$159+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PDX
Oct 8 — Oct 151
Round-trip
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Milwaukee to Portland
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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 September 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 September 8, 2026.
This Delta deal was found by Cheapflights users on 9/7. 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.
Tue 10/2012:36 pm -
1 stop11h 13m
Sat 10/316:50 am -
1 stop8h 35m
Deal found 9/7![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Sat 10/32:20 pm -
2 stops8h 50m
Tue 10/67:02 am -
1 stop6h 09m
Deal found 9/3![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/171:55 pm -
2 stops11h 30m
Wed 1/66:20 am -
2 stops8h 25m
Deal found 9/7![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 10/234:56 pm -
1 stop7h 06m
Thu 10/2911:51 am -
1 stop7h 22m
Deal found 9/7![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 9/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/282:55 pm -
1 stop8h 52m
Thu 10/112:25 am -
1 stop7h 39m
Deal found 9/3![Delta logo]()
$332
This American Airlines deal was found by Cheapflights users on 9/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:00 am -
1 stop9h 22m
Sat 10/245:20 am -
1 stop9h 37m
Deal found 9/4![American Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 9/3. 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.
Fri 10/2310:25 am -
2 stops14h 45m
Tue 10/272:15 pm -
1 stop7h 40m
Deal found 9/3![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 10/234:56 pm -
1 stop7h 06m
Fri 10/301:10 pm -
1 stop6h 46m
Deal found 9/7![Delta logo]()
$345
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 10/11:18 pm -
1 stop8h 18m
Thu 10/810:55 pm -
1 stop7h 12m
Deal found 9/3![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Mon 9/285:00 am -
1 stop6h 31m
Wed 9/3012:45 pm -
2 stops8h 14m
Deal found 9/3![United Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 9/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:52 pm -
1 stop11h 04m
Tue 12/811:23 pm -
1 stop7h 50m
Deal found 9/3![Delta logo]()
$352
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 September 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 September 8, 2026.
This Delta deal was found by Cheapflights users on 9/7. 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.
Wed 10/2112:36 pm -
1 stop11h 13m
Wed 10/283:31 pm -
2 stops15h 09m
Deal found 9/7![Delta logo]()
$385
This United Airlines deal was found by Cheapflights users on 9/5. 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 11/125:45 pm -
1 stop7h 24m
Mon 11/162:34 pm -
1 stop5h 41m
Deal found 9/5![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 9/6. 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 11/231:55 pm -
2 stops11h 05m
Fri 11/275:00 am -
1 stop6h 15m
Deal found 9/6![Southwest logo]()
$422
This Alaska Airlines deal was found by Cheapflights users on 9/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:53 pm -
1 stop19h 54m
Sun 10/2511:03 am -
1 stop27h 16m
Deal found 9/5![Alaska Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 10/155:00 am -
1 stop6h 31m
Sat 10/178:25 am -
2 stops12h 34m
Deal found 9/3![United Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 9/6. 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.
Thu 10/225:00 pm -
1 stop9h 15m
Sat 10/242:40 pm -
1 stop7h 35m
Deal found 9/6![Southwest logo]()
$452
This Delta deal was found by Cheapflights users on 9/5. 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.
Fri 10/234:56 pm -
2 stops9h 03m
Mon 10/268:44 pm -
2 stops11h 25m
Deal found 9/5![Delta logo]()
$473
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Fri 12/49:15 am -
1 stop8h 11m
Mon 12/147:21 pm -
2 stops10h 14m
Deal found 9/3![United Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 9/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:36 pm -
1 stop8h 33m
Sun 10/2511:00 pm -
1 stop8h 11m
Deal found 9/4![Delta logo]()
$483
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Mon 10/195:00 am -
1 stop6h 31m
Mon 10/2611:33 pm -
1 stop8h 40m
Deal found 9/3![United Airlines logo]()
$482
This Delta deal was found by Cheapflights users on 9/5. 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.
