$165+ Cheap flights from Oregon to Milwaukee (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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Jun 14 — Jun 211
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Oregon 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 Oregon to Milwaukee
Cheapest
Best
Last-minute
One-way
Cheapest flights from Oregon to MilwaukeeExplore the most affordable flight options available from Oregon to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2026.
Explore the most affordable flight options available from Oregon to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2026.
This American Airlines deal was found by Cheapflights users on 5/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:55 am
PDX
- MKE
1 stop7h 15m
American Airlines
Tue 9/1512:22 pm
MKE
- PDX
1 stop8h 39m
American Airlines
Deal found 5/13![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 6/310:51 am
PDX
- MKE
1 stop8h 05m
United Airlines
Sat 6/61:30 pm
MKE
- PDX
1 stop7h 17m
United Airlines
Deal found 5/13![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 5/12. 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 9/26:35 am
PDX
- MKE
2 stops8h 05m
Southwest
Sat 9/56:15 am
MKE
- PDX
1 stop6h 25m
Southwest
Deal found 5/12![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 5/12. 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 7/810:40 am
PDX
- MKE
2 stops9h 35m
Southwest
Wed 7/156:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 5/12![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 5/10. 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.
Sat 6/66:00 am
PDX
- MKE
1 stop7h 09m
Delta
Sat 6/203:58 pm
MKE
- PDX
1 stop6h 19m
Delta
Deal found 5/10![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 5/11. 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 6/35:20 am
BOI
- MKE
1 stop5h 00m
Delta
Wed 6/35:48 pm
MKE
- BOI
1 stop8h 00m
Delta
Deal found 5/11![Delta logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Wed 6/1010:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Tue 6/306:50 pm
MKE
- PDX
1 stop6h 57m
American Airlines
Deal found 5/14![American Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 5/11. 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 8/2512:32 pm
RDM
- MKE
1 stop7h 11m
Delta
Tue 9/17:15 am
MKE
- RDM
1 stop6h 39m
Delta
Deal found 5/11![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 5/13. 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 8/1711:30 pm
PDX
- MKE
2 stops10h 30m
Southwest
Thu 8/206:20 pm
MKE
- PDX
1 stop7h 05m
Southwest
Deal found 5/13![Southwest logo]()
$360
This Southwest deal was found by Cheapflights users on 5/13. 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.
Thu 6/49:20 pm
PDX
- MKE
1 stop12h 30m
Southwest
Wed 6/107:05 pm
MKE
- PDX
1 stop7h 00m
Southwest
Deal found 5/13![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 5/11. 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 8/196:20 am
RDM
- MKE
2 stops13h 23m
Delta
Wed 8/267:30 am
MKE
- RDM
1 stop6h 20m
Delta
Deal found 5/11![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Wed 7/110:59 pm
PDX
- MKE
1 stop7h 03m
American Airlines
Mon 7/66:55 pm
MKE
- PDX
1 stop7h 09m
American Airlines
Deal found 5/14![American Airlines logo]()
$365
Best flights from Oregon to MilwaukeeDiscover carefully curated flight deals from Oregon to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 15, 2026.
Discover carefully curated flight deals from Oregon to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 15, 2026.
This Delta deal was found by Cheapflights users on 5/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:20 am
RDM
- MKE
2 stops13h 23m
Delta
Wed 8/267:30 am
MKE
- RDM
1 stop6h 20m
Delta
Deal found 5/14![Delta logo]()
$364
This Alaska Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:45 pm
EUG
- MKE
1 stop8h 14m
Alaska Airlines
Tue 6/97:00 am
MKE
- EUG
1 stop8h 08m
Alaska Airlines
Deal found 5/11![Alaska Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 5/10. 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 6/52:45 pm
EUG
- MKE
1 stop5h 40m
Southwest
Tue 6/95:00 am
MKE
- EUG
1 stop6h 50m
Southwest
Deal found 5/10![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 9/92:15 pm
PDX
- MKE
1 stop6h 21m
United Airlines
Tue 9/152:35 pm
MKE
- PDX
2 stops10h 25m
United Airlines
Deal found 5/13![United Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 5/12. 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 7/86:00 am
EUG
- MKE
2 stops11h 31m
Delta
Sat 7/117:00 am
MKE
- EUG
1 stop6h 48m
Delta
Deal found 5/12![Delta logo]()
$388
This Alaska Airlines deal was found by Cheapflights users on 5/11. 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 6/41:45 pm
EUG
- MKE
1 stop8h 14m
Alaska Airlines
Wed 6/106:02 am
MKE
- EUG
1 stop8h 59m
Alaska Airlines
Deal found 5/11![Alaska Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 5/13. 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.
