$152+ Cheap flights from Milwaukee to Portland, ME (MKE - PWM)
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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Portland 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
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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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Best
Last-minute
One-way
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 October 25, 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 October 25, 2026.
This Delta deal was found by Cheapflights users on 10/21. 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 11/118:10 am -
1 stop6h 06m
Mon 11/164:50 pm -
1 stop4h 25m
Deal found 10/21![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 10/23. 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 12/14:35 pm -
1 stop4h 15m
Sun 12/65:10 pm -
1 stop7h 25m
Deal found 10/23![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 10/22. 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 11/145:45 am -
2 stops8h 00m
Mon 11/235:10 pm -
2 stops7h 10m
Deal found 10/22![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 10/22. 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 12/46:20 am -
2 stops7h 25m
Mon 12/73:25 pm -
2 stops7h 55m
Deal found 10/22![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 10/20. 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 12/233:57 pm -
1 stop6h 13m
Wed 12/305:35 am -
1 stop7h 25m
Deal found 10/20![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 10/24. 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 12/36:35 am -
1 stop4h 35m
Mon 12/73:25 pm -
1 stop7h 00m
Deal found 10/24![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:40 pm -
2 stops10h 12m
Mon 12/74:53 pm -
2 stops8h 06m
Deal found 10/24![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/106:47 am -
1 stop6h 29m
Wed 11/115:08 pm -
1 stop6h 07m
Deal found 10/22![United Airlines logo]()
$367
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 October 25, 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 October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/22. 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 11/147:05 am -
1 stop6h 40m
Mon 11/235:10 pm -
1 stop7h 25m
Deal found 10/22![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 10/20. 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 11/115:20 am -
2 stops8h 56m
Mon 11/164:50 pm -
1 stop4h 25m
Deal found 10/20![Delta logo]()
$272
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/106:47 am -
1 stop6h 29m
Wed 11/115:08 pm -
1 stop6h 07m
Deal found 10/22![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 10/20. 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 12/233:57 pm -
1 stop6h 13m
Wed 12/305:35 am -
1 stop7h 25m
Deal found 10/20![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 10/24. 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 12/46:35 am -
1 stop7h 10m
Mon 12/73:25 pm -
1 stop7h 00m
Deal found 10/24![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:40 pm -
2 stops10h 12m
Mon 12/74:53 pm -
2 stops8h 06m
Deal found 10/24![Delta logo]()
$349
Last-minute flights from Milwaukee to PortlandDiscover last-minute flight deals from Milwaukee to Portland. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Portland. Data last updated October 25, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/62:23 pm -
1 stop6h 29m
Tue 11/105:50 am -
1 stop5h 33m
Deal found 10/22![United Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 10/23. 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 11/75:25 am -
2 stops8h 20m
Wed 11/1112:45 pm -
2 stops9h 45m
Deal found 10/23![Southwest logo]()
$412
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/106:47 am -
1 stop6h 29m
Wed 11/115:08 pm -
1 stop6h 07m
Deal found 10/22![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 10/21. 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 11/118:10 am -
1 stop6h 06m
Mon 11/164:50 pm -
1 stop4h 25m
Deal found 10/21![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 10/22. 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 11/145:45 am -
2 stops8h 00m
Mon 11/235:10 pm -
2 stops7h 10m
Deal found 10/22![Southwest logo]()
$291
This United Airlines deal was found by Cheapflights users on 10/23. 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 11/202:23 pm -
1 stop6h 29m
Fri 11/278:29 am -
1 stop6h 03m
Deal found 10/23![United Airlines logo]()
$369
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 October 25, 2026.
Search for one-way flight options from Milwaukee to Portland. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/20. 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 12/66:55 am -
1 stop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$152
This Delta deal was found by Cheapflights users on 10/24. 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 12/27:45 am -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$170
This United Airlines deal was found by Cheapflights users on 10/24. 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 12/26:00 am -
2 stops7h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![United Airlines logo]()
$175
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/58:00 am -
1 stop5h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![United Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/55:27 pm -
3 stops47h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$399
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 (PWM). 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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $267 (Delta) |
One-way from | $152 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $416 |
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 October 25, 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 - PWM Portland
MKEPWM
Milwaukee-Mitchell
Sun 12/6
5:30 am-1:05 pm
2 stops6h 35m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Wed 12/2
7:45 am-3:20 pm
1 stop6h 35m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$170
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Wed 12/2
6:35 am-2:45 pm
1 stop7h 10m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$170
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Wed 12/2
6:00 am-2:37 pm
2 stops7h 37m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$175
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Sat 11/14
7:05 am-2:45 pm
1 stop6h 40m
Portland
Mon 11/23
5:10 pm-11:35 pm
1 stop7h 25m
$267
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Mon 11/9
5:04 am-11:53 am
1 stop5h 49m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$269
Quickest round-trip
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Thu 11/5
8:00 am-2:16 pm
1 stop5h 16m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$269
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Wed 11/11
5:20 am-3:16 pm
2 stops8h 56m
Portland
Mon 11/16
4:50 pm-8:15 pm
1 stop4h 25m
$272
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Mon 11/9
5:20 am-4:38 pm
2 stops10h 18m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$274
MilwaukeePortland
MKE Milwaukee-Mitchell - PWM Portland
MKEPWM
Milwaukee-Mitchell
Fri 11/6
2:23 pm-11:21 pm
2 stops7h 58m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$274
Showing 1-10 of 15 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 October.
| 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 Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Milwaukee-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milwaukee-Portland, Maine flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Milwaukee-Portland, Maine 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, Maine 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-PWM
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
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 October 25, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Milwaukee to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.4
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.4
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.4
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.4
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.4
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 locationsLewiston
North Conway
Brunswick
Conway
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Milwaukee and Portland flights
Browse other Milwaukee and Portland flight options. Last updated on October 25, 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 October 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 October 25, 2026.
Top 4 airlines flying from Milwaukee to Portland
Discover the top 4 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 October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$280 | Average$437 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$303 | Average$423 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$324 | Average$462 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$386 | Average$536 | FlexibilityNo cancel fee | On-time63% |