$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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PDX
Dec 5 — Dec 121
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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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 November 5, 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 November 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 11/2. 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.
Mon 11/234:33 pm -
1 stop8h 25m
Fri 11/278:22 am -
1 stop13h 37m
Deal found 11/2![Alaska Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 11/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:38 pm -
2 stops10h 07m
Mon 12/72:26 pm -
1 stop6h 29m
Deal found 11/4![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 10/31. 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 12/247:33 am -
1 stop7h 23m
Wed 1/65:00 am -
1 stop7h 08m
Deal found 10/31![American Airlines logo]()
$340
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/14:25 pm -
1 stop6h 29m
Mon 12/77:18 pm -
1 stop18h 09m
Deal found 11/3![Alaska Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 10/31. 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 12/177:40 pm -
1 stop7h 45m
Thu 12/2411:25 am -
2 stops8h 25m
Deal found 10/31![Southwest logo]()
$363
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/45:00 am -
1 stop9h 37m
Sun 12/611:39 pm -
1 stop9h 40m
Deal found 11/2![American Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 11/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:38 pm -
2 stops10h 07m
Sun 12/65:00 am -
1 stop6h 24m
Deal found 11/4![United Airlines logo]()
$371
This Southwest deal was found by Cheapflights users on 11/3. 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 12/145:15 am -
1 stop7h 35m
Mon 12/212:00 pm -
2 stops9h 25m
Deal found 11/3![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 11/2. 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 12/42:15 pm -
2 stops10h 05m
Sun 12/612:10 pm -
2 stops9h 00m
Deal found 11/2![Southwest logo]()
$376
This Orbitz deal was found by Cheapflights users on 10/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:00 am -
2 stops13h 48m
Wed 12/239:45 pm -
1 stop15h 48m
Deal found 10/31![Alaska Airlines logo]()
$378
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 November 5, 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 November 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/74:25 pm -
1 stop7h 27m
Tue 12/87:30 am -
1 stop5h 57m
Deal found 11/4![Alaska Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Thu 1/288:21 am -
1 stop7h 06m
Mon 2/17:10 am -
1 stop6h 00m
Deal found 11/2![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 11/2. 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.
Thu 1/283:20 pm -
1 stop8h 55m
Mon 2/16:20 am -
2 stops9h 50m
Deal found 11/2![Southwest logo]()
$322
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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 stop6h 18m
Fri 11/278:22 am -
1 stop13h 37m
Deal found 10/31![Alaska Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 11/4. 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.
Fri 12/42:15 pm -
2 stops10h 05m
Fri 12/111:25 pm -
2 stops9h 20m
Deal found 11/4![Southwest logo]()
$380
This Alaska Airlines deal was found by Cheapflights users on 11/2. 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.
Thu 1/283:17 pm -
2 stops24h 25m
Mon 2/16:30 am -
1 stop5h 49m
Deal found 11/2![Alaska Airlines logo]()
$395
This Southwest deal was found by Cheapflights users on 11/3. 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.
Tue 12/12:15 pm -
2 stops10h 05m
Tue 12/811:40 am -
2 stops7h 50m
Deal found 11/3![Southwest logo]()
$438
This United Airlines deal was found by Cheapflights users on 10/31. 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 11/239:17 am -
2 stops13h 45m
Fri 11/277:00 am -
1 stop5h 58m
Deal found 10/31![United Airlines logo]()
$483
This Southwest deal was found by Cheapflights users on 11/1. 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 12/15:15 am -
1 stop7h 35m
Sun 12/202:00 pm -
2 stops9h 25m
Deal found 11/1![Southwest logo]()
$466
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/224:27 pm -
1 stop8h 32m
Mon 12/285:53 pm -
2 stops19h 36m
Deal found 11/4![Alaska Airlines logo]()
$497
Last-minute flights from Milwaukee to PortlandDiscover last-minute flight deals from Milwaukee to Portland. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Portland. Data last updated November 5, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 11/2. 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.
