$106+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Sep 1 — Sep 81
Round-trip
1 adult, Economy
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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
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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 August 2, 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 August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/25:56 pm
PDX
- STL
1 stop23h 17m
Frontier
Wed 9/98:10 pm
STL
- PDX
1 stop17h 33m
Frontier
Deal found 7/29![Frontier logo]()
$234
This CheapOair deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:39 pm
PDX
- STL
1 stop20h 53m
Frontier
Sun 9/131:02 pm
STL
- PDX
1 stop24h 41m
Frontier
Deal found 7/30![Frontier logo]()
$240
This CheapOair deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/1012:38 pm
PDX
- STL
1 stop28h 39m
Frontier
Sun 9/131:02 pm
STL
- PDX
1 stop24h 41m
Frontier
Deal found 7/29![Frontier logo]()
$258
This CheapOair deal was found by Cheapflights users on 8/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:38 pm
PDX
- STL
1 stop28h 39m
Frontier
Sun 10/412:27 pm
STL
- PDX
1 stop25h 27m
Frontier
Deal found 8/1![Frontier logo]()
$259
This Expedia deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/1511:16 am
PDX
- STL
Nonstop3h 54m
Alaska Airlines
Wed 9/236:29 am
STL
- PDX
2 stops12h 07m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$265
This CheapOair deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:34 pm
PDX
- STL
1 stop25h 43m
Frontier
Sat 10/178:10 pm
STL
- PDX
1 stop22h 25m
Frontier
Deal found 7/28![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1312:38 pm
PDX
- STL
2 stops25h 56m
Frontier
Sun 9/208:10 pm
STL
- PDX
1 stop17h 33m
Frontier
Deal found 7/30![Frontier logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:20 pm
PDX
- STL
1 stop28h 53m
Frontier
Sat 9/128:10 pm
STL
- PDX
1 stop17h 33m
Frontier
Deal found 7/31![Frontier logo]()
$274
This CheapOair deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/136:49 pm
PDX
- STL
1 stop21h 26m
Frontier
Sun 8/167:10 pm
STL
- PDX
1 stop23h 44m
Frontier
Deal found 7/28![Frontier logo]()
$278
This WAYA deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:38 pm
PDX
- ORD
1 stop9h 45m
Multiple Airlines
Thu 10/12:22 pm
ORD
- PDX
Nonstop4h 28m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/15:56 pm
PDX
- ORD
1 stop17h 40m
Multiple Airlines
Tue 9/152:22 pm
ORD
- PDX
Nonstop4h 28m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$321
This CheapOair deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/412:20 pm
PDX
- ORD
1 stop23h 16m
Frontier
Sun 9/69:20 pm
ORD
- PDX
1 stop16h 15m
Frontier
Deal found 7/30![Frontier logo]()
$322
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 August 2, 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 August 2, 2026.
This Southwest deal was found by Cheapflights users on 8/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:20 am
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 11/35:20 am
MDW
- PDX
2 stops10h 05m
Southwest
Deal found 8/1![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Sun 8/3011:02 pm
PDX
- ORD
Nonstop4h 01m
United Airlines
Thu 9/35:00 am
ORD
- PDX
1 stop6h 32m
United Airlines
Deal found 8/1![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:00 pm
PDX
- ORD
1 stop8h 34m
Delta
Thu 10/87:00 am
ORD
- PDX
1 stop7h 09m
Delta
Deal found 8/2![Delta logo]()
$327
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/35:18 am
PDX
- MLI
1 stop8h 44m
American Airlines
Mon 9/76:45 pm
MLI
- PDX
1 stop7h 14m
American Airlines
Deal found 7/30![American Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:55 am
PDX
- ORD
1 stop9h 26m
Alaska Airlines
Thu 10/156:00 am
ORD
- PDX
1 stop9h 24m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:56 pm
PDX
- RFD
2 stops24h 49m
Multiple Airlines
Sun 8/239:35 pm
RFD
- PDX
1 stop21h 46m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 8/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Tue 9/298:20 am
MDW
- PDX
2 stops8h 40m
Southwest
Deal found 8/1![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 7/31. 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.
