$109+ Cheap flights from Milwaukee to Portland (MKE - PDX)
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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PDX
May 18 — May 251
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 April 18, 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 April 18, 2026.
This Delta deal was found by Cheapflights users on 4/13. 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 6/246:30 am
MKE
- PDX
1 stop6h 14m
Delta
Wed 7/12:10 pm
PDX
- MKE
1 stop7h 49m
Delta
Deal found 4/13![Delta logo]()
$317
This American Airlines deal was found by Cheapflights users on 4/16. 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 6/176:21 pm
MKE
- PDX
1 stop8h 29m
American Airlines
Tue 6/2310:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Deal found 4/16![American Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 4/16. 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 5/95:30 am
MKE
- PDX
1 stop6h 45m
Southwest
Wed 5/136:40 am
PDX
- MKE
1 stop5h 30m
Southwest
Deal found 4/16![Southwest logo]()
$325
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/75:37 pm
MKE
- PDX
1 stop8h 11m
American Airlines
Mon 5/1111:47 pm
PDX
- MKE
1 stop5h 54m
American Airlines
Deal found 4/14![American Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 4/16. 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 6/32:45 pm
MKE
- PDX
2 stops10h 25m
Southwest
Mon 6/811:30 pm
PDX
- MKE
1 stop9h 25m
Southwest
Deal found 4/16![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 4/14. 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 5/122:40 pm
MKE
- PDX
1 stop10h 20m
Southwest
Tue 5/1911:15 am
PDX
- MKE
2 stops8h 20m
Southwest
Deal found 4/14![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 4/14. 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 5/117:05 pm
MKE
- PDX
1 stop7h 50m
Southwest
Tue 5/1911:15 am
PDX
- MKE
2 stops8h 20m
Southwest
Deal found 4/14![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 4/17. 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 5/165:00 pm
MKE
- PDX
1 stop7h 02m
Delta
Wed 5/203:10 pm
PDX
- MKE
1 stop5h 45m
Delta
Deal found 4/17![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 4/16. 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 5/123:55 pm
MKE
- PDX
1 stop9h 15m
Southwest
Sat 5/166:25 am
PDX
- MKE
2 stops8h 25m
Southwest
Deal found 4/16![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 4/13. 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 9/26:50 am
MKE
- PDX
2 stops10h 35m
Southwest
Tue 9/85:50 am
PDX
- MKE
1 stop8h 50m
Southwest
Deal found 4/13![Southwest logo]()
$372
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 April 18, 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 April 18, 2026.
This Delta deal was found by Cheapflights users on 4/13. 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 6/246:30 am
MKE
- PDX
1 stop6h 14m
Delta
Wed 7/12:10 pm
PDX
- MKE
1 stop7h 49m
Delta
Deal found 4/13![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 4/14. 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 5/117:05 pm
MKE
- PDX
1 stop7h 50m
Southwest
Tue 5/195:30 am
PDX
- MKE
1 stop6h 35m
Southwest
Deal found 4/14![Southwest logo]()
$325
This United Airlines deal was found by Cheapflights users on 4/17. 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 6/25:29 pm
MKE
- PDX
1 stop8h 24m
United Airlines
Wed 6/311:40 pm
PDX
- MKE
1 stop8h 17m
United Airlines
Deal found 4/17![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 4/16. 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 5/95:30 am
MKE
- PDX
2 stops9h 25m
Southwest
Wed 5/136:40 am
PDX
- MKE
1 stop8h 45m
Southwest
Deal found 4/16![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 4/17. 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 5/165:00 pm
MKE
- PDX
1 stop7h 02m
Delta
Wed 5/203:10 pm
PDX
- MKE
1 stop5h 45m
Delta
