$74+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Mar 25 — Apr 11
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 February 23, 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 February 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Thu 4/1611:48 am
PDX
- STL
1 stop29h 33m
Frontier
Sat 4/188:17 pm
STL
- PDX
1 stop16h 03m
Frontier
Deal found 2/20![Frontier logo]()
$179
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/1512:30 am
PDX
- STL
1 stop6h 16m
Delta
Sat 4/1812:23 pm
STL
- PDX
1 stop7h 09m
Delta
Deal found 2/23![Delta logo]()
$190
This American Airlines deal was found by Cheapflights users on 2/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/612:59 am
PDX
- STL
1 stop8h 38m
American Airlines
Tue 4/75:21 pm
STL
- PDX
1 stop8h 36m
American Airlines
Deal found 2/22![American Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 4/95:19 pm
PDX
- STL
2 stops14h 29m
Frontier
Mon 4/138:19 pm
STL
- PDX
1 stop18h 43m
Frontier
Deal found 2/19![Frontier logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1612:04 pm
PDX
- ORD
1 stop10h 53m
Frontier
Thu 3/1910:53 am
ORD
- PDX
1 stop26h 16m
Frontier
Deal found 2/21![Frontier logo]()
$217
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/111:59 pm
PDX
- STL
1 stop6h 56m
American Airlines
Mon 4/66:33 pm
STL
- PDX
1 stop7h 42m
American Airlines
Deal found 2/23![American Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/141:39 pm
PDX
- ORD
1 stop9h 20m
United Airlines
Sat 3/218:04 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 2/22![United Airlines logo]()
$218
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/712:30 am
PDX
- ORD
1 stop6h 10m
Delta
Sat 4/187:15 am
ORD
- PDX
1 stop7h 37m
Delta
Deal found 2/23![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/712:30 am
PDX
- MDW
1 stop6h 20m
Delta
Sat 4/182:12 pm
MDW
- PDX
1 stop7h 55m
Delta
Deal found 2/23![Delta logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Mon 5/1112:52 pm
PDX
- ORD
1 stop14h 58m
Multiple Airlines
Wed 5/136:20 am
ORD
- PDX
2 stops28h 39m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$220
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/911:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Thu 4/169:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/23![Southwest logo]()
$220
This CheapOair deal was found by Cheapflights users on 2/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:54 pm
PDX
- ORD
1 stop12h 56m
Frontier
Sun 4/267:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Deal found 2/20![Frontier logo]()
$222
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 February 23, 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 February 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 4/1611:48 am
PDX
- STL
2 stops18h 06m
Frontier
Sat 4/188:17 pm
STL
- PDX
1 stop16h 03m
Frontier
Deal found 2/19![Frontier logo]()
$186
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/141:52 pm
PDX
- STL
1 stop7h 07m
American Airlines
Tue 4/214:30 pm
STL
- PDX
1 stop9h 27m
American Airlines
Deal found 2/19![American Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:45 am
PDX
- STL
1 stop5h 38m
Delta
Fri 5/16:45 pm
STL
- PDX
1 stop7h 08m
Delta
Deal found 2/19![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 4/288:40 am
PDX
- STL
2 stops10h 28m
United Airlines
Fri 5/15:59 pm
STL
- PDX
1 stop6h 55m
United Airlines
Deal found 2/19![United Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Thu 4/307:46 pm
PDX
- RFD
1 stop21h 59m
Allegiant Air
Wed 5/62:51 pm
RFD
- PDX
1 stop30h 05m
Allegiant Air
Deal found 2/22![Allegiant Air logo]()
$252
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 3/125:20 am
PDX
- MDW
Nonstop3h 55m
Southwest
Sun 3/159:40 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/19![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 3/317:14 pm
PDX
- ORD
1 stop9h 06m
United Airlines
Wed 4/157:55 pm
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 2/19![United Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3012:30 am
PDX
- MDW
1 stop6h 20m
Delta
Tue 4/72:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/19![Delta logo]()
$251
This United Airlines deal was found by Cheapflights users on 2/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1811:59 pm
PDX
- STL
1 stop7h 31m
United Airlines
Sat 5/235:41 pm
STL
- PDX
1 stop6h 50m
United Airlines
Deal found 2/21![United Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Fri 3/279:53 am
PDX
- RFD
1 stop25h 10m
Multiple Airlines
