$168+ Cheap flights from Portland (PDX) to O'Hare Intl (ORD)
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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Sep 25 — Oct 21
Round-trip
1 adult, Economy
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Find cheap flights from Portland to O'Hare Intl with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Portland to Chicago O'Hare Intl are usually found in February or January, booked 72 days in advance, depart on a Wednesday or Thursday and return on a Tuesday
Cheap flight deals from Portland to O'Hare Intl
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Best
Last-minute
One-way
Cheapest flights from Portland to O'Hare IntlExplore the most affordable flight options available from Portland to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2026.
Explore the most affordable flight options available from Portland to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2026.
This CheapOair deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Thu 10/1512:11 pm -
1 stop15h 05m
Sun 10/186:30 am -
1 stop6h 24m
Deal found 8/25![Frontier logo]()
$309
This Expedia deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:39 pm -
1 stop14h 59m
Fri 9/258:55 pm -
1 stop16h 41m
Deal found 8/21![Frontier logo]()
$312
This Expedia deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/911:06 am -
1 stop17h 28m
Tue 10/136:30 am -
1 stop6h 24m
Deal found 8/25![Frontier logo]()
$313
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Mon 9/2112:39 pm -
1 stop14h 59m
Wed 9/231:21 pm -
1 stop24h 15m
Deal found 8/24![Frontier logo]()
$314
This Expedia deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:13 am -
1 stop8h 08m
Fri 9/188:55 pm -
1 stop16h 41m
Deal found 8/21![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1912:25 pm -
2 stops16h 09m
Wed 10/218:01 pm -
1 stop16h 10m
Deal found 8/21![Frontier logo]()
$316
This Expedia deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:38 pm -
1 stop9h 45m
Sun 9/136:30 am -
1 stop7h 13m
Deal found 8/21![Frontier logo]()
$317
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/911:06 am -
1 stop17h 28m
Sun 10/116:30 am -
1 stop6h 24m
Deal found 8/21![Frontier logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/511:02 am -
2 stops33h 57m
Thu 10/158:01 pm -
1 stop16h 10m
Deal found 8/21![Frontier logo]()
$320
This Orbitz deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:38 pm -
1 stop9h 45m
Mon 9/146:30 am -
1 stop7h 13m
Deal found 8/24![Frontier logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/55:56 pm -
1 stop10h 03m
Tue 9/157:20 am -
1 stop8h 28m
Deal found 8/24![Multiple Airlines logo]()
$322
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/223:03 pm -
1 stop20h 19m
Wed 9/302:18 pm -
1 stop8h 31m
Deal found 8/25![Alaska Airlines logo]()
$323
Best flights from Portland to O'Hare IntlDiscover carefully curated flight deals from Portland to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
Discover carefully curated flight deals from Portland to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/287:09 am -
1 stop9h 44m
Tue 11/37:20 am -
1 stop13h 37m
Deal found 8/22![Alaska Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/72:27 pm -
Nonstop4h 13m
Wed 10/148:55 am -
Nonstop4h 38m
Deal found 8/24![United Airlines logo]()
$357
This Sun Country Air deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:12 pm -
1 stop13h 39m
Sat 11/2810:00 am -
1 stop14h 59m
Deal found 8/23![Sun Country Air logo]()
$435
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/72:08 pm -
1 stop7h 49m
Mon 9/217:07 am -
1 stop7h 45m
Deal found 8/22![Delta logo]()
$440
This Alaska Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/167:55 am -
1 stop9h 26m
Wed 9/237:20 am -
1 stop17h 25m
Deal found 8/23![Alaska Airlines logo]()
$323
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/309:13 am -
1 stop8h 08m
Tue 10/67:20 am -
1 stop12h 58m
Deal found 8/25![Alaska Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/710:43 am -
1 stop6h 47m
Mon 10/127:45 pm -
Nonstop4h 38m
Deal found 8/22![United Airlines logo]()
$390
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/249:13 am -
1 stop8h 08m
Mon 9/282:18 pm -
1 stop10h 27m
Deal found 8/25![Alaska Airlines logo]()
$377
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:33 am -
1 stop11h 26m
Tue 9/157:20 am -
1 stop11h 33m
Deal found 8/21![Alaska Airlines logo]()
$386
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/27:06 am -
Nonstop4h 20m
Sun 9/62:22 pm -
Nonstop4h 28m
Deal found 8/25![Alaska Airlines logo]()
$433
