$159+ Cheap flights from Chicago (CHI) to Portland (PDX)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Aug 12 — Aug 191
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 77 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to Portland
Cheapest
Best
Last-minute
One-way
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 July 13, 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 July 13, 2026.
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 9/45:51 pm
ORD
- PDX
1 stop7h 03m
United Airlines
Mon 9/77:16 am
PDX
- ORD
Nonstop4h 13m
United Airlines
Deal found 7/10![United Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:20 pm
ORD
- PDX
1 stop16h 15m
Frontier
Sun 9/65:56 pm
PDX
- ORD
1 stop10h 03m
Frontier
Deal found 7/11![Frontier logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/79:57 pm
ORD
- PDX
1 stop20h 54m
Frontier
Tue 8/115:16 pm
PDX
- ORD
2 stops12h 46m
Frontier
Deal found 7/9![Frontier logo]()
$311
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/107:35 pm
MDW
- PDX
1 stop6h 05m
Southwest
Wed 8/121:25 pm
PDX
- MDW
1 stop7h 25m
Southwest
Deal found 7/10![Southwest logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 10/2011:06 am
ORD
- PDX
1 stop7h 29m
Frontier
Mon 11/99:03 pm
PDX
- ORD
2 stops10h 58m
Frontier
Deal found 7/11![Frontier logo]()
$312
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/712:46 pm
MDW
- PDX
1 stop8h 09m
Delta
Thu 8/1312:35 am
PDX
- MDW
1 stop6h 04m
Delta
Deal found 7/10![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/86:00 am
ORD
- PDX
1 stop6h 47m
Delta
Fri 8/1412:35 am
PDX
- ORD
1 stop5h 55m
Delta
Deal found 7/8![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 9/84:20 pm
MDW
- PDX
1 stop8h 00m
Southwest
Tue 9/155:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Deal found 7/8![Southwest logo]()
$314
This Travelocity deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:57 pm
ORD
- PDX
1 stop20h 34m
Frontier
Mon 7/275:36 pm
PDX
- ORD
1 stop10h 41m
Frontier
Deal found 7/8![Frontier logo]()
$314
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/245:00 pm
MDW
- PDX
2 stops8h 40m
Southwest
Mon 8/3111:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/10![Southwest logo]()
$315
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 9/43:54 pm
ORD
- PDX
1 stop9h 15m
American Airlines
Tue 9/811:09 pm
PDX
- ORD
Nonstop4h 23m
American Airlines
Deal found 7/9![American Airlines logo]()
$315
This CheapOair deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:12 pm
ORD
- PDX
Nonstop4h 35m
Alaska Airlines
Sat 8/810:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$316
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 July 13, 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 July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/245:00 pm
MDW
- PDX
2 stops8h 40m
Southwest
Mon 8/3111:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/10![Southwest logo]()
$315
This Alaska Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 7/298:20 pm
ORD
- PDX
1 stop13h 17m
Alaska Airlines
Wed 8/510:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 7/9![Alaska Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 9/47:25 pm
MDW
- PDX
1 stop5h 55m
Delta
Mon 9/712:25 am
PDX
- MDW
1 stop6h 23m
Delta
Deal found 7/9![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/87:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Sat 8/153:43 pm
PDX
- ORD
1 stop7h 16m
United Airlines
Deal found 7/9![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 9/206:00 am
ORD
- PDX
1 stop6h 49m
Delta
Thu 9/241:27 pm
PDX
- ORD
1 stop6h 25m
Delta
Deal found 7/9![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/2610:30 am
MDW
- PDX
2 stops9h 20m
Southwest
Sun 8/306:45 am
PDX
- MDW
2 stops8h 05m
Southwest
Deal found 7/10![Southwest logo]()
$338
This United Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 9/188:12 pm
ORD
- PDX
Nonstop4h 40m
United Airlines
Mon 9/212:27 pm
PDX
- ORD
Nonstop4h 13m
United Airlines
Deal found 7/12![United Airlines logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 10/107:49 pm
ORD
- PDX
1 stop15h 42m
Alaska Airlines
Mon 10/1210:30 am
PDX
- ORD
1 stop11h 29m
Alaska Airlines
Deal found 7/11![Alaska Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 9/36:15 am
MDW
- PDX
2 stops10h 30m
Southwest
Mon 9/77:00 pm
PDX
- MDW
1 stop8h 40m
Southwest
Deal found 7/8![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/317:40 pm
ORD
- PDX
1 stop6h 04m
Delta
Tue 8/41:25 pm
PDX
- ORD
1 stop8h 23m
Delta
Deal found 7/8![Delta logo]()
$363