Thu 6/49:20 pm
PDX
- MKE
1 stop12h 30m
Southwest
Tue 6/95:00 am
MKE
- PDX
2 stops9h 00m
Southwest
Deal found 5/13![Southwest logo]()
$397
This Delta deal was found by Cheapflights users on 5/12. 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 7/226:01 am
MFR
- MKE
2 stops12h 19m
Delta
Mon 7/273:59 pm
MKE
- MFR
2 stops9h 12m
Delta
Deal found 5/12![Delta logo]()
$396
This Southwest deal was found by Cheapflights users on 5/12. 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 7/72:35 pm
PDX
- MKE
1 stop5h 40m
Southwest
Fri 7/175:15 pm
MKE
- PDX
1 stop8h 40m
Southwest
Deal found 5/12![Southwest logo]()
$403
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 9/296:20 am
BOI
- MKE
1 stop6h 47m
Alaska Airlines
Wed 9/303:03 pm
MKE
- BOI
1 stop8h 35m
Alaska Airlines
Deal found 5/12![Alaska Airlines logo]()
$403
This United Airlines deal was found by Cheapflights users on 5/11. 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 6/55:46 pm
BOI
- MKE
1 stop5h 13m
United Airlines
Tue 6/97:27 am
MKE
- BOI
2 stops10h 17m
United Airlines
Deal found 5/11![United Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 5/13. 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.
Fri 5/296:15 am
MFR
- MKE
2 stops13h 18m
Delta
Tue 6/25:01 pm
MKE
- MFR
2 stops8h 41m
Delta
Deal found 5/13![Delta logo]()
$409
This Southwest deal was found by Cheapflights users on 5/12. 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 7/92:45 pm
EUG
- MKE
1 stop5h 40m
Southwest
Sun 7/125:20 am
MKE
- EUG
1 stop6h 15m
Southwest
Deal found 5/12![Southwest logo]()
$411
This Alaska Airlines deal was found by Cheapflights users on 5/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:45 pm
EUG
- MKE
1 stop8h 14m
Alaska Airlines
Sat 5/307:00 am
MKE
- EUG
1 stop8h 08m
Alaska Airlines
Deal found 5/10![Alaska Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 5/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:00 am
RDM
- MKE
1 stop6h 25m
United Airlines
Tue 6/26:20 am
MKE
- RDM
2 stops10h 31m
United Airlines
Deal found 5/14![United Airlines logo]()
$503
This Southwest deal was found by Cheapflights users on 5/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:50 am
PDX
- MKE
2 stops10h 20m
Southwest
Sat 10/314:50 pm
MKE
- PDX
1 stop7h 10m
Southwest
Deal found 5/9![Southwest logo]()
$424
This Delta deal was found by Cheapflights users on 5/12. 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 7/152:50 pm
BOI
- MKE
1 stop5h 51m
Delta
Mon 7/206:30 am
MKE
- BOI
1 stop5h 27m
Delta
Deal found 5/12![Delta logo]()
$425
This Southwest deal was found by Cheapflights users on 5/12. 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 7/81:40 pm
EUG
- MKE
1 stop9h 15m
Southwest
Sun 7/125:20 am
MKE
- EUG
1 stop6h 15m
Southwest
Deal found 5/12![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 5/12. 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 6/102:50 pm
BOI
- MKE
1 stop5h 38m
Delta
Sun 6/146:20 am
MKE
- BOI
1 stop5h 43m
Delta
Deal found 5/12![Delta logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 5/11. 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 6/188:15 am
BOI
- MKE
1 stop14h 44m
Alaska Airlines
Mon 6/226:02 am
MKE
- BOI
1 stop9h 05m
Alaska Airlines
Deal found 5/11![Alaska Airlines logo]()
$480
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 9/95:05 am
PDX
- MKE
2 stops12h 32m
Alaska Airlines
Tue 9/156:26 am
MKE
- PDX
2 stops10h 01m
Alaska Airlines
Deal found 5/12![Alaska Airlines logo]()
$483
