$111+ Cheap flights from Portland (PDX) to Illinois
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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Jun 21 — Jun 281
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Portland to Illinois 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.Cheap flight deals from Portland to Illinois
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to IllinoisExplore the most affordable flight options available from Portland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 22, 2026.
Explore the most affordable flight options available from Portland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 22, 2026.
This CheapOair deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/118:42 pm
PDX
- STL
1 stop15h 24m
Frontier
Wed 6/177:46 pm
STL
- PDX
1 stop26h 01m
Frontier
Deal found 5/17![Frontier logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 9/283:22 pm
PDX
- ORD
1 stop16h 39m
Frontier
Mon 10/51:02 pm
ORD
- PDX
1 stop9h 37m
Frontier
Deal found 5/20![Frontier logo]()
$304
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/277:00 am
PDX
- ORD
Nonstop4h 13m
United Airlines
Thu 5/287:55 pm
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 5/18![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/2711:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Thu 5/289:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 5/18![Southwest logo]()
$305
This Orbitz deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:42 pm
PDX
- ORD
1 stop10h 35m
Multiple Airlines
Wed 8/57:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2710:59 pm
PDX
- ORD
Nonstop4h 01m
American Airlines
Fri 7/37:20 pm
ORD
- PDX
Nonstop4h 30m
American Airlines
Deal found 5/18![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/114:25 pm
PDX
- STL
1 stop6h 10m
Southwest
Sat 7/255:35 pm
STL
- PDX
Nonstop4h 05m
Southwest
Deal found 5/20![Southwest logo]()
$309
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/410:40 pm
PDX
- ORD
Nonstop4h 07m
United Airlines
Sat 7/117:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 5/20![United Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/111:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Wed 7/159:10 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 5/20![Southwest logo]()
$310
This Travelocity deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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.
Fri 9/189:34 pm
PDX
- STL
1 stop12h 17m
Multiple Airlines
Tue 9/226:08 pm
STL
- PDX
Nonstop4h 12m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$310
This Orbitz deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:59 pm
PDX
- ORD
1 stop8h 29m
Multiple Airlines
Wed 8/57:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/279:20 am
PDX
- STL
1 stop6h 40m
Southwest
Mon 8/315:45 am
STL
- PDX
1 stop6h 15m
Southwest
Deal found 5/17![Southwest logo]()
$314
Best flights from Portland to IllinoisDiscover carefully curated flight deals from Portland to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 22, 2026.
Discover carefully curated flight deals from Portland to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 22, 2026.
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/222:25 pm
PDX
- ORD
Nonstop4h 13m
United Airlines
Wed 7/291:30 pm
ORD
- PDX
Nonstop4h 27m
United Airlines
Deal found 5/18![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/275:40 am
PDX
- MDW
Nonstop3h 55m
Southwest
Thu 5/284:35 pm
MDW
- PDX
2 stops10h 20m
Southwest
Deal found 5/18![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/110:53 am
PDX
- ORD
1 stop10h 25m
Delta
Tue 8/47:00 am
ORD
- PDX
1 stop6h 40m
Delta
Deal found 5/18![Delta logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/285:16 pm
PDX
- RFD
2 stops24h 43m
Multiple Airlines
Wed 8/58:58 pm
RFD
- PDX
1 stop23h 10m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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.