Mon 3/308:50 pm
RFD
- PDX
1 stop14h 08m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:32 pm
PDX
- STL
2 stops12h 10m
Delta
Tue 4/216:45 pm
STL
- PDX
1 stop7h 08m
Delta
Deal found 2/19![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 2/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1211:15 am
PDX
- STL
2 stops8h 30m
Southwest
Tue 5/195:45 am
STL
- PDX
1 stop7h 20m
Southwest
Deal found 2/22![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 2/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:55 pm
PDX
- ORD
Nonstop4h 07m
United Airlines
Sun 5/107:55 pm
ORD
- PDX
Nonstop4h 35m
United Airlines
Deal found 2/22![United Airlines logo]()
$267
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Tue 3/1711:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Wed 3/254:40 pm
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 2/20![United Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/213:10 pm
PDX
- STL
1 stop6h 11m
Delta
Wed 5/276:21 am
STL
- PDX
1 stop8h 09m
Delta
Deal found 2/22![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 2/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:50 pm
PDX
- MDW
1 stop6h 55m
Southwest
Mon 4/134:35 pm
MDW
- PDX
2 stops10h 20m
Southwest
Deal found 2/22![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Mon 4/137:14 pm
PDX
- ORD
1 stop8h 13m
United Airlines
Fri 4/174:05 pm
ORD
- PDX
Nonstop4h 29m
United Airlines
Deal found 2/19![United Airlines logo]()
$277
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/1012:04 pm
PDX
- PIA
1 stop9h 09m
American Airlines
Sat 3/145:22 pm
PIA
- PDX
1 stop7h 44m
American Airlines
Deal found 2/23![American Airlines logo]()
$425
This Southwest deal was found by Cheapflights users on 2/20. 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.
Mon 4/67:15 pm
PDX
- MDW
1 stop7h 45m
Southwest
Mon 4/134:35 pm
MDW
- PDX
2 stops10h 20m
Southwest
Deal found 2/20![Southwest logo]()
$362
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2512:30 am
PDX
- ORD
1 stop6h 10m
Delta
Tue 3/317:10 pm
ORD
- PDX
1 stop6h 44m
Delta
Deal found 2/19![Delta logo]()
$343
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/181:39 pm
PDX
- ORD
1 stop7h 59m
United Airlines
Tue 3/249:06 am
ORD
- PDX
Nonstop4h 45m
United Airlines
Deal found 2/19![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/189:39 pm
PDX
- MDW
1 stop10h 21m
Delta
Fri 5/2912:51 pm
MDW
- PDX
1 stop10h 55m
Delta
Deal found 2/23![Delta logo]()
$343
This United Airlines deal was found by Cheapflights users on 2/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1411:40 pm
PDX
- PIA
1 stop8h 30m
United Airlines
Tue 7/285:33 pm
PIA
- PDX
1 stop6h 57m
United Airlines
Deal found 2/21![United Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 2/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/181:45 pm
PDX
- EVV
1 stop8h 11m
American Airlines
Sat 6/205:30 pm
EVV
- PDX
1 stop7h 23m
American Airlines
Deal found 2/22![American Airlines logo]()
$503
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Fri 5/223:10 pm
PDX
- RFD
2 stops19h 01m
Multiple Airlines
Sun 5/241:11 pm
RFD
- PDX
1 stop9h 58m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$571
This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/712:05 am
PDX
- ORD
1 stop5h 35m
Delta
Thu 3/192:20 pm
ORD
- PDX
1 stop8h 39m
Delta
Deal found 2/22![Delta logo]()
$366
This United Airlines deal was found by Cheapflights users on 2/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:51 am
PDX
- PIA
1 stop6h 35m
United Airlines
Sat 5/305:33 pm
PIA
- PDX
1 stop6h 58m
United Airlines
Deal found 2/22![United Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 2/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:10 am
PDX
- MDW
2 stops10h 25m
Southwest
Sun 3/89:40 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/22![Southwest logo]()
$491
This United Airlines deal was found by Cheapflights users on 2/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:00 am
PDX
- STL
1 stop7h 23m
United Airlines
Tue 3/175:15 am
STL
- PDX
2 stops9h 18m
United Airlines
Deal found 2/21![United Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/712:09 pm
PDX
- BMI
1 stop7h 57m
Delta
Wed 3/114:04 pm
BMI
- PDX
1 stop8h 04m
Delta
Deal found 2/22![Delta logo]()
$404
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated February 23, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated February 23, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Sat 3/1411:59 pm
PDX
- STL
1 stop6h 56m
American Airlines
Tue 3/176:00 am
