$177+ Cheap flights from Portland (PDX) to O'Hare Intl (ORD)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Oct 10 — Oct 171
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 60 days in advance, depart on a Wednesday or Friday and return on a Tuesday
Cheap flight deals from Portland to O'Hare Intl
Cheapest
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 September 10, 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 September 10, 2026.
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:38 pm -
2 stops10h 21m
Tue 12/83:47 pm -
2 stops9h 52m
Deal found 9/7![Delta logo]()
$313
This Frontier deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:49 am -
1 stop10h 35m
Sun 10/186:30 am -
1 stop6h 24m
Deal found 9/7![Frontier logo]()
$315
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Thu 10/1511:06 am -
1 stop17h 28m
Sun 10/186:30 am -
1 stop6h 24m
Deal found 9/7![Frontier logo]()
$317
This Priceline deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 11/1212:02 pm -
1 stop10h 19m
Sun 11/156:30 am -
1 stop6h 42m
Deal found 9/5![Frontier logo]()
$319
This CheapOair deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/811:06 am -
1 stop17h 28m
Tue 10/136:30 am -
1 stop6h 24m
Deal found 9/6![Frontier logo]()
$325
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/1911:06 am -
1 stop17h 28m
Thu 10/228:01 pm -
1 stop16h 10m
Deal found 9/7![Frontier logo]()
$326
This CheapOair deal was found by Cheapflights users on 9/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:38 pm -
1 stop9h 45m
Wed 10/71:21 pm -
1 stop24h 05m
Deal found 9/9![Frontier logo]()
$327
This Trip.com deal was found by Cheapflights users on 9/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:06 am -
1 stop17h 28m
Wed 10/148:01 pm -
1 stop16h 10m
Deal found 9/8![Frontier logo]()
$328
This Travelocity deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Thu 11/512:31 pm -
1 stop14h 42m
Sun 11/86:30 am -
1 stop6h 42m
Deal found 9/5![Frontier logo]()
$329
This Alaska Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/176:09 am -
1 stop21h 31m
Sat 10/242:14 pm -
Nonstop4h 37m
Deal found 9/7![Alaska Airlines logo]()
$330
This CheapOair deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/3012:31 pm -
1 stop14h 42m
Tue 11/36:30 am -
1 stop6h 37m
Deal found 9/7![Frontier logo]()
$331
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 September 10, 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 September 10, 2026.
This United Airlines deal was found by Cheapflights users on 9/8. 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 9/298:30 am -
Nonstop4h 13m
Wed 9/301:30 pm -
Nonstop4h 26m
Deal found 9/8![United Airlines logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/258:09 am -
1 stop8h 11m
Wed 10/282:14 pm -
Nonstop4h 37m
Deal found 9/5![Alaska Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 11/311:25 am -
2 stops10h 32m
Sat 11/73:30 pm -
2 stops9h 12m
Deal found 9/7![Delta logo]()
$363
This Sun Country Air deal was found by Cheapflights users on 9/9. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:20 pm -
1 stop18h 43m
Tue 10/135:25 pm -
1 stop26h 11m
Deal found 9/9![Sun Country Air logo]()
$375
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/177:02 am -
Nonstop4h 13m
Mon 10/197:45 pm -
Nonstop4h 38m
Deal found 9/7![United Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:25 am -
2 stops8h 40m
Tue 10/1312:50 pm -
1 stop9h 10m
Deal found 9/5![Delta logo]()
$368
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 2/246:07 am -
1 stop15h 52m
Sun 2/282:03 pm -
Nonstop4h 34m
Deal found 9/5![Alaska Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Thu 12/34:05 pm -
1 stop5h 54m
Tue 12/88:44 am -
1 stop6h 31m
Deal found 9/8![United Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 9/9. 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.
Wed 10/212:20 pm -
1 stop7h 37m
Wed 10/286:20 am -
1 stop6h 14m
Deal found 9/9![Delta logo]()
$377
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/2411:59 pm -
Nonstop4h 00m
Mon 10/267:45 pm -
Nonstop4h 42m
Deal found 9/6![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 9/8. 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.