Thu 8/135:18 am
PDX
- BMI
1 stop9h 00m
American Airlines
Sat 8/154:48 pm
BMI
- PDX
1 stop8h 19m
American Airlines
Deal found 5/16![American Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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
Wed 8/58:58 pm
RFD
- PDX
1 stop23h 10m
Allegiant Air
Deal found 5/18![Allegiant Air logo]()
$351
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:06 am
PDX
- ORD
Nonstop4h 20m
Alaska Airlines
Tue 9/292:22 pm
ORD
- PDX
Nonstop4h 28m
Alaska Airlines
Deal found 5/21![Alaska Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/511:40 pm
PDX
- STL
1 stop6h 54m
United Airlines
Wed 8/195:30 pm
STL
- PDX
1 stop7h 52m
United Airlines
Deal found 5/20![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/2711:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Fri 7/34:40 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 5/19![Southwest logo]()
$321
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:35 am
PDX
- ORD
1 stop10h 10m
Delta
Wed 7/155:55 pm
ORD
- PDX
1 stop7h 59m
Delta
Deal found 5/21![Delta logo]()
$335
This Alaska Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/710:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Tue 8/117:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/1111:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Wed 7/156:10 am
ORD
- PDX
1 stop7h 57m
United Airlines
Deal found 5/19![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:50 am
PDX
- STL
1 stop10h 00m
Southwest
Tue 8/255:35 am
STL
- PDX
2 stops11h 50m
Southwest
Deal found 5/21![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:15 pm
PDX
- ORD
1 stop6h 42m
Delta
Mon 7/66:55 am
ORD
- PDX
1 stop6h 47m
Delta
Deal found 5/21![Delta logo]()
$341
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Thu 6/412:40 am
PDX
- MLI
1 stop7h 59m
American Airlines
Wed 6/104:24 pm
MLI
- PDX
1 stop9h 35m
American Airlines
Deal found 5/20![American Airlines logo]()
$384
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/81:14 pm
PDX
- ORD
1 stop7h 45m
United Airlines
Sun 7/127:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 5/17![United Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 7/145:05 am
MDW
- PDX
1 stop6h 55m
Southwest
Deal found 5/17![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:33 am
PDX
- ORD
1 stop5h 57m
Delta
Fri 8/77:00 am
ORD
- PDX
1 stop6h 40m
Delta
Deal found 5/17![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/1311:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Fri 6/196:45 am
ORD
- PDX
Nonstop4h 25m
United Airlines
Deal found 5/19![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1011:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Mon 8/178:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 5/21![Southwest logo]()
$337
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Thu 6/45:10 am
PDX
- CMI
1 stop7h 05m
American Airlines
Mon 6/86:43 pm
CMI
- PDX
1 stop7h 04m
American Airlines
Deal found 5/20![American Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:32 am
PDX
- ORD
1 stop5h 58m
Delta
Sat 8/159:20 am
ORD
- PDX
1 stop9h 14m
Delta
Deal found 5/21![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/294:25 pm
PDX
- STL
1 stop7h 30m
Southwest
Sat 7/115:35 pm
STL
- PDX
Nonstop4h 05m
Southwest
Deal found 5/17![Southwest logo]()
$338
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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.
Wed 7/225:07 am
PDX
- CMI
1 stop7h 09m
American Airlines
Sun 7/266:36 pm
CMI
- PDX
1 stop7h 29m
American Airlines
Deal found 5/18![American Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/292:27 pm
PDX
- MLI
1 stop6h 07m
United Airlines
Wed 6/31:15 pm
MLI
- PDX
2 stops9h 39m
United Airlines
Deal found 5/18![United Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/510:34 am
PDX
- PIA
2 stops21h 27m
Allegiant Air
Sat 6/138:04 pm
PIA
- PDX
1 stop24h 23m
Allegiant Air
Deal found 5/17![Allegiant Air logo]()
$508
This Expedia deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:49 am
PDX
- STL
Nonstop3h 48m
Alaska Airlines
Tue 8/253:04 pm
STL
- PDX
1 stop6h 46m
Alaska Airlines
Deal found 5/21![Alaska Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:20 pm
PDX
- RFD
2 stops22h 04m
Multiple Airlines
Sat 7/1812:58 pm
RFD
- PDX
1 stop30h 50m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:32 am
PDX
- MDW
1 stop6h 08m
Delta
Fri 8/147:25 pm
MDW
- PDX
1 stop6h 00m
Delta
Deal found 5/21![Delta logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/51:45 pm
PDX
- BMI
1 stop8h 50m
American Airlines
Tue 6/96:02 pm
BMI
- PDX
1 stop7h 45m
American Airlines
Deal found 5/21![American Airlines logo]()
$419