Sat 9/263:59 pm -
1 stop6h 17m
Fri 10/28:44 pm -
2 stops10h 04m
Deal found 9/5![Delta logo]()
$485
Last-minute flights from Milwaukee to PortlandDiscover last-minute flight deals from Milwaukee to Portland. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Portland. Data last updated September 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/282:55 pm -
1 stop8h 52m
Thu 10/112:25 am -
1 stop7h 39m
Deal found 9/3![Delta logo]()
$332
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Mon 9/285:00 am -
1 stop6h 31m
Wed 9/3012:45 pm -
2 stops8h 14m
Deal found 9/3![United Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 10/11:18 pm -
1 stop8h 18m
Thu 10/810:55 pm -
1 stop7h 12m
Deal found 9/3![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Sat 10/32:20 pm -
2 stops8h 50m
Tue 10/67:02 am -
1 stop6h 09m
Deal found 9/3![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 9/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:00 am -
1 stop9h 22m
Sat 10/245:20 am -
1 stop9h 37m
Deal found 9/4![American Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 9/7. 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.
Tue 10/205:45 pm -
1 stop7h 59m
Mon 10/2611:00 pm -
1 stop8h 11m
Deal found 9/7![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 9/7. 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.
Wed 10/2112:36 pm -
1 stop11h 13m
Fri 10/305:49 pm -
2 stops14h 20m
Deal found 9/7![Delta logo]()
$385
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 10/234:56 pm -
1 stop7h 06m
Thu 10/2911:51 am -
1 stop7h 22m
Deal found 9/7![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 9/3. 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.
Fri 10/2310:25 am -
2 stops14h 45m
Tue 10/272:15 pm -
1 stop7h 40m
Deal found 9/3![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 10/234:56 pm -
1 stop7h 06m
Fri 10/301:10 pm -
1 stop6h 46m
Deal found 9/7![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 10/233:20 pm -
1 stop6h 42m
Sun 11/15:49 pm -
2 stops12h 51m
Deal found 9/7![Delta logo]()
$399
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 September 8, 2026.
Search for one-way flight options from Milwaukee to Portland. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 9/245:00 am -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![United Airlines logo]()
$159
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:30 pm -
2 stops10h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 9/3. 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.
Fri 10/28:00 pm -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$174
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Tue 10/62:20 pm -
2 stops8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![United Airlines logo]()
$206
This Trip.com deal was found by Cheapflights users on 9/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:53 pm -
1 stop9h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Alaska Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 9/7. 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 9/283:59 pm -
1 stop6h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 9/6. 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 10/196:30 am -
2 stops10h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Southwest logo]()
$214
This Sun Country Air deal was found by Cheapflights users on 9/4. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:35 pm -
1 stop24h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Sun Country Air logo]()
$218
This United Airlines deal was found by Cheapflights users on 9/5. 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.
Mon 10/195:00 am -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![United Airlines logo]()
$228
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 September 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (Delta) |
One-way from | $159 (United Airlines) |
Popular in | July |
Cheapest in | May |
Average price | $434 |
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 September 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
Thu 10/22
12:36 pm-7:09 pm
1 stop8h 33m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Tue 10/20
2:30 pm-11:10 pm
2 stops10h 40m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$164
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Tue 10/6
2:20 pm-9:10 pm
2 stops8h 50m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$206
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Mon 11/2
5:45 pm-11:44 pm
1 stop7h 59m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$209
Quickest round-trip
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Thu 10/8
5:00 am-9:31 am
1 stop6h 31m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$209
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Mon 10/19
6:30 am-2:50 pm
2 stops10h 20m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$214
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Wed 10/21
4:00 pm-11:40 pm
2 stops9h 40m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$214
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Mon 11/2
6:10 pm-1:20 am
2 stops9h 10m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$214
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Sun 10/11
6:35 pm-5:17 pm
1 stop24h 42m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$218
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Mon 10/19
5:00 am-9:31 am
1 stop6h 31m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$228
Showing 1-10 of 21 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 September.
| 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
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 $387). 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 $344 and $552 in October.The cheapest round-trip price found within the last 5 days was $317 on Delta (Oct 20-Oct 31).
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 September 8, 2026.
Read through reviews of airlines operating flights from Milwaukee to Portland, such as Southwest,Alaska Airlines, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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
Lincoln City
Durham
Longview
Lake Oswego
Kelso
Clackamas
Troutdale
Vancouver
Cannon Beach
McMinnville
The Dalles
Wilsonville
Stevenson
Tillamook
Hillsboro
Astoria
Gresham
Silverton
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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 September 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$254 | Average$442 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$259 | Average$417 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$266 | Average$482 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$305 | Average$486 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$319 | Average$504 | FlexibilityNo cancel fee | On-time63% |