$153+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Jul 5 — Jul 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 55 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 June 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 June 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Wed 7/227:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Tue 7/2810:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$309
This Priceline deal was found by Cheapflights users on 6/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sun 7/1910:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$310
This Booking.com deal was found by Cheapflights users on 6/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Wed 7/85:21 pm
PDX
- ORD
1 stop25h 31m
Frontier
Deal found 6/3![Frontier logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Wed 7/227:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sat 7/2510:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$314
This Southwest deal was found by Cheapflights users on 6/2. 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.
Sat 7/46:05 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Sat 7/1111:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 6/2![Southwest logo]()
$315
This Alaska Airlines deal was found by Cheapflights users on 6/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Tue 8/187:00 am
PDX
- ORD
Nonstop4h 13m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Mon 8/315:42 pm
PDX
- ORD
1 stop10h 37m
Frontier
Deal found 6/3![Frontier logo]()
$316
This American Airlines deal was found by Cheapflights users on 5/31. 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.
Sat 7/48:20 am
ORD
- PDX
Nonstop4h 29m
American Airlines
Sat 7/1111:15 pm
PDX
- ORD
Nonstop3h 59m
American Airlines
Deal found 5/31![American Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Tue 9/15:42 pm
PDX
- ORD
2 stops24h 13m
Frontier
Deal found 6/3![Frontier logo]()
$318
This Mytrip deal was found by Cheapflights users on 6/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:57 pm
ORD
- PDX
1 stop20h 54m
Frontier
Wed 8/195:42 pm
PDX
- ORD
1 stop25h 11m
Frontier
Deal found 6/3![Frontier logo]()
$319
This CheapOair deal was found by Cheapflights users on 6/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:13 pm
ORD
- PDX
1 stop16h 22m
Frontier
Wed 7/295:21 pm
PDX
- ORD
1 stop25h 31m
Frontier
Deal found 6/2![Frontier logo]()
$320
This Priceline deal was found by Cheapflights users on 6/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sun 7/2610:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$321
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 June 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 June 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/2. 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.
Sat 7/47:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Tue 7/710:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/2![Alaska Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 6/1. 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 7/229:10 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Tue 7/287:50 pm
PDX
- MDW
1 stop7h 55m
Southwest
Deal found 6/1![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 6/4. 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.
Wed 8/57:00 am
ORD
- PDX
1 stop9h 45m
Delta
Wed 8/121:30 pm
PDX
- ORD
1 stop6h 17m
Delta
Deal found 6/4![Delta logo]()
$345
This United Airlines deal was found by Cheapflights users on 5/31. 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.
Mon 6/157:55 pm
ORD
- PDX
Nonstop4h 34m
United Airlines
Thu 6/1811:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 5/31![United Airlines logo]()
$445
This KAYAK deal was found by Cheapflights users on 6/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:00 am
ORD
- PDX
Nonstop4h 25m
American Airlines
Fri 6/1910:59 pm
PDX
- ORD
Nonstop4h 01m
American Airlines
Deal found 6/2![American Airlines logo]()
$487
This Southwest deal was found by Cheapflights users on 6/4. 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.
Fri 8/218:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Sat 8/2211:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 6/4![Southwest logo]()
$326
This Alaska Airlines deal was found by Cheapflights users on 6/1. 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 8/186:00 am
ORD
- PDX
1 stop7h 21m
Alaska Airlines
Tue 8/257:06 am
PDX
- ORD
Nonstop4h 20m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 6/3. 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 7/316:55 am
ORD
- PDX
1 stop6h 46m
Delta
Wed 8/512:20 pm
PDX
- ORD
1 stop9h 08m
Delta
Deal found 6/3![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 5/31. 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.
Wed 7/295:05 am
MDW
- PDX
1 stop6h 55m
Southwest
Tue 8/46:25 pm
PDX
- MDW
1 stop9h 20m
Southwest
Deal found 5/31![Southwest logo]()
$335
This Alaska Airlines deal was found by Cheapflights users on 6/1. 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.
Fri 7/37:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Mon 7/610:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 5/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:06 pm
MDW
- PDX
1 stop6h 12m
Delta
Sat 7/1812:33 am
PDX
- MDW
1 stop6h 04m
Delta
Deal found 5/31![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 6/4. 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 7/149:10 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Fri 7/1711:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 6/4![Southwest logo]()
$336
This Alaska Airlines deal was found by Cheapflights users on 6/4. 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.
