$159+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
May 30 — Jun 61
Round-trip
1 adult, Economy
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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 April 30, 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 April 30, 2026.
This Delta deal was found by Cheapflights users on 4/28. 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 5/2011:12 pm
PDX
- MKE
1 stop7h 37m
Delta
Tue 5/265:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 4/28![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 4/26. 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 8/257:00 am
PDX
- MKE
1 stop6h 04m
United Airlines
Tue 9/110:45 am
MKE
- PDX
2 stops8h 58m
United Airlines
Deal found 4/26![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 4/29. 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 6/31:34 pm
PDX
- MKE
1 stop8h 00m
American Airlines
Sat 6/68:00 am
MKE
- PDX
1 stop8h 38m
American Airlines
Deal found 4/29![American Airlines logo]()
$325
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/192:38 pm
PDX
- MKE
1 stop5h 55m
United Airlines
Wed 5/202:38 pm
MKE
- PDX
1 stop8h 31m
United Airlines
Deal found 4/28![United Airlines logo]()
$328
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 5/239:44 am
PDX
- MKE
1 stop12h 15m
Alaska Airlines
Thu 5/284:40 pm
MKE
- PDX
1 stop6h 48m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 4/29. 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 4/29![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 4/27. 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 6/163:40 pm
PDX
- MKE
1 stop7h 15m
Southwest
Tue 6/236:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 4/27![Southwest logo]()
$348
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/201:07 pm
EUG
- MKE
1 stop5h 46m
United Airlines
Wed 5/276:20 am
MKE
- EUG
1 stop7h 27m
United Airlines
Deal found 4/28![United Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 4/28. 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 6/246:50 pm
MKE
- PDX
1 stop6h 57m
American Airlines
Deal found 4/28![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 4/29. 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 5/275:20 am
BOI
- MKE
1 stop5h 00m
Delta
Wed 6/36:45 am
MKE
- BOI
1 stop6h 11m
Delta
Deal found 4/29![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 4/28. 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 5/2611:55 pm
PDX
- MKE
1 stop9h 00m
Southwest
Tue 6/26:10 am
MKE
- PDX
2 stops9h 30m
Southwest
Deal found 4/28![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 4/26. 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 8/2511:30 pm
PDX
- MKE
1 stop9h 35m
Southwest
Tue 9/112:40 pm
MKE
- PDX
2 stops9h 10m
Southwest
Deal found 4/26![Southwest logo]()
$359
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 April 30, 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 April 30, 2026.
This United Airlines deal was found by Cheapflights users on 4/25. 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 5/235:00 am
PDX
- MKE
1 stop6h 25m
United Airlines
Sat 5/301:30 pm
MKE
- PDX
1 stop7h 17m
United Airlines
Deal found 4/25![United Airlines logo]()
$333
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 5/301:45 pm
EUG
- MKE
1 stop8h 14m
Alaska Airlines
Fri 6/54:40 pm
MKE
- EUG
1 stop9h 19m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 4/30. 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 7/107:25 pm
RDM
- MKE
2 stops12h 54m
Delta
Mon 7/134:49 pm
MKE
- RDM
2 stops9h 09m
Delta
Deal found 4/30![Delta logo]()
$389
This Southwest deal was found by Cheapflights users on 4/27. 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 6/124:25 pm
PDX
- MKE
1 stop7h 30m
Southwest
Tue 6/166:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 4/27![Southwest logo]()
$397
This Delta deal was found by Cheapflights users on 4/26. 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 7/95:20 am
RDM
- MKE
2 stops12h 11m
Delta
Tue 7/147:00 am
MKE
- RDM
1 stop6h 35m
Delta
Deal found 4/26![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 4/30. 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 6/46:10 am
