$109+ Cheap flights from Oregon to Midway (MDW)
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 — MDW
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from Oregon to Midway 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 Midway
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Cheapest flights from Oregon to MidwayExplore the most affordable flight options available from Oregon to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
Explore the most affordable flight options available from Oregon to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
This Delta deal was found by Cheapflights users on 1/31. 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 4/1411:15 pm
PDX
- MDW
1 stop7h 32m
Delta
Sat 4/182:12 pm
MDW
- PDX
1 stop7h 53m
Delta
Deal found 1/31![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 2/1. 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 2/2810:00 am
PDX
- MDW
1 stop6h 10m
Southwest
Sat 3/78:10 pm
MDW
- PDX
1 stop7h 30m
Southwest
Deal found 2/1![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:00 pm
PDX
- MDW
1 stop10h 25m
Southwest
Sat 4/186:05 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/2![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 2/1. 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 8/2611:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sat 8/2910:15 am
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 2/1![Southwest logo]()
$224
This Delta deal was found by Cheapflights users on 2/2. 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 3/2512:30 am
PDX
- MDW
1 stop6h 20m
Delta
Tue 3/312:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/2![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/2. 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 3/2411:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 3/315:10 pm
MDW
- PDX
1 stop9h 05m
Southwest
Deal found 2/2![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 1/31. 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 3/32:15 pm
PDX
- MDW
1 stop5h 35m
Southwest
Tue 3/105:45 am
MDW
- PDX
2 stops10h 45m
Southwest
Deal found 1/31![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 2/2. 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.
Sun 3/112:40 am
PDX
- MDW
1 stop6h 26m
Delta
Mon 3/910:45 am
MDW
- PDX
1 stop10h 15m
Delta
Deal found 2/2![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/1. 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 3/256:00 pm
PDX
- MDW
1 stop9h 20m
Southwest
Wed 4/15:35 pm
MDW
- PDX
1 stop6h 35m
Southwest
Deal found 2/1![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 2/1. 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 4/117:05 pm
PDX
- MDW
1 stop8h 35m
Southwest
Mon 4/137:40 pm
MDW
- PDX
1 stop7h 15m
Southwest
Deal found 2/1![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 2/2. 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 2/219:45 pm
PDX
- MDW
1 stop10h 09m
Delta
Mon 2/231:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Deal found 2/2![Delta logo]()
$244
This Delta deal was found by Cheapflights users on 2/2. 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 3/31:43 pm
BOI
- MDW
1 stop7h 50m
Delta
Tue 3/179:30 am
MDW
- BOI
1 stop5h 35m
Delta
Deal found 2/2![Delta logo]()
$269
Best flights from Oregon to MidwayDiscover carefully curated flight deals from Oregon to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Oregon to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This Delta deal was found by Cheapflights users on 2/2. 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 2/286:00 am
PDX
- MDW
1 stop8h 14m
Delta
Tue 3/102:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/2![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:00 pm
PDX
- MDW
1 stop10h 25m
Southwest
Tue 4/218:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/2![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 1/31. 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 4/1411:15 pm
PDX
- MDW
1 stop7h 32m
Delta
Sat 4/182:12 pm
MDW
- PDX
1 stop7h 53m
Delta
Deal found 1/31![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 2/2. 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 3/2411:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 3/315:10 pm
MDW
- PDX
1 stop9h 05m
Southwest
Deal found 2/2![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 2/2. 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 3/1712:30 am
PDX
- MDW
1 stop6h 20m
Delta
Wed 3/252:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/2![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 1/31. 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 3/32:15 pm
PDX
- MDW
1 stop5h 35m
Southwest
Tue 3/105:45 am
MDW
- PDX
2 stops10h 45m
Southwest
Deal found 1/31![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 2/2. 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 3/1812:30 am
PDX
- MDW
1 stop6h 20m
Delta
Wed 3/252:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/2![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 2/2. 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 4/3012:30 am
PDX
- MDW
1 stop6h 21m
Delta
Tue 5/52:12 pm
MDW
- PDX
1 stop7h 53m
Delta