This Southwest deal was found by Cheapflights users on 5/12. 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 9/167:05 am
BOI
- MKE
2 stops10h 25m
Southwest
Sun 9/2012:50 pm
MKE
- BOI
1 stop9h 50m
Southwest
Deal found 5/12![Southwest logo]()
$440
This Delta deal was found by Cheapflights users on 5/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:40 am
BOI
- MKE
1 stop7h 31m
Delta
Mon 9/75:55 pm
MKE
- BOI
1 stop6h 34m
Delta
Deal found 5/14![Delta logo]()
$463
This Southwest deal was found by Cheapflights users on 5/11. 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 9/188:00 am
PDX
- MKE
1 stop7h 00m
Southwest
Mon 9/218:00 am
MKE
- PDX
2 stops10h 35m
Southwest
Deal found 5/11![Southwest logo]()
$453
This Alaska Airlines deal was found by Cheapflights users on 5/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:28 pm
BOI
- MKE
2 stops10h 21m
Alaska Airlines
Tue 8/257:00 am
MKE
- BOI
1 stop8h 22m
Alaska Airlines
Deal found 5/13![Alaska Airlines logo]()
$508
This Delta deal was found by Cheapflights users on 5/12. 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 7/96:15 am
EUG
- MKE
2 stops9h 45m
Delta
Sun 7/127:00 am
MKE
- EUG
1 stop6h 48m
Delta
Deal found 5/12![Delta logo]()
$466
This Southwest deal was found by Cheapflights users on 5/10. 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 9/247:30 am
BOI
- MKE
2 stops9h 15m
Southwest
Sun 9/2711:35 am
MKE
- BOI
1 stop5h 35m
Southwest
Deal found 5/10![Southwest logo]()
$457
This Delta deal was found by Cheapflights users on 5/12. 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 7/86:00 am
EUG
- MKE
2 stops10h 16m
Delta
Sun 7/127:00 am
MKE
- EUG
2 stops12h 05m
Delta
Deal found 5/12![Delta logo]()
$472
This Alaska Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:35 pm
MFR
- MKE
2 stops10h 07m
Alaska Airlines
Sat 6/202:59 pm
MKE
- MFR
1 stop11h 05m
Alaska Airlines
Deal found 5/12![Alaska Airlines logo]()
$549
This Southwest deal was found by Cheapflights users on 5/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/54:25 pm
BOI
- MKE
1 stop5h 00m
Southwest
Mon 6/87:30 pm
MKE
- BOI
1 stop6h 40m
Southwest
Deal found 5/9![Southwest logo]()
$464
Last-minute flights from Oregon to MilwaukeeDiscover last-minute flight deals from Oregon to Milwaukee. Data last updated May 15, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Milwaukee. Data last updated May 15, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:00 am
PDX
- MKE
1 stop8h 44m
Alaska Airlines
Wed 6/34:40 pm
MKE
- PDX
1 stop6h 48m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$329
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 6/25:00 am
PDX
- MKE
1 stop8h 44m
Alaska Airlines
Sat 6/64:40 pm
MKE
- PDX
1 stop6h 48m
Alaska Airlines
Deal found 5/12![Alaska Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 6/310:51 am
PDX
- MKE
1 stop8h 05m
United Airlines
Sat 6/61:30 pm
MKE
- PDX
1 stop7h 17m
United Airlines
Deal found 5/13![United Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 5/11. 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 6/35:20 am
BOI
- MKE
1 stop5h 00m
Delta
Wed 6/35:48 pm
MKE
- BOI
1 stop8h 00m
Delta
Deal found 5/11![Delta logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 5/11. 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 6/31:45 pm
EUG
- MKE
1 stop8h 14m
Alaska Airlines
Tue 6/97:00 am
MKE
- EUG
1 stop8h 08m
Alaska Airlines
Deal found 5/11![Alaska Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 5/13. 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.