EUG
- MKE
1 stop11h 35m
Southwest
Mon 6/155:15 am
MKE
- EUG
1 stop6h 20m
Southwest
Deal found 4/30![Southwest logo]()
$408
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:51 am
PDX
- MKE
1 stop7h 00m
United Airlines
Wed 6/35:00 am
MKE
- PDX
1 stop6h 39m
United Airlines
Deal found 4/25![United Airlines logo]()
$417
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 5/271:26 pm
MFR
- MKE
1 stop8h 33m
Alaska Airlines
Sat 5/304:40 pm
MKE
- MFR
1 stop9h 19m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$441
This Delta deal was found by Cheapflights users on 4/28. 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 7/155:30 am
BOI
- MKE
1 stop4h 47m
Delta
Tue 7/216:59 pm
MKE
- BOI
1 stop5h 47m
Delta
Deal found 4/28![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 4/26. 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 7/134:55 pm
EUG
- MKE
1 stop7h 00m
Southwest
Sat 7/189:45 am
MKE
- EUG
2 stops14h 05m
Southwest
Deal found 4/26![Southwest logo]()
$422
This United Airlines deal was found by Cheapflights users on 4/25. 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 5/141:07 pm
EUG
- MKE
1 stop6h 58m
United Airlines
Sun 5/175:50 am
MKE
- EUG
1 stop8h 10m
United Airlines
Deal found 4/25![United Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 4/29. 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 6/22:23 pm
BOI
- MKE
1 stop7h 32m
Delta
Fri 6/196:59 pm
MKE
- BOI
1 stop5h 48m
Delta
Deal found 4/29![Delta logo]()
$412
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 8/191:28 pm
RDM
- MKE
1 stop8h 31m
Alaska Airlines
Mon 8/247:00 am
MKE
- RDM
1 stop7h 34m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$460
This Southwest deal was found by Cheapflights users on 4/26. 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 6/303:40 pm
PDX
- MKE
1 stop7h 15m
Southwest
Sun 7/55:30 am
MKE
- PDX
1 stop8h 45m
Southwest
Deal found 4/26![Southwest logo]()
$425
This United Airlines deal was found by Cheapflights users on 4/30. 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 5/2011:55 pm
PDX
- MKE
1 stop8h 02m
United Airlines
Wed 5/275:29 pm
MKE
- PDX
1 stop7h 00m
United Airlines
Deal found 4/30![United Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 4/30. 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 8/215:55 am
RDM
- MKE
2 stops8h 12m
Delta
Sun 8/233:15 pm
MKE
- RDM
2 stops10h 17m
Delta
Deal found 4/30![Delta logo]()
$420
This Alaska Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:25 am
EUG
- MKE
2 stops10h 50m
Alaska Airlines
Wed 5/274:40 pm
MKE
- EUG
1 stop9h 19m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$467
This Southwest deal was found by Cheapflights users on 4/29. 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 7/1810:25 am
EUG
- MKE
1 stop11h 15m
Southwest
Wed 7/225:00 am
MKE
- EUG
2 stops10h 00m
Southwest
Deal found 4/29![Southwest logo]()
$432
This United Airlines deal was found by Cheapflights users on 4/26. 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 5/2612:38 pm
EUG
- MKE
1 stop7h 56m
United Airlines
Wed 5/272:35 pm
MKE
- EUG
1 stop8h 46m
United Airlines
Deal found 4/26![United Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 4/26. 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 8/224:40 pm
EUG
- MKE
2 stops14h 40m
Delta
Sat 9/59:10 am
MKE
- EUG
2 stops8h 48m
Delta
Deal found 4/26![Delta logo]()
$422
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 5/131:53 pm
RDM
- MKE
1 stop8h 06m
Alaska Airlines
Sun 5/177:00 am
MKE
- RDM
1 stop7h 59m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$469
This Southwest deal was found by Cheapflights users on 4/28. 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 7/181:10 pm
PDX
- MKE
1 stop9h 05m
Southwest
Wed 7/226:55 pm
MKE
- PDX
1 stop6h 55m
Southwest
Deal found 4/28![Southwest logo]()
$447
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:00 am
BOI
- MKE
2 stops11h 51m
United Airlines
Wed 6/310:38 am
MKE
- BOI
2 stops12h 27m
United Airlines
Deal found 4/26![United Airlines logo]()
$458
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 8/201:28 pm
RDM
- MKE
1 stop8h 31m