Deal found 2/2![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/1. 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 3/311:20 am
BOI
- MDW
1 stop7h 35m
Southwest
Tue 3/176:35 pm
MDW
- BOI
1 stop6h 55m
Southwest
Deal found 2/1![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 2/2. 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 3/412:40 am
PDX
- MDW
1 stop6h 26m
Delta
Wed 3/112:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/2![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/1. 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 2/274:25 pm
BOI
- MDW
1 stop7h 10m
Southwest
Mon 3/28:10 am
MDW
- BOI
1 stop14h 05m
Southwest
Deal found 2/1![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 2/2. 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 3/29:45 pm
PDX
- MDW
1 stop10h 09m
Delta
Mon 3/910:45 am
MDW
- PDX
1 stop10h 15m
Delta
Deal found 2/2![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 1/31. 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 4/86:35 am
EUG
- MDW
2 stops8h 25m
Southwest
Wed 4/155:30 pm
MDW
- EUG
1 stop6h 30m
Southwest
Deal found 1/31![Southwest logo]()
$288
This Delta deal was found by Cheapflights users on 2/2. 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 3/21:43 pm
BOI
- MDW
1 stop7h 48m
Delta
Mon 3/99:30 am
MDW
- BOI
1 stop5h 34m
Delta
Deal found 2/2![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 2/2. 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 3/101:35 pm
EUG
- MDW
1 stop5h 40m
Southwest
Fri 3/135:40 am
MDW
- EUG
1 stop6h 30m
Southwest
Deal found 2/2![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 2/2. 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 4/305:34 am
BOI
- MDW
1 stop6h 58m
Delta
Mon 5/49:31 am
MDW
- BOI
1 stop5h 55m
Delta
Deal found 2/2![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 2/1. 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 2/186:35 am
EUG
- MDW
2 stops11h 20m
Southwest
Wed 3/115:55 am
MDW
- EUG
1 stop6h 15m
Southwest
Deal found 2/1![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 2/1. 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 2/186:07 am
EUG
- MDW
2 stops9h 30m
Delta
Tue 3/102:05 pm
MDW
- EUG
2 stops11h 44m
Delta
Deal found 2/1![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 2/1. 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 2/176:07 am
EUG
- MDW
2 stops9h 30m
Delta
Tue 3/101:10 pm
MDW
- EUG
2 stops11h 36m
Delta
Deal found 2/1![Delta logo]()
$273
This Southwest deal was found by Cheapflights users on 1/31. 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 3/311:35 pm
EUG
- MDW
2 stops8h 30m
Southwest
Tue 4/76:30 am
MDW
- EUG
1 stop6h 15m
Southwest
Deal found 1/31![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 2/2. 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 2/263:30 pm
EUG
- MDW
1 stop5h 40m
Southwest
Tue 3/32:10 pm
MDW
- EUG
2 stops9h 05m
Southwest
Deal found 2/2![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 2/2. 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 3/35:20 am
BOI
- MDW
2 stops11h 17m
Delta
Tue 3/179:30 am
MDW
- BOI
1 stop5h 35m
Delta
Deal found 2/2![Delta logo]()
$274
This Delta deal was found by Cheapflights users on 2/1. 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 2/275:20 am
BOI
- MDW
2 stops11h 17m
Delta
Mon 3/26:00 am
MDW
- BOI
1 stop7h 28m
Delta
Deal found 2/1![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 2/1. 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 4/1511:20 am
EUG
- MDW
2 stops10h 00m
Southwest
Sun 4/266:00 am
MDW
- EUG
1 stop6h 15m
Southwest
Deal found 2/1![Southwest logo]()
$334
This Delta deal was found by Cheapflights users on 2/1. 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 3/1011:30 pm
BOI
- MDW
1 stop9h 26m
Delta
Sun 3/156:00 am
MDW
- BOI
1 stop7h 38m
Delta
Deal found 2/1![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 2/1. 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 3/115:30 am
BOI
- MDW
1 stop6h 55m
Delta
Sun 3/156:00 am
MDW
- BOI
1 stop7h 38m
Delta
Deal found 2/1![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 2/1. 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 4/175:34 am
BOI
- MDW
2 stops11h 24m
Delta
Mon 4/202:12 pm
MDW
- BOI
1 stop7h 49m
Delta
Deal found 2/1![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 2/2. 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 2/266:07 am
EUG
- MDW
2 stops9h 30m
Delta
Tue 3/31:49 pm
MDW
- EUG
2 stops11h 06m
Delta
Deal found 2/2![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 2/3. 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 5/306:14 am
MFR
- MDW
2 stops9h 42m
Delta
Mon 6/81:00 pm
MDW
- MFR
2 stops12h 13m
Delta
Deal found 2/3![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 2/3. 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 5/306:14 am
MFR
- MDW
2 stops9h 42m
Delta
Tue 6/91:00 pm
MDW
- MFR
2 stops12h 13m
Delta
Deal found 2/3![Delta logo]()
$417
Last-minute flights from Oregon to MidwayDiscover last-minute flight deals from Oregon to Midway. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Midway. Data last updated February 3, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/1. 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 2/146:00 am
