$177+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Dec 5 — Dec 121
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 76 days in advance, depart on a Tuesday or Saturday 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 November 5, 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 November 5, 2026.
This Expedia deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/238:59 pm -
1 stop13h 30m
Wed 12/309:22 pm -
1 stop13h 57m
Deal found 11/4![Alaska Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:05 am -
2 stops8h 40m
Wed 12/910:10 am -
2 stops7h 30m
Deal found 11/4![Southwest logo]()
$359
This Kissandfly.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:00 am -
2 stops13h 56m
Wed 12/91:17 pm -
2 stops13h 44m
Deal found 11/3![Frontier logo]()
$359
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:20 pm -
2 stops11h 00m
Sun 12/67:35 am -
2 stops8h 00m
Deal found 11/3![Southwest logo]()
$360
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:00 am -
1 stop9h 24m
Wed 12/307:05 am -
1 stop14h 54m
Deal found 11/2![Alaska Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:00 am -
1 stop7h 53m
Tue 12/85:10 pm -
2 stops26h 50m
Deal found 11/4![Frontier logo]()
$361
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:00 pm -
1 stop14h 28m
Fri 11/271:58 pm -
1 stop13h 12m
Deal found 11/1![Frontier logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:15 am -
1 stop30h 17m
Tue 12/15:09 pm -
2 stops26h 26m
Deal found 11/2![Frontier logo]()
$363
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:20 pm -
2 stops11h 00m
Wed 12/910:10 am -
2 stops7h 30m
Deal found 11/3![Southwest logo]()
$364
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/612:58 pm -
1 stop6h 21m
Tue 12/811:17 pm -
1 stop6h 42m
Deal found 11/4![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/159:45 am -
Nonstop4h 52m
Tue 12/2211:31 pm -
Nonstop3h 54m
Deal found 10/31![American Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/248:40 pm -
Nonstop4h 45m
Mon 12/2811:30 pm -
Nonstop3h 45m
Deal found 11/2![Southwest logo]()
$367
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 November 5, 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 November 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:00 am -
1 stop11h 50m
Mon 12/287:00 am -
Nonstop4h 10m
Deal found 11/1![Alaska Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:00 am -
1 stop8h 35m
Wed 12/3011:30 pm -
Nonstop3h 45m
Deal found 11/3![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/171:41 pm -
2 stops10h 25m
Thu 12/241:00 pm -
1 stop7h 22m
Deal found 11/2![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:58 pm -
Nonstop4h 49m
Tue 12/2911:50 pm -
Nonstop4h 09m
Deal found 11/2![United Airlines logo]()
$396
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:40 pm -
Nonstop4h 45m
Tue 12/86:00 am -
Nonstop3h 50m
Deal found 11/3![Southwest logo]()
$374
This Alaska Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/172:17 pm -
1 stop8h 33m
Fri 1/16:09 am -
1 stop6h 12m
Deal found 11/4![Alaska Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/74:15 pm -
Nonstop4h 44m
Sat 1/1610:46 am -
Nonstop4h 07m
Deal found 11/1![United Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:40 pm -
Nonstop4h 45m
Thu 12/1711:30 pm -
Nonstop3h 45m
Deal found 11/1![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/175:02 pm -
2 stops8h 37m
Thu 12/245:30 am -
2 stops12h 48m
Deal found 11/2![Delta logo]()
$438
This Alaska Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:00 am -
1 stop9h 24m
Wed 12/307:00 am -
Nonstop4h 10m
Deal found 11/1![Alaska Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2510:15 am -
2 stops9h 50m
Thu 1/76:30 am -
Nonstop3h 55m
Deal found 11/1![Southwest logo]()
$389
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:41 pm -
2 stops10h 58m
Wed 12/95:30 am -
2 stops10h 36m
Deal found 11/2![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:49 pm -
Nonstop4h 34m
Mon 11/2311:30 pm -
Nonstop3h 49m
Deal found 10/31![United Airlines logo]()
$452
This Alaska Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/236:00 am -
1 stop11h 16m
Wed 12/301:52 pm -
1 stop8h 07m
Deal found 11/1![Alaska Airlines logo]()
$420
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/286:55 pm -
1 stop7h 35m
Thu 3/46:00 am -
2 stops10h 10m
Deal found 11/3![Southwest logo]()
$402
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/194:15 pm -
Nonstop4h 45m
Sat 12/2611:59 pm -
1 stop8h 11m
Deal found 10/31![United Airlines logo]()
$465
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/151:05 pm -
1 stop11h 21m
Tue 4/2010:55 pm -
1 stop7h 50m
Deal found 11/1![Delta logo]()
$484
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:50 am -
2 stops9h 35m
Wed 12/910:10 am -
2 stops7h 30m
Deal found 11/2![Southwest logo]()
$404
This Alaska Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:26 am -
1 stop18h 01m
Fri 11/277:00 am -
Nonstop4h 08m
Deal found 11/1![Alaska Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:00 pm -
2 stops7h 55m
Thu 12/316:55 am -
2 stops8h 25m
Deal found 11/4![Southwest logo]()
$445
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:00 am -
1 stop8h 35m
Mon 12/76:00 am -
Nonstop3h 50m
Deal found 10/31![Southwest logo]()
$451
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:40 pm -
Nonstop4h 45m
Mon 11/2311:30 pm -
Nonstop3h 45m
Deal found 10/31![Southwest logo]()
$452
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:10 pm -
1 stop7h 40m
Thu 11/266:15 am -
1 stop6h 50m
Deal found 11/1![Southwest logo]()
$457
Last-minute flights from Chicago to PortlandDiscover last-minute flight deals from Chicago to Portland. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Portland. Data last updated November 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:15 am -
1 stop30h 17m
Tue 12/15:09 pm -
2 stops26h 26m
Deal found 11/2![Frontier logo]()
$363
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:00 pm -
1 stop14h 28m
Fri 11/271:58 pm -
1 stop13h 12m
Deal found 11/1![Frontier logo]()
$362
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:05 am -
2 stops8h 40m
Wed 12/910:10 am -
2 stops7h 30m
Deal found 11/4![Southwest logo]()
$359
This Kissandfly.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:00 am -
2 stops13h 56m
Wed 12/91:17 pm -
2 stops13h 44m
Deal found 11/3![Frontier logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:00 am -
1 stop7h 53m
Tue 12/85:10 pm -