Alaska Airlines
Sun 8/237:00 am
MKE
- RDM
1 stop7h 34m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 4/27. 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 5/121:40 pm
MFR
- MKE
1 stop5h 53m
Delta
Sat 5/166:45 am
MKE
- MFR
2 stops11h 48m
Delta
Deal found 4/27![Delta logo]()
$434
This Southwest deal was found by Cheapflights users on 4/30. 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 7/223:40 pm
PDX
- MKE
1 stop7h 15m
Southwest
Sat 7/256:55 pm
MKE
- PDX
1 stop7h 00m
Southwest
Deal found 4/30![Southwest logo]()
$447
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/276:35 pm
MFR
- MKE
2 stops13h 22m
United Airlines
Sat 5/301:30 pm
MKE
- MFR
2 stops11h 29m
United Airlines
Deal found 4/28![United Airlines logo]()
$460
This Delta deal was found by Cheapflights users on 4/26. 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 8/271:25 pm
MFR
- MKE
1 stop5h 59m
Delta
Mon 8/315:55 pm
MKE
- MFR
2 stops7h 46m
Delta
Deal found 4/26![Delta logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 8/256:01 am
MKE
- BOI
2 stops10h 30m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$493
This Southwest deal was found by Cheapflights users on 4/27. 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 7/295:10 am
PDX
- MKE
1 stop6h 55m
Southwest
Mon 8/36:30 pm
MKE
- PDX
2 stops8h 50m
Southwest
Deal found 4/27![Southwest logo]()
$452
Last-minute flights from Oregon to MilwaukeeDiscover last-minute flight deals from Oregon to Milwaukee. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Milwaukee. Data last updated April 30, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/192:38 pm
PDX
- MKE
1 stop5h 55m
United Airlines
Wed 5/202:38 pm
MKE
- PDX
1 stop8h 31m
United Airlines
Deal found 4/28![United Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 4/28. 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 5/2011:12 pm
PDX
- MKE
1 stop7h 37m
Delta
Tue 5/265:01 pm
MKE
- PDX
1 stop7h 01m
Delta
Deal found 4/28![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/201:07 pm
EUG
- MKE
1 stop5h 46m
United Airlines
Wed 5/276:20 am
MKE
- EUG
1 stop7h 27m
United Airlines
Deal found 4/28![United Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/2011:40 pm
PDX
- MKE
1 stop9h 36m
American Airlines
Tue 5/265:00 am
MKE
- PDX
1 stop6h 57m
American Airlines
Deal found 4/29![American Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 4/29. 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 5/207:00 am
PDX
- MKE
2 stops8h 25m
Southwest
Wed 5/275:45 pm
MKE
- PDX
1 stop7h 15m
Southwest
Deal found 4/29![Southwest logo]()
$363
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 5/239:44 am
PDX
- MKE
1 stop12h 15m
Alaska Airlines
Thu 5/284:40 pm
MKE
- PDX
1 stop6h 48m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 4/25. 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 5/238:50 am
PDX
- MKE
1 stop6h 14m
United Airlines
Sat 5/3010:38 am
MKE
- PDX
2 stops9h 08m
United Airlines
Deal found 4/25![United Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 4/28. 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.
Mon 5/259:39 pm
PDX
- MKE
1 stop9h 29m
Delta
Wed 5/2712:15 pm
MKE
- PDX
1 stop7h 00m
Delta
Deal found 4/28![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 4/28. 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 5/2611:55 pm
PDX
- MKE
1 stop9h 00m
Southwest
Tue 6/26:10 am
MKE
- PDX
2 stops9h 30m
Southwest
Deal found 4/28![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 4/26. 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 5/267:20 pm
RDM
- MKE
2 stops11h 11m
Delta
Tue 6/21:08 pm
MKE
- RDM
2 stops11h 44m
Delta
Deal found 4/26![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 4/29. 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 5/275:20 am
BOI
- MKE
1 stop5h 00m
Delta
Wed 6/36:45 am
MKE
- BOI
1 stop6h 11m
Delta
Deal found 4/29![Delta logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 5/301:45 pm
EUG
- MKE
1 stop8h 14m
Alaska Airlines
Fri 6/54:40 pm
MKE
- EUG
1 stop9h 19m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$370
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 April 30, 2026.
