$179+ Cheap flights from Portland (PDX) to Chicago (CHI)
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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Oct 21 — Oct 281
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Chicago 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.Cheapflights Tip: The best prices from Portland to Chicago are usually found in January or February, booked 58 days in advance, depart on a Wednesday or Thursday and return on a Tuesday
Cheap flight deals from Portland to Chicago
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Cheapest flights from Portland to ChicagoExplore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/1011:25 am -
2 stops8h 40m
Tue 10/137:20 am -
1 stop10h 55m
Deal found 9/17![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/2811:35 pm -
Nonstop3h 50m
Sat 10/3111:00 am -
Nonstop4h 25m
Deal found 9/16![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/1211:35 pm -
Nonstop3h 50m
Wed 10/148:40 pm -
Nonstop4h 30m
Deal found 9/16![Southwest logo]()
$333
This Expedia deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:49 am -
1 stop10h 35m
Mon 10/197:49 pm -
1 stop15h 42m
Deal found 9/17![Multiple Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:44 pm -
2 stops10h 00m
Thu 10/295:31 pm -
1 stop8h 13m
Deal found 9/16![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/31:10 pm -
1 stop6h 55m
Fri 11/68:29 am -
2 stops10h 35m
Deal found 9/17![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/276:50 am -
2 stops8h 00m
Fri 10/305:15 am -
2 stops9h 20m
Deal found 9/16![Southwest logo]()
$335
This Gotogate deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:24 pm -
1 stop15h 14m
Wed 10/212:14 pm -
Nonstop4h 37m
Deal found 9/16![Multiple Airlines logo]()
$336
This Alaska Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 12/319:35 pm -
1 stop7h 05m
Wed 1/62:11 pm -
Nonstop4h 40m
Deal found 9/17![Alaska Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/216:05 pm -
1 stop8h 55m
Mon 10/269:45 pm -
Nonstop4h 30m
Deal found 9/17![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/158:44 pm -
2 stops10h 09m
Tue 10/202:03 pm -
2 stops11h 56m
Deal found 9/17![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/105:55 pm -
1 stop9h 05m
Sat 10/176:35 am -
2 stops10h 05m
Deal found 9/17![Southwest logo]()
$338
Best flights from Portland to ChicagoDiscover carefully curated flight deals from Portland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
Discover carefully curated flight deals from Portland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/136:00 am -
1 stop8h 47m
Tue 10/2012:49 pm -
1 stop8h 20m
Deal found 9/16![Delta logo]()
$346
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 10/138:30 am -
Nonstop4h 13m
Sat 10/171:30 pm -
Nonstop4h 26m
Deal found 9/19![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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
Sat 10/247:15 pm -
Nonstop4h 30m
Deal found 9/18![Southwest logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/511:06 am -
2 stops21h 27m
Sun 11/88:37 pm -
1 stop16h 59m
Deal found 9/17![Multiple Airlines logo]()
$398
This Sun Country Air deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:50 pm -
1 stop12h 58m
Tue 12/296:40 pm -
1 stop24h 20m
Deal found 9/16![Sun Country Air logo]()
$445
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/2311:51 am -
1 stop7h 36m
Mon 10/267:15 pm -
1 stop6h 32m
Deal found 9/16![Delta logo]()
$349
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.
Tue 10/2011:35 pm -
Nonstop3h 50m
Fri 11/69:15 pm -
Nonstop4h 40m
Deal found 9/20![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/2911:52 am -
1 stop8h 41m
Thu 11/512:27 pm -
2 stops9h 33m
Deal found 9/16![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/27:02 am -
Nonstop4h 13m
Tue 10/68:55 am -
Nonstop4h 38m
Deal found 9/16![United Airlines logo]()
$398
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/42:15 pm -
1 stop6h 25m
Sun 11/89:15 pm -
Nonstop4h 40m
Deal found 9/17![Southwest logo]()
$374
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.
Tue 10/2011:49 am -
2 stops20h 25m
Sun 10/258:53 pm -
1 stop16h 47m
Deal found 9/19![Multiple Airlines logo]()
$449
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.
