$66+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Mar 14 — Mar 211
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 12, 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 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:48 am
PDX
- STL
1 stop29h 24m
Frontier
Sat 5/168:12 pm
STL
- PDX
1 stop16h 51m
Frontier
Deal found 2/10![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:48 am
PDX
- STL
1 stop29h 24m
Frontier
Sat 4/188:12 pm
STL
- PDX
2 stops17h 45m
Frontier
Deal found 2/10![Frontier logo]()
$201
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/75:20 am
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 3/105:45 am
MDW
- PDX
2 stops10h 45m
Southwest
Deal found 2/9![Southwest logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/199:53 am
PDX
- ORD
1 stop17h 57m
Multiple Airlines
Tue 4/217:41 am
ORD
- PDX
2 stops31h 21m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$214
This Super.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:24 am
PDX
- ORD
1 stop17h 25m
Frontier
Wed 3/117:39 pm
ORD
- PDX
1 stop18h 13m
Frontier
Deal found 2/9![Frontier logo]()
$215
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:59 pm
PDX
- ORD
1 stop5h 53m
Delta
Wed 3/42:46 pm
ORD
- PDX
1 stop9h 22m
Delta
Deal found 2/8![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:40 am
PDX
- MDW
1 stop6h 26m
Delta
Wed 3/41:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Deal found 2/8![Delta logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:48 pm
PDX
- ORD
2 stops17h 24m
Multiple Airlines
Thu 4/167:21 pm
ORD
- PDX
1 stop18h 36m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/104:15 pm
PDX
- ORD
1 stop6h 43m
United Airlines
Wed 5/209:15 pm
ORD
- PDX
Nonstop4h 35m
United Airlines
Deal found 2/9![United Airlines logo]()
$220
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:55 am
PDX
- MDW
1 stop5h 35m
Southwest
Sat 3/710:30 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/8![Southwest logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1712:52 pm
PDX
- ORD
1 stop15h 55m
Frontier
Mon 4/209:18 pm
ORD
- PDX
2 stops17h 44m
Frontier
Deal found 2/9![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:48 am
PDX
- ORD
2 stops19h 24m
Multiple Airlines
Sun 4/268:53 pm
ORD
- PDX
1 stop14h 06m
Multiple Airlines
Deal found 2/10![Multiple Airlines 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 12, 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 12, 2026.
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/62:05 pm
PDX
- ORD
1 stop7h 54m
United Airlines
Tue 3/109:06 am
ORD
- PDX
Nonstop4h 45m
United Airlines
Deal found 2/9![United Airlines logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:00 am
PDX
- ORD
Nonstop4h 11m
Alaska Airlines
Mon 3/92:07 pm
ORD
- PDX
Nonstop4h 43m
Alaska Airlines
Deal found 2/8![Alaska Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:45 pm
PDX
- ORD
1 stop10h 29m
Delta
Tue 3/1012:15 pm
ORD
- PDX
1 stop7h 24m
Delta
Deal found 2/8![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2711:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Mon 4/139:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/8![Southwest logo]()
$217
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:52 pm
PDX
- STL
1 stop7h 30m
American Airlines
Mon 3/94:13 pm
STL
- PDX
1 stop8h 56m
American Airlines
Deal found 2/10![American Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stops24h 24m
Frontier
Sat 4/188:12 pm
STL
- PDX
1 stop16h 51m
Frontier
Deal found 2/11![Frontier logo]()
$251
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1711:59 pm
PDX
- ORD
Nonstop4h 04m
United Airlines
Mon 4/209:25 pm
ORD
- PDX
Nonstop4h 33m
United Airlines
Deal found 2/9![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sun 5/39:45 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/8![Southwest logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/63:52 pm
PDX
- ORD
1 stop6h 04m
Alaska Airlines
Mon 3/92:07 pm
ORD
- PDX
Nonstop4h 43m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:15 pm
PDX
- ORD
1 stop8h 54m
Delta
Tue 4/211:36 pm
ORD
- PDX
1 stop10h 06m
Delta
Deal found 2/9![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:10 am
PDX
- MDW
Nonstop3h 55m
Southwest
Thu 4/309:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/8![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:15 pm
PDX
- ORD
1 stop6h 43m
United Airlines
Sun 5/109:15 pm
ORD
- PDX
Nonstop4h 35m
United Airlines
Deal found 2/9![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1411:15 pm
PDX
- MDW
1 stop7h 32m
Delta
Sat 4/182:12 pm
MDW
- PDX
1 stop7h 53m
Delta
Deal found 2/9![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:55 am
PDX
- MDW
1 stop5h 35m
Southwest
Sat 3/710:30 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/8![Southwest logo]()
$220
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/112:05 pm
PDX
- ORD
1 stop7h 54m
United Airlines
Sat 3/148:04 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 2/9![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:59 am