Search for one-way flight options from Oregon to Milwaukee. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/1911:23 pm
PDX
- MKE
1 stop10h 07m
American Airlines
Deal found 4/28![American Airlines logo]()
$159
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/1810:23 pm
PDX
- MKE
1 stop9h 46m
American Airlines
Deal found 4/28![American Airlines logo]()
$167
This United Airlines deal was found by Cheapflights users on 4/26. 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 9/155:00 am
MFR
- MKE
1 stop6h 24m
United Airlines
Deal found 4/26![United Airlines logo]()
$175
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 6/94:08 pm
EUG
- MKE
1 stop5h 51m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$179
This Expedia deal was found by Cheapflights users on 4/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:53 pm
RDM
- MKE
1 stop8h 06m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/274:05 pm
BOI
- MKE
1 stop6h 29m
American Airlines
Deal found 4/29![American Airlines logo]()
$179
This Delta deal was found by Cheapflights users on 4/28. 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 6/95:30 am
EUG
- MKE
2 stops10h 49m
Delta
Deal found 4/28![Delta logo]()
$184
This Southwest deal was found by Cheapflights users on 4/27. 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 4/27![Southwest logo]()
$184
This Delta deal was found by Cheapflights users on 4/27. 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 4/27![Delta logo]()
$185
This Southwest deal was found by Cheapflights users on 4/27. 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 6/101:40 pm
EUG
- MKE
1 stop9h 15m
Southwest
Deal found 4/27![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 4/29. 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 9/155:40 am
BOI
- MKE
1 stop4h 31m
Delta
Deal found 4/29![Delta logo]()
$192
This Delta deal was found by Cheapflights users on 4/27. 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 6/106:13 am
EUG
- MKE
2 stops10h 06m
Delta
Deal found 4/27![Delta logo]()
$197
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 April 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (Delta) |
One-way from | $159 (American Airlines) |
Popular in | February |
Cheapest in | January |
Average price | $421 |
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 April 30, 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
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Sat 5/23
5:00 am-1:25 pm
1 stop6h 25m
Milwaukee-Mitchell
Sat 5/30
1:30 pm-6:47 pm
1 stop7h 17m
$333
EugeneMilwaukee
EUG - MKE
EUGMKE
Eugene
Sat 5/30
1:45 pm-11:59 pm
1 stop8h 14m
Milwaukee-Mitchell
Fri 6/5
4:40 pm-11:59 pm
1 stop9h 19m
$370
RedmondMilwaukee
RDM - MKE
RDMMKE
Bend/Redmond
Fri 7/10
7:25 pm-10:19 am
2 stops12h 54m
Milwaukee-Mitchell
Mon 7/13
4:49 pm-11:58 pm
2 stops9h 09m
$389
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Fri 6/12
4:25 pm-1:55 am
1 stop7h 30m
Milwaukee-Mitchell
Tue 6/16
6:55 pm-11:50 pm
1 stop6h 55m
$397
RedmondMilwaukee
RDM - MKE
RDMMKE
Bend/Redmond
Thu 7/9
5:20 am-7:31 pm
2 stops12h 11m
Milwaukee-Mitchell
Tue 7/14
7:00 am-11:35 am
1 stop6h 35m
$399
Quickest round-trip
BoiseMilwaukee
BOI - MKE
BOIMKE
Boise Air Term. Gowen Fld
Wed 7/15
5:30 am-11:17 am
1 stop4h 47m
Milwaukee-Mitchell
Tue 7/21
6:59 pm-11:46 pm
1 stop5h 47m
$407
EugeneMilwaukee
EUG - MKE
EUGMKE
Eugene
Thu 6/4
6:10 am-7:45 pm
1 stop11h 35m
Milwaukee-Mitchell
Mon 6/15
5:15 am-9:35 am
1 stop6h 20m
$408
BoiseMilwaukee
BOI - MKE
BOIMKE
Boise Air Term. Gowen Fld
Tue 6/2
2:23 pm-10:55 pm
1 stop7h 32m
Milwaukee-Mitchell
Fri 6/19
6:59 pm-11:47 pm
1 stop5h 48m
$412
PortlandMilwaukee
PDX - MKE
PDXMKE
Portland
Tue 6/2
10:51 am-7:51 pm
1 stop7h 00m
Milwaukee-Mitchell
Wed 6/3
5:00 am-9:39 am
1 stop6h 39m
$417
RedmondMilwaukee
RDM - MKE
RDMMKE
Bend/Redmond
Fri 8/21
5:55 am-4:07 pm
2 stops8h 12m
Milwaukee-Mitchell
Sun 8/23
3:15 pm-11:32 pm
2 stops10h 17m
$420
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.
EUG-MKE
MFR-MKE
BOI-MKE
PDX-MKE
RDM-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
EUG-MKE
MFR-MKE
BOI-MKE
PDX-MKE
How far ahead should I book a flight from Oregon to Milwaukee?
Booking 33 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.
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Milwaukee flight routes
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Alternative routes for Oregon to Milwaukee
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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.
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 April 30, 2026.
Oregon and Milwaukee flights
Browse other Oregon and Milwaukee flight options. Last updated on April 30, 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 April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$566 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$405 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$242 | Average$483 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$288 | Average$458 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$465 | FlexibilityNo cancel fee | On-time75% |