Sun 7/57:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sun 7/1210:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 6/2. 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.
Wed 8/198:35 am
MDW
- PDX
2 stops8h 50m
Southwest
Tue 8/257:50 am
PDX
- MDW
2 stops10h 00m
Southwest
Deal found 6/2![Southwest logo]()
$345
This Delta deal was found by Cheapflights users on 6/4. 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.
Fri 7/37:16 pm
MDW
- PDX
1 stop6h 02m
Delta
Sun 7/512:33 am
PDX
- MDW
1 stop6h 04m
Delta
Deal found 6/4![Delta logo]()
$388
This Alaska Airlines deal was found by Cheapflights users on 6/1. 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.
Fri 8/216:00 am
ORD
- PDX
1 stop9h 10m
Alaska Airlines
Thu 8/277:55 am
PDX
- ORD
1 stop9h 26m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 6/3. 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 7/24:40 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Mon 7/611:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 6/3![Southwest logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 6/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:17 pm
ORD
- PDX
1 stop15h 13m
Alaska Airlines
Mon 8/247:22 pm
PDX
- ORD
1 stop8h 58m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 6/1. 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.
Tue 7/77:06 pm
MDW
- PDX
1 stop6h 12m
Delta
Sat 7/1112:33 am
PDX
- MDW
1 stop6h 04m
Delta
Deal found 6/1![Delta logo]()
$397
This Southwest deal was found by Cheapflights users on 6/3. 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 8/216:30 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Mon 8/2412:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Deal found 6/3![Southwest logo]()
$368
This Delta deal was found by Cheapflights users on 6/3. 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.
Wed 6/246:30 am
ORD
- PDX
1 stop8h 10m
Delta
Fri 6/266:30 am
PDX
- ORD
1 stop9h 00m
Delta
Deal found 6/3![Delta logo]()
$448
This Southwest deal was found by Cheapflights users on 6/1. 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.
Sun 8/169:20 pm
MDW
- PDX
Nonstop4h 10m
Southwest
Sun 8/2311:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 6/1![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 5/31. 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.
Fri 7/36:25 pm
MDW
- PDX
2 stops8h 05m
Southwest
Sun 7/55:10 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 5/31![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 6/1. 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.
Tue 8/187:00 am
ORD
- PDX
1 stop6h 40m
Delta
Tue 8/257:05 am
PDX
- ORD
2 stops12h 53m
Delta
Deal found 6/1![Delta logo]()
$494
Last-minute flights from Chicago to PortlandDiscover last-minute flight deals from Chicago to Portland. Data last updated June 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Portland. Data last updated June 5, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 6/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Wed 6/245:20 pm
PDX
- ORD
1 stop25h 23m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$323
This Booking.com deal was found by Cheapflights users on 6/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Wed 7/85:21 pm
PDX
- ORD
1 stop25h 31m
Frontier
Deal found 6/3![Frontier logo]()
$313
This Southwest deal was found by Cheapflights users on 6/2. 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.
Sat 7/46:05 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Sat 7/1111:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 6/2![Southwest logo]()
$315
This Alaska Airlines deal was found by Cheapflights users on 6/2. 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.
Sat 7/47:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Tue 7/710:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/2![Alaska Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 5/31. 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.
Sat 7/48:20 am
ORD
- PDX
Nonstop4h 29m
American Airlines
Sat 7/1111:15 pm
PDX
- ORD
Nonstop3h 59m
American Airlines
Deal found 5/31![American Airlines logo]()
$317
This Gotogate deal was found by Cheapflights users on 5/31. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:57 pm
ORD
- PDX
1 stop20h 39m
Frontier
Sat 7/115:36 pm
PDX
- ORD
1 stop10h 41m
Frontier
Deal found 5/31![Frontier logo]()
$324
This Priceline deal was found by Cheapflights users on 6/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sun 7/1910:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$310
This Alaska Airlines deal was found by Cheapflights users on 6/2. 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.