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated May 22, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/277:00 am
PDX
- ORD
Nonstop4h 13m
United Airlines
Thu 5/287:55 pm
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 5/18![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/2711:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Thu 5/289:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 5/18![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/278:50 am
PDX
- ORD
1 stop8h 00m
Southwest
Thu 5/287:20 pm
ORD
- PDX
1 stop7h 35m
Southwest
Deal found 5/18![Southwest logo]()
$325
This Expedia deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/511:15 am
PDX
- STL
1 stop6h 56m
Multiple Airlines
Sun 6/75:33 pm
STL
- PDX
Nonstop4h 17m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$325
This CheapOair deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/118:42 pm
PDX
- STL
1 stop15h 24m
Frontier
Wed 6/177:46 pm
STL
- PDX
1 stop26h 01m
Frontier
Deal found 5/17![Frontier logo]()
$299
This CheapOair deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:42 pm
PDX
- STL
1 stop20h 09m
Frontier
Mon 6/227:38 pm
STL
- PDX
1 stop22h 57m
Frontier
Deal found 5/18![Frontier logo]()
$318
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/2011:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Sat 6/276:59 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 5/19![United Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Fri 6/261:45 pm
PDX
- ORD
Nonstop4h 21m
American Airlines
Fri 7/38:00 am
ORD
- PDX
Nonstop4h 36m
American Airlines
Deal found 5/20![American Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2710:59 pm
PDX
- ORD
Nonstop4h 01m
American Airlines
Fri 7/37:20 pm
ORD
- PDX
Nonstop4h 30m
American Airlines
Deal found 5/18![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/2711:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Fri 7/39:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 5/19![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/294:25 pm
PDX
- STL
1 stop7h 30m
Southwest
Sat 7/117:35 pm
STL
- PDX
1 stop6h 20m
Southwest
Deal found 5/17![Southwest logo]()
$319
This Alaska Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3010:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Tue 7/77:59 pm
ORD
- PDX
1 stop15h 30m
Alaska Airlines
Deal found 5/19![Alaska Airlines logo]()
$320
One-way flights from Portland to IllinoisSearch for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/812:35 pm
PDX
- STL
1 stop28h 48m
Frontier
Deal found 5/18![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/112:38 pm
PDX
- STL
2 stops40h 14m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$133
This CheapOair deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:16 pm
PDX
- STL
1 stop24h 07m
Frontier
Deal found 5/18![Frontier logo]()
$146
This Alaska Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1410:49 am
PDX
- STL
Nonstop3h 48m
Alaska Airlines
Deal found 5/21![Alaska Airlines logo]()
$150
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/2911:53 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 5/18![United Airlines logo]()
$153
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/295:10 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 5/18![Southwest logo]()
$153
This Frontier deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/95:42 pm
PDX
- ORD
1 stop10h 35m
Frontier
Deal found 5/17![Frontier logo]()
$154
This Frontier deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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.
Fri 7/106:59 pm
PDX
- ORD
1 stop8h 29m
Frontier
Deal found 5/18![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/95:20 pm
PDX
- STL
2 stops22h 58m
Frontier
Deal found 5/17![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/1212:26 pm
PDX
- ORD
1 stop30h 17m
Frontier
Deal found 5/18![Frontier logo]()
$157
This Alaska Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1410:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$158
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1411:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 5/17![Southwest logo]()
$158
Find flight deals from Portland to Illinois
Keep the following information in mind while searching for Portland to Illinois flight deals. Data was last updated May 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (CheapOair) |
One-way from | $111 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $334 |
Good round-trip deal | $373 or less |
Good one-way deal | $199 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Illinois 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 May 22, 2026.
