$60+ Cheap flights from Portland (PDX) to Illinois
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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Mrz 4 — Mrz 111
1 adult, Economy
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Cheapest flights from Portland to IllinoisExplore the most affordable flight options available from Portland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on Februar 2, 2026.
Explore the most affordable flight options available from Portland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on Februar 2, 2026.
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.
So 4/197:46 pm
PDX
- ORD
1 stop19h 07m
Multiple Airlines
Sa 4/257:21 pm
ORD
- PDX
1 stop18h 36m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$216
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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.
Di 4/77:03 am
PDX
- ORD
Nonstop4h 10m
Alaska Airlines
Fr 4/174:10 pm
ORD
- PDX
1 stop9h 49m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$217
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.
Di 3/1712:30 am
PDX
- MDW
1 stop6h 20m
Delta
Mi 3/252:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/1![Delta logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 4/125:14 pm
PDX
- ORD
1 stop10h 25m
Frontier
Do 4/2310:55 am
ORD
- PDX
1 stop26h 08m
Frontier
Deal found 1/30![Frontier logo]()
$220
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.
Sa 2/2810:00 am
PDX
- MDW
1 stop6h 10m
Southwest
Sa 3/78:10 pm
MDW
- PDX
1 stop7h 30m
Southwest
Deal found 2/1![Southwest logo]()
$220
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/2311:48 am
PDX
- ORD
1 stop20h 02m
Frontier
Mo 4/2710:55 am
ORD
- PDX
1 stop28h 07m
Frontier
Deal found 1/31![Frontier logo]()
$222
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/151:48 pm
PDX
- STL
1 stop27h 24m
Frontier
Sa 4/188:12 pm
STL
- PDX
1 stop16h 51m
Frontier
Deal found 2/1![Frontier logo]()
$222
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 2/183:50 pm
PDX
- ORD
1 stop6h 09m
United Airlines
Mi 3/188:04 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 1/31![United Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 1/30. 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.
Mi 4/297:55 pm
PDX
- MDW
1 stop7h 05m
Southwest
Sa 5/21:55 pm
MDW
- PDX
1 stop6h 50m
Southwest
Deal found 1/30![Southwest logo]()
$224
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 3/139:26 pm
PDX
- ORD
1 stop15h 32m
Alaska Airlines
Di 3/172:07 pm
ORD
- PDX
Nonstop4h 43m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 3/912:52 pm
PDX
- ORD
1 stop15h 16m
Multiple Airlines
Mi 3/188:58 pm
ORD
- PDX
2 stops40h 11m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$226
This Delta deal was found by Cheapflights users on 1/30. 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.
Mi 4/812:30 am
PDX
- ORD
1 stop6h 10m
Delta
Di 4/147:15 am
ORD
- PDX
1 stop9h 35m
Delta
Deal found 1/30![Delta logo]()
$227
Best flights from Portland to IllinoisDiscover carefully curated flight deals from Portland to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated Februar 2, 2026.
Discover carefully curated flight deals from Portland to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated Februar 2, 2026.
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 3/611:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Mo 3/98:04 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 1/31![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 1/30. 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.
Mi 4/81:45 pm
PDX
- ORD
1 stop5h 49m
Delta
Di 4/147:12 pm
ORD
- PDX
1 stop6h 41m
Delta
Deal found 1/30![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.
Fr 3/611:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
So 3/89:40 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/1![Southwest logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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.
Mo 5/41:52 pm
PDX
- ORD
1 stop8h 07m
Alaska Airlines
Fr 5/153:43 pm
ORD
- PDX
1 stop10h 09m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$237
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 2/251:52 pm
PDX
- MLI
1 stop7h 36m
American Airlines
Sa 2/287:09 pm
MLI
- PDX
1 stop7h 08m
American Airlines
Deal found 1/31![American Airlines logo]()
$251
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 3/611:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
So 3/88:04 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 2/1![United Airlines 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.
So 3/16:45 am
PDX
- MDW
Nonstop3h 55m
Southwest
So 3/89:40 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 1/31![Southwest logo]()
$217
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.