Deal found 4/17![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 4/17. 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 6/246:30 am
MKE
- PDX
1 stop6h 14m
Delta
Mon 7/611:15 pm
PDX
- MKE
1 stop7h 35m
Delta
Deal found 4/17![Delta logo]()
$397
This United Airlines deal was found by Cheapflights users on 4/13. 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 4/2810:45 am
MKE
- PDX
2 stops8h 59m
United Airlines
Tue 5/52:41 pm
PDX
- MKE
1 stop5h 49m
United Airlines
Deal found 4/13![United Airlines logo]()
$458
This Southwest deal was found by Cheapflights users on 4/13. 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 6/236:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Sun 6/281:10 pm
PDX
- MKE
1 stop10h 30m
Southwest
Deal found 4/13![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 4/17. 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 5/175:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Sun 5/2411:58 am
PDX
- MKE
1 stop5h 49m
Delta
Deal found 4/17![Delta logo]()
$447
This Southwest deal was found by Cheapflights users on 4/13. 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 6/155:50 am
MKE
- PDX
1 stop8h 35m
Southwest
Fri 6/199:20 pm
PDX
- MKE
1 stop10h 05m
Southwest
Deal found 4/13![Southwest logo]()
$477
Last-minute flights from Milwaukee to PortlandDiscover last-minute flight deals from Milwaukee to Portland. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Portland. Data last updated April 18, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/75:37 pm
MKE
- PDX
1 stop8h 11m
American Airlines
Mon 5/1111:47 pm
PDX
- MKE
1 stop5h 54m
American Airlines
Deal found 4/14![American Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 4/16. 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 5/95:30 am
MKE
- PDX
1 stop6h 45m
Southwest
Wed 5/136:40 am
PDX
- MKE
1 stop5h 30m
Southwest
Deal found 4/16![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 4/14. 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 5/117:05 pm
MKE
- PDX
1 stop7h 50m
Southwest
Tue 5/1911:15 am
PDX
- MKE
2 stops8h 20m
Southwest
Deal found 4/14![Southwest logo]()
$351
This Alaska Airlines deal was found by Cheapflights users on 4/14. 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 5/127:00 am
MKE
- PDX
1 stop7h 52m
Alaska Airlines
Tue 5/195:00 am
PDX
- MKE
1 stop8h 44m
Alaska Airlines
Deal found 4/14![Alaska Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 4/14. 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 5/122:40 pm
MKE
- PDX
1 stop10h 20m
Southwest
Tue 5/1911:15 am
PDX
- MKE
2 stops8h 20m
Southwest
Deal found 4/14![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 4/16. 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 5/123:55 pm
MKE
- PDX
1 stop9h 15m
Southwest
Sat 5/166:25 am
PDX
- MKE
2 stops8h 25m
Southwest
Deal found 4/16![Southwest logo]()
$367
This American Airlines deal was found by Cheapflights users on 4/15. 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 5/144:26 pm
MKE
- PDX
1 stop8h 21m
American Airlines
Sun 5/1711:47 pm
PDX
- MKE
1 stop8h 56m
American Airlines
Deal found 4/15![American Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 4/17. 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 5/165:00 pm
MKE
- PDX
1 stop7h 02m
Delta
Wed 5/203:10 pm
PDX
- MKE
1 stop5h 45m
Delta
Deal found 4/17![Delta logo]()
$357
This American Airlines deal was found by Cheapflights users on 4/16. 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 5/226:45 pm
MKE
- PDX
1 stop7h 07m
American Airlines
Tue 5/261:45 pm
PDX
- MKE
1 stop6h 39m
American Airlines
Deal found 4/16![American Airlines logo]()
$397
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 April 18, 2026.
Search for one-way flight options from Milwaukee to Portland. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
This Trip.com deal was found by Cheapflights users on 4/13. 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.
