$110+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
May 9 — May 161
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 April 9, 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 April 9, 2026.
This CheapOair deal was found by Cheapflights users on 4/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:48 am
PDX
- MKE
1 stop27h 46m
Frontier
Mon 4/275:05 pm
MKE
- PDX
1 stop20h 47m
Frontier
Deal found 4/9![Frontier logo]()
$216
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Tue 5/56:00 am
PDX
- MKE
1 stop9h 01m
American Airlines
Tue 5/124:26 pm
MKE
- PDX
1 stop8h 21m
American Airlines
Deal found 4/6![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 4/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:37 am
PDX
- MKE
1 stop8h 58m
American Airlines
Tue 6/306:21 pm
MKE
- PDX
1 stop8h 29m
American Airlines
Deal found 4/5![American Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/52:35 pm
PDX
- MKE
1 stop6h 35m
Southwest
Tue 5/126:10 am
MKE
- PDX
2 stops9h 30m
Southwest
Deal found 4/6![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 4/7. 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 5/511:00 am
PDX
- MKE
1 stop6h 30m
Southwest
Sat 5/912:40 pm
MKE
- PDX
1 stop8h 05m
Southwest
Deal found 4/7![Southwest logo]()
$325
This American Airlines deal was found by Cheapflights users on 4/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:37 am
PDX
- MKE
1 stop8h 58m
American Airlines
Wed 6/245:00 am
MKE
- PDX
1 stop6h 59m
American Airlines
Deal found 4/5![American Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 4/6. 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 5/411:35 am
PDX
- MKE
1 stop8h 45m
Southwest
Mon 5/116:30 pm
MKE
- PDX
1 stop7h 55m
Southwest
Deal found 4/6![Southwest logo]()
$333
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 April 9, 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 April 9, 2026.
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/52:35 pm
PDX
- MKE
1 stop6h 35m
Southwest
Tue 5/126:10 am
MKE
- PDX
2 stops9h 30m
Southwest
Deal found 4/6![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 4/6. 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 5/1110:55 pm
PDX
- MKE
1 stop6h 54m
United Airlines
Thu 5/146:56 pm
MKE
- PDX
1 stop6h 59m
United Airlines
Deal found 4/6![United Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:45 pm
PDX
- MKE
1 stop5h 58m
Delta
Sat 6/1311:04 am
MKE
- PDX
1 stop8h 33m
Delta
Deal found 4/9![Delta logo]()
$397
This Alaska Airlines deal was found by Cheapflights users on 4/5. 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.
Wed 4/296:00 am
PDX
- MKE
1 stop6h 13m
Alaska Airlines
Sat 5/27:00 am
MKE
- PDX
1 stop7h 52m
Alaska Airlines
Deal found 4/5![Alaska Airlines logo]()
$410
This United Airlines deal was found by Cheapflights users on 4/4. 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.
Tue 4/282:30 pm
PDX
- MKE
1 stop6h 00m
United Airlines
Wed 4/295:10 am
MKE
- PDX
1 stop8h 36m
United Airlines
Deal found 4/4![United Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 4/7. 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 6/1012:31 am
PDX
- MKE
1 stop6h 44m
Delta
Tue 6/166:30 am
MKE
- PDX
1 stop8h 10m
Delta
Deal found 4/7![Delta logo]()
$417
This Alaska Airlines deal was found by Cheapflights users on 4/4. 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 4/288:45 am
PDX
- MKE
2 stops9h 21m
Alaska Airlines
Wed 4/297:00 am
MKE
- PDX
1 stop7h 52m
Alaska Airlines
Deal found 4/4![Alaska Airlines logo]()
$430
This United Airlines deal was found by Cheapflights users on 4/7. 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.
Wed 4/298:40 am
PDX
- MKE
1 stop6h 23m
United Airlines
Sat 5/25:56 pm
MKE
- PDX
1 stop6h 39m
United Airlines
Deal found 4/7![United Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:30 am
PDX
- MKE
3 stops13h 57m
United Airlines
Thu 5/75:55 am
MKE
- PDX
2 stops11h 08m
United Airlines
Deal found 4/8![United Airlines logo]()
$441
Last-minute flights from Portland to MilwaukeeDiscover last-minute flight deals from Portland to Milwaukee. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Milwaukee. Data last updated April 9, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 4/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:48 am
PDX
- MKE
1 stop27h 46m
Frontier
Mon 4/275:05 pm
MKE
- PDX
1 stop20h 47m
Frontier
Deal found 4/9![Frontier logo]()
$216
This Southwest deal was found by Cheapflights users on 4/6. 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 5/411:35 am
PDX
- MKE
1 stop8h 45m
Southwest
Mon 5/116:30 pm
MKE
- PDX
1 stop7h 55m
Southwest
Deal found 4/6![Southwest logo]()
$333
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Tue 5/56:00 am
PDX
- MKE
1 stop9h 01m
American Airlines
Tue 5/124:26 pm
MKE
- PDX
1 stop8h 21m
American Airlines
Deal found 4/6![American Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/52:35 pm
PDX
- MKE
1 stop6h 35m
Southwest
Tue 5/126:10 am
MKE
- PDX
2 stops9h 30m
Southwest
Deal found 4/6![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 4/7. 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 5/511:00 am
PDX
- MKE
1 stop6h 30m
Southwest
Sat 5/912:40 pm
MKE
- PDX
1 stop8h 05m
Southwest
Deal found 4/7![Southwest logo]()
$325
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 April 9, 2026.