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/117:06 am -
Nonstop4h 20m
Tue 9/152:22 pm -
Nonstop4h 28m
Deal found 8/25![Alaska Airlines logo]()
$433
This KAYAK deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:32 pm -
1 stop6h 48m
Fri 9/182:18 pm -
1 stop10h 27m
Deal found 8/21![Alaska Airlines logo]()
$450
Last-minute flights from Portland to O'Hare IntlDiscover last-minute flight deals from Portland to O'Hare Intl. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to O'Hare Intl. Data last updated August 26, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 8/255:56 pm -
1 stop17h 40m
Sat 8/299:20 pm -
1 stop16h 15m
Deal found 8/22![Frontier logo]()
$328
This Booking.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Thu 9/31:47 pm -
1 stop27h 15m
Mon 9/146:30 am -
1 stop7h 13m
Deal found 8/24![Frontier logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/55:56 pm -
1 stop10h 03m
Tue 9/157:20 am -
1 stop8h 28m
Deal found 8/24![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/55:56 pm -
1 stop10h 03m
Sat 9/123:50 pm -
2 stops21h 53m
Deal found 8/24![Frontier logo]()
$326
This Orbitz deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:38 pm -
1 stop9h 45m
Mon 9/146:30 am -
1 stop7h 13m
Deal found 8/24![Frontier logo]()
$321
This CheapOair deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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.
Sat 9/1212:24 pm -
1 stop15h 14m
Sun 9/206:30 am -
1 stop7h 13m
Deal found 8/22![Frontier logo]()
$318
This Expedia deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:13 am -
1 stop8h 08m
Fri 9/188:55 pm -
1 stop16h 41m
Deal found 8/21![Multiple Airlines logo]()
$315
This Expedia deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/1812:38 pm -
1 stop9h 45m
Sun 9/206:30 am -
1 stop7h 13m
Deal found 8/25![Frontier logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/1912:24 pm -
1 stop15h 14m
Tue 9/222:18 pm -
1 stop8h 31m
Deal found 8/25![Multiple Airlines logo]()
$313
This Expedia deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:39 pm -
1 stop14h 59m
Fri 9/258:55 pm -
1 stop16h 41m
Deal found 8/21![Frontier logo]()
$312
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Mon 9/2112:39 pm -
1 stop14h 59m
Wed 9/231:21 pm -
1 stop24h 15m
Deal found 8/24![Frontier logo]()
$314
This Alaska Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/223:03 pm -
1 stop20h 19m
Wed 9/302:18 pm -
1 stop8h 31m
Deal found 8/25![Alaska Airlines logo]()
$323
One-way flights from Portland to O'Hare IntlSearch for one-way flight options from Portland to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
Search for one-way flight options from Portland to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This Super.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:38 pm -
1 stop9h 45m
Deal found 8/21![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1212:25 pm -
2 stops16h 09m
Deal found 8/25![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/2312:25 pm -
1 stop14h 51m
Deal found 8/25![Frontier logo]()
$170
This Priceline deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:55 am -
1 stop9h 26m
Deal found 8/21![Alaska Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2711:02 am -
2 stops33h 57m
Deal found 8/21![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/1812:38 pm -
2 stops32h 21m
Deal found 8/25![Frontier logo]()
$174
This Frontier deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Sun 10/2511:49 am -
1 stop10h 35m
Deal found 8/25![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/1112:38 pm -
1 stop9h 45m
Deal found 8/22![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2611:06 am -
2 stops35h 15m
Deal found 8/22![Frontier logo]()
$177
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:02 am -
Nonstop4h 13m
Deal found 8/21![United Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Sun 9/276:01 am -
Nonstop4h 14m
Deal found 8/23![American Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/2111:02 am -
2 stops33h 57m
Deal found 8/24![Frontier logo]()
$181
Find flight deals from Portland to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to O'Hare Intl (ORD). 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 August 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (CheapOair) |
One-way from | $168 (Super.com) |
Popular in | December |
Cheapest in | February |
Average price | $388 |
Good round-trip deal | $380 or less |
Good one-way deal | $213 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to O'Hare Intl 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 August 26, 2026.