Mon 4/275:05 pm
MKE
- PDX
1 stop20h 47m
Frontier
Deal found 4/13![Frontier logo]()
$109
This United Airlines deal was found by Cheapflights users on 4/13. 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 5/125:10 am
MKE
- PDX
1 stop8h 27m
United Airlines
Deal found 4/13![United Airlines logo]()
$159
This United Airlines deal was found by Cheapflights users on 4/13. 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 5/116:56 pm
MKE
- PDX
1 stop6h 59m
United Airlines
Deal found 4/13![United Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/129:56 am
MKE
- PDX
3 stops56h 50m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$177
This United Airlines deal was found by Cheapflights users on 4/17. 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 5/265:00 am
MKE
- PDX
1 stop6h 39m
United Airlines
Deal found 4/17![United Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Thu 5/72:50 pm
MKE
- PDX
2 stops27h 56m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$233
This United Airlines deal was found by Cheapflights users on 4/16. 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 6/61:30 pm
MKE
- PDX
2 stops11h 18m
United Airlines
Deal found 4/16![United Airlines logo]()
$234
This American Airlines deal was found by Cheapflights users on 4/14. 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 6/137:25 am
MKE
- PDX
1 stop9h 13m
American Airlines
Deal found 4/14![American Airlines logo]()
$239
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 April 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (Delta) |
One-way from | $109 (Trip.com) |
Popular in | November |
Cheapest in | September |
Average price | $426 |
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 2,558,603 searches. Data last updated April 18, 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 - PDX
MKEPDX
Milwaukee-Mitchell
Wed 6/24
6:30 am-10:44 am
1 stop6h 14m
Portland
Wed 7/1
2:10 pm-11:59 pm
1 stop7h 49m
$317
MilwaukeePortland
MKE - PDX
MKEPDX
Milwaukee-Mitchell
Mon 5/11
7:05 pm-12:55 am
1 stop7h 50m
Portland
Tue 5/19
5:30 am-2:05 pm
1 stop6h 35m
$325
MilwaukeePortland
MKE - PDX
MKEPDX
Milwaukee-Mitchell
Sat 5/9
5:30 am-12:55 pm
2 stops9h 25m
Portland
Wed 5/13
6:40 am-5:25 pm
1 stop8h 45m
$330
Quickest round-trip
MilwaukeePortland
MKE - PDX
MKEPDX
Milwaukee-Mitchell
Sat 5/16
5:00 pm-10:02 pm
1 stop7h 02m
Portland
Wed 5/20
3:10 pm-10:55 pm
1 stop5h 45m
$357
MilwaukeePortland
MKE - PDX
MKEPDX
Milwaukee-Mitchell
Wed 6/24
6:30 am-10:44 am
1 stop6h 14m
Portland
Mon 7/6
11:15 pm-8:50 am
1 stop7h 35m
$397
MilwaukeePortland
MKE - PDX
MKEPDX
Milwaukee-Mitchell
Tue 6/2
5:29 pm-11:53 pm
1 stop8h 24m
Portland
Wed 6/3
11:40 pm-9:57 am
1 stop8h 17m
$417
MilwaukeePortland
MKE - PDX
MKEPDX
Milwaukee-Mitchell
Tue 6/23
6:55 pm-11:50 pm
1 stop6h 55m
Portland
Sun 6/28
1:10 pm-1:40 am
1 stop10h 30m
$417
MilwaukeePortland
MKE - PDX
MKEPDX
Milwaukee-Mitchell
Sun 5/17
5:01 pm-10:02 pm
1 stop7h 01m
Portland
Sun 5/24
11:58 am-7:47 pm
1 stop5h 49m
$447
MilwaukeePortland
MKE - PDX
MKEPDX
Milwaukee-Mitchell
Tue 4/28
10:45 am-5:44 pm
2 stops8h 59m
Portland
Tue 5/5
2:41 pm-10:30 pm
1 stop5h 49m
$458
MilwaukeePortland
MKE - PDX
MKEPDX
Milwaukee-Mitchell
Mon 6/15
5:50 am-12:25 pm
1 stop8h 35m
Portland
Fri 6/19
9:20 pm-9:25 am
1 stop10h 05m
$477
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 April.
| 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?
Use this chart to determine the optimal time to book a round-trip flight from Milwaukee to Portland. Price data was last updated on April 10, 2026.
The best time to book flights from Milwaukee to Portland is 72 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, September is the cheapest month in which you can book a flight from Milwaukee to Portland (average of $353). Flying from Milwaukee to Portland in November is currently the most expensive (average of $497). 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?
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.
Chicago (ORD) is the most affordable 1-stop option, with an average round-trip price of $396.
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 Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 6h 05m.
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 Chicago (ORD) offer the fastest connection on this route, with an average layover time of 0h 53m.
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 April 18, 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.
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Vancouver
Lincoln City
Longview
Lake Oswego
Hillsboro
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Pacific City
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Milwaukee and Portland flights
Browse other Milwaukee and Portland flight options. Last updated on April 18, 2026.
Other flights from Milwaukee
Browse through other flights departing from Milwaukee. Flights are based on user searches made on Cheapflights and were last updated on April 18, 2026.
Popular flight searches
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Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 18, 2026.
Top 6 airlines flying from Milwaukee to Portland
Discover the top 6 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 2,558,603 searches. Data last updated April 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$278 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$236 | Average$383 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$268 | Average$421 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$276 | Average$435 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$278 | Average$450 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$319 | Average$443 | FlexibilityNo cancel fee | On-time63% |