Search for one-way flight options from Portland to Milwaukee. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Trip.com deal was found by Cheapflights users on 4/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2611:15 am
PDX
- MKE
1 stop26h 55m
Frontier
Deal found 4/7![Frontier logo]()
$110
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Tue 5/191:23 pm
PDX
- MKE
1 stop6h 36m
American Airlines
Deal found 4/6![American Airlines logo]()
$159
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Tue 6/2310:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Deal found 4/6![American Airlines logo]()
$162
This Southwest deal was found by Cheapflights users on 4/7. 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 4/286:30 am
PDX
- MKE
2 stops13h 25m
Southwest
Deal found 4/7![Southwest logo]()
$164
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Mon 5/411:47 pm
PDX
- MKE
1 stop5h 54m
American Airlines
Deal found 4/6![American Airlines logo]()
$167
This Southwest deal was found by Cheapflights users on 4/7. 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.
Sat 5/99:35 am
PDX
- MKE
2 stops10h 15m
Southwest
Deal found 4/7![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 4/6. 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 5/46:00 am
PDX
- MKE
2 stops14h 20m
Southwest
Deal found 4/6![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:15 am
PDX
- MKE
2 stops8h 20m
Southwest
Deal found 4/5![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/910:40 am
PDX
- MKE
2 stops9h 35m
Southwest
Deal found 4/4![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:45 pm
PDX
- MKE
2 stops12h 00m
United Airlines
Deal found 4/8![United Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 4/4. 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.
Mon 6/812:15 pm
PDX
- MKE
2 stops9h 30m
Southwest
Deal found 4/4![Southwest logo]()
$217
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 April 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $216 (CheapOair) |
One-way from | $110 (Trip.com) |
Popular in | February |
Cheapest in | January |
Average price | $404 |
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 April 9, 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 - MKE
PDXMKE
Portland
Tue 5/5
2:35 pm-11:10 pm
1 stop6h 35m
Milwaukee-Mitchell
Tue 5/12
6:10 am-1:40 pm
2 stops9h 30m
$322
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Mon 5/11
10:55 pm-7:49 am
1 stop6h 54m
Milwaukee-Mitchell
Thu 5/14
6:56 pm-11:55 pm
1 stop6h 59m
$333
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 6/10
1:45 pm-9:43 pm
1 stop5h 58m
Milwaukee-Mitchell
Sat 6/13
11:04 am-5:37 pm
1 stop8h 33m
$397
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 4/29
6:00 am-2:13 pm
1 stop6h 13m
Milwaukee-Mitchell
Sat 5/2
7:00 am-12:52 pm
1 stop7h 52m
$410
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 4/28
2:30 pm-10:30 pm
1 stop6h 00m
Milwaukee-Mitchell
Wed 4/29
5:10 am-11:46 am
1 stop8h 36m
$417
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 6/10
12:31 am-9:15 am
1 stop6h 44m
Milwaukee-Mitchell
Tue 6/16
6:30 am-12:40 pm
1 stop8h 10m
$417
Quickest round-trip
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 4/29
8:40 am-5:03 pm
1 stop6h 23m
Milwaukee-Mitchell
Sat 5/2
5:56 pm-10:35 pm
1 stop6h 39m
$425
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 4/28
8:45 am-8:06 pm
2 stops9h 21m
Milwaukee-Mitchell
Wed 4/29
7:00 am-12:52 pm
1 stop7h 52m
$430
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 5/5
5:30 am-9:27 pm
3 stops13h 57m
Milwaukee-Mitchell
Thu 5/7
5:55 am-3:03 pm
2 stops11h 08m
$441
Cheapest one-way
Quickest one-way
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Wed 6/10
1:45 pm-9:43 pm
1 stop5h 58m
$159
Showing 1-10 of 19 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 April.
| 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?
Use this chart to determine the optimal time to book a round-trip flight from Portland to Milwaukee. Price data was last updated on April 3, 2026.
Booking 35 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, August is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $88). Flying from Portland to Milwaukee in July is currently the most expensive (average of $238). 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?
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 April 9, 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
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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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Complete your trip
Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
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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 April 9, 2026.
Portland and Milwaukee flights
Browse other Portland and Milwaukee flight options. Last updated on April 9, 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 April 9, 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 April 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$428 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$379 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$278 | Average$457 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$307 | Average$422 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$322 | Average$499 | FlexibilityNo cancel fee | On-time63% |