Use the filters below to find and compare flights from Portland to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 7/22
2:25 pm-8:38 pm
Nonstop4h 13m
Chicago O'Hare Intl
Wed 7/29
1:30 pm-3:57 pm
Nonstop4h 27m
$315
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Wed 8/5
11:40 pm-8:34 am
1 stop6h 54m
Lambert-St Louis
Wed 8/19
5:30 pm-11:22 pm
1 stop7h 52m
$319
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 5/27
5:40 am-11:35 am
Nonstop3h 55m
Chicago Midway
Thu 5/28
4:35 pm-12:55 am
2 stops10h 20m
$320
Quickest round-trip
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 6/27
11:30 pm-5:20 am
Nonstop3h 50m
Chicago Midway
Fri 7/3
4:40 pm-7:00 pm
Nonstop4h 20m
$321
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 7/11
11:40 pm-5:45 am
Nonstop4h 05m
Chicago O'Hare Intl
Wed 7/15
6:10 am-12:07 pm
1 stop7h 57m
$325
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 8/1
10:53 am-11:18 pm
1 stop10h 25m
Chicago O'Hare Intl
Tue 8/4
7:00 am-11:40 am
1 stop6h 40m
$335
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 7/8
6:35 am-6:45 pm
1 stop10h 10m
Chicago O'Hare Intl
Wed 7/15
5:55 pm-11:54 pm
1 stop7h 59m
$335
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Tue 8/4
5:50 am-5:50 pm
1 stop10h 00m
Lambert-St Louis
Tue 8/25
5:35 am-3:25 pm
2 stops11h 50m
$335
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 7/8
1:14 pm-10:59 pm
1 stop7h 45m
Chicago O'Hare Intl
Sun 7/12
7:00 am-9:34 am
Nonstop4h 34m
$336
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 7/10
11:30 pm-5:20 am
Nonstop3h 50m
Chicago Midway
Tue 7/14
5:05 am-10:00 am
1 stop6h 55m
$336
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Portland to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Portland with our price prediction graph.
PDX-STL
PDX-ORD
PDX-MDW
PDX-RFD
PDX-BMI
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 Illinois
PDX-USIL
PDX-STL
PDX-ORD
PDX-MDW
PDX-RFD
What is the cheapest month to book a flight from Portland to Illinois?
Currently, May is the cheapest month in which you can book a flight from Portland to Illinois (average of $102). Flying from Portland to Illinois in September is currently the most expensive (average of $755). 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 IL?
Find hourly flight availability from Portland to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 22, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 16% on the flight price compared to flying in the morning, which is usually more expensive.
Weekly flight availability from Portland to Illinois
Explore weekly flight availability from Portland to Illinois. 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 May 22, 2026.
The most flights from PDX to USIL are scheduled on a Thursday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 on average).
How much does it cost to fly round-trip from Portland to Illinois?
How far ahead should I book a flight from Portland to Illinois?
To ensure you get the cheapest price possible for a flight from Portland to Illinois, you should look to book at least 89 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Portland to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Portland to Illinois. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their Portland to Illinois flight should consider departing on Wednesday afternoons 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.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated May 22, 2026.
Read reviews from past customers who have flown Alaska Airlines,Southwest, andHawaiian Airlines from Portland to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Food
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Related info for your journey
Find useful and relevant information for your journey from Portland to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Portland to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Illinois by cabin class
Find flights from Portland to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Illinois flights
Browse other Portland and Illinois flight options. Last updated on May 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Portland to Illinois flights
Consider these flights traveling from Portland to Illinois.
Top 7 airlines flying from Portland to Illinois
Discover the top 7 airlines that operate flights from Portland to Illinois. 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 May 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$249 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$96 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$433 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$171 | Average$435 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$209 | Average$337 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$217 | Average$357 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$446 | FlexibilityNo cancel fee | On-time69% |