$156+ Cheap flights from Milwaukee to Portland (MKE - PDX)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PDX
Nov 7 — Nov 141
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 Milwaukee to PortlandExplore the most affordable flight options available from Milwaukee to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 8, 2026.
Explore the most affordable flight options available from Milwaukee to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 8, 2026.
This United Airlines deal was found by Cheapflights users on 10/8. 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 10/296:47 am -
1 stop7h 00m
Wed 11/411:30 pm -
1 stop7h 06m
Deal found 10/8![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:15 pm -
1 stop9h 05m
Tue 11/102:10 pm -
1 stop6h 35m
Deal found 10/4![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 10/8. 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.
Sat 11/71:24 pm -
2 stops11h 18m
Sat 11/145:30 am -
2 stops8h 53m
Deal found 10/8![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Sat 11/72:23 pm -
2 stops9h 05m
Sat 11/145:00 am -
1 stop6h 34m
Deal found 10/8![United Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 10/4. 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 11/45:15 am -
1 stop7h 35m
Mon 11/911:30 pm -
1 stop9h 30m
Deal found 10/4![Southwest logo]()
$318
This United Airlines deal was found by Cheapflights users on 10/8. 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 11/52:35 pm -
1 stop8h 38m
Tue 11/1011:30 pm -
1 stop7h 06m
Deal found 10/8![United Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Thu 11/55:45 pm -
1 stop7h 24m
Mon 11/92:34 pm -
1 stop5h 41m
Deal found 10/5![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 10/8. 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 10/298:00 pm -
1 stop7h 25m
Wed 11/410:15 am -
2 stops9h 35m
Deal found 10/8![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 10/8. 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.
Fri 10/304:56 pm -
2 stops9h 03m
Mon 11/26:00 am -
1 stop8h 31m
Deal found 10/8![Delta logo]()
$342
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Fri 12/257:05 am -
1 stop8h 07m
Thu 12/311:46 pm -
1 stop6h 36m
Deal found 10/6![American Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 10/8. 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.
Thu 11/1210:53 am -
2 stops13h 04m
Mon 11/167:35 pm -
2 stops12h 37m
Deal found 10/8![Delta logo]()
$344
Best flights from Milwaukee to PortlandDiscover carefully curated flight deals from Milwaukee to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 8, 2026.
Discover carefully curated flight deals from Milwaukee to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 8, 2026.
This Southwest deal was found by Cheapflights users on 10/5. 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.
Sat 11/75:35 am -
1 stop7h 00m
Sat 11/146:55 am -
1 stop5h 40m
Deal found 10/5![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 10/8. 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.
Sun 11/85:45 pm -
1 stop8h 20m
Sat 11/147:00 am -
2 stops11h 15m
Deal found 10/8![Delta logo]()
$430
This Alaska Airlines deal was found by Cheapflights users on 10/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:33 pm -
1 stop7h 21m
Fri 11/276:22 am -
1 stop7h 13m
Deal found 10/6![Alaska Airlines logo]()
$443
This Southwest deal was found by Cheapflights users on 10/4. 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 11/412:45 pm -
2 stops10h 45m
Mon 11/911:30 pm -
1 stop9h 30m
Deal found 10/4![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 10/7. 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.
Thu 12/247:09 am -
2 stops13h 50m
Mon 1/46:40 am -
2 stops12h 45m
Deal found 10/7![Delta logo]()
$439
This Southwest deal was found by Cheapflights users on 10/6. 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.
Mon 11/237:40 pm -
1 stop7h 45m
Fri 11/275:45 am -
2 stops9h 30m
Deal found 10/6![Southwest logo]()
$400
This Alaska Airlines deal was found by Cheapflights users on 10/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/223:59 pm -
1 stop8h 59m
Tue 12/299:35 pm -
1 stop15h 26m
Deal found 10/3![Alaska Airlines logo]()
$487
This Southwest deal was found by Cheapflights users on 10/5. 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.