Mon 11/234:33 pm -
1 stop8h 25m
Fri 11/278:22 am -
1 stop13h 37m
Deal found 11/2![Alaska Airlines logo]()
$317
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/14:25 pm -
1 stop6h 29m
Mon 12/77:18 pm -
1 stop18h 09m
Deal found 11/3![Alaska Airlines logo]()
$358
This United Airlines deal was found by Cheapflights users on 11/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:38 pm -
2 stops10h 07m
Mon 12/72:26 pm -
1 stop6h 29m
Deal found 11/4![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/45:00 am -
1 stop9h 37m
Sun 12/611:39 pm -
1 stop9h 40m
Deal found 11/2![American Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/43:59 pm -
1 stop7h 16m
Sun 12/65:00 am -
2 stops8h 03m
Deal found 11/3![United Airlines logo]()
$371
This Southwest deal was found by Cheapflights users on 11/2. 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 12/42:15 pm -
2 stops10h 05m
Sun 12/612:10 pm -
2 stops9h 00m
Deal found 11/2![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 11/3. 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 12/145:15 am -
1 stop7h 35m
Mon 12/212:00 pm -
2 stops9h 25m
Deal found 11/3![Southwest logo]()
$375
This Orbitz deal was found by Cheapflights users on 10/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:00 am -
2 stops13h 48m
Wed 12/239:45 pm -
1 stop15h 48m
Deal found 10/31![Alaska Airlines logo]()
$378
This Southwest deal was found by Cheapflights users on 10/31. 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 12/177:40 pm -
1 stop7h 45m
Thu 12/2411:25 am -
2 stops8h 25m
Deal found 10/31![Southwest logo]()
$363
This American Airlines deal was found by Cheapflights users on 10/31. 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 12/247:33 am -
1 stop7h 23m
Wed 1/65:00 am -
1 stop7h 08m
Deal found 10/31![American Airlines logo]()
$340
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 November 5, 2026.
Search for one-way flight options from Milwaukee to Portland. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Thu 11/266:47 am -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![United Airlines logo]()
$159
This Southwest deal was found by Cheapflights users on 10/31. 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 12/176:25 pm -
2 stops17h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 11/4. 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.
Thu 12/244:20 pm -
1 stop9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:11 pm -
2 stops42h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$178
This American Airlines deal was found by Cheapflights users on 10/31. 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 12/247:33 am -
1 stop7h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![American Airlines logo]()
$182
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/39:15 am -
2 stops10h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![United Airlines logo]()
$191
This Priceline deal was found by Cheapflights users on 11/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/14:25 pm -
1 stop7h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Alaska Airlines logo]()
$200
This Southwest deal was found by Cheapflights users on 11/3. 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.
Tue 11/248:00 pm -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$258
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 November 5, 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 | $554 |
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 November 5, 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
Fri 12/25
7:15 am-12:23 pm
1 stop7h 08m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Thu 11/26
6:47 am-11:47 am
1 stop7h 00m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
Quickest round-trip
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Thu 12/3
6:24 am-10:48 am
1 stop6h 24m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$159
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Wed 12/9
10:38 am-6:23 pm
2 stops9h 45m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$164
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Thu 12/17
6:25 pm-10:15 am
2 stops17h 50m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$170
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Thu 12/24
4:20 pm-11:25 pm
1 stop9h 05m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$171
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Thu 12/3
9:15 am-6:07 pm
2 stops10h 52m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$191
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Fri 12/25
6:00 am-1:24 pm
1 stop9h 24m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$200
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Fri 12/25
6:20 am-1:10 pm
2 stops8h 50m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$259
MilwaukeePortland
MKE Milwaukee-Mitchell - PDX Portland
MKEPDX
Milwaukee-Mitchell
Tue 12/22
6:15 pm-1:15 am
2 stops9h 00m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$259
Showing 1-10 of 20 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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 $468 and $649 in January.The cheapest round-trip price found within the last 5 days was $317 on Delta (Jan 7-Jan 11).
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 November 5, 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
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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
Cannon Beach
Longview
Lake Oswego
Lincoln City
Vancouver
Kelso
Troutdale
Clackamas
McMinnville
The Dalles
Wilsonville
Stevenson
Hillsboro
Astoria
Tillamook
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Milwaukee and Portland flights
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Other flights from Milwaukee
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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 November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$254 | Average$442 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$305 | Average$506 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$306 | Average$493 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$316 | Average$434 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$336 | Average$516 | FlexibilityNo cancel fee | On-time63% |