$161+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Dec 5 — Dec 121
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
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 November 5, 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 November 5, 2026.
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:30 pm -
1 stop6h 26m
Sat 12/57:05 am -
1 stop7h 20m
Deal found 11/3![Delta logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/67:51 pm -
2 stops27h 03m
Thu 12/106:21 am -
1 stop7h 32m
Deal found 11/4![Frontier logo]()
$346
This Cheapflightsfares deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:10 pm -
1 stop29h 00m
Mon 11/2310:00 pm -
1 stop14h 28m
Deal found 11/4![Frontier logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:51 pm -
2 stops27h 03m
Wed 12/96:21 am -
1 stop31h 32m
Deal found 11/3![Frontier logo]()
$348
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:38 pm -
2 stops10h 21m
Tue 12/83:47 pm -
1 stop6h 37m
Deal found 11/3![Delta logo]()
$349
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:31 pm -
1 stop14h 42m
Sat 11/2110:00 pm -
1 stop14h 28m
Deal found 11/2![Frontier logo]()
$350
This Alaska Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:00 am -
Nonstop4h 10m
Sat 12/122:08 pm -
Nonstop4h 57m
Deal found 11/4![Alaska Airlines logo]()
$351
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:02 pm -
1 stop10h 19m
Sat 11/2110:00 pm -
1 stop14h 28m
Deal found 11/2![Frontier logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2412:52 pm -
2 stops14h 18m
Tue 12/87:25 am -
1 stop10h 45m
Deal found 11/3![Frontier logo]()
$353
This Alaska Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:26 am -
1 stop8h 05m
Sun 12/66:00 am -
1 stop7h 24m
Deal found 11/4![Alaska Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/112:26 pm -
Nonstop4h 02m
Fri 12/187:58 pm -
Nonstop4h 49m
Deal found 11/3![United Airlines logo]()
$355
This Mytrip deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:51 pm -
2 stops27h 02m
Wed 12/97:25 am -
2 stops30h 28m
Deal found 11/3![Frontier logo]()
$356
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 November 5, 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 November 5, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:50 pm -
1 stop17h 29m
Fri 12/256:00 am -
1 stop9h 24m
Deal found 10/31![Alaska Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:23 am -
2 stops10h 12m
Sun 12/66:20 am -
2 stops9h 15m
Deal found 11/3![Delta logo]()
$364
This Alaska Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:05 am -
1 stop14h 54m
Sun 12/202:17 pm -
1 stop8h 33m
Deal found 11/2![Alaska Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/269:58 am -
2 stops11h 22m
Fri 11/277:30 am -
2 stops11h 40m
Deal found 11/4![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/251:05 pm -
1 stop8h 50m
Fri 11/277:30 am -
2 stops13h 25m
Deal found 10/31![Delta logo]()
$433
This Alaska Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/259:22 am -
1 stop6h 37m
Fri 1/16:00 am -
1 stop17h 59m
Deal found 11/3![Alaska Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/315:30 am -
2 stops12h 48m
Sun 1/32:27 pm -
1 stop8h 33m
Deal found 11/3![Delta logo]()
$452
This Alaska Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:00 am -
Nonstop4h 10m
Sun 1/36:00 am -
1 stop9h 24m
Deal found 11/3![Alaska Airlines logo]()
$462
This Alaska Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/257:00 am -
Nonstop4h 10m
Sun 1/36:00 am -
1 stop9h 24m
Deal found 11/1![Alaska Airlines logo]()
$462
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2111:20 pm -
2 stops10h 28m
Thu 11/2610:00 am -
2 stops11h 38m
Deal found 11/4![Delta logo]()
$468
This Alaska Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:05 am -
1 stop6h 16m
Thu 12/317:00 am -
1 stop14h 12m
Deal found 11/1![Alaska Airlines logo]()
$465
Last-minute flights from Portland to O'Hare IntlDiscover last-minute flight deals from Portland to O'Hare Intl. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to O'Hare Intl. Data last updated November 5, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:02 pm -
1 stop10h 19m
Sat 11/2110:00 pm -
1 stop14h 28m
Deal found 11/2![Frontier logo]()
$352
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:31 pm -
1 stop14h 42m
Sat 11/2110:00 pm -
1 stop14h 28m
Deal found 11/2![Frontier logo]()
$350
This Cheapflightsfares deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:10 pm -
1 stop29h 00m
Mon 11/2310:00 pm -
1 stop14h 28m
Deal found 11/4![Frontier logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2412:52 pm -
2 stops14h 18m
Tue 12/87:25 am -
1 stop10h 45m
Deal found 11/3![Frontier logo]()
$353
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:30 pm -
1 stop6h 26m
Sat 12/57:05 am -
1 stop7h 20m
Deal found 11/3![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:38 pm -
2 stops10h 21m
Tue 12/83:47 pm -
1 stop6h 37m
Deal found 11/3![Delta logo]()
$349
This Mytrip deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:51 pm -
2 stops27h 02m
Wed 12/97:25 am -
2 stops30h 28m
Deal found 11/3![Frontier logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:51 pm -
2 stops27h 03m
Wed 12/96:21 am -
1 stop31h 32m
Deal found 11/3![Frontier logo]()
$348
This Alaska Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:26 am -
1 stop8h 05m
Sun 12/66:00 am -
1 stop7h 24m
Deal found 11/4![Alaska Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/67:51 pm -
2 stops27h 03m
Thu 12/106:21 am -
1 stop7h 32m