Tue 11/35:15 am -
2 stops10h 10m
Thu 11/511:20 am -
2 stops8h 50m
Deal found 10/5![Southwest logo]()
$428
This Alaska Airlines deal was found by Cheapflights users on 10/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/114:40 pm -
1 stop8h 20m
Mon 11/166:08 am -
1 stop7h 34m
Deal found 10/3![Alaska Airlines logo]()
$487
This Alaska Airlines deal was found by Cheapflights users on 10/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:00 am -
2 stops10h 38m
Sat 12/57:30 am -
1 stop5h 57m
Deal found 10/6![Alaska Airlines logo]()
$500
This Southwest deal was found by Cheapflights users on 10/6. 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 11/2412:55 pm -
2 stops10h 10m
Fri 11/275:45 am -
2 stops9h 30m
Deal found 10/6![Southwest logo]()
$518
This Southwest deal was found by Cheapflights users on 10/3. 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.
Thu 10/296:30 pm -
1 stop6h 15m
Sat 10/318:15 am -
1 stop6h 30m
Deal found 10/3![Southwest logo]()
$547
Last-minute flights from Milwaukee to PortlandDiscover last-minute flight deals from Milwaukee to Portland. Data last updated October 8, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Portland. Data last updated October 8, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/8. 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 10/296:47 am -
1 stop7h 00m
Wed 11/411:30 pm -
1 stop7h 06m
Deal found 10/8![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 10/8. 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 10/298:00 pm -
1 stop7h 25m
Wed 11/410:15 am -
2 stops9h 35m
Deal found 10/8![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 10/8. 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.
Fri 10/304:56 pm -
2 stops9h 03m
Mon 11/26:00 am -
1 stop8h 31m
Deal found 10/8![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:15 pm -
1 stop9h 05m
Tue 11/102:10 pm -
1 stop6h 35m
Deal found 10/4![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 10/4. 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 11/45:15 am -
1 stop7h 35m
Mon 11/911:30 pm -
1 stop9h 30m
Deal found 10/4![Southwest logo]()
$318
This United Airlines deal was found by Cheapflights users on 10/8. 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 11/52:35 pm -
1 stop8h 38m
Tue 11/1011:30 pm -
1 stop7h 06m
Deal found 10/8![United Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Thu 11/55:45 pm -
1 stop7h 24m
Mon 11/92:34 pm -
1 stop5h 41m
Deal found 10/5![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 10/8. 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.
Sat 11/71:24 pm -
2 stops11h 18m
Sat 11/145:30 am -
2 stops8h 53m
Deal found 10/8![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Sat 11/72:23 pm -
2 stops9h 05m
Sat 11/145:00 am -
1 stop6h 34m
Deal found 10/8![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 10/8. 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.
Thu 11/1210:53 am -
2 stops13h 04m
Mon 11/167:35 pm -
2 stops12h 37m
Deal found 10/8![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 10/7. 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 11/2310:53 am -
2 stops13h 04m
Fri 11/277:00 am -
2 stops9h 10m
Deal found 10/7![Delta logo]()
$354
One-way flights from Milwaukee to PortlandSearch for one-way flight options from Milwaukee to Portland. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
Search for one-way flight options from Milwaukee to Portland. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
This Southwest deal was found by Cheapflights users on 10/5. 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.
Wed 11/412:45 pm -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Southwest logo]()
$156
This United Airlines deal was found by Cheapflights users on 10/5. 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 11/410:48 am -
2 stops9h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![United Airlines logo]()
$161
This Southwest deal was found by Cheapflights users on 10/5. 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.
Sat 11/76:15 am -
2 stops10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Southwest logo]()
$162
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Thu 10/299:18 am -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![United Airlines logo]()
$174
This Southwest deal was found by Cheapflights users on 10/5. 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.
Mon 11/26:10 pm -
2 stops9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Southwest logo]()
$180
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Fri 11/612:03 pm -
1 stop9h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![United Airlines logo]()
$200
This Southwest deal was found by Cheapflights users on 10/8. 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.
