$113+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Jul 7 — Jul 141
Round-trip
1 adult, Economy
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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 June 7, 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 June 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:42 pm
PDX
- STL
1 stop23h 41m
Frontier
Tue 9/18:08 pm
STL
- PDX
1 stop22h 49m
Frontier
Deal found 6/4![Frontier logo]()
$238
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:07 am
PDX
- MLI
1 stop9h 07m
American Airlines
Sat 7/116:50 pm
MLI
- PDX
1 stop8h 00m
American Airlines
Deal found 6/6![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 10/69:45 pm
PDX
- MLI
1 stop10h 41m
Delta
Sat 10/175:55 am
MLI
- PDX
2 stops12h 32m
Delta
Deal found 6/4![Delta logo]()
$306
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 10/76:15 am
PDX
- MLI
2 stops14h 15m
Delta
Sat 10/175:55 am
MLI
- PDX
2 stops12h 32m
Delta
Deal found 6/4![Delta logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 10/1212:34 pm
PDX
- STL
1 stop28h 41m
Frontier
Wed 10/218:10 pm
STL
- PDX
1 stop22h 25m
Frontier
Deal found 6/3![Frontier logo]()
$314
This American Airlines deal was found by Cheapflights users on 6/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:15 pm
PDX
- ORD
Nonstop3h 59m
American Airlines
Wed 7/1510:15 pm
ORD
- PDX
Nonstop4h 35m
American Airlines
Deal found 6/2![American Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Tue 9/15:42 pm
PDX
- ORD
1 stop25h 11m
Frontier
Sat 9/59:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Deal found 6/2![Frontier logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:42 pm
PDX
- ORD
2 stops25h 11m
Frontier
Tue 8/259:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Deal found 6/3![Frontier logo]()
$318
This Mytrip deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:16 pm
PDX
- ORD
1 stop25h 36m
Frontier
Tue 8/189:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Deal found 6/3![Frontier logo]()
$319
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/25:24 pm
PDX
- STL
1 stop5h 19m
Delta
Tue 7/77:55 pm
STL
- PDX
1 stop5h 49m
Delta
Deal found 6/4![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/45:07 am
PDX
- MLI
1 stop9h 07m
American Airlines
Fri 7/106:50 pm
MLI
- PDX
1 stop8h 00m
American Airlines
Deal found 6/5![American Airlines logo]()
$320
This CheapOair deal was found by Cheapflights users on 6/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:21 pm
PDX
- ORD
1 stop25h 31m
Frontier
Wed 7/159:13 pm
ORD
- PDX
1 stop16h 22m
Frontier
Deal found 6/2![Frontier logo]()
$320
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 June 7, 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 June 7, 2026.
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 10/22:27 pm
PDX
- STL
1 stop6h 32m
United Airlines
Tue 10/61:29 pm
STL
- PDX
1 stop7h 22m
United Airlines
Deal found 6/5![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/103:25 pm
PDX
- STL
1 stop6h 25m
Southwest
Mon 9/1411:55 am
STL
- PDX
1 stop9h 20m
Southwest
Deal found 6/3![Southwest logo]()
$319
This Alaska Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1210:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Wed 7/157:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:55 pm
PDX
- STL
1 stop8h 41m
Delta
Mon 11/97:55 pm
STL
- PDX
1 stop5h 56m
Delta
Deal found 6/6![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3111:15 pm
PDX
- PIA
1 stop8h 02m
American Airlines
Tue 8/46:58 pm
PIA
- PDX
1 stop7h 52m
American Airlines
Deal found 6/6![American Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/166:58 pm
PDX
- RFD
1 stop23h 36m
Multiple Airlines
Thu 8/209:35 pm
RFD
- PDX
1 stop21h 49m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 6/217:21 pm
PDX
- RFD
1 stop22h 59m
Allegiant Air
Sat 7/111:03 pm
RFD
- PDX
1 stop30h 45m
Allegiant Air
Deal found 6/5![Allegiant Air logo]()
$496
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:16 am
PDX
- STL
1 stop6h 22m
United Airlines
Mon 8/315:30 pm
STL
- PDX
1 stop7h 22m
United Airlines
Deal found 6/6![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:20 am
PDX
- STL
1 stop7h 05m
Southwest
Thu 8/2011:55 am
STL
- PDX
2 stops9h 25m
Southwest