PDX
- MLI
1 stop8h 35m
American Airlines
Fri 5/83:48 pm
MLI
- PDX
1 stop10h 06m
American Airlines
Deal found 2/9![American Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/71:55 pm
PDX
- ORD
1 stop8h 45m
Delta
Thu 4/97:10 pm
ORD
- PDX
1 stop6h 44m
Delta
Deal found 2/10![Delta logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:25 am
PDX
- STL
Nonstop3h 48m
Alaska Airlines
Tue 8/116:20 pm
STL
- PDX
Nonstop4h 10m
Alaska Airlines
Deal found 2/11![Alaska Airlines logo]()
$278
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/211:55 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Tue 5/512:44 pm
ORD
- PDX
Nonstop4h 29m
United Airlines
Deal found 2/10![United Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1410:24 am
PDX
- RFD
2 stops23h 31m
Multiple Airlines
Sat 3/219:28 pm
RFD
- PDX
1 stop23h 38m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$622
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:30 pm
PDX
- ORD
1 stop8h 00m
Delta
Thu 4/97:10 pm
ORD
- PDX
1 stop6h 44m
Delta
Deal found 2/9![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:25 pm
PDX
- MDW
1 stop9h 35m
Southwest
Sat 3/149:40 pm
MDW
- PDX
1 stop11h 15m
Southwest
Deal found 2/9![Southwest logo]()
$242
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/93:16 pm
PDX
- MLI
1 stop6h 38m
American Airlines
Wed 4/157:25 am
MLI
- PDX
1 stop7h 33m
American Airlines
Deal found 2/9![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/44:00 pm
PDX
- ORD
1 stop5h 59m
United Airlines
Sat 3/72:45 pm
ORD
- PDX
1 stop8h 25m
United Airlines
Deal found 2/9![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:40 am
PDX
- MDW
1 stop6h 26m
Delta
Mon 3/92:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/9![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/135:20 am
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 3/178:45 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/10![Southwest logo]()
$249
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/93:16 pm
PDX
- MLI
1 stop6h 38m
American Airlines
Tue 4/1412:52 pm
MLI
- PDX
1 stop9h 27m
American Airlines
Deal found 2/9![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/112:40 am
PDX
- MDW
1 stop6h 26m
Delta
Mon 3/92:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/8![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:10 am
PDX
- MDW
Nonstop3h 55m
Southwest
Sat 5/210:15 am
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/11![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1311:59 pm
PDX
- STL
1 stop8h 37m
United Airlines
Fri 3/206:05 pm
STL
- PDX
1 stop6h 55m
United Airlines
Deal found 2/11![United Airlines logo]()
$249
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated February 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:55 am
PDX
- MDW
1 stop5h 35m
Southwest
Sat 3/710:30 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/8![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/112:40 am
PDX
- MDW
1 stop6h 26m
Delta
Thu 3/51:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Deal found 2/8![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:45 pm
PDX
- MDW
1 stop10h 09m
Delta
Wed 3/41:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Deal found 2/8![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/39:45 pm
PDX
- MDW
1 stop10h 09m
Delta
Tue 3/102:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/8![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/49:44 pm
PDX
- STL
1 stop8h 51m
American Airlines
Mon 3/96:00 am
STL
- PDX
1 stop6h 48m
American Airlines
Deal found 2/9![American Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:20 am
PDX
- MDW
Nonstop3h 55m
Southwest
Wed 3/118:45 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/8![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/75:20 am
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 3/105:45 am
MDW
- PDX
2 stops10h 45m
Southwest
Deal found 2/9![Southwest logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/912:52 pm
PDX
- STL
1 stop28h 19m
Frontier
Mon 3/238:12 pm
STL
- PDX
2 stops38h 46m
Frontier
Deal found 2/10![Frontier logo]()
$255
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/103:52 pm
PDX
- STL
1 stop5h 42m
United Airlines
Tue 3/175:15 am
STL
- PDX
2 stops9h 18m
United Airlines
Deal found 2/10![United Airlines logo]()
$254
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:25 pm
PDX
- MDW
1 stop9h 35m
Southwest
Sat 3/149:40 pm
MDW
- PDX
1 stop11h 15m
Southwest
Deal found 2/9![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:20 am
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 3/1712:25 pm
MDW
- PDX
1 stop11h 45m
Southwest
Deal found 2/9![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:05 am
PDX
- STL
1 stop6h 19m
Delta
Mon 3/236:12 pm
STL
- PDX
1 stop7h 42m
Delta
Deal found 2/11![Delta logo]()
$259
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 12, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/811:48 am
PDX
- STL
1 stop29h 24m
Frontier
Deal found 2/10![Frontier logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:48 pm
