![United Airlines logo]()
$477
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated June 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Fri 7/33:58 pm
MKE
- PDX
1 stop6h 19m
Delta
Deal found 6/7![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3010:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Tue 7/76:01 am
MKE
- PDX
1 stop6h 35m
American Airlines
Deal found 6/9![American Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 7/147:20 am
MKE
- PDX
2 stops9h 20m
Southwest
Deal found 6/9![Southwest logo]()
$408
This American Airlines deal was found by Cheapflights users on 6/6. 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 6/6![American Airlines logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sat 7/45:02 am
MKE
- PDX
1 stop6h 43m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:33 am
PDX
- MKE
1 stop6h 42m
Delta
Wed 7/156:59 pm
MKE
- PDX
1 stop6h 19m
Delta
Deal found 6/9![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:33 am
PDX
- MKE
1 stop6h 42m
Delta
Sat 7/1111:04 am
MKE
- PDX
1 stop8h 31m
Delta
Deal found 6/9![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 6/6. 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
Sat 7/115:45 am
MKE
- PDX
2 stops10h 40m
Southwest
Deal found 6/6![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Tue 7/1411:30 am
MKE
- PDX
2 stops9h 30m
Southwest
Deal found 6/9![Southwest logo]()
$414
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.
Tue 7/2811:15 pm
PDX
- MKE
1 stop6h 47m
American Airlines
Tue 8/45:02 am
MKE
- PDX
1 stop7h 34m
American Airlines
Deal found 6/10![American Airlines logo]()
$317
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:32 am
PDX
- MKE
2 stops11h 29m
Alaska Airlines
Tue 8/46:02 am
MKE
- PDX
1 stop7h 19m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$372
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 10, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:57 pm
PDX
- MKE
1 stop7h 48m
United Airlines
Deal found 6/9![United Airlines logo]()
$153
This Southwest 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 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
Deal found 6/10![Southwest logo]()
$159
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.
Fri 7/31:45 pm
PDX
- MKE
1 stop6h 36m
American Airlines
Deal found 6/10![American Airlines logo]()
$165
This Southwest 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 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 6/10![Southwest logo]()
$170
This Delta deal was found by Cheapflights users on 6/6. 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 6/6![Delta logo]()
$180
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:02 pm
PDX
- MKE
1 stop6h 05m
United Airlines
Deal found 6/8![United Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:20 am
PDX
- MKE
2 stops9h 25m
Southwest
Deal found 6/8![Southwest logo]()
$191
This Southwest 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 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 6/10![Southwest logo]()
$192
This Southwest 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 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 6/10![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/152:08 pm
PDX
- MKE
1 stop7h 48m
Delta
Deal found 6/8![Delta logo]()
$210
This Southwest deal was found by Cheapflights users on 6/6. 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 6/3010:25 am
PDX
- MKE
2 stops9h 50m
Southwest
Deal found 6/6![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:15 am
PDX
- MKE
1 stop6h 54m
Delta
Deal found 6/9![Delta logo]()
$217
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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (Delta) |
One-way from | $153 (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 10, 2026.
Use the filters below to find and compare flights from Portland to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 10/14
11:55 am-9:09 pm
1 stop7h 14m
Milwaukee-Mitchell
Tue 10/20
5:50 pm-11:47 pm
1 stop7h 57m
$305
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 10/21
11:55 am-9:09 pm
1 stop7h 14m
Milwaukee-Mitchell
Sat 10/31
6:45 am-12:29 pm
1 stop7h 44m
$344
Quickest round-trip
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 10/16
6:15 am-2:13 pm
1 stop5h 58m
Milwaukee-Mitchell
Tue 10/20
5:00 pm-9:53 pm
1 stop6h 53m
$369
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
$415
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Thu 8/6
5:15 pm-9:40 am
2 stops14h 25m
Milwaukee-Mitchell
Sun 8/9
5:45 am-2:05 pm
2 stops10h 20m
$434
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Thu 10/15
7:30 am-10:50 pm
2 stops13h 20m
Milwaukee-Mitchell
Sun 10/18
12:10 pm-7:00 pm
1 stop8h 50m
$435
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/30
10:58 am-11:37 pm
1 stop10h 39m
Milwaukee-Mitchell
Sat 10/3
12:05 pm-10:57 pm
2 stops12h 52m
$449
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 9/18
2:27 pm-10:36 pm
1 stop6h 09m
Milwaukee-Mitchell
Sun 9/20
5:00 am-11:28 am
1 stop8h 28m
$455
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 10/21
10:43 am-9:25 pm
1 stop8h 42m
Milwaukee-Mitchell
Sat 10/31
10:45 am-5:38 pm
2 stops8h 53m
$459
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 9/30
5:07 am-2:07 pm
1 stop7h 00m
Milwaukee-Mitchell
Sat 10/3
3:54 pm-9:59 pm
1 stop8h 05m
$477
Showing 1-10 of 22 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 10, 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.
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.5
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.5
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.5
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.5
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.5
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.5
Entertainment
7.0
Comfort
7.8
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
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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 10, 2026.
Portland and Milwaukee flights
Browse other Portland and Milwaukee flight options. Last updated on June 10, 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 10, 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 10, 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$439 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$307 | Average$427 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$322 | Average$535 | FlexibilityNo cancel fee | On-time63% |