$159+ 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 6/22. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Jun 3 — Jun 101
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 May 4, 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 May 4, 2026.
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:15 pm
PDX
- MKE
1 stop7h 56m
United Airlines
Tue 9/155:50 pm
MKE
- PDX
1 stop7h 02m
United Airlines
Deal found 5/1![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:34 pm
PDX
- MKE
1 stop8h 00m
American Airlines
Sat 6/68:00 am
MKE
- PDX
1 stop8h 38m
American Airlines
Deal found 4/29![American Airlines logo]()
$325
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/192:38 pm
PDX
- MKE
1 stop5h 55m
United Airlines
Wed 5/202:38 pm
MKE
- PDX
1 stop8h 31m
United Airlines
Deal found 4/28![United Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:45 pm
PDX
- MKE
1 stop6h 39m
American Airlines
Thu 5/288:12 am
MKE
- PDX
1 stop8h 23m
American Airlines
Deal found 4/30![American Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:40 am
PDX
- MKE
2 stops9h 35m
Southwest
Tue 6/166:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 4/29![Southwest logo]()
$342
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1710:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Wed 6/246:21 pm
MKE
- PDX
1 stop8h 29m
American Airlines
Deal found 5/1![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1710:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Tue 6/306:50 pm
MKE
- PDX
1 stop6h 57m
American Airlines
Deal found 5/1![American Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:30 pm
PDX
- MKE
1 stop9h 30m
Southwest
Tue 9/153:40 pm
MKE
- PDX
2 stops8h 35m
Southwest
Deal found 5/1![Southwest logo]()
$359
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:40 pm
PDX
- MKE
1 stop9h 36m
American Airlines
Tue 5/265:00 am
MKE
- PDX
1 stop6h 57m
American Airlines
Deal found 4/29![American Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:00 am
PDX
- MKE
2 stops8h 25m
Southwest
Wed 5/275:45 pm
MKE
- PDX
1 stop7h 15m
Southwest
Deal found 4/29![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3011:40 pm
PDX
- MKE
1 stop8h 18m
United Airlines
Sat 7/41:30 pm
MKE
- PDX
1 stop7h 17m
United Airlines
Deal found 4/30![United Airlines logo]()
$367
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 May 4, 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 May 4, 2026.
This American Airlines deal was found by Cheapflights users on 5/3. 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 6/31:34 pm
PDX
- MKE
1 stop8h 00m
American Airlines
Sat 6/65:00 am
MKE
- PDX
1 stop7h 22m
American Airlines
Deal found 5/3![American Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 5/2. 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 6/103:40 pm
PDX
- MKE
1 stop7h 15m
Southwest
Tue 6/163:40 pm
MKE
- PDX
2 stops8h 55m
Southwest
Deal found 5/2![Southwest logo]()
$393
This United Airlines deal was found by Cheapflights users on 5/3. 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 6/311:05 am
PDX
- MKE
2 stops9h 14m
United Airlines
Sat 6/62:35 pm
MKE
- PDX
1 stop8h 35m
United Airlines
Deal found 5/3![United Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:12 pm
PDX
- MKE
1 stop7h 37m
Delta
Mon 5/255:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 5/2![Delta logo]()
$484
This Southwest deal was found by Cheapflights users on 5/2. 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 7/2210:40 am
PDX
- MKE
2 stops9h 35m
Southwest
Tue 7/286:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 5/2![Southwest logo]()
$422
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stops9h 30m
Southwest
Tue 7/76:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 4/30![Southwest logo]()
$422
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1810:10 am
PDX
- MKE
2 stops11h 30m
Southwest
Wed 7/226:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 4/29![Southwest logo]()
$452
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2110:25 am
PDX
- MKE
2 stops9h 35m
Southwest
Fri 7/241:50 pm
MKE
- PDX
2 stops10h 20m
Southwest
Deal found 4/30![Southwest logo]()
$457
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:15 pm
PDX
- MKE
2 stops8h 10m
Southwest
Tue 6/93:40 pm
MKE
- PDX
2 stops8h 55m
Southwest
Deal found 4/29![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:15 pm
PDX
- MKE
2 stops8h 10m
Southwest
Sun 6/75:20 am
MKE
- PDX
1 stop6h 10m
Southwest
Deal found 4/30![Southwest logo]()
$482
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated May 4, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/192:38 pm
PDX
- MKE
1 stop5h 55m
United Airlines
Wed 5/202:38 pm
MKE
- PDX
1 stop8h 31m
United Airlines
Deal found 4/28![United Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 4/28. 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.