Thu 6/49:20 pm
PDX
- MKE
1 stop12h 30m
Southwest
Wed 6/107:05 pm
MKE
- PDX
1 stop7h 00m
Southwest
Deal found 5/13![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 5/10. 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.
Sat 6/66:00 am
PDX
- MKE
1 stop7h 09m
Delta
Sat 6/203:58 pm
MKE
- PDX
1 stop6h 19m
Delta
Deal found 5/10![Delta logo]()
$355
This Southwest deal was found by Cheapflights users on 5/10. 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 6/910:40 am
PDX
- MKE
2 stops9h 35m
Southwest
Tue 6/166:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 5/10![Southwest logo]()
$347
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Wed 6/1010:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Tue 6/306:50 pm
MKE
- PDX
1 stop6h 57m
American Airlines
Deal found 5/14![American Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 5/11. 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 6/101:15 pm
PDX
- MKE
1 stop8h 20m
Southwest
Wed 6/176:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 5/11![Southwest logo]()
$373
This American Airlines deal was found by Cheapflights users on 5/14. 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 6/1110:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Thu 6/186:50 pm
MKE
- PDX
1 stop6h 57m
American Airlines
Deal found 5/14![American Airlines logo]()
$368
This American Airlines deal was found by Cheapflights users on 5/12. 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 6/1710:59 pm
PDX
- MKE
1 stop6h 43m
American Airlines
Wed 6/246:21 pm
MKE
- PDX
1 stop8h 29m
American Airlines
Deal found 5/12![American Airlines logo]()
$378
One-way flights from Oregon to MilwaukeeSearch for one-way flight options from Oregon to Milwaukee. Find affordable one-way fares based on user searches. Data last updated May 15, 2026.
Search for one-way flight options from Oregon to Milwaukee. Find affordable one-way fares based on user searches. Data last updated May 15, 2026.
This Delta deal was found by Cheapflights users on 5/10. 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 7/221:15 pm
PDX
- MKE
1 stop6h 28m
Delta
Deal found 5/10![Delta logo]()
$165
This United Airlines deal was found by Cheapflights users on 5/11. 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 6/311:05 am
PDX
- MKE
2 stops9h 16m
United Airlines
Deal found 5/11![United Airlines logo]()
$170
This Delta deal was found by Cheapflights users on 5/10. 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 7/2311:15 pm
PDX
- MKE
1 stop7h 35m
Delta
Deal found 5/10![Delta logo]()
$178
This American Airlines deal was found by Cheapflights users on 5/11. 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 6/34:05 pm
BOI
- MKE
1 stop6h 29m
American Airlines
Deal found 5/11![American Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Wed 8/265:30 am
RDM
- MKE
1 stop6h 26m
American Airlines
Deal found 5/14![American Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 5/12. 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 6/136:00 am
PDX
- MKE
1 stop7h 08m
Delta
Deal found 5/12![Delta logo]()
$183
This Delta deal was found by Cheapflights users on 5/11. 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 7/87:25 pm
RDM
- MKE
2 stops11h 33m
Delta
Deal found 5/11![Delta logo]()
$185
This Delta deal was found by Cheapflights users on 5/11. 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 7/912:15 pm
RDM
- MKE
1 stop7h 28m
Delta
Deal found 5/11![Delta logo]()
$190
This Delta deal was found by Cheapflights users on 5/12. 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 5/271:35 pm
EUG
- MKE
1 stop5h 58m
Delta
Deal found 5/12![Delta logo]()
$192
This United Airlines deal was found by Cheapflights users on 5/11. 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 6/310:41 am
BOI
- MKE
2 stops10h 40m
United Airlines
Deal found 5/11![United Airlines logo]()
$197
This Alaska Airlines deal was found by Cheapflights users on 5/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:45 am
MFR
- MKE
1 stop7h 59m
Alaska Airlines
Deal found 5/13![Alaska Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Tue 10/2012:10 pm
BOI
- MKE
1 stop8h 00m
American Airlines
Deal found 5/14![American Airlines logo]()
$202
Find flight deals from Oregon to Milwaukee
Keep the following information in mind while searching for Oregon to Milwaukee flight deals. Data was last updated May 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $329 (American Airlines) |
One-way from | $165 (Delta) |
Popular in | February |
Cheapest in | January |
Average price | $436 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oregon 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 May 15, 2026.
