$156+ Cheap flights from Portland to Milwaukee (PDX - MKE)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Sep 10 — Sep 171
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Milwaukee with Cheapflights
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Portland to Milwaukee
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Cheapest flights from Portland to MilwaukeeExplore the most affordable flight options available from Portland to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 11, 2026.
Explore the most affordable flight options available from Portland to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 11, 2026.
This Southwest deal was found by Cheapflights users on 8/10. 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 9/56:00 am -
1 stop11h 50m
Fri 9/116:20 pm -
1 stop7h 00m
Deal found 8/10![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 8/10. 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 9/111:30 pm -
1 stop5h 55m
Mon 9/146:25 pm -
1 stop7h 20m
Deal found 8/10![Southwest logo]()
$288
This Delta deal was found by Cheapflights users on 8/10. 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 10/136:00 am -
1 stop6h 30m
Tue 10/205:45 pm -
1 stop7h 59m
Deal found 8/10![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 8/10. 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 9/108:00 am -
1 stop7h 00m
Mon 9/144:25 pm -
1 stop8h 45m
Deal found 8/10![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 8/10. 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 9/1012:25 am -
1 stop6h 53m
Wed 9/162:55 pm -
1 stop8h 52m
Deal found 8/10![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 8/10. 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 10/2011:15 am -
2 stops8h 30m
Tue 10/275:55 am -
1 stop6h 40m
Deal found 8/10![Southwest logo]()
$318
Best flights from Portland to MilwaukeeDiscover carefully curated flight deals from Portland to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 11, 2026.
Discover carefully curated flight deals from Portland to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 11, 2026.
This Southwest deal was found by Cheapflights users on 8/10. 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 9/108:00 am -
1 stop7h 00m
Mon 9/144:25 pm -
1 stop8h 45m
Deal found 8/10![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:20 pm -
1 stop7h 33m
Thu 11/55:30 am -
1 stop10h 08m
Deal found 8/6![Delta logo]()
$347
This United Airlines deal was found by Cheapflights users on 8/9. 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 9/512:45 pm -
1 stop6h 18m
Wed 9/92:18 pm -
2 stops8h 47m
Deal found 8/9![United Airlines logo]()
$407
This Alaska Airlines deal was found by Cheapflights users on 8/6. 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 10/277:09 am -
1 stop7h 10m
Tue 11/34:44 pm -
2 stops19h 06m
Deal found 8/6![Alaska Airlines logo]()
$438
This Southwest deal was found by Cheapflights users on 8/8. 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.
Sat 9/59:00 am -
1 stop8h 50m
Fri 9/116:20 pm -
1 stop7h 00m
Deal found 8/8![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 8/10. 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 10/22:10 pm -
1 stop7h 38m
Mon 10/52:55 pm -
1 stop8h 52m
Deal found 8/10![Delta logo]()
$355
This Southwest deal was found by Cheapflights users on 8/7. 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.
Wed 9/165:50 am -
1 stop8h 50m
Sat 9/191:30 pm -
2 stops9h 55m
Deal found 8/7![Southwest logo]()
$352
This United Airlines deal was found by Cheapflights users on 8/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/511:30 pm -
1 stop8h 37m
Sun 10/115:00 am -
1 stop6h 31m
Deal found 8/6![United Airlines logo]()
$417
This United Airlines deal was found by Cheapflights users on 8/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:30 pm -
1 stop6h 09m
Thu 12/108:29 am -
1 stop8h 54m
Deal found 8/7![United Airlines logo]()
$447
This Southwest deal was found by Cheapflights users on 8/10. 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 10/168:00 am -
1 stop9h 25m
Fri 10/2310:25 am -
2 stops14h 40m
Deal found 8/10![Southwest logo]()
$411
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated August 11, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated August 11, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/10. 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 9/56:00 am -
1 stop11h 50m
Fri 9/116:20 pm -
1 stop7h 00m
Deal found 8/10![Southwest logo]()
$269
This American Airlines deal was found by Cheapflights users on 8/10. 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 9/1011:08 pm -
1 stop6h 53m
Mon 9/145:43 pm -
1 stop7h 40m
Deal found 8/10![American Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 8/10. 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 9/108:00 am -
1 stop7h 00m
Mon 9/144:25 pm -
1 stop8h 45m
Deal found 8/10![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 8/10. 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 9/1012:25 am -
1 stop6h 53m
Wed 9/162:55 pm -
1 stop8h 52m
Deal found 8/10![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 8/10. 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 9/111:30 pm -
1 stop5h 55m
Mon 9/146:25 pm -
1 stop7h 20m
Deal found 8/10![Southwest logo]()
$288
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:54 am -
1 stop6h 11m
Tue 9/152:55 pm -
1 stop8h 52m
Deal found 8/6![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 8/6. 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.
Fri 9/1111:35 am -
1 stop7h 50m
Tue 9/154:25 pm -
2 stops7h 50m
Deal found 8/6![Southwest logo]()
$337
One-way flights from Portland to MilwaukeeSearch for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated August 11, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated August 11, 2026.