This Alaska Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 10/82:17 pm
ORD
- PDX
Nonstop4h 37m
Alaska Airlines
Tue 10/137:06 am
PDX
- ORD
1 stop9h 14m
Alaska Airlines
Deal found 7/12![Alaska Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 7/176:40 pm
MDW
- PDX
1 stop8h 45m
Southwest
Thu 8/1312:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Deal found 7/9![Southwest logo]()
$370
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 7/314:15 pm
ORD
- PDX
Nonstop4h 32m
United Airlines
Sat 8/111:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 7/8![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/81:51 pm
MDW
- PDX
1 stop8h 26m
Delta
Sat 8/1510:55 pm
PDX
- MDW
1 stop9h 04m
Delta
Deal found 7/8![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/216:30 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Mon 8/2411:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/12![Southwest logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/37:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Mon 8/1010:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 7/12![Alaska Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 10/86:55 am
ORD
- PDX
1 stop7h 14m
Delta
Tue 10/131:38 pm
PDX
- ORD
1 stop5h 54m
Delta
Deal found 7/12![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 9/146:30 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Fri 9/188:00 am
PDX
- MDW
1 stop7h 00m
Southwest
Deal found 7/12![Southwest logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/36:42 pm
ORD
- PDX
1 stop6h 48m
Alaska Airlines
Sat 8/810:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$445
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 9/122:15 pm
MDW
- PDX
2 stops9h 05m
Southwest
Mon 9/1412:20 pm
PDX
- MDW
2 stops9h 00m
Southwest
Deal found 7/12![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 7/315:54 pm
ORD
- PDX
1 stop7h 24m
Delta
Sat 8/112:33 am
PDX
- ORD
1 stop5h 57m
Delta
Deal found 7/10![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/136:15 am
MDW
- PDX
2 stops10h 30m
Southwest
Sun 8/1611:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/11![Southwest logo]()
$388
Last-minute flights from Chicago to PortlandDiscover last-minute flight deals from Chicago to Portland. Data last updated July 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Portland. Data last updated July 13, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Fri 7/179:13 pm
ORD
- PDX
1 stop16h 22m
Multiple Airlines
Thu 8/1310:59 pm
PDX
- ORD
Nonstop4h 01m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$309
This Travelocity deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:57 pm
ORD
- PDX
1 stop20h 34m
Frontier
Mon 7/275:36 pm
PDX
- ORD
1 stop10h 41m
Frontier
Deal found 7/8![Frontier logo]()
$314
This CheapOair deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:12 pm
ORD
- PDX
Nonstop4h 35m
Alaska Airlines
Sat 8/810:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:30 pm
ORD
- PDX
Nonstop4h 29m
American Airlines
Wed 8/1211:34 pm
PDX
- ORD
Nonstop3h 58m
American Airlines
Deal found 7/9![American Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/68:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Thu 8/1311:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/9![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/79:57 pm
ORD
- PDX
1 stop20h 54m
Frontier
Tue 8/115:16 pm
PDX
- ORD
2 stops12h 46m
Frontier
Deal found 7/9![Frontier logo]()
$311
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/76:15 pm
MDW
- PDX
1 stop7h 00m
Southwest
Fri 8/147:55 pm
PDX
- MDW
1 stop7h 50m
Southwest
Deal found 7/10![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/86:00 am
ORD
- PDX
1 stop6h 47m
Delta
Fri 8/1412:35 am
PDX
- ORD
1 stop5h 55m
Delta
Deal found 7/8![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/107:35 pm
MDW
- PDX
1 stop6h 05m
Southwest
Wed 8/121:25 pm
PDX
- MDW
1 stop7h 25m
Southwest
Deal found 7/10![Southwest logo]()
$312
This CheapOair deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:57 pm
ORD
- PDX
1 stop20h 39m
Frontier
Thu 8/136:49 pm
PDX
- ORD
1 stop8h 48m
Frontier
Deal found 7/12![Frontier logo]()
$312
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/245:00 pm
MDW
- PDX
2 stops8h 40m
Southwest
Mon 8/3111:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/10![Southwest logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:20 pm
ORD
- PDX
1 stop16h 15m
Frontier
Sun 9/65:56 pm
PDX
- ORD
1 stop10h 03m
Frontier
Deal found 7/11![Frontier logo]()
$310
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 July 13, 2026.
