$142+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Oct 2 — Oct 91
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Illinois with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 September 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 September 2, 2026.
This CheapOair deal was found by Cheapflights users on 8/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:11 pm -
1 stop22h 24m
Mon 10/198:00 pm -
1 stop16h 54m
Deal found 8/30![Frontier logo]()
$280
This CheapOair deal was found by Cheapflights users on 8/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:38 pm -
1 stop28h 39m
Wed 10/712:17 pm -
1 stop25h 09m
Deal found 8/28![Frontier logo]()
$289
This Trip.com deal was found by Cheapflights users on 8/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:38 pm -
1 stop28h 39m
Thu 9/2412:27 pm -
1 stop25h 27m
Deal found 8/28![Frontier logo]()
$293
This United Airlines deal was found by Cheapflights users on 8/31. 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.
Sat 10/172:27 pm -
1 stop6h 11m
Sat 10/242:28 pm -
1 stop9h 55m
Deal found 8/31![United Airlines logo]()
$301
This Frontier deal was found by Cheapflights users on 8/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:02 pm -
1 stop10h 19m
Tue 11/36:30 am -
1 stop6h 37m
Deal found 8/28![Frontier logo]()
$310
This Frontier deal was found by Cheapflights users on 8/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:49 am -
1 stop10h 35m
Tue 10/206:30 am -
1 stop6h 24m
Deal found 8/29![Frontier logo]()
$311
This Frontier deal was found by Cheapflights users on 8/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:02 pm -
1 stop10h 19m
Tue 11/36:30 am -
1 stop6h 37m
Deal found 8/31![Frontier logo]()
$315
This Priceline deal was found by Cheapflights users on 8/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:38 pm -
1 stop9h 45m
Tue 10/67:20 am -
1 stop8h 30m
Deal found 8/31![Multiple Airlines logo]()
$316
This Orbitz deal was found by Cheapflights users on 8/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:38 pm -
1 stop9h 45m
Sun 9/276:30 am -
1 stop7h 13m
Deal found 8/28![Frontier logo]()
$317
This Expedia deal was found by Cheapflights users on 9/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:00 am -
Nonstop4h 18m
Tue 10/136:30 am -
1 stop6h 24m
Deal found 9/1![Multiple Airlines logo]()
$318
This Frontier deal was found by Cheapflights users on 8/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:38 pm -
1 stop9h 45m
Sun 10/46:30 am -
1 stop7h 13m
Deal found 8/28![Frontier logo]()
$320
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:25 pm -
1 stop14h 51m
Sun 10/256:30 am -
1 stop6h 24m
Deal found 9/2![Frontier logo]()
$321
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 September 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 September 2, 2026.
This Southwest deal was found by Cheapflights users on 8/28. 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 10/2710:45 am -
2 stops9h 25m
Thu 10/295:05 am -
1 stop6h 45m
Deal found 8/28![Southwest logo]()
$354
This Alaska Airlines deal was found by Cheapflights users on 9/1. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:06 am -
Nonstop4h 20m
Tue 9/297:20 am -
1 stop28h 10m
Deal found 9/1![Alaska Airlines logo]()
$360
This United Airlines deal was found by Cheapflights users on 8/28. 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 11/47:00 am -
Nonstop4h 07m
Sat 11/78:55 am -
1 stop7h 42m
Deal found 8/28![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 9/1. 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.
Mon 10/511:10 pm -
1 stop8h 39m
Wed 10/77:00 pm -
1 stop6h 47m
Deal found 9/1![Delta logo]()
$369
This KAYAK deal was found by Cheapflights users on 8/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/511:49 pm -
1 stop7h 31m
Thu 10/811:31 am -
1 stop10h 10m
Deal found 8/31![American Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Thu 10/2912:02 pm -
2 stops21h 25m
Sun 11/18:53 pm -
1 stop16h 43m
Deal found 9/1![Multiple Airlines logo]()
$398
This Southwest deal was found by Cheapflights users on 9/1. 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.
Thu 10/295:20 am -
Nonstop3h 50m
Mon 11/29:15 pm -
Nonstop4h 40m
Deal found 9/1![Southwest logo]()
$357
This United Airlines deal was found by Cheapflights users on 8/28. 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.