Di 4/1411:15 pm
PDX
- MDW
1 stop7h 32m
Delta
Sa 4/182:12 pm
MDW
- PDX
1 stop7h 53m
Delta
Deal found 1/31![Delta logo]()
$217
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 3/2711:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Di 3/3112:40 pm
ORD
- PDX
Nonstop4h 29m
United Airlines
Deal found 2/2![United Airlines 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.
Di 4/212:35 pm
PDX
- MDW
1 stop6h 45m
Southwest
Do 4/239:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 1/31![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 1/30. 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.
Di 3/105:30 am
PDX
- ORD
1 stop5h 54m
Delta
Fr 3/137:10 pm
ORD
- PDX
1 stop6h 44m
Delta
Deal found 1/30![Delta logo]()
$227
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/2211:59 pm
PDX
- ORD
Nonstop4h 04m
United Airlines
Di 4/287:40 am
ORD
- PDX
1 stop8h 50m
United Airlines
Deal found 1/31![United Airlines 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.
Do 4/95:10 am
PDX
- MDW
Nonstop3h 55m
Southwest
Mo 4/139:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 1/31![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 1/30. 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.
Mi 4/812:30 am
PDX
- ORD
1 stop6h 10m
Delta
Mi 4/157:12 pm
ORD
- PDX
1 stop6h 41m
Delta
Deal found 1/30![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 1/30. 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.
Mi 4/297:55 pm
PDX
- MDW
1 stop7h 05m
Southwest
Sa 5/21:55 pm
MDW
- PDX
1 stop6h 50m
Southwest
Deal found 1/30![Southwest logo]()
$224
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 3/127:49 pm
PDX
- ORD
1 stop7h 18m
United Airlines
Mo 3/164:40 pm
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 1/31![United Airlines logo]()
$227
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.
Sa 4/115:45 am
PDX
- ORD
1 stop7h 33m
Delta
Mo 4/137:12 pm
ORD
- PDX
1 stop6h 41m
Delta
Deal found 2/1![Delta logo]()
$227
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 2/2012:04 pm
PDX
- MLI
1 stop8h 49m
American Airlines
Di 2/243:33 pm
MLI
- PDX
1 stop8h 19m
American Airlines
Deal found 2/2![American Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 1/30. 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.
Do 4/163:00 pm
PDX
- MDW
1 stop6h 55m
Southwest
Sa 4/186:00 am
MDW
- PDX
1 stop6h 15m
Southwest
Deal found 1/30![Southwest logo]()
$227
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.
Fr 4/1711:15 pm
PDX
- MDW
1 stop7h 32m
Delta
Di 4/212:12 pm
MDW
- PDX
1 stop7h 53m
Delta
Deal found 1/31![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Do 7/2311:40 pm
PDX
- STL
1 stop8h 54m
United Airlines
Di 7/285:15 am
STL
- PDX
1 stop6h 05m
United Airlines
Deal found 1/30![United Airlines logo]()
$249
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.
Mi 3/115:25 am
PDX
- MDW
Nonstop3h 55m
Southwest
So 3/159:40 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/1![Southwest logo]()
$232
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.
Mi 4/812:30 am
PDX
- ORD
1 stop6h 10m
Delta
Mo 4/1312:46 pm
ORD
- PDX
1 stop6h 24m
Delta
Deal found 1/31![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Sa 2/217:00 am
PDX
- STL
1 stop7h 02m
United Airlines
Di 2/246:25 am
STL
- PDX
1 stop7h 30m
United Airlines
Deal found 1/30![United Airlines logo]()
$249
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.
Di 3/32:15 pm
PDX
- MDW
1 stop5h 35m
Southwest
Di 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 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.
Mi 4/112:30 am
PDX
- STL
1 stop6h 31m
Delta
So 4/56:12 pm
STL
- PDX
1 stop7h 42m
Delta
Deal found 1/31![Delta logo]()
$249
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/1611:59 pm
PDX
- STL
1 stop6h 36m
United Airlines
Sa 4/188:30 am
STL
- PDX
1 stop8h 01m
United Airlines
Deal found 2/1![United Airlines logo]()
$249
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 2/242:05 pm
PDX
- EVV
1 stop7h 12m
American Airlines
Mi 3/183:50 pm
EVV
- PDX
1 stop9h 19m
American Airlines
Deal found 1/31![American Airlines logo]()
$430
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.
