$179+ Cheap flights from Illinois to Portland (PDX)
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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PDX
Oct 24 — Oct 311
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Illinois to Portland with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Illinois to Portland
Cheapest
Best
Last-minute
One-way
Cheapest flights from Illinois to PortlandExplore the most affordable flight options available from Illinois to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
Explore the most affordable flight options available from Illinois to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/205:03 pm -
1 stop8h 56m
Sat 10/241:12 pm -
1 stop8h 59m
Deal found 9/20![American Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/215:03 pm -
1 stop8h 56m
Tue 10/271:12 pm -
1 stop8h 59m
Deal found 9/20![American Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sat 10/248:01 pm -
1 stop16h 10m
Thu 10/2912:31 pm -
1 stop14h 42m
Deal found 9/20![Frontier logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Sat 10/108:01 pm -
1 stop16h 10m
Sat 10/179:31 am -
1 stop6h 49m
Deal found 9/19![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sat 10/178:01 pm -
1 stop16h 10m
Tue 10/207:00 am -
Nonstop4h 18m
Deal found 9/20![Multiple Airlines logo]()
$342
This Priceline deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/56:30 am -
1 stop6h 37m
Sat 11/77:01 am -
Nonstop4h 08m
Deal found 9/19![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/296:30 am -
1 stop6h 37m
Sat 10/319:03 am -
1 stop7h 50m
Deal found 9/20![Multiple Airlines logo]()
$344
This Cheapflightsfares deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Sun 10/186:30 am -
1 stop6h 24m
Sun 10/2511:49 am -
1 stop10h 35m
Deal found 9/19![Frontier logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/206:30 am -
1 stop6h 24m
Tue 10/2712:02 pm -
2 stops28h 14m
Deal found 9/20![Frontier logo]()
$346
This Orbitz deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/163:49 pm -
1 stop9h 13m
Mon 10/1911:06 am -
1 stop17h 28m
Deal found 9/20![Multiple Airlines logo]()
$347
This Cheapflightsfares deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/86:30 am -
1 stop6h 24m
Tue 10/1311:49 am -
1 stop10h 35m
Deal found 9/19![Frontier logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/308:46 am -
1 stop6h 36m
Sat 11/79:00 am -
2 stops10h 22m
Deal found 9/20![United Airlines logo]()
$355
Best flights from Illinois to PortlandDiscover carefully curated flight deals from Illinois to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
Discover carefully curated flight deals from Illinois to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/217:00 am -
Nonstop4h 31m
Tue 10/277:00 am -
Nonstop4h 07m
Deal found 9/21![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/309:45 pm -
Nonstop4h 30m
Mon 11/211:30 pm -
Nonstop3h 45m
Deal found 9/23![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/2011:08 am -
1 stop10h 01m
Sat 10/246:00 am -
2 stops14h 30m
Deal found 9/23![Delta logo]()
$376
This American Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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.
Mon 1/2512:37 pm -
1 stop7h 29m
Sat 1/306:00 am -
1 stop8h 32m
Deal found 9/24![American Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/52:15 pm -
1 stop10h 37m
Sun 11/810:34 am -
1 stop11h 15m
Deal found 9/23![Alaska Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/712:42 pm -
1 stop7h 42m
Wed 11/112:34 pm -
Nonstop4h 06m
Deal found 9/21![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/155:30 pm -
1 stop6h 26m
Mon 10/1912:29 pm -
1 stop9h 05m
Deal found 9/20![Delta logo]()
$377
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/43:58 pm -
1 stop9h 45m
Thu 11/1211:57 am -
1 stop9h 20m
Deal found 9/23![American Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/78:25 am -
1 stop10h 20m
Wed 11/1110:15 am -
2 stops10h 10m
Deal found 9/21![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/511:08 am -
1 stop10h 01m
Thu 11/1211:10 pm -
1 stop9h 09m
Deal found 9/21![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/99:55 pm -
1 stop13h 35m
Wed 11/185:25 pm -
2 stops10h 30m
Deal found 9/23![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 12/127:25 am -
2 stops11h 11m
Tue 12/151:55 pm -
1 stop5h 40m
Deal found 9/21![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/168:55 am -
Nonstop4h 38m
Sun 10/187:02 am -
Nonstop4h 13m
Deal found 9/21![United Airlines logo]()
$431
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/195:45 pm -
1 stop6h 35m
Mon 11/2311:30 pm -
Nonstop3h 45m
Deal found 9/23![Southwest logo]()
$395
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/177:35 am -
2 stops11h 29m
Thu 10/2211:12 pm -
1 stop6h 29m
Deal found 9/22![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/208:25 am -
2 stops13h 45m
Sat 10/2411:59 pm -
1 stop7h 45m
Deal found 9/19![United Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/29:59 am -
2 stops8h 11m
Thu 11/53:31 pm -
1 stop6h 03m
Deal found 9/23![Delta logo]()
$382
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/66:48 pm -
1 stop7h 11m
Sat 10/106:01 am -
1 stop6h 55m
Deal found 9/21![American Airlines logo]()
$510
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/159:45 pm -