Fri 10/307:00 am -
Nonstop4h 07m
Wed 11/44:25 pm -
Nonstop4h 47m
Deal found 8/28![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 9/1. 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 11/45:33 am -
1 stop5h 59m
Sun 11/82:38 pm -
1 stop9h 24m
Deal found 9/1![Delta logo]()
$369
This Alaska Airlines deal was found by Cheapflights users on 8/31. 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.
Fri 10/25:38 pm -
1 stop17h 47m
Mon 10/52:21 pm -
1 stop10h 26m
Deal found 8/31![Alaska Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 8/28. 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 10/172:40 pm -
1 stop6h 15m
Mon 10/195:10 am -
2 stops9h 25m
Deal found 8/28![Southwest logo]()
$358
This American Airlines deal was found by Cheapflights users on 8/29. 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.
Thu 10/151:12 pm -
1 stop8h 59m
Sun 10/186:00 am -
1 stop8h 22m
Deal found 8/29![American Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 8/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 pm -
Nonstop4h 01m
Sun 10/117:00 am -
Nonstop4h 31m
Deal found 8/29![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 9/1. 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.
Thu 10/1511:12 pm -
1 stop6h 29m
Mon 10/192:45 pm -
1 stop9h 34m
Deal found 9/1![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 8/28. 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 10/2710:45 am -
2 stops9h 25m
Mon 11/24:00 pm -
2 stops10h 10m
Deal found 8/28![Southwest logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Thu 10/1512:11 pm -
2 stops21h 16m
Sun 10/189:33 pm -
1 stop16h 07m
Deal found 8/31![Multiple Airlines logo]()
$445
This Delta deal was found by Cheapflights users on 8/31. 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 11/36:00 am -
1 stop8h 47m
Sat 11/76:04 am -
1 stop9h 34m
Deal found 8/31![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 8/29. 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 9/266:50 am -
2 stops6h 45m
Sat 10/38:25 am -
2 stops10h 55m
Deal found 8/29![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Sat 1/307:01 am -
1 stop8h 59m
Tue 2/28:15 am -
1 stop9h 15m
Deal found 9/1![United Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 9/1. 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.
Thu 10/11:49 pm -
1 stop7h 42m
Mon 10/58:55 am -
2 stops10h 14m
Deal found 9/1![Delta logo]()
$382
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:00 am -
1 stop7h 02m
Fri 12/112:32 pm -
1 stop9h 26m
Deal found 9/1![American Airlines logo]()
$474
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 10/412:38 pm -
2 stops19h 16m
Thu 10/89:03 pm -
1 stop16h 37m
Deal found 8/31![Multiple Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 8/28. 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.
Mon 10/122:55 pm -
2 stops8h 20m
Thu 10/159:45 pm -
Nonstop4h 30m
Deal found 8/28![Southwest logo]()
$372
This United Airlines deal was found by Cheapflights users on 8/31. 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.
Sat 10/177:29 pm -
2 stops12h 43m
Sat 10/2410:49 am -
2 stops12h 11m
Deal found 8/31![United Airlines logo]()
$411
This Delta deal was found by Cheapflights users on 9/1. 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.
Thu 10/295:30 am -
2 stops10h 40m
Mon 11/212:50 pm -
1 stop9h 10m
Deal found 9/1![Delta logo]()
$382
This American Airlines deal was found by Cheapflights users on 8/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:00 am -
1 stop9h 21m
Sat 11/146:40 am -
1 stop7h 48m
Deal found 8/30![American Airlines logo]()
$475
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:06 am -
2 stops22h 21m
Sun 10/119:33 pm -
1 stop16h 07m
Deal found 8/28![Multiple Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 8/31. 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.
Thu 10/12:35 pm -
1 stop7h 40m
Tue 10/65:45 am -
1 stop8h 05m
Deal found 8/31![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 8/31. 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.
Thu 10/18:44 pm -
2 stops9h 12m
Tue 10/62:45 pm -
1 stop9h 34m
Deal found 8/31![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 8/30. 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.