Use the filters below to find and compare flights from Portland to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 10/28
7:09 am-6:53 pm
1 stop9h 44m
Chicago O'Hare Intl
Tue 11/3
7:20 am-6:57 pm
1 stop13h 37m
$323
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 9/16
7:55 am-7:21 pm
1 stop9h 26m
Chicago O'Hare Intl
Wed 9/23
7:20 am-10:45 pm
1 stop17h 25m
$323
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 9/30
9:13 am-7:21 pm
1 stop8h 08m
Chicago O'Hare Intl
Tue 10/6
7:20 am-6:18 pm
1 stop12h 58m
$323
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 10/7
2:27 pm-8:40 pm
Nonstop4h 13m
Chicago O'Hare Intl
Wed 10/14
8:55 am-11:33 am
Nonstop4h 38m
$357
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 9/24
9:13 am-7:21 pm
1 stop8h 08m
Chicago O'Hare Intl
Mon 9/28
2:18 pm-10:45 pm
1 stop10h 27m
$377
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 9/10
10:33 am-11:59 pm
1 stop11h 26m
Chicago O'Hare Intl
Tue 9/15
7:20 am-4:53 pm
1 stop11h 33m
$386
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 10/7
10:43 am-7:30 pm
1 stop6h 47m
Chicago O'Hare Intl
Mon 10/12
7:45 pm-10:23 pm
Nonstop4h 38m
$390
Quickest round-trip
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 9/2
7:06 am-1:26 pm
Nonstop4h 20m
Chicago O'Hare Intl
Sun 9/6
2:22 pm-4:50 pm
Nonstop4h 28m
$433
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Fri 9/11
7:06 am-1:26 pm
Nonstop4h 20m
Chicago O'Hare Intl
Tue 9/15
2:22 pm-4:50 pm
Nonstop4h 28m
$433
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Tue 11/24
6:12 pm-9:51 am
1 stop13h 39m
Chicago O'Hare Intl
Sat 11/28
10:00 am-10:59 pm
1 stop14h 59m
$435
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Portland to O'Hare Intl
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to O'Hare Intl in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Portland-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Portland with our price prediction graph.
PDX-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Chicago O'Hare Intl Airport
Prices
Airlines
How far ahead should I book a flight from Portland to Chicago O'Hare Intl Airport?
Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Portland to Chicago O'Hare Intl Airport?
Currently, February is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $257). Flying from Portland to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $440). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from PDX to ORD?
Find hourly flight availability from Portland to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 26, 2026.
When flying from Portland to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 22% versus a flight at noon.
What is the cheapest day to fly from Portland to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from Portland to O'Hare Intl. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Portland to Chicago O'Hare Intl Airport flight should consider departing on Wednesday 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 Portland to Chicago O'Hare Intl Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Portland to Chicago O'Hare Intl Airport trip
Our travel experts
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated August 26, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Delta, andUnited Airlines from Portland to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
7.9
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Boarding
8.1
Overall
7.9
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Boarding
8.1
Overall
7.9
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Boarding
8.1
Overall
7.9
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Boarding
8.1
Overall
7.9
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Boarding
8.1
Overall
7.9
Food
7.0
Crew
8.5
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Related info for your journey
Find useful and relevant information for your journey from Portland to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBenton Harbor
Rosemont
Naperville
Lake Geneva
Schaumburg
Oak Brook
Oakbrook Terrace
Delavan
South Holland
Libertyville
Glenview
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
Racine
Great Lakes
Janesville
Gurnee
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Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 26, 2026.
Portland and O'Hare Intl flights
Browse other Portland and O'Hare Intl flight options. Last updated on August 26, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on August 26, 2026.
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Top 6 airlines flying from Portland to O'Hare Intl
Discover the top 6 airlines that operate flights from Portland to O'Hare Intl. 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 August 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$208 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$326 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$125 | Average$368 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$216 | Average$365 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$227 | Average$386 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$400 | FlexibilityNo cancel fee | On-time69% |