$161+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Dec 5 — Dec 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 November 5, 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 November 5, 2026.
This Delta deal was found by Cheapflights users on 11/2. 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 12/911:10 pm -
1 stop9h 16m
Wed 12/1611:08 am -
1 stop10h 09m
Deal found 11/2![Delta logo]()
$341
This Delta deal was found by Cheapflights users on 11/3. 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 12/11:30 pm -
1 stop6h 26m
Sat 12/57:05 am -
1 stop7h 20m
Deal found 11/3![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 11/4. 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.
Tue 12/111:17 pm -
1 stop8h 20m
Tue 12/81:02 pm -
1 stop10h 56m
Deal found 11/4![Delta logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Sun 12/67:51 pm -
2 stops27h 03m
Thu 12/106:21 am -
1 stop7h 32m
Deal found 11/4![Frontier logo]()
$346
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
Sat 11/2110:10 pm -
1 stop29h 00m
Mon 11/2310:00 pm -
1 stop14h 28m
Deal found 11/4![Frontier logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:51 pm -
2 stops27h 03m
Wed 12/96:21 am -
1 stop31h 32m
Deal found 11/3![Frontier logo]()
$348
This Delta deal was found by Cheapflights users on 11/3. 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 12/17:38 pm -
2 stops10h 21m
Tue 12/83:47 pm -
1 stop6h 37m
Deal found 11/3![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 11/4. 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.
Thu 12/32:10 pm -
1 stop8h 05m
Mon 12/76:05 am -
1 stop6h 35m
Deal found 11/4![Southwest logo]()
$349
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:31 pm -
1 stop14h 42m
Sat 11/2110:00 pm -
1 stop14h 28m
Deal found 11/2![Frontier logo]()
$350
This Southwest deal was found by Cheapflights users on 11/4. 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 12/410:10 am -
2 stops7h 30m
Fri 12/113:40 pm -
1 stop7h 20m
Deal found 11/4![Southwest logo]()
$350
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 12/107:00 am -
Nonstop4h 10m
Sat 12/122:08 pm -
Nonstop4h 57m
Deal found 11/4![Alaska Airlines logo]()
$351
This Frontier deal was found by Cheapflights users on 11/2. 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 11/1212:02 pm -
1 stop10h 19m
Sat 11/2110:00 pm -
1 stop14h 28m
Deal found 11/2![Frontier logo]()
$352
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 November 5, 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 November 5, 2026.
This Delta deal was found by Cheapflights users on 11/4. 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.
Wed 12/911:10 pm -
1 stop9h 16m
Wed 12/1611:08 am -
2 stops12h 59m
Deal found 11/4![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:10 am -
2 stops7h 30m
Wed 12/96:05 am -
2 stops10h 55m
Deal found 11/2![Southwest logo]()
$354
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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.
Mon 12/215:50 pm -
1 stop17h 29m
Fri 12/256:00 am -
1 stop9h 24m
Deal found 10/31![Alaska Airlines logo]()
$360
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Mon 12/72:26 pm -
1 stop6h 33m
Mon 12/148:33 am -
1 stop8h 46m
Deal found 11/1![United Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/282:06 pm -
1 stop8h 05m
Wed 2/312:37 pm -
1 stop10h 21m
Deal found 11/4![American Airlines logo]()
$389
This Southwest deal was found by Cheapflights users on 11/3. 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.
Fri 12/41:50 pm -
1 stop5h 40m
Sun 12/612:45 pm -
2 stops9h 35m
Deal found 11/3![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 11/3. 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.
Thu 12/39:23 am -
2 stops10h 12m
Sun 12/66:20 am -
2 stops9h 15m
Deal found 11/3![Delta logo]()
$364
This Alaska Airlines deal was found by Cheapflights users on 11/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:05 am -
1 stop14h 54m
Sun 12/202:17 pm -
1 stop8h 33m
Deal found 11/2![Alaska Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 11/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/317:02 am -
1 stop8h 54m
Tue 1/56:30 am -
1 stop7h 01m
Deal found 11/4![United Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 11/2. 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.
Wed 12/3011:30 pm -
Nonstop3h 45m
Sun 1/106:15 am -
2 stops9h 45m
Deal found 11/2![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 11/4. 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.