Mon 9/2812:25 am -
1 stop6h 05m
Thu 10/1512:50 pm -
1 stop6h 14m
Deal found 9/8![Delta logo]()
$377
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 11/2611:55 am -
1 stop5h 44m
Tue 12/17:18 pm -
1 stop6h 43m
Deal found 9/9![Delta logo]()
$377
Last-minute flights from Portland to O'Hare IntlDiscover last-minute flight deals from Portland to O'Hare Intl. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to O'Hare Intl. Data last updated September 10, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:38 pm -
1 stop9h 45m
Wed 10/71:21 pm -
1 stop24h 05m
Deal found 9/9![Frontier logo]()
$327
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Thu 10/112:38 pm -
1 stop9h 45m
Sun 10/113:30 pm -
1 stop22h 10m
Deal found 9/7![Frontier logo]()
$329
This CheapOair deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/811:06 am -
1 stop17h 28m
Tue 10/136:30 am -
1 stop6h 24m
Deal found 9/6![Frontier logo]()
$325
This Trip.com deal was found by Cheapflights users on 9/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:06 am -
1 stop17h 28m
Wed 10/148:01 pm -
1 stop16h 10m
Deal found 9/8![Frontier logo]()
$328
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:10 am -
2 stops12h 55m
Tue 10/2712:30 pm -
2 stops11h 26m
Deal found 9/5![Delta logo]()
$313
This Expedia deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Sat 10/107:00 am -
Nonstop4h 18m
Tue 10/136:30 am -
1 stop6h 24m
Deal found 9/5![Multiple Airlines logo]()
$334
This Frontier deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:49 am -
1 stop10h 35m
Sun 10/186:30 am -
1 stop6h 24m
Deal found 9/7![Frontier logo]()
$315
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Thu 10/1511:06 am -
1 stop17h 28m
Sun 10/186:30 am -
1 stop6h 24m
Deal found 9/7![Frontier logo]()
$317
This Alaska Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/176:09 am -
1 stop21h 31m
Sat 10/242:14 pm -
Nonstop4h 37m
Deal found 9/7![Alaska Airlines logo]()
$330
This Expedia deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Sun 10/1811:06 am -
1 stop17h 28m
Sun 10/256:30 am -
1 stop6h 24m
Deal found 9/5![Frontier logo]()
$320
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/1911:06 am -
1 stop17h 28m
Thu 10/228:01 pm -
1 stop16h 10m
Deal found 9/7![Frontier logo]()
$326
This CheapOair deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/3012:31 pm -
1 stop14h 42m
Tue 11/36:30 am -
1 stop6h 37m
Deal found 9/7![Frontier logo]()
$331
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 September 10, 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 September 10, 2026.
This CheapOair deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Sun 10/2512:11 pm -
1 stop15h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$177
This Sun Country Air deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Fri 10/96:20 pm -
1 stop18h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Sun Country Air logo]()
$178
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Thu 10/1511:30 pm -
Nonstop4h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![United Airlines logo]()
$179
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/13:21 pm -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Delta logo]()
$182
This United Airlines deal was found by Cheapflights users on 9/8. 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 9/2912:45 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![United Airlines logo]()
$184
This Super.com deal was found by Cheapflights users on 9/9. 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.
Mon 9/2112:39 pm -
1 stop14h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Thu 12/105:45 pm -
1 stop16h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$186
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:44 pm -
1 stop15h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$187
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:06 pm -
1 stop8h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$189
This Priceline deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Fri 9/1812:38 pm -
1 stop9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$190
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 September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $313 (Delta) |
One-way from | $177 (CheapOair) |
Popular in | December |
Cheapest in | February |
Average price | $390 |
Good round-trip deal | $378 or less |
Good one-way deal | $207 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 September 10, 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
Tue 10/6
10:55 pm-5:07 am
Nonstop4h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
Quickest round-trip
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 11/12
11:30 pm-5:19 am
Nonstop3h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Sat 10/3
7:00 am-1:18 pm
Nonstop4h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 10/7
3:31 pm-11:34 pm
1 stop6h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$182
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Wed 10/28
9:00 am-8:22 pm
1 stop9h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$184
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Sat 10/3
5:30 am-9:30 pm
2 stops14h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$187
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Mon 10/19
8:44 pm-8:53 am
2 stops10h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$187
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Mon 10/26
8:44 pm-7:41 am
2 stops8h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$187
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Fri 10/9
8:44 pm-7:41 am
2 stops8h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$187
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Sat 10/24
10:43 am-9:18 pm
1 stop8h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
Showing 1-10 of 23 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 September.
| 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 59 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 $444). 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 September 10, 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 24% 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 September 5, 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 September 10, 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.
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Comfort
7.8
Boarding
8.1
Overall
7.9
Crew
8.5
Food
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
Lake Geneva
Naperville
Des Plaines
Glenview
Schaumburg
Oakbrook Terrace
Delavan
Oak Brook
Libertyville
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
South Holland
Elgin
Racine
Janesville
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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 September 10, 2026.
Portland and O'Hare Intl flights
Browse other Portland and O'Hare Intl flight options. Last updated on September 10, 2026.
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Top 5 airlines flying from Portland to O'Hare Intl
Discover the top 5 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 September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$256 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$217 | Average$371 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$228 | Average$392 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$237 | Average$409 | FlexibilityNo cancel fee | On-time69% |