PDX
- MDW
1 stop8h 14m
Delta
Tue 2/1710:49 am
MDW
- PDX
1 stop10h 27m
Delta
Deal found 2/1![Delta logo]()
$251
This Delta deal was found by Cheapflights users on 2/1. 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 2/216:00 am
PDX
- MDW
1 stop8h 14m
Delta
Mon 2/231:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Deal found 2/1![Delta logo]()
$244
This Southwest deal was found by Cheapflights users on 2/1. 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 2/2810:00 am
PDX
- MDW
1 stop6h 10m
Southwest
Sat 3/78:10 pm
MDW
- PDX
1 stop7h 30m
Southwest
Deal found 2/1![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 2/2. 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.
Sun 3/112:40 am
PDX
- MDW
1 stop6h 26m
Delta
Mon 3/910:45 am
MDW
- PDX
1 stop10h 15m
Delta
Deal found 2/2![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 1/31. 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 3/16:45 am
PDX
- MDW
Nonstop3h 55m
Southwest
Sun 3/85:55 am
MDW
- PDX
1 stop6h 15m
Southwest
Deal found 1/31![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 2/3. 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 3/311:05 am
PDX
- MDW
1 stop6h 50m
Southwest
Tue 3/105:45 am
MDW
- PDX
2 stops10h 45m
Southwest
Deal found 2/3![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 2/1. 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 3/311:20 am
BOI
- MDW
1 stop7h 35m
Southwest
Tue 3/176:35 pm
MDW
- BOI
1 stop6h 55m
Southwest
Deal found 2/1![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 1/31. 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 3/1311:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Wed 3/185:45 am
MDW
- PDX
2 stops10h 45m
Southwest
Deal found 1/31![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 2/1. 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 3/1712:30 am
PDX
- MDW
1 stop6h 20m
Delta
Wed 3/252:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/1![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 2/2. 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 3/2411:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 3/315:10 pm
MDW
- PDX
1 stop9h 05m
Southwest
Deal found 2/2![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 2/1. 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 3/2512:30 am
PDX
- MDW
1 stop6h 20m
Delta
Tue 3/312:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/1![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/1. 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 3/256:00 pm
PDX
- MDW
1 stop9h 20m
Southwest
Wed 4/15:35 pm
MDW
- PDX
1 stop6h 35m
Southwest
Deal found 2/1![Southwest logo]()
$241
One-way flights from Oregon to MidwaySearch for one-way flight options from Oregon to Midway. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Oregon to Midway. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Delta deal was found by Cheapflights users on 2/1. 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 2/259:45 pm
PDX
- MDW
1 stop10h 09m
Delta
Deal found 2/1![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 2/2. 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 2/287:15 am
PDX
- MDW
Nonstop4h 00m
Southwest
Deal found 2/2![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/92:40 pm
PDX
- MDW
1 stop6h 25m
Southwest
Deal found 1/31![Southwest logo]()
$111
This Southwest deal was found by Cheapflights users on 2/1. 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 2/288:30 am
BOI
- MDW
1 stop5h 00m
Southwest
Deal found 2/1![Southwest logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sun 4/2611:48 am
PDX
- MDW
2 stops25h 01m
Frontier
Deal found 2/3![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sun 5/37:46 pm
PDX
- MDW
1 stop17h 03m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:56 am
BOI
- MDW
2 stops26h 23m
Frontier
Deal found 2/1![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:04 pm
PDX
- MDW
2 stops32h 20m
Frontier
Deal found 2/3![Frontier logo]()
$116
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:20 pm
PDX
- MDW
1 stop14h 15m
Southwest
Deal found 1/31![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 2/2. 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 3/412:40 am
PDX
- MDW
1 stop6h 26m
Delta
Deal found 2/2![Delta logo]()
$119
This Southwest deal was found by Cheapflights users on 2/2. 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 3/1010:45 am
EUG
- MDW
1 stop9h 30m
Southwest
Deal found 2/2![Southwest logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Sun 5/1011:48 am
PDX
- MDW
2 stops32h 33m
Frontier
Deal found 1/31![Frontier logo]()
$121
Find flight deals from Oregon to Midway
Keep the following information in mind while searching for Oregon to Midway flight deals. Data was last updated February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Delta) |
One-way from | $109 (Delta) |
Popular in | March |
Cheapest in | August |
Average price | $326 |
Good round-trip deal | $319 or less |
Good one-way deal | $174 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Oregon to Midway 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 February 3, 2026.