Thu 11/269:58 am -
2 stops11h 22m
Fri 11/277:30 am -
2 stops11h 40m
Deal found 11/4![Delta logo]()
$387
This United Airlines deal was found by Cheapflights users on 11/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:26 pm -
1 stop6h 16m
Tue 1/56:27 am -
1 stop7h 04m
Deal found 11/4![United Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 10/31. 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.
Sat 11/72:34 pm -
1 stop7h 15m
Sat 11/144:43 pm -
1 stop7h 27m
Deal found 10/31![American Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 11/1. 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 12/76:00 am -
2 stops15h 01m
Mon 12/146:10 am -
2 stops12h 27m
Deal found 11/1![Delta logo]()
$389
This United Airlines deal was found by Cheapflights users on 11/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2810:46 am -
1 stop8h 29m
Wed 2/36:27 am -
2 stops10h 09m
Deal found 11/4![United Airlines logo]()
$394
This Southwest deal was found by Cheapflights users on 11/3. 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.
Fri 12/117:35 am -
2 stops8h 00m
Fri 12/1812:30 pm -
2 stops9h 05m
Deal found 11/3![Southwest logo]()
$400
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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.
Fri 12/259:22 am -
1 stop6h 37m
Fri 1/16:00 am -
1 stop17h 59m
Deal found 11/3![Alaska Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 11/4. 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 1/16:50 am -
1 stop7h 32m
Wed 1/611:07 am -
2 stops14h 51m
Deal found 11/4![Delta logo]()
$394
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 11/1910:47 am -
1 stop8h 35m
Wed 12/95:00 am -
1 stop8h 41m
Deal found 11/3![United Airlines logo]()
$395
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 12/247:00 am -
Nonstop4h 10m
Sun 1/36:00 am -
1 stop9h 24m
Deal found 11/3![Alaska Airlines logo]()
$462
This Southwest deal was found by Cheapflights users on 11/4. 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 12/410:10 am -
2 stops7h 30m
Fri 12/1112:45 pm -
2 stops9h 35m
Deal found 11/4![Southwest logo]()
$437
This Alaska Airlines deal was found by Cheapflights users on 11/1. 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.
Fri 12/257:00 am -
Nonstop4h 10m
Sun 1/36:00 am -
1 stop9h 24m
Deal found 11/1![Alaska Airlines logo]()
$462
This Delta deal was found by Cheapflights users on 10/31. 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.
Wed 11/251:05 pm -
1 stop8h 50m
Fri 11/277:30 am -
2 stops13h 25m
Deal found 10/31![Delta logo]()
$433
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 11/1911:30 pm -
1 stop8h 35m
Mon 11/232:31 pm -
1 stop9h 56m
Deal found 11/3![United Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 11/1. 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.
Fri 12/256:05 am -
1 stop6h 16m
Thu 12/317:00 am -
1 stop14h 12m
Deal found 11/1![Alaska Airlines logo]()
$465
This Southwest deal was found by Cheapflights users on 11/3. 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.
Mon 11/2311:30 pm -
Nonstop3h 45m
Sun 12/610:10 am -
1 stop8h 45m
Deal found 11/3![Southwest logo]()
$482
This Delta deal was found by Cheapflights users on 11/3. 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.
Thu 12/315:30 am -
2 stops12h 48m
Sun 1/32:27 pm -
1 stop8h 33m
Deal found 11/3![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Wed 11/1810:59 am -
2 stops10h 14m
Sun 11/226:25 am -
1 stop7h 22m
Deal found 11/3![United Airlines logo]()
$454
This American Airlines deal was found by Cheapflights users on 10/31. 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.
Tue 12/15:00 am -
1 stop6h 59m
Sat 12/55:59 am -
1 stop8h 38m
Deal found 10/31![American Airlines logo]()
$676
This Southwest deal was found by Cheapflights users on 11/3. 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.
Fri 12/186:20 am -
2 stops9h 30m
Fri 12/186:50 pm -
1 stop7h 45m
Deal found 11/3![Southwest logo]()
$493
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated November 5, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 11/2. 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 11/1212:02 pm -
1 stop10h 19m
Sat 11/2110:00 pm -
1 stop14h 28m
Deal found 11/2![Frontier logo]()
$352
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:31 pm -
1 stop14h 42m
Sat 11/2110:00 pm -
1 stop14h 28m
Deal found 11/2![Frontier logo]()
$350
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
Sat 11/2110:10 pm -
1 stop29h 00m
Mon 11/2310:00 pm -
1 stop14h 28m
Deal found 11/4![Frontier logo]()
$347
This Delta deal was found by Cheapflights users on 11/3. 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 12/11:30 pm -
1 stop6h 26m
Sat 12/57:05 am -
1 stop7h 20m
Deal found 11/3![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 11/4. 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.