Sun 12/134:50 pm -
1 stop9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$208
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Fri 10/309:18 am -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![United Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:15 am -
2 stops51h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$225
Find flight deals from Milwaukee to Portland
Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Portland (PDX). 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 October 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $311 (United Airlines) |
One-way from | $156 (Southwest) |
Popular in | July |
Cheapest in | May |
Average price | $422 |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee to Portland 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 7,457,451 searches. Data last updated October 8, 2026.
Use the filters below to find and compare flights from Milwaukee to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Sat 11/7
12:42 pm-9:49 pm
1 stop11h 07m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$156
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Sat 10/31
6:25 am-3:45 pm
2 stops11h 20m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$180
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Tue 11/3
10:48 am-9:13 pm
3 stops12h 25m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$226
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Tue 12/29
8:00 pm-1:10 am
1 stop7h 10m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$244
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Sun 11/15
6:10 pm-1:25 am
2 stops9h 15m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$249
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Sun 11/1
5:00 am-12:05 pm
1 stop9h 05m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$274
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Sun 10/18
6:15 pm-5:27 pm
1 stop25h 12m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$298
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Sat 11/7
5:35 am-10:35 am
1 stop7h 00m
Portland
Sat 11/14
6:55 am-2:35 pm
1 stop5h 40m
$312
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Thu 10/22
2:39 pm-9:10 pm
1 stop8h 31m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$314
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Sun 12/13
6:00 am-6:23 pm
3 stops14h 23m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$314
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Milwaukee to Portland
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 Milwaukee to Portland in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Milwaukee-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milwaukee-Portland flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Milwaukee-Portland 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 Milwaukee-Portland 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 Milwaukee to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Milwaukee with our price prediction graph.
MKE-PDX
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 Milwaukee to Portland
Prices
More
How far ahead should I book a flight from Milwaukee to Portland?
The best time to book flights from Milwaukee to Portland is 22 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Milwaukee to Portland?
Currently, May is the cheapest month in which you can book a flight from Milwaukee to Portland (average of $395). Flying from Milwaukee to Portland in July 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 Milwaukee to Portland?
Airfare is below average for this route at the moment.
Milwaukee to Portland flights typically cost between $365 and $517 in October.The cheapest round-trip price found within the last 5 days was $311 on United Airlines (Oct 29-Nov 4).
What’s the top layover airport for flights from Milwaukee to Portland?
Share of 1-stop round-trip flights from Milwaukee to Portland chosen by Cheapflights users in the past 12 months, using the same layover each way.
Chicago (ORD) – chosen by Cheapflights users on 50% of 1-stop itineraries from Milwaukee to Portland on Cheapflights.
What’s the cheapest layover airport for flights from Milwaukee to Portland?
Average round-trip fare for 1-stop flights from Milwaukee to Portland, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Minneapolis (MSP) is the most affordable 1-stop option, with an average round-trip price of $282.
What’s the fastest layover option from Milwaukee to Portland?
Shortest average travel time for 1-stop one-way flights from Milwaukee to Portland, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 6h 12m.
Which airport typically offers the quickest layover for flights from Milwaukee to Portland?
Average layover duration for 1-stop one-way flights from Milwaukee to Portland, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 0h 46m.
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated October 8, 2026.
Read through reviews of airlines operating flights from Milwaukee to Portland, such as Alaska Airlines,Southwest, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Overall
7.9
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Overall
7.9
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Overall
7.9
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Overall
7.9
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Overall
7.9
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Overall
7.9
Entertainment
7.0
Boarding
8.1
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Portland. 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 Portland?
Book flights to Portland if you plan to visit one of these locationsBeaverton
Seaside
Durham
Longview
Lake Oswego
Cannon Beach
Vancouver
Kelso
Troutdale
Lincoln City
Clackamas
McMinnville
The Dalles
Wilsonville
Stevenson
Tillamook
Hillsboro
Astoria
Gresham
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Milwaukee and Portland flights
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Top 5 airlines flying from Milwaukee to Portland
Discover the top 5 airlines that operate flights from Milwaukee to Portland. 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 7,457,451 searches. Data last updated October 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$254 | Average$452 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$305 | Average$486 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$306 | Average$486 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$316 | Average$434 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$320 | Average$505 | FlexibilityNo cancel fee | On-time63% |