$179+ Cheap flights from Portland (PDX) to Illinois
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Nov 5 — Nov 121
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 October 6, 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 October 6, 2026.
This Delta deal was found by Cheapflights users on 10/3. 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.
Tue 12/156:00 am -
2 stops15h 01m
Sat 1/911:00 am -
1 stop10h 08m
Deal found 10/3![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 10/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:37 pm -
1 stop6h 22m
Sat 11/73:39 pm -
1 stop8h 48m
Deal found 10/3![United Airlines logo]()
$350
This CheapOair deal was found by Cheapflights users on 10/2. 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.
Tue 10/2712:02 pm -
1 stop10h 19m
Thu 10/295:15 pm -
1 stop20h 21m
Deal found 10/2![Frontier logo]()
$352
This Alaska Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 12/57:00 am -
Nonstop4h 10m
Sun 12/136:00 am -
1 stop9h 28m
Deal found 10/5![Alaska Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/511:30 pm -
Nonstop3h 45m
Mon 11/99:15 pm -
Nonstop4h 40m
Deal found 10/5![Southwest logo]()
$353
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares 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 10/1![Frontier logo]()
$354
This Delta deal was found by Cheapflights users on 10/3. 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.
Tue 12/156:00 am -
2 stops15h 01m
Fri 1/811:00 am -
1 stop10h 08m
Deal found 10/3![Delta logo]()
$355
This Frontier deal was found by Cheapflights users on 10/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:49 am -
1 stop10h 35m
Sun 11/16:30 am -
1 stop6h 42m
Deal found 10/2![Frontier logo]()
$356
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 11/69:25 pm -
1 stop6h 30m
Mon 11/99:55 pm -
1 stop13h 35m
Deal found 10/4![Southwest logo]()
$356
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Thu 10/292:34 pm -
Nonstop4h 06m
Tue 11/312:49 pm -
Nonstop4h 34m
Deal found 9/30![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 10/1. 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 10/2211:35 pm -
Nonstop3h 50m
Wed 10/2810:05 am -
Nonstop4h 25m
Deal found 10/1![Southwest logo]()
$357
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Thu 10/2210:55 pm -
Nonstop4h 12m
Wed 10/284:59 pm -
Nonstop4h 42m
Deal found 10/1![American Airlines logo]()
$358
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 October 6, 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 October 6, 2026.
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/3011:35 pm -
Nonstop3h 50m
Mon 11/29:55 pm -
1 stop13h 35m
Deal found 10/5![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/305:33 am -
2 stops8h 59m
Mon 11/26:20 am -
1 stop6h 14m
Deal found 10/5![Delta logo]()
$367
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Wed 10/211:12 pm -
1 stop8h 58m
Tue 10/2712:31 pm -
1 stop8h 58m
Deal found 10/1![American Airlines logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:00 am -
Nonstop4h 10m
Tue 1/52:11 pm -
Nonstop4h 40m
Deal found 10/4![Alaska Airlines logo]()
$418
This United Airlines deal was found by Cheapflights users on 10/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:47 am -
Nonstop4h 06m
Fri 11/209:05 am -
Nonstop4h 47m
Deal found 10/3![United Airlines logo]()
$418
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/1911:40 am -
2 stops7h 55m
Sun 11/229:15 pm -
Nonstop4h 40m
Deal found 10/5![Southwest logo]()
$368
This Delta deal was found by Cheapflights users on 10/1. 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 11/35:33 am -
2 stops8h 59m
Sat 11/76:35 am -
1 stop7h 14m
Deal found 10/1![Delta logo]()
$382
This Southwest deal was found by Cheapflights users on 10/2. 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 11/36:00 am -
Nonstop3h 50m
Wed 11/118:40 pm -
Nonstop4h 45m
Deal found 10/2![Southwest logo]()
$377
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/911:57 am -
1 stop8h 07m
Tue 12/1511:58 am -
1 stop9h 57m
Deal found 10/5![American Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/269:58 am -
2 stops11h 22m
Tue 12/13:47 pm -
2 stops10h 12m
Deal found 10/5![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/67:10 am -
1 stop8h 56m
Tue 2/96:30 am -
1 stop7h 01m
Deal found 10/3![United Airlines logo]()
$441