PDX
- STL
1 stop27h 24m
Frontier
Deal found 2/9![Frontier logo]()
$77
This Trip.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/812:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 2/11![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1011:48 am
PDX
- STL
1 stop29h 24m
Frontier
Deal found 2/10![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/912:27 pm
PDX
- STL
1 stop28h 45m
Frontier
Deal found 2/9![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:48 pm
PDX
- STL
1 stop27h 24m
Frontier
Deal found 2/10![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1512:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 2/9![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:48 am
PDX
- STL
1 stop29h 24m
Frontier
Deal found 2/11![Frontier logo]()
$100
This Orbitz deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1712:52 pm
PDX
- STL
1 stop24h 29m
Frontier
Deal found 2/10![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2011:48 am
PDX
- STL
2 stops41h 02m
Frontier
Deal found 2/10![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:48 am
PDX
- STL
1 stop29h 24m
Frontier
Deal found 2/9![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 24m
Frontier
Deal found 2/11![Frontier logo]()
$105
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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $157 (Kiwi.com) |
One-way from | $66 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $327 |
Good round-trip deal | $315 or less |
Good one-way deal | $161 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 12, 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
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 3/6
2:05 pm-11:59 pm
1 stop7h 54m
Chicago O'Hare Intl
Tue 3/10
9:06 am-11:51 am
Nonstop4h 45m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 3/1
7:00 am-1:11 pm
Nonstop4h 11m
Chicago O'Hare Intl
Mon 3/9
2:07 pm-4:50 pm
Nonstop4h 43m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 3/3
9:45 pm-10:14 am
1 stop10h 29m
Chicago O'Hare Intl
Tue 3/10
12:15 pm-5:39 pm
1 stop7h 24m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 3/27
11:55 pm-5:45 am
Nonstop3h 50m
Chicago Midway
Mon 4/13
9:50 pm-12:10 am
Nonstop4h 20m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 4/17
11:59 pm-6:03 am
Nonstop4h 04m
Chicago O'Hare Intl
Mon 4/20
9:25 pm-11:58 pm
Nonstop4h 33m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 5/1
11:55 pm-5:50 am
Nonstop3h 55m
Chicago Midway
Sun 5/3
9:45 pm-12:05 am
Nonstop4h 20m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 4/27
5:10 am-11:05 am
Nonstop3h 55m
Chicago Midway
Thu 4/30
9:50 pm-12:10 am
Nonstop4h 20m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 2/28
6:55 am-2:30 pm
1 stop5h 35m
Chicago Midway
Sat 3/7
10:30 pm-12:55 am
Nonstop4h 25m
$220
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 3/6
3:52 pm-11:56 pm
1 stop6h 04m
Chicago O'Hare Intl
Mon 3/9
2:07 pm-4:50 pm
Nonstop4h 43m
$227
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 4/15
11:15 pm-10:09 am
1 stop8h 54m
Chicago O'Hare Intl
Tue 4/21
1:36 pm-9:42 pm
1 stop10h 06m
$227
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-MDW
PDX-STL
PDX-ORD
PDX-MLI
PDX-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Illinois
PDX-USIL
PDX-MDW
PDX-STL
PDX-ORD
PDX-MLI
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 12, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 19% on the flight price compared to flying in the evening, 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 7, 2026.
Travelers seeking maximum savings on their Portland to Illinois flight should consider departing on Tuesday evenings 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 12, 2026.
The most flights from PDX to USIL are scheduled on a Thursday (19 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 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 12, 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.
Food
7.1
Overall
8.0
Crew
8.5
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Food
7.1
Overall
8.0
Crew
8.5
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Food
7.1
Overall
8.0
Crew
8.5
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Food
7.1
Overall
8.0
Crew
8.5
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Food
7.1
Overall
8.0
Crew
8.5
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Food
7.1
Overall
8.0
Crew
8.5
Boarding
8.1
Entertainment
7.0
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 12, 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$333 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$194 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$125 | Average$283 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$196 | Average$453 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$205 | Average$451 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$212 | Average$347 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$231 | Average$379 | FlexibilityNo cancel fee | On-time63% |