$167+ Cheap flights from Portland (PDX) to Chicago (CHI)
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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Aug 10 — Aug 171
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Portland to Chicago 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 are usually found in January or February, booked 71 days in advance, depart on a Wednesday or Thursday and return on a Tuesday
Cheap flight deals from Portland to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to ChicagoExplore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 11, 2026.
Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:59 pm
PDX
- ORD
Nonstop4h 01m
Multiple Airlines
Sat 8/89:13 pm
ORD
- PDX
1 stop16h 22m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:21 pm
PDX
- MDW
2 stops25h 11m
Multiple Airlines
Sun 8/168:20 pm
MDW
- PDX
1 stop17h 15m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:36 pm
PDX
- ORD
1 stop10h 41m
Frontier
Mon 7/209:57 pm
ORD
- PDX
1 stop20h 34m
Frontier
Deal found 7/8![Frontier logo]()
$326
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Fri 8/218:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/9![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:16 am
PDX
- ORD
Nonstop4h 13m
United Airlines
Wed 8/268:50 am
ORD
- PDX
Nonstop4h 38m
United Airlines
Deal found 7/8![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/411:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 8/116:00 am
MDW
- PDX
1 stop7h 20m
Southwest
Deal found 7/8![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/610:55 pm
PDX
- ORD
1 stop7h 09m
Delta
Tue 12/811:10 am
ORD
- PDX
1 stop9h 58m
Delta
Deal found 7/9![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:35 am
PDX
- MDW
1 stop6h 04m
Delta
Sun 8/307:25 pm
MDW
- PDX
1 stop5h 55m
Delta
Deal found 7/8![Delta logo]()
$328
This KAYAK deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:45 am
PDX
- ORD
1 stop6h 34m
Delta
Wed 8/192:36 pm
ORD
- PDX
1 stop9h 36m
Delta
Deal found 7/8![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 7/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Wed 8/125:20 pm
MDW
- PDX
1 stop7h 00m
Southwest
Deal found 7/7![Southwest logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:17 pm
PDX
- ORD
2 stops17h 19m
Frontier
Sun 8/239:20 pm
ORD
- PDX
1 stop16h 15m
Frontier
Deal found 7/8![Frontier logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1010:59 pm
PDX
- ORD
Nonstop4h 01m
Multiple Airlines
Sun 7/129:57 pm
ORD
- PDX
1 stop20h 54m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$331
Best flights from Portland to ChicagoDiscover carefully curated flight deals from Portland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 11, 2026.
Discover carefully curated flight deals from Portland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 11, 2026.
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:27 pm
PDX
- ORD
Nonstop4h 13m
United Airlines
Mon 8/247:00 am
ORD
- PDX
Nonstop4h 29m
United Airlines
Deal found 7/8![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:35 am
PDX
- MDW
1 stop6h 04m
Delta
Tue 8/2512:46 pm
MDW
- PDX
1 stop8h 09m
Delta
Deal found 7/8![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 7/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/811:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sat 8/156:00 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/6![Southwest logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 7/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:06 am
PDX
- ORD
1 stop9h 47m
Alaska Airlines
Mon 10/127:49 pm
ORD
- PDX
1 stop15h 42m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:16 pm
PDX
- RFD
2 stops37h 13m
Multiple Airlines
Sun 7/261:14 pm
RFD
- PDX
1 stop29h 40m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$430
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:50 am
PDX
- ORD
1 stop9h 10m
United Airlines
Sat 8/227:00 am
ORD
- PDX
Nonstop4h 29m
United Airlines
Deal found 7/8![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/711:20 pm
PDX
- ORD
1 stop9h 22m
Delta
Sun 8/96:00 am
ORD
- PDX
1 stop6h 41m
Delta
Deal found 7/10![Delta logo]()
$361
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:30 pm
PDX
- ORD
Nonstop4h 04m
United Airlines
Sun 12/1312:40 pm
ORD
- PDX
Nonstop4h 43m
United Airlines
Deal found 7/10![United Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 7/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Tue 8/258:20 am
MDW
- PDX
2 stops8h 40m
Southwest
Deal found 7/6![Southwest logo]()
$385
This Delta deal was found by Cheapflights users on 7/7. 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 11/36:00 am
PDX
- MDW
1 stop8h 39m
Delta
Sat 11/712:28 pm
MDW
- PDX
1 stop9h 17m
Delta
Deal found 7/7![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 7/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Thu 8/208:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/6![Southwest logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:38 pm
PDX
- RFD
1 stop23h 45m
Multiple Airlines
Sun 8/29:19 am
RFD
- PDX
2 stops9h 32m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 7/7. 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.