Use the filters below to find and compare flights from Oregon to Chicago Midway Airport that are best for you.
Fly from
Oregon
Fly to
Midway
Route
Depart
Return
Price
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 2/28
6:00 am-4:14 pm
1 stop8h 14m
Chicago Midway
Tue 3/10
2:05 pm-8:25 pm
1 stop8h 20m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 4/14
11:15 pm-8:47 am
1 stop7h 32m
Chicago Midway
Sat 4/18
2:12 pm-8:05 pm
1 stop7h 53m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 3/17
12:30 am-8:50 am
1 stop6h 20m
Chicago Midway
Wed 3/25
2:05 pm-8:25 pm
1 stop8h 20m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 4/14
5:00 pm-5:25 am
1 stop10h 25m
Chicago Midway
Tue 4/21
8:50 pm-11:10 pm
Nonstop4h 20m
$223
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 3/18
12:30 am-8:50 am
1 stop6h 20m
Chicago Midway
Wed 3/25
2:05 pm-8:25 pm
1 stop8h 20m
$227
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 4/30
12:30 am-8:51 am
1 stop6h 21m
Chicago Midway
Tue 5/5
2:12 pm-8:05 pm
1 stop7h 53m
$227
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 3/4
12:40 am-9:06 am
1 stop6h 26m
Chicago Midway
Wed 3/11
2:05 pm-8:25 pm
1 stop8h 20m
$227
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 3/24
11:55 pm-5:45 am
Nonstop3h 50m
Chicago Midway
Tue 3/31
5:10 pm-12:15 am
1 stop9h 05m
$231
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 3/3
2:15 pm-9:50 pm
1 stop5h 35m
Chicago Midway
Tue 3/10
5:45 am-2:30 pm
2 stops10h 45m
$232
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 3/2
9:45 pm-9:54 am
1 stop10h 09m
Chicago Midway
Mon 3/9
10:45 am-7:00 pm
1 stop10h 15m
$237
Showing 1-10 of 60 results
Best time to book a flight from Oregon to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Oregon with our price prediction graph.
PDX-MDW
EUG-MDW
BOI-MDW
RDM-MDW
MFR-MDW
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 Chicago Midway Airport
USOR-MDW
PDX-MDW
EUG-MDW
BOI-MDW
RDM-MDW
What is the cheapest month to book a flight from Oregon to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Oregon to Chicago Midway Airport (average of $141). Flying from Oregon to Chicago Midway Airport in March is currently the most expensive (average of $292). 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.
What is the cheapest time of day to fly from OR to MDW?
Find hourly flight availability from Oregon to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 3, 2026.
When flying from Oregon to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 27% versus a flight in the evening.
Related info for your journey
Find useful and relevant information for your journey from Oregon to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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 for Oregon to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Oregon to Midway
Discover the top 2 airlines that operate flights from Oregon to Midway. 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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$231 | Average$424 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$268 | Average$377 | FlexibilityNo cancel fee | On-timeN/A |