Tue 5/1911:15 am
PDX
- MKE
2 stops8h 20m
Southwest
Wed 5/205:45 pm
MKE
- PDX
1 stop7h 15m
Southwest
Deal found 4/28![Southwest logo]()
$402
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:54 pm
PDX
- MKE
1 stop8h 25m
United Airlines
Wed 5/275:00 am
MKE
- PDX
1 stop6h 39m
United Airlines
Deal found 4/29![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:40 pm
PDX
- MKE
1 stop9h 36m
American Airlines
Tue 5/265:00 am
MKE
- PDX
1 stop6h 57m
American Airlines
Deal found 4/29![American Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:00 am
PDX
- MKE
2 stops8h 25m
Southwest
Wed 5/275:45 pm
MKE
- PDX
1 stop7h 15m
Southwest
Deal found 4/29![Southwest logo]()
$363
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:43 pm
PDX
- MKE
1 stop9h 38m
American Airlines
Mon 5/255:00 am
MKE
- PDX
1 stop6h 59m
American Airlines
Deal found 5/1![American Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:45 pm
PDX
- MKE
1 stop6h 39m
American Airlines
Thu 5/288:12 am
MKE
- PDX
1 stop8h 23m
American Airlines
Deal found 4/30![American Airlines logo]()
$333
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:44 am
PDX
- MKE
1 stop12h 15m
Alaska Airlines
Thu 5/287:00 am
MKE
- PDX
2 stops11h 30m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:39 pm
PDX
- MKE
1 stop9h 29m
Delta
Wed 5/2712:15 pm
MKE
- PDX
1 stop7h 00m
Delta
Deal found 4/28![Delta logo]()
$325
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/2911:59 am
PDX
- MKE
1 stop9h 35m
American Airlines
Mon 6/15:00 am
MKE
- PDX
1 stop6h 59m
American Airlines
Deal found 5/2![American Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:25 am
PDX
- MKE
2 stops9h 25m
Southwest
Mon 6/17:05 pm
MKE
- PDX
1 stop7h 50m
Southwest
Deal found 5/2![Southwest logo]()
$403
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 May 4, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2212:33 am
PDX
- MKE
1 stop6h 42m
Delta
Deal found 4/29![Delta logo]()
$159
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/811:15 pm
PDX
- MKE
1 stop7h 36m
Delta
Deal found 5/1![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:40 am
PDX
- MKE
2 stops9h 35m
Southwest
Deal found 5/1![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 5/3. 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 6/16:00 am
PDX
- MKE
2 stops14h 20m
Southwest
Deal found 5/3![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:33 am
PDX
- MKE
1 stop6h 42m
Delta
Deal found 5/1![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 5/2. 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 5/2![Southwest logo]()
$214
This United Airlines deal was found by Cheapflights users on 5/2. 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 6/811:30 pm
PDX
- MKE
2 stops13h 06m
United Airlines
Deal found 5/2![United Airlines logo]()
$222
This Alaska Airlines deal was found by Cheapflights users on 5/2. 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.
Sat 5/239:44 am
PDX
- MKE
2 stops10h 40m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$234
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1310:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Deal found 4/30![American Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:25 pm
PDX
- MKE
2 stops8h 00m
Southwest
Deal found 5/1![Southwest logo]()
$244
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:43 pm
PDX
- MKE
1 stop9h 38m
American Airlines
Deal found 5/1![American Airlines logo]()
$254
This CheapOair deal was found by Cheapflights users on 5/3. 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.
Sat 5/232:30 pm
PDX
- MKE
1 stop15h 21m
JetBlue
Deal found 5/3![JetBlue logo]()
$258
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 May 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (United Airlines) |
One-way from | $159 (Delta) |
Popular in | February |
Cheapest in | January |
Average price | $506 |
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 May 4, 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 6/3
1:34 pm-11:34 pm
1 stop8h 00m
Milwaukee-Mitchell
Sat 6/6
5:00 am-10:22 am
1 stop7h 22m
$325
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 6/10
3:40 pm-12:55 am
1 stop7h 15m
Milwaukee-Mitchell
Tue 6/16
3:40 pm-10:35 pm
2 stops8h 55m
$393
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 7/22
10:40 am-10:15 pm
2 stops9h 35m
Milwaukee-Mitchell
Tue 7/28
6:55 pm-11:50 pm
1 stop6h 55m
$422
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 7/3
12:15 pm-11:45 pm
2 stops9h 30m
Milwaukee-Mitchell
Tue 7/7
6:55 pm-11:50 pm
1 stop6h 55m
$422
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 6/3
11:05 am-10:19 pm
2 stops9h 14m
Milwaukee-Mitchell
Sat 6/6
2:35 pm-9:10 pm
1 stop8h 35m
$430
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Sat 7/18
10:10 am-11:40 pm
2 stops11h 30m
Milwaukee-Mitchell
Wed 7/22
6:55 pm-11:50 pm
1 stop6h 55m
$452
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 7/21
10:25 am-10:00 pm
2 stops9h 35m
Milwaukee-Mitchell
Fri 7/24
1:50 pm-10:10 pm
2 stops10h 20m
$457
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 6/5
12:15 pm-10:25 pm
2 stops8h 10m
Milwaukee-Mitchell
Tue 6/9
3:40 pm-10:35 pm
2 stops8h 55m
$472
Quickest round-trip
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 6/5
12:15 pm-10:25 pm
2 stops8h 10m
Milwaukee-Mitchell
Sun 6/7
5:20 am-9:30 am
1 stop6h 10m
$482
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 5/22
11:12 pm-8:49 am
1 stop7h 37m
Milwaukee-Mitchell
Mon 5/25
5:01 pm-10:02 pm
1 stop7h 01m
$484
Showing 1-10 of 20 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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Milwaukee flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Portland with our price prediction graph.
PDX-MKE
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Milwaukee
How far ahead should I book a flight from Portland to Milwaukee?
Booking 34 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Milwaukee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Portland to Milwaukee?
Currently, January is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $324). Flying from Portland to Milwaukee in February is currently the most expensive (average of $570). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Portland to Milwaukee?
Reviews of airlines servicing Milwaukee
Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated May 4, 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.
Boarding
8.1
Overall
7.9
Food
7.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Overall
7.9
Food
7.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Overall
7.9
Food
7.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Overall
7.9
Food
7.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Overall
7.9
Food
7.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Overall
7.9
Food
7.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
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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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 May 4, 2026.
Portland and Milwaukee flights
Browse other Portland and Milwaukee flight options. Last updated on May 4, 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 May 4, 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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$434 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$405 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$298 | Average$451 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$307 | Average$406 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$322 | Average$492 | FlexibilityNo cancel fee | On-time63% |