Deal found 11/4![Frontier logo]()
$346
This Alaska Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:00 am -
Nonstop4h 10m
Sat 12/122:08 pm -
Nonstop4h 57m
Deal found 11/4![Alaska Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/112:26 pm -
Nonstop4h 02m
Fri 12/187:58 pm -
Nonstop4h 49m
Deal found 11/3![United Airlines logo]()
$355
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 November 5, 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 November 5, 2026.
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:30 am -
2 stops12h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$161
This Mytrip deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:51 pm -
2 stops27h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$164
This Mytrip deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:10 pm -
1 stop29h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$166
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/297:02 am -
Nonstop4h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![United Airlines logo]()
$169
This Alaska Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:05 am -
1 stop9h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Alaska Airlines logo]()
$172
This Alaska Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/199:22 pm -
1 stop24h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Alaska Airlines logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/216:53 pm -
1 stop8h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$178
This Alaska Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/257:00 am -
Nonstop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Alaska Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:51 pm -
2 stops27h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$181
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2211:50 pm -
Nonstop4h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![United Airlines logo]()
$182
This Super.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2010:28 pm -
1 stop29h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$183
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:38 pm -
2 stops10h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Delta logo]()
$184
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 November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $344 (Delta) |
One-way from | $161 (Delta) |
Popular in | November |
Cheapest in | February |
Average price | $527 |
Good round-trip deal | $431 or less |
Good one-way deal | $231 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 November 5, 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 12/29
2:26 pm-8:33 pm
Nonstop4h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 11/26
6:00 am-2:55 pm
1 stop6h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
Quickest round-trip
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Sun 1/10
7:10 am-1:15 pm
Nonstop4h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Mon 11/23
1:05 pm-11:55 pm
1 stop8h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$189
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Thu 12/24
5:30 am-8:18 pm
2 stops12h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Fri 12/25
9:43 am-9:39 pm
2 stops9h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Sun 2/7
9:45 am-9:36 pm
2 stops9h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$204
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Sat 3/27
7:02 am-1:09 pm
Nonstop4h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$225
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Sat 3/27
1:38 pm-11:46 pm
1 stop8h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$235
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Mon 12/21
5:50 pm-1:19 pm
1 stop17h 29m
Chicago O'Hare Intl
Fri 12/25
6:00 am-1:24 pm
1 stop9h 24m
$360
Showing 1-10 of 20 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- 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 November is currently the most expensive (average of $527). 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 November 5, 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 30% 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 October 31, 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 November 5, 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.
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Comfort
7.8
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
Des Plaines
Glenview
Oak Brook
Aurora
Oakbrook Terrace
Delavan
Schaumburg
Libertyville
Rockford
Hoffman Estates
Gurnee
Orland Park
South Holland
Beloit
Elgin
Racine
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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 November 5, 2026.
Portland and O'Hare Intl flights
Browse other Portland and O'Hare Intl flight options. Last updated on November 5, 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 November 5, 2026.
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Check out other popular destinations found by fellow travelers in 2026
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 November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$125 | Average$368 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$216 | Average$357 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$375 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$232 | Average$418 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$247 | Average$436 | FlexibilityNo cancel fee | On-time69% |