Nonstop4h 30m
Sun 10/1811:35 pm -
Nonstop3h 50m
Deal found 9/19![Southwest logo]()
$431
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/208:25 am -
2 stops15h 02m
Tue 10/272:34 pm -
1 stop6h 25m
Deal found 9/20![United Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 11/66:06 am -
1 stop9h 32m
Sat 11/76:00 am -
2 stops14h 36m
Deal found 9/24![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/309:45 am -
Nonstop4h 25m
Sun 11/17:35 am -
2 stops8h 00m
Deal found 9/20![Southwest logo]()
$433
This American Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/282:59 pm -
1 stop6h 42m
Tue 11/31:22 pm -
1 stop8h 48m
Deal found 9/24![American Airlines logo]()
$525
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 12/56:42 am -
2 stops13h 25m
Tue 12/88:50 am -
2 stops12h 09m
Deal found 9/23![United Airlines logo]()
$451
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/212:03 pm -
2 stops9h 53m
Sat 10/246:00 am -
2 stops8h 26m
Deal found 9/19![Delta logo]()
$387
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 12/235:10 am -
1 stop9h 46m
Wed 12/301:46 pm -
1 stop8h 31m
Deal found 9/21![American Airlines logo]()
$525
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/212:28 pm -
2 stops10h 29m
Wed 10/2811:10 pm -
2 stops12h 45m
Deal found 9/20![United Airlines logo]()
$451
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/1010:35 am -
2 stops8h 45m
Sat 10/1710:40 am -
1 stop8h 20m
Deal found 9/22![Southwest logo]()
$452
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/306:35 am -
1 stop7h 14m
Mon 11/29:55 am -
2 stops12h 02m
Deal found 9/23![Delta logo]()
$396
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Sun 11/15:00 am -
2 stops10h 22m
Sun 11/811:30 pm -
1 stop8h 35m
Deal found 9/23![United Airlines logo]()
$464
Last-minute flights from Illinois to PortlandDiscover last-minute flight deals from Illinois to Portland. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Portland. Data last updated September 24, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/86:30 am -
1 stop6h 24m
Tue 10/1311:49 am -
1 stop10h 35m
Deal found 9/19![Frontier logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Sat 10/108:01 pm -
1 stop16h 10m
Sat 10/179:31 am -
1 stop6h 49m
Deal found 9/19![Multiple Airlines logo]()
$339
This Orbitz deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/163:49 pm -
1 stop9h 13m
Mon 10/1911:06 am -
1 stop17h 28m
Deal found 9/20![Multiple Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sat 10/178:01 pm -
1 stop16h 10m
Tue 10/207:00 am -
Nonstop4h 18m
Deal found 9/20![Multiple Airlines logo]()
$342
This Cheapflightsfares deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Sun 10/186:30 am -
1 stop6h 24m
Sun 10/2511:49 am -
1 stop10h 35m
Deal found 9/19![Frontier logo]()
$345
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/205:03 pm -
1 stop8h 56m
Sat 10/241:12 pm -
1 stop8h 59m
Deal found 9/20![American Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/206:30 am -
1 stop6h 24m
Tue 10/2712:02 pm -
2 stops28h 14m
Deal found 9/20![Frontier logo]()
$346
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/215:03 pm -
1 stop8h 56m
Tue 10/271:12 pm -
1 stop8h 59m
Deal found 9/20![American Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sat 10/248:01 pm -
1 stop16h 10m
Thu 10/2912:31 pm -
1 stop14h 42m
Deal found 9/20![Frontier logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/296:30 am -
1 stop6h 37m
Sat 10/319:03 am -
1 stop7h 50m
Deal found 9/20![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/296:30 am -
1 stop6h 37m
Tue 11/312:02 pm -
2 stops28h 14m
Deal found 9/21![Frontier logo]()
$351
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/308:46 am -
1 stop6h 36m
Sat 11/79:00 am -
2 stops10h 22m
Deal found 9/20![United Airlines logo]()
$355
One-way flights from Illinois to PortlandSearch for one-way flight options from Illinois to Portland. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
Search for one-way flight options from Illinois to Portland. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/2010:05 am -
Nonstop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/224:20 pm -
Nonstop4h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![United Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Wed 10/216:30 am -
1 stop30h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$180
This Super.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Sat 9/267:32 pm -
1 stop18h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$181
This Super.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Wed 10/71:21 pm -
1 stop24h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$182
This Super.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 9/276:30 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Sun 10/116:30 am -
1 stop6h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$184
This Trip.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Sat 11/77:20 am -
1 stop8h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Alaska Airlines logo]()
$185
This Mytrip deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Mon 9/286:30 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$186
This Super.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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.