Sat 10/103:34 pm -
1 stop6h 20m
Sat 10/179:30 am -
1 stop8h 49m
Deal found 9/19![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/294:20 pm -
1 stop6h 55m
Sun 11/19:55 am -
2 stops9h 00m
Deal found 9/16![Southwest logo]()
$409
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/311:52 am -
1 stop8h 41m
Sat 11/75:31 pm -
1 stop8h 13m
Deal found 9/18![Delta logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/112:38 pm -
2 stops17h 21m
Sun 10/49:36 pm -
1 stop16h 18m
Deal found 9/16![Multiple Airlines logo]()
$493
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.
Mon 10/192:55 pm -
2 stops8h 20m
Thu 10/225:15 am -
2 stops9h 20m
Deal found 9/20![Southwest logo]()
$411
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.
Tue 11/35:33 am -
2 stops8h 59m
Sat 11/76:35 am -
1 stop7h 14m
Deal found 9/20![Delta logo]()
$382
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 11/59:00 pm -
1 stop6h 40m
Sun 11/87:25 am -
2 stops9h 50m
Deal found 9/19![Southwest logo]()
$433
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 9/306:45 am -
1 stop10h 00m
Tue 10/66:35 am -
1 stop7h 14m
Deal found 9/16![Delta logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/2110:10 pm -
1 stop11h 37m
Mon 11/308:51 pm -
2 stops21h 16m
Deal found 9/17![Multiple Airlines logo]()
$578
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Sun 10/185:20 am -
Nonstop3h 50m
Tue 10/201:05 pm -
2 stops9h 05m
Deal found 9/18![Southwest logo]()
$437
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/49:55 am -
2 stops12h 02m
Sun 11/88:29 am -
2 stops10h 35m
Deal found 9/16![Delta logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/59:25 am -
2 stops49h 52m
Thu 10/89:03 pm -
1 stop16h 37m
Deal found 9/18![Multiple Airlines logo]()
$600
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:44 pm -
2 stops9h 46m
Mon 10/55:10 pm -
1 stop6h 49m
Deal found 9/16![Delta logo]()
$443
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 9/2712:38 pm -
2 stops29h 16m
Sun 10/49:36 pm -
1 stop16h 18m
Deal found 9/17![Multiple Airlines logo]()
$622
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 9/2412:38 pm -
2 stops18h 14m
Sun 9/279:29 pm -
1 stop16h 25m
Deal found 9/16![Multiple Airlines logo]()
$715
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/312:24 pm -
1 stop30h 22m
Thu 10/89:03 pm -
1 stop16h 37m
Deal found 9/18![Multiple Airlines logo]()
$889
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/206:50 pm -
2 stops23h 05m
Tue 12/299:02 pm -
1 stop22h 07m
Deal found 9/16![Multiple Airlines logo]()
$926
Last-minute flights from Portland to ChicagoDiscover last-minute flight deals from Portland to Chicago. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Chicago. Data last updated September 21, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/911:00 pm -
2 stops9h 24m
Tue 10/135:30 pm -
1 stop8h 29m
Deal found 9/17![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/1011:43 am -
2 stops10h 14m
Wed 10/1412:50 pm -
1 stop9h 10m
Deal found 9/17![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/105:55 pm -
1 stop9h 05m
Sat 10/176:35 am -
2 stops10h 05m
Deal found 9/17![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/1211:35 pm -
Nonstop3h 50m
Wed 10/148:40 pm -
Nonstop4h 30m
Deal found 9/16![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/138:44 pm -
2 stops8h 57m
Wed 10/217:35 am -
2 stops11h 29m
Deal found 9/16![Delta logo]()
$337
This Expedia deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:49 am -
1 stop10h 35m
Mon 10/197:49 pm -
1 stop15h 42m
Deal found 9/17![Multiple Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/158:44 pm -
2 stops10h 09m
Tue 10/202:03 pm -
2 stops11h 56m
Deal found 9/17![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:12 pm -
1 stop6h 29m
Mon 10/196:35 am -
1 stop7h 14m
Deal found 9/16![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/216:05 pm -
1 stop8h 55m
Mon 10/269:45 pm -
Nonstop4h 30m
Deal found 9/17![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:44 pm -
2 stops10h 00m
Thu 10/295:31 pm -
1 stop8h 13m
Deal found 9/16![Delta logo]()
$334
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/276:50 am -
2 stops8h 00m
Fri 10/305:15 am -
2 stops9h 20m
Deal found 9/16![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/2811:35 pm -
Nonstop3h 50m
Sat 10/3111:00 am -
Nonstop4h 25m
Deal found 9/16![Southwest logo]()
$332
One-way flights from Portland to ChicagoSearch for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
Search for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/1511:30 pm -
Nonstop4h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![United Airlines logo]()
$179
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/1511:35 pm -
Nonstop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/2712:02 pm -
2 stops31h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/2712:02 pm -
2 stops18h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/298:44 pm -
2 stops10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$180
This Super.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/312:24 pm -
1 stop15h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$182
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/136:00 am -
1 stop8h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$182
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 10/2412:45 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$184
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Fri 10/911:49 pm -