STL
- PDX
1 stop6h 48m
American Airlines
Deal found 2/21![American Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/141:39 pm
PDX
- ORD
1 stop9h 20m
United Airlines
Sat 3/218:04 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 2/22![United Airlines logo]()
$218
This United Airlines deal was found by Cheapflights users on 2/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1411:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Sun 3/158:04 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 2/22![United Airlines logo]()
$233
This Southwest deal was found by Cheapflights users on 2/21. 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.
Sat 3/1411:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 3/178:45 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/21![Southwest logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1612:04 pm
PDX
- ORD
1 stop10h 53m
Frontier
Thu 3/1910:53 am
ORD
- PDX
1 stop26h 16m
Frontier
Deal found 2/21![Frontier logo]()
$217
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/2511:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Wed 4/18:45 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/23![Southwest logo]()
$238
This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2812:30 am
PDX
- STL
1 stop6h 31m
Delta
Fri 4/36:12 pm
STL
- PDX
1 stop7h 42m
Delta
Deal found 2/22![Delta logo]()
$237
This Travelocity deal was found by Cheapflights users on 2/20. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3010:08 am
PDX
- ORD
1 stop16h 51m
Multiple Airlines
Tue 4/72:09 pm
ORD
- PDX
Nonstop4h 41m
Multiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$246
This Alaska Airlines deal was found by Cheapflights users on 2/19. 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.
Mon 3/307:03 am
PDX
- ORD
Nonstop4h 10m
Alaska Airlines
Tue 4/72:09 pm
ORD
- PDX
Nonstop4h 41m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Tue 3/3111:59 pm
PDX
- ORD
Nonstop3h 57m
American Airlines
Tue 4/79:26 pm
ORD
- PDX
Nonstop4h 31m
American Airlines
Deal found 2/21![American Airlines logo]()
$231
This Alaska Airlines deal was found by Cheapflights users on 2/19. 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 3/311:35 pm
PDX
- ORD
1 stop8h 24m
Alaska Airlines
Tue 4/72:09 pm
ORD
- PDX
Nonstop4h 41m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:55 pm
PDX
- ORD
1 stop8h 45m
Delta
Tue 4/72:20 pm
ORD
- PDX
1 stop8h 39m
Delta
Deal found 2/19![Delta logo]()
$251
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 February 23, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated February 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Wed 4/151:48 pm
PDX
- STL
1 stop27h 33m
Frontier
Deal found 2/20![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Fri 3/1312:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 2/20![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/2512:27 pm
PDX
- STL
1 stop28h 54m
Frontier
Deal found 2/23![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Sun 5/311:15 am
PDX
- STL
1 stop30h 17m
Frontier
Deal found 2/20![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Fri 4/1711:48 am
PDX
- STL
1 stop29h 44m
Frontier
Deal found 2/20![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/1212:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 2/19![Frontier logo]()
$86
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/76:05 am
PDX
- STL
1 stop6h 19m
Delta
Deal found 2/23![Delta logo]()
$91
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:48 am
PDX
- STL
1 stop5h 33m
Frontier
Deal found 2/20![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Tue 3/319:43 am
PDX
- STL
2 stops22h 05m
Frontier
Deal found 2/20![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Sat 5/912:27 pm
PDX
- STL
1 stop28h 45m
Frontier
Deal found 2/20![Frontier logo]()
$98
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:45 am
PDX
- STL
1 stop7h 16m
Delta
Deal found 2/20![Delta logo]()
$99
This Super.com deal was found by Cheapflights users on 2/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1912:45 pm
PDX
- ORD
1 stop15h 38m
Frontier
Deal found 2/20![Frontier logo]()
$100
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 February 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $179 (Kiwi.com) |
One-way from | $74 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $327 |
Good round-trip deal | $328 or less |
Good one-way deal | $168 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 February 23, 2026.