Mon 9/2812:25 am
PDX
- MDW
1 stop6h 23m
Delta
Thu 10/155:31 pm
MDW
- PDX
1 stop8h 13m
Delta
Deal found 7/31![Delta logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Wed 9/309:00 am
PDX
- STL
1 stop7h 43m
United Airlines
Mon 10/51:36 pm
STL
- PDX
1 stop6h 10m
United Airlines
Deal found 8/1![United Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Mon 9/216:15 am
MDW
- PDX
2 stops10h 30m
Southwest
Deal found 7/31![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 8/1. 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.
Sun 8/306:20 am
PDX
- ORD
1 stop9h 20m
Delta
Thu 9/32:36 pm
ORD
- PDX
1 stop9h 36m
Delta
Deal found 8/1![Delta logo]()
$337
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 11/65:40 pm
PDX
- STL
1 stop18h 35m
Alaska Airlines
Mon 11/97:00 am
STL
- PDX
2 stops11h 50m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:27 pm
PDX
- PIA
1 stop6h 46m
United Airlines
Thu 10/14:05 pm
PIA
- PDX
1 stop8h 18m
United Airlines
Deal found 7/31![United Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 8/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:45 am
PDX
- MDW
2 stops9h 25m
Southwest
Mon 10/266:15 pm
MDW
- PDX
1 stop9h 05m
Southwest
Deal found 8/1![Southwest logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:56 pm
PDX
- RFD
2 stops17h 23m
Multiple Airlines
Sun 9/139:29 pm
RFD
- PDX
1 stop16h 25m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/2012:40 pm
PDX
- STL
1 stop9h 10m
Southwest
Fri 8/216:05 am
STL
- PDX
2 stops10h 55m
Southwest
Deal found 7/29![Southwest logo]()
$334
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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 9/2411:16 am
PDX
- STL
Nonstop3h 54m
Alaska Airlines
Mon 9/286:08 pm
STL
- PDX
Nonstop4h 12m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/52:27 pm
PDX
- ORD
Nonstop4h 13m
United Airlines
Sun 9/68:50 am
ORD
- PDX
Nonstop4h 38m
United Airlines
Deal found 7/30![United Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/1212:35 am
PDX
- STL
1 stop6h 02m
Delta
Tue 9/13:50 pm
STL
- PDX
2 stops10h 06m
Delta
Deal found 7/29![Delta logo]()
$390
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:20 pm
PDX
- STL
1 stop8h 20m
Southwest
Sun 8/309:55 pm
STL
- PDX
Nonstop4h 10m
Southwest
Deal found 7/31![Southwest logo]()
$339
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:26 pm
PDX
- MLI
1 stop6h 51m
American Airlines
Sun 10/187:00 am
MLI
- PDX
1 stop8h 32m
American Airlines
Deal found 7/31![American Airlines logo]()
$509
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/2511:30 pm
PDX
- ORD
Nonstop4h 01m
United Airlines
Thu 10/17:00 am
ORD
- PDX
Nonstop4h 31m
United Airlines
Deal found 7/30![United Airlines logo]()
$388
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/1110:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Wed 8/127:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/48:24 pm
PDX
- STL
2 stops11h 59m
Delta
Sun 9/66:20 am
STL
- PDX
1 stop6h 29m
Delta
Deal found 7/29![Delta logo]()
$396
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 10/295:30 am
PDX
- STL
2 stops10h 00m
Southwest
Sun 11/17:15 pm
STL
- PDX
1 stop6h 40m
Southwest
Deal found 7/29![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/912:40 pm
PDX
- MLI
1 stop6h 23m
United Airlines
Tue 1/126:45 am
MLI
- PDX
1 stop7h 08m
United Airlines
Deal found 7/31![United Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:59 am
PDX
- SPI
1 stop6h 22m
American Airlines
Sat 9/56:08 am
SPI
- PDX
1 stop7h 25m
American Airlines
Deal found 8/1![American Airlines logo]()
$542
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:44 pm
PDX
- STL
2 stops11h 50m
Delta
Mon 9/212:25 pm
STL
- PDX
2 stops9h 37m
Delta
Deal found 8/2![Delta logo]()
$409
This Alaska Airlines deal was found by Cheapflights users on 8/1. 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 8/710:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Sun 8/97:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 8/1![Alaska Airlines logo]()
$483
This Southwest deal was found by Cheapflights users on 8/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:55 pm