Tue 10/1310:43 am -
2 stops10h 15m
Sat 10/176:15 am -
1 stop7h 18m
Deal found 8/30![United Airlines logo]()
$430
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated September 2, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 8/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:38 pm -
1 stop28h 39m
Thu 9/2412:27 pm -
1 stop25h 27m
Deal found 8/28![Frontier logo]()
$293
This Orbitz deal was found by Cheapflights users on 8/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:38 pm -
1 stop9h 45m
Sun 9/276:30 am -
1 stop7h 13m
Deal found 8/28![Frontier logo]()
$317
This CheapOair deal was found by Cheapflights users on 8/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:38 pm -
1 stop28h 39m
Wed 10/712:17 pm -
1 stop25h 09m
Deal found 8/28![Frontier logo]()
$289
This Priceline deal was found by Cheapflights users on 8/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:38 pm -
1 stop9h 45m
Tue 10/67:20 am -
1 stop8h 30m
Deal found 8/31![Multiple Airlines logo]()
$316
This Expedia deal was found by Cheapflights users on 8/31. 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.
Thu 10/112:38 pm -
1 stop9h 45m
Thu 10/88:01 pm -
1 stop16h 10m
Deal found 8/31![Frontier logo]()
$320
This Expedia deal was found by Cheapflights users on 9/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:00 am -
Nonstop4h 18m
Tue 10/136:30 am -
1 stop6h 24m
Deal found 9/1![Multiple Airlines logo]()
$318
This Frontier deal was found by Cheapflights users on 8/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:49 am -
1 stop10h 35m
Tue 10/206:30 am -
1 stop6h 24m
Deal found 8/29![Frontier logo]()
$311
This Super.com deal was found by Cheapflights users on 8/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:49 am -
1 stop10h 35m
Sat 10/178:01 pm -
1 stop16h 10m
Deal found 8/30![Frontier logo]()
$322
This CheapOair deal was found by Cheapflights users on 8/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:11 pm -
1 stop22h 24m
Mon 10/198:00 pm -
1 stop16h 54m
Deal found 8/30![Frontier logo]()
$280
This United Airlines deal was found by Cheapflights users on 8/31. 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.
Sat 10/172:27 pm -
1 stop6h 11m
Sat 10/242:28 pm -
1 stop9h 55m
Deal found 8/31![United Airlines logo]()
$301
This Frontier deal was found by Cheapflights users on 8/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:02 pm -
1 stop10h 19m
Tue 11/36:30 am -
1 stop6h 37m
Deal found 8/29![Frontier logo]()
$310
This Frontier deal was found by Cheapflights users on 8/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:02 pm -
1 stop10h 19m
Tue 11/36:30 am -
1 stop6h 37m
Deal found 8/31![Frontier logo]()
$315
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 September 2, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:38 pm -
1 stop28h 39m
Deal found 9/2![Frontier logo]()
$142
This CheapOair deal was found by Cheapflights users on 8/31. 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.
Mon 9/2812:39 pm -
1 stop20h 53m
Deal found 8/31![Frontier logo]()
$143
This CheapOair deal was found by Cheapflights users on 9/1. 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.
Sun 10/412:24 pm -
1 stop20h 53m
Deal found 9/1![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Tue 12/14:35 pm -
1 stop24h 19m
Deal found 8/31![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Tue 10/2011:49 am -
1 stop25h 35m
Deal found 9/1![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Thu 10/2912:02 pm -
2 stops27h 38m
Deal found 9/1![Frontier logo]()
$158
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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 9/2911:16 am -
Nonstop3h 54m
Deal found 8/30![Alaska Airlines logo]()
$159
This CheapOair deal was found by Cheapflights users on 8/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:38 pm -
1 stop28h 39m
Deal found 8/28![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:38 pm -
1 stop28h 39m
Deal found 8/28![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Fri 10/212:38 pm -
1 stop28h 39m
Deal found 8/30![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Tue 12/14:35 pm -
1 stop26h 46m
Deal found 8/31![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 10/3012:31 pm -
1 stop14h 42m
Deal found 9/1![Frontier logo]()
$171
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 September 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $280 (CheapOair) |
One-way from | $142 (CheapOair) |
Popular in | November |
Cheapest in | January |
Average price | $365 |
Good round-trip deal | $376 or less |
Good one-way deal | $209 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 7,457,451 searches. Data last updated September 2, 2026.