2 stops26h 50m
Deal found 11/4![Frontier logo]()
$361
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:20 pm -
2 stops11h 00m
Wed 12/910:10 am -
2 stops7h 30m
Deal found 11/3![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:20 pm -
2 stops11h 00m
Sun 12/67:35 am -
2 stops8h 00m
Deal found 11/3![Southwest logo]()
$360
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:02 pm -
1 stop7h 05m
Mon 12/71:30 pm -
1 stop6h 26m
Deal found 11/4![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/159:45 am -
Nonstop4h 52m
Tue 12/2211:31 pm -
Nonstop3h 54m
Deal found 10/31![American Airlines logo]()
$366
This Expedia deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/238:59 pm -
1 stop13h 30m
Wed 12/309:22 pm -
1 stop13h 57m
Deal found 11/4![Alaska Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/248:40 pm -
Nonstop4h 45m
Mon 12/2811:30 pm -
Nonstop3h 45m
Deal found 11/2![Southwest logo]()
$367
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:00 am -
1 stop9h 24m
Wed 12/307:05 am -
1 stop14h 54m
Deal found 11/2![Alaska Airlines logo]()
$360
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 November 5, 2026.
Search for one-way flight options from Chicago to Portland. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/132:13 pm -
1 stop21h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Alaska Airlines logo]()
$177
This Super.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:05 am -
1 stop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$178
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:25 pm -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:45 pm -
Nonstop4h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![United Airlines logo]()
$179
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:30 am -
1 stop6h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$180
This Super.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:15 am -
1 stop9h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$187
This Super.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:30 am -
1 stop6h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$188
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:29 pm -
1 stop8h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$189
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:20 am -
1 stop6h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$189
This Super.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:15 pm -
1 stop20h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$191
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:25 pm -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:05 am -
2 stops10h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$194
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 November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $357 (Expedia) |
One-way from | $177 (Alaska Airlines) |
Popular in | October |
Cheapest in | January |
Average price | $436 |
Good round-trip deal | $357 or less |
Good one-way deal | $224 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 November 5, 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
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Wed 11/25
9:25 pm-12:10 am
Nonstop4h 45m
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
Wed 11/25
7:45 pm-10:27 pm
Nonstop4h 42m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Mon 12/21
9:30 pm-12:15 am
Nonstop4h 45m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Thu 12/24
8:40 pm-11:25 pm
Nonstop4h 45m
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
Mon 11/23
5:15 am-12:36 pm
1 stop9h 21m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$186
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Fri 12/18
6:20 am-10:39 am
1 stop6h 19m
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 11/21
3:47 pm-10:26 pm
2 stops8h 39m
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 11/25
2:44 pm-11:51 pm
2 stops11h 07m
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
Tue 12/1
9:44 am-12:26 pm
Nonstop4h 42m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$229
Quickest round-trip
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sat 11/21
10:05 am-12:40 pm
Nonstop4h 35m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$229
Showing 1-10 of 41 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 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 $296). Flying from Chicago to Portland in October is currently the most expensive (average of $445). 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 November 5, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 47% 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 November 5, 2026.
The most flights from CHI to PDX are scheduled on a Monday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Chicago to Portland?
Airfare is below average for this route at the moment.
Chicago to Portland flights typically cost between $362 and $572 in March.The cheapest round-trip price found within the last 5 days was $357 on Southwest (Mar 6-Mar 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 63 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 October 31, 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 November 5, 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.
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
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
Durham
Cannon Beach
Longview
Lake Oswego
Lincoln City
Vancouver
Kelso
Troutdale
Clackamas
McMinnville
The Dalles
Wilsonville
Stevenson
Hillsboro
Astoria
Tillamook
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Search flights from Chicago to Portland by cabin class
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Chicago and Portland flights
Browse other Chicago and Portland flight options. Last updated on November 5, 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 November 5, 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 November 5, 2026.
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 November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$155 | Average$250 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$343 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$217 | Average$394 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$222 | Average$403 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$239 | Average$374 | FlexibilityNo cancel fee | On-time63% |