Use the filters below to find and compare flights from Oregon to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
RedmondMilwaukee
RDM - MKE
RDMMKE
Bend/Redmond
Wed 8/19
6:20 am-9:43 pm
2 stops13h 23m
Milwaukee-Mitchell
Wed 8/26
7:30 am-11:50 am
1 stop6h 20m
$364
EugeneMilwaukee
EUG - MKE
EUGMKE
Eugene
Mon 6/1
1:45 pm-11:59 pm
1 stop8h 14m
Milwaukee-Mitchell
Tue 6/9
7:00 am-1:08 pm
1 stop8h 08m
$388
EugeneMilwaukee
EUG - MKE
EUGMKE
Eugene
Fri 6/5
2:45 pm-10:25 pm
1 stop5h 40m
Milwaukee-Mitchell
Tue 6/9
5:00 am-9:50 am
1 stop6h 50m
$388
EugeneMilwaukee
EUG - MKE
EUGMKE
Eugene
Wed 7/8
6:00 am-7:31 pm
2 stops11h 31m
Milwaukee-Mitchell
Sat 7/11
7:00 am-11:48 am
1 stop6h 48m
$388
EugeneMilwaukee
EUG - MKE
EUGMKE
Eugene
Thu 6/4
1:45 pm-11:59 pm
1 stop8h 14m
Milwaukee-Mitchell
Wed 6/10
6:02 am-1:01 pm
1 stop8h 59m
$393
MedfordMilwaukee
MFR - MKE
MFRMKE
Medford
Wed 7/22
6:01 am-8:20 pm
2 stops12h 19m
Milwaukee-Mitchell
Mon 7/27
3:59 pm-11:11 pm
2 stops9h 12m
$396
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Thu 6/4
9:20 pm-11:50 am
1 stop12h 30m
Milwaukee-Mitchell
Tue 6/9
5:00 am-12:00 pm
2 stops9h 00m
$397
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 7/7
2:35 pm-10:15 pm
1 stop5h 40m
Milwaukee-Mitchell
Fri 7/17
5:15 pm-11:55 pm
1 stop8h 40m
$403
BoiseMilwaukee
BOI - MKE
BOIMKE
Boise Air Term. Gowen Fld
Tue 9/29
6:20 am-2:07 pm
1 stop6h 47m
Milwaukee-Mitchell
Wed 9/30
3:03 pm-10:38 pm
1 stop8h 35m
$403
MedfordMilwaukee
MFR - MKE
MFRMKE
Medford
Fri 5/29
6:15 am-9:33 pm
2 stops13h 18m
Milwaukee-Mitchell
Tue 6/2
5:01 pm-11:42 pm
2 stops8h 41m
$409
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Oregon to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Oregon with our price prediction graph.
PDX-MKE
BOI-MKE
RDM-MKE
EUG-MKE
MFR-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 Oregon to Milwaukee
USOR-MKE
PDX-MKE
BOI-MKE
RDM-MKE
EUG-MKE
How far ahead should I book a flight from Oregon to Milwaukee?
Booking 32 days in advance of your planned departure date is, on average, the best time to get cheap flights from Oregon 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 Oregon to Milwaukee?
Currently, August is the cheapest month in which you can book a flight from Oregon to Milwaukee (average of $88). Flying from Oregon to Milwaukee in February is currently the most expensive (average of $339). 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 Oregon to Milwaukee?
Related info for your journey
Find useful and relevant information for your journey from Oregon 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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Milwaukee flight routes
Other flight options
Popular flights
Top destinations
Alternative routes for Oregon to Milwaukee
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oregon to Milwaukee by cabin class
Find flights from Oregon to Milwaukee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 May 15, 2026.
Oregon and Milwaukee flights
Browse other Oregon and Milwaukee flight options. Last updated on May 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oregon to Milwaukee flights
Consider these flights traveling from Oregon to Milwaukee.
Top 5 airlines flying from Oregon to Milwaukee
Discover the top 5 airlines that operate flights from Oregon 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 May 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$562 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$416 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$242 | Average$477 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$278 | Average$458 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$454 | FlexibilityNo cancel fee | On-time75% |