Fr 2/271:53 pm
PDX
- STL
1 stop7h 30m
Delta
Mo 3/26:40 pm
STL
- PDX
1 stop7h 13m
Delta
Deal found 2/1![Delta logo]()
$249
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 7/1811:59 pm
PDX
- STL
1 stop7h 54m
United Airlines
Sa 7/256:55 pm
STL
- PDX
1 stop6h 57m
United Airlines
Deal found 2/1![United Airlines logo]()
$249
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated Februar 2, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated Februar 2, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 1/30. 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.
Di 2/179:45 pm
PDX
- ORD
1 stop8h 56m
Delta
Mi 2/257:40 am
ORD
- PDX
1 stop7h 02m
Delta
Deal found 1/30![Delta logo]()
$234
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 2/183:50 pm
PDX
- ORD
1 stop6h 09m
United Airlines
Sa 2/219:10 am
ORD
- PDX
Nonstop4h 45m
United Airlines
Deal found 1/31![United Airlines logo]()
$224
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.
Mi 2/187:25 am
PDX
- MDW
1 stop7h 50m
Southwest
Mi 3/185:45 am
MDW
- PDX
1 stop10h 05m
Southwest
Deal found 1/31![Southwest logo]()
$234
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.
Mi 2/187:25 am
PDX
- MDW
1 stop7h 50m
Southwest
Sa 2/218:30 pm
MDW
- PDX
Nonstop4h 30m
Southwest
Deal found 1/31![Southwest logo]()
$235
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.
Sa 2/216:00 am
PDX
- MDW
1 stop8h 14m
Delta
Fr 3/202:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 1/31![Delta logo]()
$227
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 2/217:00 am
PDX
- ORD
Nonstop4h 11m
Alaska Airlines
Mo 3/162:07 pm
ORD
- PDX
Nonstop4h 43m
Alaska Airlines
Deal found 1/31![Alaska Airlines 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.
Mi 2/253:59 pm
PDX
- ORD
1 stop5h 53m
Delta
Mi 3/42:20 pm
ORD
- PDX
1 stop8h 35m
Delta
Deal found 2/2![Delta logo]()
$217
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.
Do 2/263:59 pm
PDX
- ORD
1 stop5h 53m
Delta
Mi 3/42:20 pm
ORD
- PDX
1 stop6h 28m
Delta
Deal found 2/2![Delta logo]()
$227
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.
Do 2/2612:40 am
PDX
- MDW
1 stop6h 26m
Delta
Mo 3/21:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Deal found 2/1![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.
Fr 2/276:45 am
PDX
- MDW
Nonstop3h 55m
Southwest
Mo 3/28:10 am
MDW
- PDX
Nonstop4h 35m
Southwest
Deal found 2/1![Southwest logo]()
$217
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.
Fr 2/275:30 am
PDX
- ORD
1 stop5h 52m
Delta
Fr 3/62:20 pm
ORD
- PDX
1 stop8h 35m
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.
Sa 2/2810:00 am
PDX
- MDW
1 stop6h 10m
Southwest
Sa 3/78:10 pm
MDW
- PDX
1 stop7h 30m
Southwest
Deal found 2/1![Southwest logo]()
$220
One-way flights from Portland to IllinoisSearch for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated Februar 2, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated Februar 2, 2026.
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.
Fr 3/612:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 1/31![Frontier logo]()
$60
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 3/1212:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 2/1![Frontier logo]()
$76
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.
Fr 3/1312:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 1/31![Frontier logo]()
$79
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 3/812:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 1/31![Frontier logo]()
$94
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.
So 3/1512:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 1/31![Frontier logo]()
$97
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/151:48 pm
PDX
- STL
1 stop27h 24m
Frontier
Deal found 1/31![Frontier logo]()
$107
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 3/111:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Deal found 2/2![United Airlines logo]()
$109
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.
Mi 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 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.
Sa 2/217:15 am
PDX
- MDW
Nonstop4h 00m
Southwest
Deal found 1/31![Southwest logo]()
$110
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 4/279:27 pm
PDX
- ORD
1 stop13h 46m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$111
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.