Search for one-way flight options from Chicago to Portland. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
This Super.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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 8/99:57 pm
ORD
- PDX
1 stop20h 54m
Frontier
Deal found 7/9![Frontier logo]()
$159
This Super.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/249:57 pm
ORD
- PDX
1 stop20h 54m
Frontier
Deal found 7/13![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 8/69:27 pm
MDW
- PDX
2 stops45h 24m
Frontier
Deal found 7/11![Frontier logo]()
$161
This Super.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/179:13 pm
ORD
- PDX
1 stop16h 22m
Frontier
Deal found 7/9![Frontier logo]()
$161
This Super.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/319:57 pm
ORD
- PDX
1 stop20h 54m
Frontier
Deal found 7/10![Frontier logo]()
$162
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/118:50 am
ORD
- PDX
Nonstop4h 38m
United Airlines
Deal found 7/8![United Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/109:13 pm
ORD
- PDX
2 stops21h 18m
Frontier
Deal found 7/8![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:26 pm
MDW
- PDX
2 stops21h 45m
Frontier
Deal found 7/11![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/279:20 am
ORD
- PDX
2 stops33h 51m
Frontier
Deal found 7/10![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/209:20 pm
ORD
- PDX
1 stop16h 15m
Frontier
Deal found 7/12![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/711:06 am
MDW
- PDX
2 stops31h 45m
Frontier
Deal found 7/8![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/89:57 pm
ORD
- PDX
1 stop20h 54m
Frontier
Deal found 7/12![Frontier logo]()
$168
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 July 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (United Airlines) |
One-way from | $159 (Super.com) |
Popular in | March |
Cheapest in | January |
Average price | $371 |
Good round-trip deal | $353 or less |
Good one-way deal | $168 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 2,558,603 searches. Data last updated July 13, 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 - PDX
MDWPDX
Chicago Midway
Mon 8/24
5:00 pm-11:40 pm
2 stops8h 40m
Portland
Mon 8/31
11:30 pm-5:25 am
Nonstop3h 55m
$315
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 7/29
8:20 pm-7:37 am
1 stop13h 17m
Portland
Wed 8/5
10:59 pm-5:00 am
Nonstop4h 01m
$327
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Fri 9/4
7:25 pm-11:20 pm
1 stop5h 55m
Portland
Mon 9/7
12:25 am-8:48 am
1 stop6h 23m
$328
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sun 9/20
6:00 am-10:49 am
1 stop6h 49m
Portland
Thu 9/24
1:27 pm-9:52 pm
1 stop6h 25m
$328
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sat 8/8
7:00 am-9:34 am
Nonstop4h 34m
Portland
Sat 8/15
3:43 pm-12:59 am
1 stop7h 16m
$337
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 8/26
10:30 am-5:50 pm
2 stops9h 20m
Portland
Sun 8/30
6:45 am-4:50 pm
2 stops8h 05m
$338
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Thu 9/3
6:15 am-2:45 pm
2 stops10h 30m
Portland
Mon 9/7
7:00 pm-5:40 am
1 stop8h 40m
$343
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 7/31
7:40 pm-11:44 pm
1 stop6h 04m
Portland
Tue 8/4
1:25 pm-11:48 pm
1 stop8h 23m
$363
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Fri 7/17
6:40 pm-1:25 am
1 stop8h 45m
Portland
Thu 8/13
12:40 pm-11:45 pm
2 stops9h 05m
$370
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 9/18
8:12 pm-10:52 pm
Nonstop4h 40m
Portland
Mon 9/21
2:27 pm-8:40 pm
Nonstop4h 13m
$373
Showing 1-10 of 43 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 July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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, August is the cheapest month in which you can book a flight from Chicago to Portland (average of $94). Flying from Chicago to Portland in June is currently the most expensive (average of $463). 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 July 13, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 7% 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 July 13, 2026.
The most flights from CHI to PDX are scheduled on a Monday (31 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (24 on average).
How much does it cost to fly round-trip from Chicago to Portland?
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 77 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 July 11, 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. Sunday 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 July 13, 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
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
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
Vancouver
Lincoln City
Longview
Lake Oswego
Hillsboro
Clackamas
Kelso
Troutdale
Cannon Beach
Long Beach
McMinnville
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Gresham
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 July 13, 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 July 13, 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 July 13, 2026.
Top 7 airlines flying from Chicago to Portland
Discover the top 7 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 2,558,603 searches. Data last updated July 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$229 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$150 | Average$338 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$196 | Average$326 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$203 | Average$343 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$205 | Average$359 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$227 | Average$372 | FlexibilityNo cancel fee | On-time63% |