Deal found 6/6![Southwest logo]()
$324
This Alaska Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:28 am
PDX
- ORD
1 stop6h 52m
Alaska Airlines
Wed 10/282:21 pm
ORD
- PDX
1 stop10h 29m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:33 am
PDX
- MDW
1 stop6h 04m
Delta
Wed 7/156:00 am
MDW
- PDX
1 stop8h 58m
Delta
Deal found 6/6![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/94:15 pm
PDX
- STL
1 stop5h 42m
United Airlines
Mon 7/137:23 pm
STL
- PDX
1 stop7h 27m
United Airlines
Deal found 6/5![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:00 am
PDX
- MDW
1 stop7h 05m
Southwest
Wed 9/308:55 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/6![Southwest logo]()
$325
This Alaska Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2610:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Thu 7/307:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/1712:33 am
PDX
- ORD
1 stop6h 02m
Delta
Mon 7/207:40 pm
ORD
- PDX
1 stop6h 04m
Delta
Deal found 6/3![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:50 pm
PDX
- ORD
1 stop6h 49m
United Airlines
Sat 7/114:15 pm
ORD
- PDX
Nonstop4h 32m
United Airlines
Deal found 6/4![United Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2211:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 7/286:40 pm
MDW
- PDX
1 stop7h 15m
Southwest
Deal found 6/6![Southwest logo]()
$325
This Alaska Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/309:32 pm
PDX
- ORD
1 stop6h 48m
Alaska Airlines
Sun 10/46:00 am
ORD
- PDX
1 stop9h 27m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/612:45 am
PDX
- EVV
1 stop9h 09m
American Airlines
Sat 7/254:35 pm
EVV
- PDX
1 stop9h 20m
American Airlines
Deal found 6/3![American Airlines logo]()
$419
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2111:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Sun 7/269:50 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/6![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/2811:02 pm
PDX
- ORD
Nonstop4h 01m
United Airlines
Sun 8/307:00 am
ORD
- PDX
Nonstop4h 29m
United Airlines
Deal found 6/5![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 6/2. 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.
Thu 7/26:00 am
PDX
- ORD
1 stop7h 05m
Delta
Mon 7/63:55 pm
ORD
- PDX
1 stop9h 23m
Delta
Deal found 6/2![Delta logo]()
$377
This Alaska Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/277:55 am
PDX
- ORD
1 stop9h 26m
Alaska Airlines
Sun 8/308:17 pm
ORD
- PDX
1 stop15h 13m
Alaska Airlines
Deal found 6/5![Alaska Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 9/911:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sun 9/135:40 am
MDW
- PDX
1 stop7h 40m
Southwest
Deal found 6/5![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2212:33 am
PDX
- MDW
1 stop6h 04m
Delta
Mon 7/271:49 pm
MDW
- PDX
1 stop8h 26m
Delta
Deal found 6/3![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:50 pm
PDX
- MDW
1 stop7h 55m
Southwest
Thu 7/309:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 6/3![Southwest logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:38 pm
PDX
- RFD
1 stop23h 45m
Multiple Airlines
Sun 8/29:19 am
RFD
- PDX
2 stops15h 24m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$545
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/2310:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Wed 7/17:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 6/3![United Airlines logo]()
$382
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/101:25 pm
PDX
- STL
1 stop7h 36m
Delta
Tue 9/158:47 am
STL
- PDX
1 stop6h 00m
Delta
Deal found 6/3![Delta logo]()
$397
This Alaska Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2310:49 am
PDX
- STL
Nonstop3h 48m
Alaska Airlines
Tue 7/285:37 pm
STL
- PDX
Nonstop4h 10m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$417
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated June 7, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated June 7, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/110:59 pm
PDX
- ORD
Nonstop4h 01m
Multiple Airlines
Tue 7/79:57 pm
ORD
- PDX
1 stop20h 39m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/25:24 pm
PDX
- STL
1 stop5h 19m
Delta
Tue 7/77:55 pm
STL
- PDX
1 stop5h 49m
Delta