1 stop9h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/168:20 pm -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$185
This Super.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 9/2812:39 pm -
1 stop14h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$187
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:50 pm -
1 stop12h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Sun Country Air logo]()
$188
Find flight deals from Portland to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $332 (Delta) |
One-way from | $179 (United Airlines) |
Popular in | November |
Cheapest in | January |
Average price | $374 |
Good round-trip deal | $388 or less |
Good one-way deal | $209 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Chicago 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 21, 2026.
Use the filters below to find and compare flights from Portland to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Sat 10/10
11:35 pm-5:25 am
Nonstop3h 50m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
Quickest round-trip
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Mon 11/23
11:30 pm-5:15 am
Nonstop3h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Fri 11/6
9:00 am-8:22 pm
1 stop9h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$180
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Thu 10/29
8:44 pm-8:44 am
2 stops10h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$180
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Sat 10/10
12:45 pm-9:18 pm
1 stop6h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$184
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Fri 11/6
2:04 pm-11:49 pm
1 stop7h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$185
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 10/15
8:44 pm-8:53 am
2 stops10h 09m
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
Sun 12/20
6:50 pm-9:48 am
1 stop12h 58m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$188
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 12/16
5:23 am-2:21 pm
1 stop6h 58m
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
Sat 10/17
5:30 am-4:53 pm
1 stop9h 23m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
Showing 1-10 of 56 resultsSorted by cheapest first
Compare providers for flights from Portland to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Portland with our price prediction graph.
PDX-CHI
PDX-MDW
PDX-ORD
PDX-RFD
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 Chicago
PDX-CHI
PDX-MDW
PDX-ORD
PDX-RFD
What is the cheapest month to book a flight from Portland to Chicago?
Currently, January is the cheapest month in which you can book a flight from Portland to Chicago (average of $276). Flying from Portland to Chicago in December is currently the most expensive (average of $427). 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 CHI?
Find hourly flight availability from Portland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 21, 2026.
A simple way to save on the total cost of your ticket is to fly from Portland to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight in the morning.
Weekly flight availability from Portland to Chicago
Explore weekly flight availability from Portland to Chicago. 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 21, 2026.
The most flights from PDX to CHI are scheduled on a Friday (30 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (19 on average).
How much does it cost to fly round-trip from Portland to Chicago?
Airfare is below average for this route at the moment.
Portland to Chicago flights typically cost between $353 and $480 in October.The cheapest round-trip price found within the last 5 days was $332 on Delta (Oct 10-Oct 13).
How far ahead should I book a flight from Portland to Chicago?
Booking 57 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Portland to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Portland to Chicago. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Portland to Chicago 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.
The best insider tips for Portland to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Portland to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 21, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andDelta from Portland to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
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 Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 21, 2026.
Complete your trip
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Search flights from Portland to Chicago by cabin class
Find flights from Portland to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Chicago flights
Browse other Portland and Chicago flight options. Last updated on September 21, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on September 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Portland to Chicago
Discover the top 7 airlines that operate flights from Portland to Chicago. 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$243 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$368 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$216 | Average$344 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$220 | Average$378 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$227 | Average$390 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$242 | Average$420 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$365 | FlexibilityNo cancel fee | On-time63% |