Use the filters below to find and compare flights from Portland to Illinois that are best for you.
Fly from
Portland
Fly to
Illinois
Route
Depart
Return
Price
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Thu 4/16
11:48 am-7:54 am
2 stops18h 06m
Lambert-St Louis
Sat 4/18
8:17 pm-10:20 am
1 stop16h 03m
$186
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Tue 4/14
1:52 pm-10:59 pm
1 stop7h 07m
Lambert-St Louis
Tue 4/21
4:30 pm-11:57 pm
1 stop9h 27m
$197
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Tue 4/28
5:45 am-1:23 pm
1 stop5h 38m
Lambert-St Louis
Fri 5/1
6:45 pm-11:53 pm
1 stop7h 08m
$217
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Tue 4/28
8:40 am-9:08 pm
2 stops10h 28m
Lambert-St Louis
Fri 5/1
5:59 pm-10:54 pm
1 stop6h 55m
$238
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 3/31
7:14 pm-6:20 am
1 stop9h 06m
Chicago O'Hare Intl
Wed 4/15
7:55 pm-10:29 pm
Nonstop4h 34m
$241
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Mon 5/18
11:59 pm-9:30 am
1 stop7h 31m
Lambert-St Louis
Sat 5/23
5:41 pm-10:31 pm
1 stop6h 50m
$243
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 3/30
12:30 am-8:50 am
1 stop6h 20m
Chicago Midway
Tue 4/7
2:05 pm-8:25 pm
1 stop8h 20m
$251
PortlandChicago
PDX - RFD
PDXRFD
Portland
Thu 4/30
7:46 pm-7:45 pm
1 stop21h 59m
Chicago Greater Rockford
Wed 5/6
2:51 pm-6:56 pm
1 stop30h 05m
$252
PortlandChicago
PDX - ORD
PDXORD
Portland
Thu 5/7
10:55 pm-5:02 am
Nonstop4h 07m
Chicago O'Hare Intl
Sun 5/10
7:55 pm-10:30 pm
Nonstop4h 35m
$267
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 3/17
11:59 pm-5:53 am
Nonstop3h 54m
Chicago O'Hare Intl
Wed 3/25
4:40 pm-7:14 pm
Nonstop4h 34m
$271
Showing 1-10 of 60 results
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-ORD
PDX-STL
PDX-MDW
PDX-RFD
PDX-PIA
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-ORD
PDX-STL
PDX-MDW
PDX-RFD
What is the cheapest month to book a flight from Portland to Illinois?
Currently, August is the cheapest month in which you can book a flight from Portland to Illinois (average of $118). Flying from Portland to Illinois in July is currently the most expensive (average of $238). 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 February 23, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 18% on the flight price compared to flying in the morning, which is usually more expensive.
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 February 21, 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 at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 February 23, 2026.
The most flights from PDX to USIL are scheduled on a Thursday (19 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (16 on average).
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 February 23, 2026.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Hawaiian Airlines from Portland to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Crew
8.5
Food
7.1
Overall
8.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
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
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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 February 23, 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 8 airlines flying from Portland to Illinois
Discover the top 8 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 February 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$93 | Average$194 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$99 | Average$333 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$286 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$180 | Average$453 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$199 | Average$449 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$340 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$231 | Average$372 | FlexibilityNo cancel fee | On-time63% |