Wed 9/2310:35 am
PDX
- ORD
Nonstop4h 13m
United Airlines
Sun 9/278:55 am
ORD
- PDX
Nonstop4h 38m
United Airlines
Deal found 7/7![United Airlines logo]()
$374
This Alaska Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/267:02 am
PDX
- ORD
Nonstop4h 07m
Alaska Airlines
Sat 1/27:00 am
ORD
- PDX
Nonstop4h 28m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$459
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/171:38 pm
PDX
- ORD
1 stop8h 08m
Delta
Sun 12/207:00 am
ORD
- PDX
1 stop6h 43m
Delta
Deal found 7/9![Delta logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:16 pm
PDX
- RFD
2 stops36h 55m
Multiple Airlines
Thu 8/279:35 pm
RFD
- PDX
1 stop21h 46m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$467
This United Airlines deal was found by Cheapflights users on 7/6. 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.
Tue 7/2811:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Fri 7/314:15 pm
ORD
- PDX
Nonstop4h 32m
United Airlines
Deal found 7/6![United Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2911:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Mon 8/39:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 7/11![Southwest logo]()
$449
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:55 pm
PDX
- MDW
1 stop9h 10m
Delta
Sat 8/11:49 pm
MDW
- PDX
1 stop8h 26m
Delta
Deal found 7/10![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Sun 9/206:10 am
MDW
- PDX
2 stops9h 10m
Southwest
Deal found 7/10![Southwest logo]()
$449
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:45 pm
PDX
- ORD
1 stop7h 07m
United Airlines
Mon 10/127:00 am
ORD
- PDX
Nonstop4h 31m
United Airlines
Deal found 7/9![United Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:25 am
PDX
- MDW
1 stop6h 23m
Delta
Sun 10/46:05 am
MDW
- PDX
1 stop8h 55m
Delta
Deal found 7/8![Delta logo]()
$436
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/274:25 pm
PDX
- MDW
1 stop7h 05m
Southwest
Thu 7/305:00 am
MDW
- PDX
1 stop6h 55m
Southwest
Deal found 7/10![Southwest logo]()
$468
This United Airlines deal was found by Cheapflights users on 7/6. 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.
Tue 11/248:46 am
PDX
- ORD
Nonstop4h 04m
United Airlines
Mon 11/308:30 pm
ORD
- PDX
Nonstop4h 42m
United Airlines
Deal found 7/6![United Airlines logo]()
$436
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3012:45 pm
PDX
- ORD
1 stop6h 33m
United Airlines
Tue 10/66:00 am
ORD
- PDX
2 stops11h 06m
United Airlines
Deal found 7/10![United Airlines logo]()
$476
Last-minute flights from Portland to ChicagoDiscover last-minute flight deals from Portland to Chicago. Data last updated July 11, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Chicago. Data last updated July 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1010:59 pm
PDX
- ORD
Nonstop4h 01m
Multiple Airlines
Sun 7/129:57 pm
ORD
- PDX
1 stop20h 54m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:36 pm
PDX
- ORD
1 stop10h 41m
Frontier
Mon 7/209:57 pm
ORD
- PDX
1 stop20h 34m
Frontier
Deal found 7/8![Frontier logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:59 pm
PDX
- ORD
Nonstop4h 01m
Multiple Airlines
Sat 8/89:13 pm
ORD
- PDX
1 stop16h 22m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/411:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 8/116:00 am
MDW
- PDX
1 stop7h 20m
Southwest
Deal found 7/8![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:25 pm
PDX
- ORD
1 stop8h 23m
Delta
Sun 8/96:00 am
ORD
- PDX
1 stop6h 41m
Delta
Deal found 7/8![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 7/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Wed 8/125:20 pm
MDW
- PDX
1 stop7h 00m
Southwest
Deal found 7/7![Southwest logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:21 pm
PDX
- MDW
2 stops25h 11m
Multiple Airlines
Sun 8/168:20 pm
MDW
- PDX
1 stop17h 15m
Multiple Airlines
Deal found 7/10![Multiple Airlines logo]()
$325
This KAYAK deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:45 am
PDX
- ORD
1 stop6h 34m
Delta
Wed 8/192:36 pm
ORD
- PDX
1 stop9h 36m
Delta
Deal found 7/8![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Fri 8/218:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/9![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:35 am
PDX
- MDW
1 stop6h 04m
Delta
Sun 8/307:25 pm
MDW
- PDX
1 stop5h 55m
Delta
Deal found 7/8![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:16 am
PDX
- ORD
Nonstop4h 13m
United Airlines
Wed 8/268:50 am
ORD
- PDX
Nonstop4h 38m
United Airlines
Deal found 7/8![United Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:17 pm
PDX
- ORD
2 stops17h 19m
Frontier
Sun 8/239:20 pm
ORD
- PDX
1 stop16h 15m
Frontier
Deal found 7/8![Frontier logo]()
$330
One-way flights from Portland to ChicagoSearch for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Data last updated July 11, 2026.