Mi 4/291:48 pm
PDX
- MDW
2 stops30h 33m
Frontier
Deal found 1/31![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/151:48 pm
PDX
- MDW
2 stops30h 33m
Frontier
Deal found 1/30![Frontier logo]()
$112
Find flight deals from Portland to Illinois
Keep the following information in mind while searching for Portland to Illinois flight deals. Data was last updated Februar 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $216 (Kiwi.com) |
One-way from | $60 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $326 |
Good round-trip deal | $318 or less |
Good one-way deal | $166 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Illinois 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 Februar 2, 2026.
Use the filters below to find and compare flights from Portland to Illinois that are best for you.
Fly from
Portland
Fly to
Illinois
Route
Depart
Return
Price
PortlandChicago
PDX - ORD
PDXORD
Portland
Fr 3/6
11:59 pm-5:53 am
Nonstop3h 54m
Chicago O'Hare Intl
Mo 3/9
8:04 pm-10:45 pm
Nonstop4h 41m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Mi 4/8
1:45 pm-9:34 pm
1 stop5h 49m
Chicago O'Hare Intl
Di 4/14
7:12 pm-11:53 pm
1 stop6h 41m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fr 3/6
11:55 pm-5:45 am
Nonstop3h 50m
Chicago Midway
So 3/8
9:40 pm-12:05 am
Nonstop4h 25m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Fr 3/6
11:59 pm-5:53 am
Nonstop3h 54m
Chicago O'Hare Intl
So 3/8
8:04 pm-10:45 pm
Nonstop4h 41m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
So 3/1
6:45 am-12:40 pm
Nonstop3h 55m
Chicago Midway
So 3/8
9:40 pm-12:05 am
Nonstop4h 25m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Di 4/14
11:15 pm-8:47 am
1 stop7h 32m
Chicago Midway
Sa 4/18
2:12 pm-8:05 pm
1 stop7h 53m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Fr 3/27
11:59 pm-5:53 am
Nonstop3h 54m
Chicago O'Hare Intl
Di 3/31
12:40 pm-3:09 pm
Nonstop4h 29m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Di 4/21
2:35 pm-11:20 pm
1 stop6h 45m
Chicago Midway
Do 4/23
9:50 pm-12:10 am
Nonstop4h 20m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Mi 4/22
11:59 pm-6:03 am
Nonstop4h 04m
Chicago O'Hare Intl
Di 4/28
7:40 am-2:30 pm
1 stop8h 50m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Do 4/9
5:10 am-11:05 am
Nonstop3h 55m
Chicago Midway
Mo 4/13
9:50 pm-12:10 am
Nonstop4h 20m
$217
Showing 1-10 of 60 results
Best time to book a flight from Portland to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Portland with our price prediction graph.
PDX-ORD
PDX-MDW
PDX-MLI
PDX-STL
PDX-PIA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Illinois
PDX-USIL
PDX-ORD
PDX-MDW
PDX-MLI
PDX-STL
What is the cheapest month to book a flight from Portland to Illinois?
Currently, August is the cheapest month in which you can book a flight from Portland to Illinois (average of $122). Flying from Portland to Illinois in July is currently the most expensive (average of $238). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from PDX to IL?
Find hourly flight availability from Portland to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated Februar 2, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 20% on the flight price compared to flying in the evening, which is usually more expensive.
What is the cheapest day to fly from Portland to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Portland to Illinois. Price data was last updated on January 31, 2026.
Travelers seeking maximum savings on their Portland to Illinois flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Portland to Illinois
Explore weekly flight availability from Portland to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated Februar 2, 2026.
The most flights from PDX to USIL are scheduled on a Thursday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated Februar 2, 2026.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Hawaiian Airlines from Portland to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Boarding
8.1
Entertainment
7.0
Crew
8.5
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Related info for your journey
Find useful and relevant information for your journey from Portland to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Portland to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Top 8 airlines flying from Portland to Illinois
Discover the top 8 airlines that operate flights from Portland to Illinois. 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 Februar 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$333 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$194 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$125 | Average$283 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$196 | Average$447 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$205 | Average$451 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$215 | Average$349 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$231 | Average$398 | FlexibilityNo cancel fee | On-time63% |