This Alaska Airlines deal was found by Cheapflights users on 10/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:00 am -
Nonstop4h 18m
Wed 10/282:14 pm -
Nonstop4h 37m
Deal found 10/3![Alaska Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 10/1. 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 12/91:00 pm -
1 stop8h 59m
Sun 12/1312:58 pm -
1 stop8h 00m
Deal found 10/1![Delta logo]()
$407
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:01 am -
1 stop5h 56m
Sat 10/243:58 pm -
1 stop9h 41m
Deal found 10/5![American Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 1/301:21 pm -
1 stop5h 49m
Tue 2/26:27 am -
1 stop7h 04m
Deal found 10/5![United Airlines logo]()
$481
This Southwest deal was found by Cheapflights users on 10/1. 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 11/125:10 am -
2 stops10h 25m
Sun 11/157:30 am -
2 stops11h 25m
Deal found 10/1![Southwest logo]()
$447
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 12/27:38 pm -
2 stops10h 21m
Mon 12/76:20 am -
1 stop6h 28m
Deal found 10/5![Delta logo]()
$422
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 12/82:26 pm -
1 stop6h 43m
Wed 12/166:30 am -
2 stops10h 08m
Deal found 10/5![United Airlines logo]()
$486
This American Airlines deal was found by Cheapflights users on 10/1. 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 12/125:00 am -
1 stop7h 01m
Thu 12/177:04 am -
1 stop8h 42m
Deal found 10/1![American Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 9/30. 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.
Mon 10/198:20 pm -
1 stop7h 30m
Thu 10/229:45 pm -
Nonstop4h 30m
Deal found 9/30![Southwest logo]()
$452
This Delta deal was found by Cheapflights users on 10/3. 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 11/145:45 am -
2 stops8h 33m
Fri 11/2012:58 pm -
1 stop7h 57m
Deal found 10/3![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 11/207:35 pm -
2 stops11h 29m
Sun 11/2212:58 pm -
1 stop7h 57m
Deal found 10/4![Delta logo]()
$447
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2311:30 pm -
Nonstop3h 45m
Mon 12/286:00 am -
1 stop8h 35m
Deal found 9/30![Southwest logo]()
$500
This American Airlines deal was found by Cheapflights users on 10/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:00 am -
1 stop7h 01m
Thu 12/242:32 pm -
1 stop7h 16m
Deal found 10/3![American Airlines logo]()
$558
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/206:00 am -
2 stops14h 36m
Sat 10/246:06 am -
1 stop9h 32m
Deal found 10/5![Delta logo]()
$454
This Southwest deal was found by Cheapflights users on 10/3. 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.
Sat 10/245:55 pm -
1 stop9h 05m
Tue 10/271:05 pm -
2 stops9h 05m
Deal found 10/3![Southwest logo]()
$502
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Thu 10/152:27 pm -
1 stop6h 11m
Sun 10/186:32 am -
1 stop7h 01m
Deal found 10/1![United Airlines logo]()
$614
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Wed 12/2311:31 pm -
1 stop8h 44m
Wed 12/304:16 pm -
1 stop9h 28m
Deal found 10/1![American Airlines logo]()
$613
This Southwest deal was found by Cheapflights users on 10/1. 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 10/131:40 pm -
1 stop7h 35m
Wed 10/2110:05 am -
Nonstop4h 25m
Deal found 10/1![Southwest logo]()
$507
This Delta deal was found by Cheapflights users on 10/2. 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 10/287:10 am -
2 stops9h 00m
Sun 11/18:29 am -
2 stops10h 35m
Deal found 10/2![Delta logo]()
$477
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated October 6, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated October 6, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares 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 10/1![Frontier logo]()
$354
This Frontier deal was found by Cheapflights users on 10/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:49 am -
1 stop10h 35m
Sun 11/16:30 am -
1 stop6h 42m
Deal found 10/2![Frontier logo]()
$356
This Southwest deal was found by Cheapflights users on 10/1. 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 10/2211:35 pm -
Nonstop3h 50m
Wed 10/2810:05 am -
Nonstop4h 25m
Deal found 10/1![Southwest logo]()
$357
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Thu 10/2210:55 pm -
Nonstop4h 12m
Wed 10/284:59 pm -
Nonstop4h 42m
Deal found 10/1![American Airlines logo]()
$358
This CheapOair deal was found by Cheapflights users on 10/2. 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.