This Delta deal was found by Cheapflights users on 8/10. 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 9/1612:25 am -
1 stop6h 53m
Deal found 8/10![Delta logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 10/293:47 pm -
2 stops25h 21m
Deal found 8/9![Frontier logo]()
$158
This Southwest deal was found by Cheapflights users on 8/10. 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 10/2712:00 pm -
2 stops8h 20m
Deal found 8/10![Southwest logo]()
$162
This American Airlines deal was found by Cheapflights users on 8/6. 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.
Sat 8/2911:58 am -
1 stop8h 59m
Deal found 8/6![American Airlines logo]()
$174
This United Airlines deal was found by Cheapflights users on 8/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:00 am -
2 stops8h 47m
Deal found 8/6![United Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Fri 10/169:34 pm -
2 stops43h 41m
Deal found 8/10![Frontier logo]()
$191
This Delta deal was found by Cheapflights users on 8/10. 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 9/411:20 pm -
1 stop7h 25m
Deal found 8/10![Delta logo]()
$200
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/411:34 pm -
1 stop6h 15m
Deal found 8/6![American Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 8/7. 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.
Sat 9/2612:25 am -
1 stop6h 53m
Deal found 8/7![Delta logo]()
$244
This Southwest deal was found by Cheapflights users on 8/8. 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 9/136:25 am -
2 stops9h 50m
Deal found 8/8![Southwest logo]()
$249
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:32 pm -
2 stops11h 35m
Deal found 8/7![Alaska Airlines logo]()
$255
Find flight deals from Portland to Milwaukee
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $269 (Southwest) |
One-way from | $156 (Delta) |
Popular in | June |
Cheapest in | January |
Average price | $423 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Milwaukee that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 11, 2026.
Use the filters below to find and compare flights from Portland to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Thu 9/10
8:00 am-5:00 pm
1 stop7h 00m
Milwaukee-Mitchell
Mon 9/14
4:25 pm-11:10 pm
1 stop8h 45m
$312
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Sat 9/5
9:00 am-7:50 pm
1 stop8h 50m
Milwaukee-Mitchell
Fri 9/11
6:20 pm-11:20 pm
1 stop7h 00m
$317
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 10/28
2:20 pm-11:53 pm
1 stop7h 33m
Milwaukee-Mitchell
Thu 11/5
5:30 am-1:38 pm
1 stop10h 08m
$347
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Wed 9/16
5:50 am-4:40 pm
1 stop8h 50m
Milwaukee-Mitchell
Sat 9/19
1:30 pm-9:25 pm
2 stops9h 55m
$352
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Fri 10/2
2:10 pm-11:48 pm
1 stop7h 38m
Milwaukee-Mitchell
Mon 10/5
2:55 pm-9:47 pm
1 stop8h 52m
$355
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Sat 9/5
12:45 pm-9:03 pm
1 stop6h 18m
Milwaukee-Mitchell
Wed 9/9
2:18 pm-9:05 pm
2 stops8h 47m
$407
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Fri 10/16
8:00 am-7:25 pm
1 stop9h 25m
Milwaukee-Mitchell
Fri 10/23
10:25 am-11:05 pm
2 stops14h 40m
$411
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Mon 10/5
11:30 pm-10:07 am
1 stop8h 37m
Milwaukee-Mitchell
Sun 10/11
5:00 am-9:31 am
1 stop6h 31m
$417
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Tue 10/27
7:09 am-4:19 pm
1 stop7h 10m
Milwaukee-Mitchell
Tue 11/3
4:44 pm-9:50 am
2 stops19h 06m
$438
Quickest round-trip
PortlandMilwaukee
PDX Portland - MKE Milwaukee-Mitchell
PDXMKE
Portland
Tue 12/8
2:30 pm-10:39 pm
1 stop6h 09m
Milwaukee-Mitchell
Thu 12/10
8:29 am-3:23 pm
1 stop8h 54m
$447
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Portland to Milwaukee
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Milwaukee in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Milwaukee flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Portland with our price prediction graph.
PDX-MKE
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Milwaukee
How far ahead should I book a flight from Portland to Milwaukee?
Booking 55 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Milwaukee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Portland to Milwaukee?
Currently, January is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $324). Flying from Portland to Milwaukee in June is currently the most expensive (average of $576). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Portland to Milwaukee?
Airfare is below average for this route at the moment.
Portland to Milwaukee flights typically cost between $344 and $536 in September.The cheapest round-trip price found within the last 5 days was $269 on Southwest (Sep 5-Sep 11).
Reviews of airlines servicing Milwaukee
Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated August 11, 2026.
Read through reviews of airlines operating flights from Portland to Milwaukee, 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
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Portland to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Milwaukee?
Book flights to Milwaukee if you plan to visit one of these locationsSheboygan
Port Washington
New Berlin
Oak Creek
Wauwatosa
Browse thousands of different options on Cheapflights for your next trip
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Other flights to Milwaukee
Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 11, 2026.
Portland and Milwaukee flights
Browse other Portland and Milwaukee flight options. Last updated on August 11, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on August 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Portland to Milwaukee
Discover the top 5 airlines that operate flights from Portland to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$478 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$211 | Average$438 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$278 | Average$454 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$406 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$322 | Average$540 | FlexibilityNo cancel fee | On-time63% |