Wed 7/158:20 pm
ORD
- PDX
1 stop13h 17m
Alaska Airlines
Wed 7/2210:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/2![Alaska Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Wed 7/227:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Tue 7/2810:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Wed 7/227:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sat 7/2510:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$314
This CheapOair deal was found by Cheapflights users on 6/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:13 pm
ORD
- PDX
1 stop16h 22m
Frontier
Tue 7/285:16 pm
PDX
- ORD
1 stop25h 36m
Frontier
Deal found 6/2![Frontier logo]()
$320
This Priceline deal was found by Cheapflights users on 6/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sun 7/2610:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$321
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 June 5, 2026.
Search for one-way flight options from Chicago to Portland. Find affordable one-way fares based on user searches. Data last updated June 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Mon 8/316:00 am
MDW
- PDX
2 stops13h 24m
Frontier
Deal found 6/4![Frontier logo]()
$153
This Priceline deal was found by Cheapflights users on 6/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 6/4![Alaska Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/98:11 pm
MDW
- PDX
1 stop17h 19m
Allegiant Air
Deal found 6/3![Allegiant Air logo]()
$154
This SmartFares deal was found by Cheapflights users on 6/1. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/49:34 pm
ORD
- PDX
2 stops46h 30m
Frontier
Deal found 6/3![Frontier logo]()
$156
This Southwest deal was found by Cheapflights users on 6/3. 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.
Sat 7/258:25 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/3![Southwest logo]()
$158
This Alaska Airlines deal was found by Cheapflights users on 6/1. 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 7/147:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 6/1![Alaska Airlines logo]()
$158
This Super.com deal was found by Cheapflights users on 6/3. 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.
Wed 7/19:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Deal found 6/3![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 6/2. 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 8/189:07 pm
ORD
- PDX
2 stops21h 50m
Frontier
Deal found 6/2![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Wed 9/29:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Deal found 6/4![Frontier logo]()
$162
This Alaska Airlines deal was found by Cheapflights users on 6/2. 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.
Wed 8/261:03 pm
ORD
- PDX
1 stop8h 47m
Alaska Airlines
Deal found 6/2![Alaska Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1211:06 am
MDW
- PDX
2 stops33h 02m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$166
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 June 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (Kiwi.com) |
One-way from | $153 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $357 |
Good round-trip deal | $315 or less |
Good one-way deal | $163 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 June 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
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sat 7/4
7:20 am-9:45 am
Nonstop4h 25m
Portland
Tue 7/7
10:59 pm-5:00 am
Nonstop4h 01m
$315
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 7/22
9:10 pm-11:35 pm
Nonstop4h 25m
Portland
Tue 7/28
7:50 pm-5:45 am
1 stop7h 55m
$325
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Fri 8/21
8:50 pm-11:05 pm
Nonstop4h 15m
Portland
Sat 8/22
11:30 pm-5:25 am
Nonstop3h 55m
$326
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 8/18
6:00 am-11:21 am
1 stop7h 21m
Portland
Tue 8/25
7:06 am-1:26 pm
Nonstop4h 20m
$335
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 7/29
5:05 am-10:00 am
1 stop6h 55m
Portland
Tue 8/4
6:25 pm-5:45 am
1 stop9h 20m
$335
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Tue 7/14
9:10 pm-11:35 pm
Nonstop4h 25m
Portland
Fri 7/17
11:30 pm-5:20 am
Nonstop3h 50m
$336
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 7/3
7:20 am-9:45 am
Nonstop4h 25m
Portland
Mon 7/6
10:59 pm-5:00 am
Nonstop4h 01m
$337
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sun 7/5
7:20 am-9:45 am
Nonstop4h 25m
Portland
Sun 7/12
10:59 pm-5:00 am
Nonstop4h 01m
$337
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 8/5
7:00 am-2:45 pm
1 stop9h 45m
Portland
Wed 8/12
1:30 pm-9:47 pm
1 stop6h 17m
$345
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 8/19
8:35 am-3:25 pm
2 stops8h 50m
Portland
Tue 8/25
7:50 am-7:50 pm
2 stops10h 00m
$345
Showing 1-10 of 46 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 June.
| 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 | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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 July is currently the most expensive (average of $697). 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 June 5, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 19% 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 June 5, 2026.
The most flights from CHI to PDX are scheduled on a Thursday (32 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (18 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 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 May 30, 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 June 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.
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Gresham
Browse thousands of different 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 June 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 June 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 June 5, 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 June 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$247 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$150 | Average$248 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$319 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$200 | Average$329 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$201 | Average$353 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$227 | Average$357 | FlexibilityNo cancel fee | On-time63% |