$179+ Cheap flights from Chicago (CHI) 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Oct 21 — Oct 281
Round-trip
1 adult, Economy
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Find cheap flights from Chicago 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.Cheapflights Tip: The best prices from Chicago to Portland are usually found in January or February, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to Portland
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Cheapest flights from Chicago to PortlandExplore the most affordable flight options available from Chicago to Portland. 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 Chicago to Portland. 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 9/16. 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 10/76:35 am -
1 stop7h 14m
Fri 10/911:12 pm -
1 stop6h 29m
Deal found 9/16![Delta logo]()
$329
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 10/612:49 pm -
1 stop11h 00m
Fri 10/98:44 pm -
2 stops10h 00m
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.
Tue 10/67:20 am -
1 stop10h 55m
Fri 10/98:44 pm -
2 stops8h 57m
Deal found 9/17![Delta logo]()
$335
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 10/71:55 pm -
2 stops11h 52m
Tue 10/138:44 pm -
2 stops8h 57m
Deal found 9/16![Delta logo]()
$337
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 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.
Fri 10/169:45 pm -
Nonstop4h 30m
Mon 10/199:15 pm -
1 stop6h 30m
Deal found 9/16![Southwest logo]()
$339
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 10/292:03 pm -
2 stops11h 56m
Mon 11/26:00 am -
2 stops8h 32m
Deal found 9/16![Delta logo]()
$339
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 10/3012:27 pm -
2 stops11h 29m
Tue 11/35:33 am -
2 stops9h 14m
Deal found 9/16![Delta logo]()
$340
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:59 pm -
Nonstop4h 42m
Mon 10/1910:55 pm -
Nonstop4h 12m
Deal found 9/16![American Airlines logo]()
$340
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 10/241:27 pm -
2 stops8h 35m
Fri 10/305:33 am -
2 stops9h 14m
Deal found 9/17![Delta logo]()
$341
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:21 pm -
Nonstop4h 38m
Mon 10/126:09 pm -
1 stop9h 50m
Deal found 9/16![American Airlines logo]()
$341
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 10/105:31 pm -
1 stop8h 13m
Sat 10/176:00 am -
1 stop8h 47m
Deal found 9/17![Delta logo]()
$342
Best flights from Chicago to PortlandDiscover carefully curated flight deals from Chicago to Portland 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 Chicago to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
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.
Sat 10/247:15 pm -
Nonstop4h 30m
Tue 10/276:15 am -
Nonstop3h 50m
Deal found 9/20![Southwest logo]()
$357
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.
Thu 10/221:30 pm -
Nonstop4h 26m
Tue 10/2711:30 pm -
Nonstop3h 49m
Deal found 9/20![United Airlines logo]()
$357
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 10/196:35 am -
1 stop7h 14m
Fri 10/238:44 pm -
2 stops10h 09m
Deal found 9/16![Delta logo]()
$364
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:14 pm -
Nonstop4h 37m
Wed 10/287:09 am -
1 stop9h 44m
Deal found 9/20![Alaska Airlines logo]()
$367
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.
Wed 10/218:40 pm -
Nonstop4h 30m
Tue 10/2711:35 pm -
Nonstop3h 50m
Deal found 9/19![Southwest logo]()
$357
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 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.
Thu 10/157:00 am -
Nonstop4h 31m
Sun 10/1811:30 pm -
Nonstop4h 01m
Deal found 9/16![United Airlines logo]()
$384
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 10/225:46 pm -
1 stop7h 16m
Sun 10/251:49 pm -
1 stop21h 36m
Deal found 9/17![Alaska Airlines logo]()
$401
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 11/59:15 pm -
Nonstop4h 40m
Sun 11/811:30 pm -
Nonstop3h 45m
Deal found 9/16![Southwest logo]()
$384
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.
Wed 10/141:27 pm -
2 stops10h 22m
Wed 10/218:44 pm -
2 stops10h 00m
Deal found 9/20![Delta logo]()
$387
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.