Tue 10/2712:02 pm -
1 stop10h 19m
Thu 10/295:15 pm -
1 stop20h 21m
Deal found 10/2![Frontier logo]()
$352
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/286:00 am -
2 stops8h 32m
Fri 10/307:35 am -
1 stop6h 28m
Deal found 10/5![Delta logo]()
$353
This United Airlines deal was found by Cheapflights users on 10/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:37 pm -
1 stop6h 22m
Sat 11/73:39 pm -
1 stop8h 48m
Deal found 10/3![United Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Tue 11/311:09 pm -
Nonstop3h 58m
Sat 11/79:45 am -
Nonstop4h 43m
Deal found 10/1![American Airlines logo]()
$357
This Expedia deal was found by Cheapflights users on 10/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:02 pm -
1 stop10h 19m
Sat 11/72:15 pm -
1 stop8h 32m
Deal found 10/2![Multiple Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/511:30 pm -
Nonstop3h 45m
Mon 11/99:15 pm -
Nonstop4h 40m
Deal found 10/5![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/511:30 pm -
Nonstop3h 45m
Wed 11/111:20 pm -
2 stops11h 00m
Deal found 10/5![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 11/69:25 pm -
1 stop6h 30m
Mon 11/99:55 pm -
1 stop13h 35m
Deal found 10/4![Southwest logo]()
$356
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 October 6, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated October 6, 2026.
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/2711:30 pm -
Nonstop3h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 9/30. 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.
Tue 10/2711:35 pm -
Nonstop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Southwest logo]()
$179
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/611:00 pm -
1 stop9h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Delta logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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.
Mon 11/912:31 pm -
2 stops33h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$181
This Super.com deal was found by Cheapflights users on 10/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2612:25 pm -
1 stop14h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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.
Mon 11/212:31 pm -
2 stops20h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 10/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2011:49 am -
1 stop10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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.
Mon 11/212:31 pm -
2 stops25h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$185
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 12/411:20 am -
Nonstop3h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Southwest logo]()
$187
This Super.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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.
Sun 10/1111:06 am -
1 stop17h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$188
This Alaska Airlines deal was found by Cheapflights users on 10/1. 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.
Tue 12/17:30 am -
1 stop7h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Alaska Airlines logo]()
$189
This Cheapflightsfares deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:49 am -
1 stop10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$190
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 October 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $326 (Delta) |
One-way from | $179 (United Airlines) |
Popular in | November |
Cheapest in | January |
Average price | $413 |
Good round-trip deal | $398 or less |
Good one-way deal | $219 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 October 6, 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
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Tue 10/27
11:35 pm-5:25 am
Nonstop3h 50m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Fri 12/4
11:17 pm-9:37 am
1 stop8h 20m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$180
Quickest round-trip
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 11/5
11:30 pm-5:19 am
Nonstop3h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$187
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 11/4
7:01 am-1:09 pm
Nonstop4h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 12/3
7:00 am-4:50 pm
1 stop7h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Tue 11/10
11:30 pm-5:19 am
Nonstop3h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Fri 11/27
7:00 am-1:08 pm
Nonstop4h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Tue 10/27
11:51 am-11:57 pm
2 stops10h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 11/4
3:31 pm-11:34 pm
1 stop6h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$199
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Tue 11/3
10:10 am-7:40 pm
2 stops7h 30m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$204
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-MLI
PDX-ORD
PDX-MDW
PDX-PIA
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-MLI
PDX-ORD
PDX-MDW
PDX-PIA
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 $285). Flying from Portland to Illinois in November is currently the most expensive (average of $439). 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 October 6, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 23% 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 October 6, 2026.
The most flights from PDX to USIL are scheduled on a Sunday (28 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (15 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 $357 and $495 in October.The cheapest round-trip price found within the last 5 days was $352 on Frontier (Oct 27-Oct 29).
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 October 3, 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. Monday 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 October 6, 2026.
Read reviews from past customers who have flown Alaska Airlines,Southwest, andDelta from Portland to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Crew
8.5
Food
7.0
Comfort
7.8
Entertainment
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
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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Search flights from Portland to Illinois by cabin class
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 October 6, 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 6 airlines flying from Portland to Illinois
Discover the top 6 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 October 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$125 | Average$368 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$216 | Average$344 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$223 | Average$493 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$232 | Average$402 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$243 | Average$462 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$370 | FlexibilityNo cancel fee | On-time63% |