Tue 12/111:17 pm -
1 stop8h 20m
Tue 12/81:02 pm -
1 stop10h 56m
Deal found 11/4![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 11/3. 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 12/17:38 pm -
2 stops10h 21m
Tue 12/83:47 pm -
1 stop6h 37m
Deal found 11/3![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 11/4. 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.
Thu 12/32:10 pm -
1 stop8h 05m
Mon 12/76:05 am -
1 stop6h 35m
Deal found 11/4![Southwest logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:51 pm -
2 stops27h 03m
Wed 12/96:21 am -
1 stop31h 32m
Deal found 11/3![Frontier logo]()
$348
This Southwest deal was found by Cheapflights users on 11/4. 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 12/410:10 am -
2 stops7h 30m
Fri 12/113:40 pm -
1 stop7h 20m
Deal found 11/4![Southwest logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Sun 12/67:51 pm -
2 stops27h 03m
Thu 12/106:21 am -
1 stop7h 32m
Deal found 11/4![Frontier logo]()
$346
This Delta deal was found by Cheapflights users on 11/2. 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 12/911:10 pm -
1 stop9h 16m
Wed 12/1611:08 am -
1 stop10h 09m
Deal found 11/2![Delta logo]()
$341
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 12/107:00 am -
Nonstop4h 10m
Sat 12/122:08 pm -
Nonstop4h 57m
Deal found 11/4![Alaska Airlines logo]()
$351
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 November 5, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Delta deal was found by Cheapflights users on 11/3. 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.
Thu 12/35:30 am -
2 stops12h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$161
This Delta deal was found by Cheapflights users on 11/3. 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 12/55:45 am -
2 stops9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$161
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:51 pm -
2 stops27h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$164
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:10 pm -
1 stop29h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$166
This Delta deal was found by Cheapflights users on 11/4. 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 12/45:30 am -
2 stops10h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Delta logo]()
$166
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/297:02 am -
Nonstop4h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![United Airlines logo]()
$169
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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.
Thu 12/177:05 am -
1 stop9h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Alaska Airlines logo]()
$172
This Alaska Airlines deal was found by Cheapflights users on 10/31. 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.
Sat 12/199:22 pm -
1 stop24h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Alaska Airlines logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
Mon 12/216:53 pm -
1 stop8h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$178
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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.
Fri 12/257:00 am -
Nonstop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Alaska Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 11/3. 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.
Thu 12/1711:30 pm -
Nonstop3h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/117:51 pm -
2 stops27h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$181
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 November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $341 (Delta) |
One-way from | $161 (Delta) |
Popular in | November |
Cheapest in | January |
Average price | $456 |
Good round-trip deal | $394 or less |
Good one-way deal | $231 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 November 5, 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
Fri 1/8
7:38 pm-9:16 am
2 stops11h 38m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$161
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Tue 12/29
2:26 pm-8:33 pm
Nonstop4h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Thu 12/31
6:00 am-11:50 am
Nonstop3h 50m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 11/26
6:00 am-2:55 pm
1 stop6h 55m
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
Sun 1/10
7:10 am-1:15 pm
Nonstop4h 05m
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
Mon 11/23
1:05 pm-11:55 pm
1 stop8h 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
Thu 12/24
5:30 am-8:18 pm
2 stops12h 48m
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
Fri 12/25
9:43 am-9:39 pm
2 stops9h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Tue 12/29
7:41 pm-8:49 am
2 stops11h 08m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Mon 12/28
8:15 pm-5:00 am
1 stop6h 45m
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-CMI
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 $290). Flying from Portland to Illinois in November is currently the most expensive (average of $480). 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 November 5, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 32% on the flight price compared to flying at noon, 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 November 5, 2026.
The most flights from PDX to USIL are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, 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 $387 and $616 in December.The cheapest round-trip price found within the last 5 days was $344 on Delta (Dec 1-Dec 5).
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 85 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 31, 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 November 5, 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.
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
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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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 November 5, 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 November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$125 | Average$368 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$216 | Average$357 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$494 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$232 | Average$418 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$247 | Average$466 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$375 | FlexibilityNo cancel fee | On-time63% |