Fri 10/28:55 pm -
1 stop16h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$188
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/2012:49 pm -
1 stop11h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$189
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/169:45 pm -
Nonstop4h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$193
Find flight deals from Illinois to Portland
Keep the following information in mind while searching for Illinois to Portland flight deals. Data was last updated September 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $308 (American Airlines) |
One-way from | $179 (Southwest) |
Popular in | March |
Cheapest in | January |
Average price | $385 |
Good round-trip deal | $374 or less |
Good one-way deal | $209 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Portland 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 24, 2026.
Use the filters below to find and compare flights from Illinois to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Thu 11/12
9:15 pm-11:55 pm
Nonstop4h 40m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
Quickest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Tue 10/27
2:14 pm-4:51 pm
Nonstop4h 37m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Thu 10/22
2:14 pm-4:51 pm
Nonstop4h 37m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Sat 10/24
2:14 pm-4:51 pm
Nonstop4h 37m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Tue 11/17
5:29 pm-11:46 pm
1 stop8h 17m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Mon 11/16
5:29 pm-11:46 pm
1 stop8h 17m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Wed 11/11
5:45 pm-10:20 pm
1 stop6h 35m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Tue 11/3
6:04 am-1:38 pm
1 stop9h 34m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Mon 11/23
5:29 pm-11:46 pm
1 stop8h 17m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Sat 10/31
3:49 pm-11:02 pm
1 stop9h 13m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Illinois with our price prediction graph.
MDW-PDX
ORD-PDX
MLI-PDX
PIA-PDX
SPI-PDX
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 Illinois to Portland
USIL-PDX
MDW-PDX
ORD-PDX
MLI-PDX
PIA-PDX
What is the cheapest month to book a flight from Illinois to Portland?
Currently, February is the cheapest month in which you can book a flight from Illinois to Portland (average of $294). Flying from Illinois to Portland in March is currently the most expensive (average of $403). 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 IL to PDX?
Find hourly flight availability from Illinois to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 24, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 48% on flights from Illinois to Portland by exploring options for tickets in the evening.
Weekly flight availability from Illinois to Portland
Explore weekly flight availability from Illinois to Portland. 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 24, 2026.
The most flights from USIL to PDX are scheduled on a Wednesday (25 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Illinois to Portland?
Airfare is typical for this route at the moment.
Illinois to Portland flights typically cost between $330 and $489 in October.The cheapest round-trip price found within the last 5 days was $338 on Frontier (Oct 24-Oct 29).
How far ahead should I book a flight from Illinois to Portland?
To ensure you get the cheapest price possible for a flight from Illinois to Portland, you should look to book at least 86 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 Illinois to Portland?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Portland. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Illinois to Portland flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Illinois to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsBeaverton
Seaside
Lincoln City
Durham
Longview
Lake Oswego
Cannon Beach
Vancouver
Kelso
Troutdale
Clackamas
McMinnville
The Dalles
Wilsonville
Stevenson
Tillamook
Hillsboro
Astoria
Gresham
Silverton
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Portland flight routes
Top destinations
Alternative routes for Illinois to Portland
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Illinois to Portland by cabin class
Find flights from Illinois to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Portland flights
Browse other Illinois and Portland flight options. Last updated on September 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 24, 2026.
Illinois to Portland flights
Consider these flights traveling from Illinois to Portland.
Top 6 airlines flying from Illinois to Portland
Discover the top 6 airlines that operate flights from Illinois to Portland. 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 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$155 | Average$338 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$205 | Average$333 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$217 | Average$441 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$222 | Average$475 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$239 | Average$375 | FlexibilityNo cancel fee | On-time63% |