PDX
- MDW
1 stop9h 05m
Southwest
Mon 10/195:15 am
MDW
- PDX
2 stops9h 20m
Southwest
Deal found 8/1![Southwest logo]()
$367
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated August 2, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/66:49 pm
PDX
- STL
1 stop21h 26m
Frontier
Wed 8/266:45 pm
STL
- PDX
1 stop20h 07m
Frontier
Deal found 7/29![Frontier logo]()
$311
This CheapOair deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:16 pm
PDX
- STL
1 stop24h 07m
Frontier
Sun 8/167:10 pm
STL
- PDX
1 stop23h 44m
Frontier
Deal found 7/28![Frontier logo]()
$298
This CheapOair deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/136:49 pm
PDX
- STL
1 stop21h 26m
Frontier
Sun 8/167:10 pm
STL
- PDX
1 stop23h 44m
Frontier
Deal found 7/28![Frontier logo]()
$278
This Expedia deal was found by Cheapflights users on 7/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:49 pm
PDX
- ORD
1 stop8h 48m
Multiple Airlines
Sat 9/52:22 pm
ORD
- PDX
Nonstop4h 28m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$321
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:36 pm
PDX
- ORD
1 stop10h 41m
Frontier
Tue 8/182:41 pm
ORD
- PDX
1 stop28h 30m
Frontier
Deal found 7/31![Frontier logo]()
$320
This CheapOair deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/201:47 pm
PDX
- STL
1 stop26h 03m
Frontier
Sun 8/236:45 pm
STL
- PDX
1 stop24h 36m
Frontier
Deal found 7/30![Frontier logo]()
$309
This CheapOair deal was found by Cheapflights users on 7/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:20 pm
PDX
- STL
1 stop28h 53m
Frontier
Sun 8/307:58 pm
STL
- PDX
1 stop23h 13m
Frontier
Deal found 7/31![Frontier logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:47 pm
PDX
- ORD
1 stop27h 15m
Frontier
Sat 8/299:20 pm
ORD
- PDX
2 stops21h 51m
Frontier
Deal found 7/31![Frontier logo]()
$322
This CheapOair deal was found by Cheapflights users on 7/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:17 pm
PDX
- STL
1 stop21h 33m
Frontier
Sun 8/307:58 pm
STL
- PDX
1 stop23h 13m
Frontier
Deal found 7/31![Frontier logo]()
$290
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/299:45 am
PDX
- STL
Nonstop3h 45m
Southwest
Sat 9/58:30 am
STL
- PDX
Nonstop4h 10m
Southwest
Deal found 7/30![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/2911:20 am
PDX
- MDW
2 stops8h 55m
Southwest
Sat 9/51:15 pm
MDW
- PDX
1 stop7h 00m
Southwest
Deal found 7/30![Southwest logo]()
$322
This CheapOair deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/301:47 pm
PDX
- STL
1 stop26h 03m
Frontier
Sat 9/56:45 pm
STL
- PDX
1 stop20h 07m
Frontier
Deal found 7/30![Frontier logo]()
$314
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 August 2, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/85:56 pm
PDX
- STL
1 stop23h 21m
Frontier
Deal found 7/30![Frontier logo]()
$106
This Alaska Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 10/1710:30 am
PDX
- STL
2 stops11h 29m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:38 pm
PDX
- STL
1 stop28h 39m
Frontier
Deal found 7/30![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:38 pm
PDX
- STL
1 stop28h 39m
Frontier
Deal found 7/28![Frontier logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:47 pm
PDX
- STL
1 stop25h 28m
Frontier
Deal found 8/2![Frontier logo]()
$123
This Trip.com deal was found by Cheapflights users on 7/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/301:47 pm
PDX
- STL
1 stop26h 03m
Frontier
Deal found 7/31![Frontier logo]()
$124
This Trip.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:03 pm
PDX
- STL
1 stop23h 36m
Frontier
Deal found 7/30![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/265:56 pm
PDX
- STL
1 stop23h 17m
Frontier
Deal found 7/28![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Wed 9/25:56 pm
PDX
- STL
1 stop23h 17m
Frontier
Deal found 8/1![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2712:24 pm
PDX
- ORD
1 stop15h 14m
Frontier
Deal found 7/29![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/85:56 pm
PDX
- ORD
2 stops18h 21m
Frontier
Deal found 7/29![Frontier logo]()
$167