Use the filters below to find and compare flights from Portland to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandSt. Louis
PDX Portland - STL Lambert-St Louis
PDXSTL
Portland
Tue 10/27
10:45 am-10:10 pm
2 stops9h 25m
Lambert-St Louis
Thu 10/29
5:05 am-9:50 am
1 stop6h 45m
$354
Quickest round-trip
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Thu 10/29
5:20 am-11:10 am
Nonstop3h 50m
Chicago Midway
Mon 11/2
9:15 pm-11:55 pm
Nonstop4h 40m
$357
PortlandSt. Louis
PDX Portland - STL Lambert-St Louis
PDXSTL
Portland
Sat 10/17
2:40 pm-10:55 pm
1 stop6h 15m
Lambert-St Louis
Mon 10/19
5:10 am-12:35 pm
2 stops9h 25m
$358
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Sat 9/26
7:06 am-1:26 pm
Nonstop4h 20m
Chicago O'Hare Intl
Tue 9/29
7:20 am-9:30 am
1 stop28h 10m
$360
PortlandSt. Louis
PDX Portland - STL Lambert-St Louis
PDXSTL
Portland
Tue 10/27
10:45 am-10:10 pm
2 stops9h 25m
Lambert-St Louis
Mon 11/2
4:00 pm-12:10 am
2 stops10h 10m
$363
PortlandSt. Louis
PDX Portland - STL Lambert-St Louis
PDXSTL
Portland
Sat 9/26
6:50 am-3:35 pm
2 stops6h 45m
Lambert-St Louis
Sat 10/3
8:25 am-5:20 pm
2 stops10h 55m
$363
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 11/4
7:00 am-1:07 pm
Nonstop4h 07m
Chicago O'Hare Intl
Sat 11/7
8:55 am-2:37 pm
1 stop7h 42m
$367
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Fri 10/30
7:00 am-1:07 pm
Nonstop4h 07m
Chicago O'Hare Intl
Wed 11/4
4:25 pm-7:12 pm
Nonstop4h 47m
$367
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 10/8
11:30 pm-5:31 am
Nonstop4h 01m
Chicago O'Hare Intl
Sun 10/11
7:00 am-9:31 am
Nonstop4h 31m
$367
PortlandSt. Louis
PDX Portland - STL Lambert-St Louis
PDXSTL
Portland
Mon 10/5
11:10 pm-9:49 am
1 stop8h 39m
Lambert-St Louis
Wed 10/7
7:00 pm-11:47 pm
1 stop6h 47m
$369
Showing 1-10 of 60 resultsSorted by cheapest first
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-STL
PDX-MLI
PDX-ORD
PDX-RFD
PDX-BMI
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-STL
PDX-MLI
PDX-ORD
PDX-RFD
What is the cheapest month to book a flight from Portland to Illinois?
Currently, January is the cheapest month in which you can book a flight from Portland to Illinois (average of $282). Flying from Portland to Illinois in December is currently the most expensive (average of $424). 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 September 2, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 13% on the flight price compared to flying in the morning, which is usually more expensive.
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 September 2, 2026.
The most flights from PDX to USIL are scheduled on a Monday (23 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (13 on average).
How much does it cost to fly round-trip from Portland to Illinois?
Airfare is below average for this route at the moment.
Portland to Illinois flights typically cost between $316 and $452 in October.The cheapest round-trip price found within the last 5 days was $310 on Frontier (Oct 27-Nov 3).
How far ahead should I book a flight from Portland to Illinois?
To ensure you get the cheapest price possible for a flight from Portland to Illinois, you should look to book at least 57 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 August 29, 2026.
Travelers seeking maximum savings on their Portland to Illinois flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 September 2, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andDelta from Portland to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
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Alternative routes for Portland to Illinois
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Complete your trip
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Find flights from Portland to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Illinois flights
Browse other Portland and Illinois flight options. Last updated on September 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Portland to Illinois flights
Consider these flights traveling from Portland to Illinois.
Top 7 airlines flying from Portland to Illinois
Discover the top 7 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 7,457,451 searches. Data last updated September 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$208 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$326 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$125 | Average$256 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$217 | Average$486 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$228 | Average$390 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$460 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$365 | FlexibilityNo cancel fee | On-time63% |