Search for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Data last updated July 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:22 pm
PDX
- ORD
1 stop16h 39m
Frontier
Deal found 7/7![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:20 pm
PDX
- ORD
2 stops39h 17m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$168
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/44:15 pm
PDX
- ORD
1 stop6h 29m
United Airlines
Deal found 7/8![United Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 7/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:55 pm
PDX
- MDW
1 stop7h 05m
Southwest
Deal found 7/7![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:56 pm
PDX
- ORD
1 stop10h 21m
Frontier
Deal found 7/8![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/143:22 pm
PDX
- MDW
2 stops41h 36m
Frontier
Deal found 7/8![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:22 pm
PDX
- ORD
2 stops18h 40m
Frontier
Deal found 7/8![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:38 pm
PDX
- RFD
1 stop23h 45m
Allegiant Air
Deal found 7/7![Allegiant Air logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:20 pm
PDX
- ORD
2 stops25h 40m
Frontier
Deal found 7/7![Frontier logo]()
$173
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:25 am
PDX
- MDW
2 stops8h 40m
Southwest
Deal found 7/8![Southwest logo]()
$174
This Booking.com deal was found by Cheapflights users on 7/6. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$175
This American Airlines deal was found by Cheapflights users on 7/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/43:31 pm
PDX
- ORD
1 stop7h 20m
American Airlines
Deal found 7/7![American Airlines logo]()
$176
Find flight deals from Portland to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $325 (Kiwi.com) |
One-way from | $167 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $363 |
Good round-trip deal | $394 or less |
Good one-way deal | $224 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 11, 2026.
Use the filters below to find and compare flights from Portland to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 8/22
2:27 pm-8:40 pm
Nonstop4h 13m
Chicago O'Hare Intl
Mon 8/24
7:00 am-9:29 am
Nonstop4h 29m
$327
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 8/22
12:35 am-8:39 am
1 stop6h 04m
Chicago Midway
Tue 8/25
12:46 pm-6:55 pm
1 stop8h 09m
$328
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 8/19
10:50 am-10:00 pm
1 stop9h 10m
Chicago O'Hare Intl
Sat 8/22
7:00 am-9:29 am
Nonstop4h 29m
$337
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 12/4
2:30 pm-8:34 pm
Nonstop4h 04m
Chicago O'Hare Intl
Sun 12/13
12:40 pm-3:23 pm
Nonstop4h 43m
$341
Quickest round-trip
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 8/8
11:30 pm-5:25 am
Nonstop3h 55m
Chicago Midway
Sat 8/15
6:00 pm-8:15 pm
Nonstop4h 15m
$359
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 8/7
11:20 pm-10:42 am
1 stop9h 22m
Chicago O'Hare Intl
Sun 8/9
6:00 am-10:41 am
1 stop6h 41m
$361
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 9/23
10:35 am-4:48 pm
Nonstop4h 13m
Chicago O'Hare Intl
Sun 9/27
8:55 am-11:33 am
Nonstop4h 38m
$374
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 11/3
6:00 am-4:39 pm
1 stop8h 39m
Chicago Midway
Sat 11/7
12:28 pm-7:45 pm
1 stop9h 17m
$379
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 8/19
5:50 am-4:35 pm
2 stops8h 45m
Chicago Midway
Tue 8/25
8:20 am-3:00 pm
2 stops8h 40m
$385
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 8/19
5:50 am-4:35 pm
2 stops8h 45m
Chicago Midway
Thu 8/20
8:50 pm-11:05 pm
Nonstop4h 15m
$385
Showing 1-10 of 55 resultsSorted by cheapest first
Compare providers for flights from Portland to Chicago
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 Chicago in July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Portland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Chicago 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 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 Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Portland with our price prediction graph.
PDX-CHI
PDX-ORD
PDX-MDW
PDX-RFD
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
PDX-CHI
PDX-ORD
PDX-MDW
PDX-RFD
What is the cheapest month to book a flight from Portland to Chicago?
Currently, November is the cheapest month in which you can book a flight from Portland to Chicago (average of $103). Flying from Portland to Chicago in October is currently the most expensive (average of $770). 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 CHI?
Find hourly flight availability from Portland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 11, 2026.
A simple way to save on the total cost of your ticket is to fly from Portland to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 13% on your trip compared to booking a flight in the morning.
Weekly flight availability from Portland to Chicago
Explore weekly flight availability from Portland to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 11, 2026.
The most flights from PDX to CHI are scheduled on a Friday (34 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (21 on average).
How much does it cost to fly round-trip from Portland to Chicago?
How far ahead should I book a flight from Portland to Chicago?
Booking 57 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Portland to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Portland to Chicago. Price data was last updated on July 11, 2026.
Travelers seeking maximum savings on their Portland to Chicago flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Portland to Chicago 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 trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 11, 2026.
Read reviews from past customers who have flown Alaska Airlines,Southwest, andDelta from Portland to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.1
Overall
7.9
Crew
8.5
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.1
Overall
7.9
Crew
8.5
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 Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Portland
Popular flights
Alternative routes for Portland to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 11, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Chicago by cabin class
Find flights from Portland to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Chicago flights
Browse other Portland and Chicago flight options. Last updated on July 11, 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 July 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Portland to Chicago
Discover the top 7 airlines that operate flights from Portland to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$217 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$96 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$256 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$170 | Average$337 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$373 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$222 | Average$385 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$231 | Average$360 | FlexibilityNo cancel fee | On-time63% |