This Frontier deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:34 pm
PDX
- ORD
1 stop12h 23m
Frontier
Deal found 7/28![Frontier logo]()
$168
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 August 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $234 (Kiwi.com) |
One-way from | $106 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $373 |
Good round-trip deal | $355 or less |
Good one-way deal | $211 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 August 2, 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 - MDW
PDXMDW
Portland
Fri 10/30
5:20 am-11:10 am
Nonstop3h 50m
Chicago Midway
Tue 11/3
5:20 am-1:25 pm
2 stops10h 05m
$322
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 9/22
5:50 am-4:35 pm
2 stops8h 45m
Chicago Midway
Tue 9/29
8:20 am-3:00 pm
2 stops8h 40m
$323
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 8/30
11:02 pm-5:03 am
Nonstop4h 01m
Chicago O'Hare Intl
Thu 9/3
5:00 am-9:32 am
1 stop6h 32m
$327
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 10/6
1:00 pm-11:34 pm
1 stop8h 34m
Chicago O'Hare Intl
Thu 10/8
7:00 am-12:09 pm
1 stop7h 09m
$327
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 9/28
12:25 am-8:48 am
1 stop6h 23m
Chicago Midway
Thu 10/15
5:31 pm-11:44 pm
1 stop8h 13m
$327
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 9/17
11:30 pm-5:25 am
Nonstop3h 55m
Chicago Midway
Mon 9/21
6:15 am-2:45 pm
2 stops10h 30m
$332
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 10/21
10:45 am-10:10 pm
2 stops9h 25m
Chicago Midway
Mon 10/26
6:15 pm-1:20 am
1 stop9h 05m
$332
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Wed 9/30
9:00 am-6:43 pm
1 stop7h 43m
Lambert-St Louis
Mon 10/5
1:36 pm-5:46 pm
1 stop6h 10m
$333
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Thu 8/20
12:40 pm-11:50 pm
1 stop9h 10m
Lambert-St Louis
Fri 8/21
6:05 am-3:00 pm
2 stops10h 55m
$334
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 8/30
6:20 am-5:40 pm
1 stop9h 20m
Chicago O'Hare Intl
Thu 9/3
2:36 pm-10:12 pm
1 stop9h 36m
$337
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-MLI
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, January is the cheapest month in which you can book a flight from Portland to Illinois (average of $280). Flying from Portland to Illinois in December is currently the most expensive (average of $405). 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 August 2, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 12% 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 August 2, 2026.
The most flights from PDX to USIL are scheduled on a Friday (29 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (14 on average).
How much does it cost to fly round-trip from Portland to Illinois?
Airfare is typical for this route at the moment.
Portland to Illinois flights typically cost between $315 and $441 in September.The cheapest round-trip price found within the last 5 days was $320 on Multiple Airlines (Sep 25-Oct 1).
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 29 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 July 25, 2026.
Travelers seeking maximum savings on their Portland to Illinois flight should consider departing on Saturday 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.
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 August 2, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andDelta from Portland to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
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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 August 2, 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 August 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$93 | Average$217 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$125 | Average$368 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$195 | Average$467 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$215 | Average$377 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$227 | Average$356 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$228 | Average$452 | FlexibilityNo cancel fee | On-time69% |