Mon 10/57:00 am -
Nonstop4h 31m
Sun 10/118:30 am -
Nonstop4h 13m
Deal found 9/16![United Airlines logo]()
$393
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:15 pm -
1 stop10h 37m
Sun 11/159:03 am -
1 stop26h 14m
Deal found 9/20![Alaska Airlines logo]()
$425
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.
Sat 10/103:30 pm -
2 stops9h 12m
Mon 10/128:44 pm -
2 stops10h 09m
Deal found 9/18![Delta logo]()
$387
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 Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:49 pm -
1 stop24h 29m
Thu 10/157:09 am -
1 stop14h 50m
Deal found 9/20![Alaska Airlines logo]()
$443
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 11/129:59 am -
2 stops10h 56m
Sun 11/152:24 pm -
1 stop7h 30m
Deal found 9/16![Delta logo]()
$409
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 12/177:30 am -
2 stops11h 25m
Fri 1/110:10 am -
2 stops7h 30m
Deal found 9/19![Southwest logo]()
$438
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 10/55:10 pm -
2 stops8h 30m
Fri 10/98:44 pm -
2 stops10h 09m
Deal found 9/16![Delta logo]()
$415
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 10/155:25 am -
1 stop9h 10m
Sun 10/185:20 am -
Nonstop3h 50m
Deal found 9/16![Southwest logo]()
$463
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 10/32:00 pm -
1 stop8h 16m
Mon 10/128:44 pm -
2 stops10h 00m
Deal found 9/19![Delta logo]()
$452
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.
Thu 10/225:25 am -
1 stop9h 10m
Sun 10/255:50 am -
2 stops10h 10m
Deal found 9/17![Southwest logo]()
$478
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 11/215:29 pm -
1 stop8h 17m
Fri 11/276:00 am -
1 stop8h 39m
Deal found 9/17![Delta logo]()
$474
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.
Fri 10/166:15 pm -
1 stop9h 10m
Sun 10/1811:35 pm -
Nonstop3h 50m
Deal found 9/18![Southwest logo]()
$478
Last-minute flights from Chicago to PortlandDiscover last-minute flight deals from Chicago to Portland. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Portland. 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.
Tue 10/612:49 pm -
1 stop11h 00m
Fri 10/98:44 pm -
2 stops10h 00m
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.
Tue 10/67:20 am -
1 stop10h 55m
Fri 10/98:44 pm -
2 stops8h 57m
Deal found 9/17![Delta logo]()
$335
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 10/71:55 pm -
2 stops11h 52m
Tue 10/138:44 pm -
2 stops8h 57m
Deal found 9/16![Delta logo]()
$337
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:21 pm -
Nonstop4h 38m
Mon 10/126:09 pm -
1 stop9h 50m
Deal found 9/16![American Airlines logo]()
$341
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.
Sat 10/105:30 pm -
1 stop8h 14m
Mon 10/123:31 pm -
1 stop6h 03m
Deal found 9/16![Delta logo]()
$329
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 10/105:31 pm -
1 stop8h 13m
Sat 10/176:00 am -
1 stop8h 47m
Deal found 9/17![Delta logo]()
$342
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.
Fri 10/169:45 pm -
Nonstop4h 30m
Mon 10/199:15 pm -
1 stop6h 30m
Deal found 9/16![Southwest logo]()
$339
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:59 pm -
Nonstop4h 42m
Mon 10/1910:55 pm -
Nonstop4h 12m
Deal found 9/16![American Airlines logo]()
$340
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 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 10/241:27 pm -
2 stops8h 35m
Fri 10/305:33 am -
2 stops9h 14m
Deal found 9/17![Delta logo]()
$341
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 10/292:03 pm -
2 stops11h 56m
Mon 11/211:00 pm -
2 stops11h 59m
Deal found 9/17![Delta logo]()
$339
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 10/3012:27 pm -
2 stops11h 29m
Tue 11/35:33 am -
2 stops9h 14m
Deal found 9/16![Delta logo]()
$340
One-way flights from Chicago to PortlandSearch for one-way flight options from Chicago to Portland. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
Search for one-way flight options from Chicago to Portland. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
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 10/107:15 pm -
Nonstop4h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$179
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:14 pm -
Nonstop4h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Alaska 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 9/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:30 am -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$183
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.
Fri 10/307:15 pm -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$185
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 10/167:15 pm -
1 stop6h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$185
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 11/196:30 am -
2 stops32h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$186
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.
Wed 10/141:27 pm -
2 stops10h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$187
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 10/197:44 pm -
2 stops17h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$188
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 10/206:05 am -
1 stop6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$189
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.
Mon 10/192:45 pm -
1 stop9h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$189
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 11/1312:30 pm -
2 stops11h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$190
Find flight deals from Chicago to Portland
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Portland (PDX). 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 | $335 (Delta) |
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 Chicago 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 21, 2026.
Use the filters below to find and compare flights from Chicago to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Thu 10/22
1:30 pm-3:56 pm
Nonstop4h 26m
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
Fri 10/16
7:15 pm-11:47 pm
1 stop6h 32m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$185
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Wed 11/18
5:20 am-10:50 am
1 stop7h 30m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Mon 10/19
5:31 pm-11:44 pm
1 stop8h 13m
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
Mon 10/19
2:45 pm-10:19 pm
1 stop9h 34m
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
Thu 12/17
7:45 am-4:24 pm
1 stop10h 39m
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
Wed 10/14
12:50 pm-8:00 pm
1 stop9h 10m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Tue 11/17
12:30 pm-6:55 pm
2 stops8h 25m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$194
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sat 10/31
9:29 am-4:10 pm
2 stops8h 41m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$194
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Wed 10/21
2:03 pm-11:59 pm
2 stops11h 56m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$194
Showing 1-10 of 45 resultsSorted by cheapest first
Compare providers for flights from Chicago to Portland
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 Chicago to Portland in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Portland flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Portland 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 Chicago-Portland 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 Chicago to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Chicago with our price prediction graph.
CHI-PDX
ORD-PDX
MDW-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 Chicago to Portland
CHI-PDX
ORD-PDX
MDW-PDX
What is the cheapest month to book a flight from Chicago to Portland?
Currently, February is the cheapest month in which you can book a flight from Chicago to Portland (average of $291). Flying from Chicago to Portland in March is currently the most expensive (average of $395). 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 CHI to PDX?
Find hourly flight availability from Chicago 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 21, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 48% on flights from Chicago to Portland by exploring options for tickets in the evening.
Weekly flight availability from Chicago to Portland
Explore weekly flight availability from Chicago 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 21, 2026.
The most flights from CHI to PDX are scheduled on a Sunday (29 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (14 on average).
How much does it cost to fly round-trip from Chicago to Portland?
Airfare is typical for this route at the moment.
Chicago to Portland flights typically cost between $318 and $482 in October.The cheapest round-trip price found within the last 5 days was $335 on Delta (Oct 6-Oct 9).
How far ahead should I book a flight from Chicago to Portland?
To ensure you get the cheapest price possible for a flight from Chicago 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 Chicago to Portland?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Portland. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Chicago 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.
The best insider tips for Chicago to Portland 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 Chicago to Portland trip
Our travel experts
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated September 21, 2026.
Read through reviews of airlines operating flights from Chicago to Portland, such as Southwest,Alaska Airlines, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago 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
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Chicago and Portland flights
Browse other Chicago and Portland flight options. Last updated on September 21, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 21, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
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Top 6 airlines flying from Chicago to Portland
Discover the top 6 airlines that operate flights from Chicago 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 21, 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$380 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$222 | Average$403 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$239 | Average$375 | FlexibilityNo cancel fee | On-time63% |