Deal found 6/4![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:07 am
PDX
- MLI
1 stop9h 07m
American Airlines
Sat 7/116:50 pm
MLI
- PDX
1 stop8h 00m
American Airlines
Deal found 6/6![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/45:07 am
PDX
- MLI
1 stop9h 07m
American Airlines
Fri 7/106:50 pm
MLI
- PDX
1 stop8h 00m
American Airlines
Deal found 6/5![American Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:00 am
PDX
- STL
2 stops9h 50m
Southwest
Fri 7/1012:40 pm
STL
- PDX
1 stop8h 20m
Southwest
Deal found 6/3![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/711:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 7/149:10 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/6![Southwest logo]()
$320
This American Airlines deal was found by Cheapflights users on 6/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:15 pm
PDX
- ORD
Nonstop3h 59m
American Airlines
Wed 7/1510:15 pm
ORD
- PDX
Nonstop4h 35m
American Airlines
Deal found 6/2![American Airlines logo]()
$315
This CheapOair deal was found by Cheapflights users on 6/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:21 pm
PDX
- ORD
1 stop25h 31m
Frontier
Wed 7/159:13 pm
ORD
- PDX
1 stop16h 22m
Frontier
Deal found 6/2![Frontier logo]()
$320
This Alaska Airlines deal was found by Cheapflights users on 6/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/810:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Wed 7/158:20 pm
ORD
- PDX
1 stop13h 17m
Alaska Airlines
Deal found 6/2![Alaska Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/1111:46 am
PDX
- ORD
Nonstop4h 06m
American Airlines
Sat 7/1810:15 pm
ORD
- PDX
Nonstop4h 35m
American Airlines
Deal found 6/5![American Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 7/1711:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Tue 7/217:55 pm
ORD
- PDX
Nonstop4h 35m
United Airlines
Deal found 6/4![United Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2211:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Wed 7/296:40 pm
MDW
- PDX
1 stop7h 15m
Southwest
Deal found 6/3![Southwest logo]()
$325
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 June 7, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated June 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:26 pm
PDX
- STL
1 stop28h 57m
Frontier
Deal found 6/4![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 8/3012:26 pm
PDX
- STL
1 stop28h 57m
Frontier
Deal found 6/4![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” 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 9/25:42 pm
PDX
- STL
1 stop23h 41m
Frontier
Deal found 6/4![Frontier logo]()
$143
This Booking.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2610:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1810:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/3![Alaska Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:19 pm
PDX
- MDW
2 stops38h 50m
Frontier
Deal found 6/4![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:22 pm
PDX
- ORD
1 stop16h 39m
Frontier
Deal found 6/6![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:42 pm
PDX
- STL
1 stop23h 41m
Frontier
Deal found 6/6![Frontier logo]()
$157
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 6/7![United Airlines logo]()
$158
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1511:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 6/3![Southwest logo]()
$158
This Super.com deal was found by Cheapflights users on 6/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:16 pm
PDX
- ORD
1 stop25h 36m
Frontier
Deal found 6/2![Frontier logo]()
$160
This United Airlines deal was found by Cheapflights users on 6/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/304:15 pm
PDX
- STL
1 stop5h 42m
United Airlines
Deal found 6/2![United Airlines logo]()
$160
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 June 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $238 (Kiwi.com) |
One-way from | $113 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $368 |
Good round-trip deal | $373 or less |
Good one-way deal | $202 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 June 7, 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
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Fri 10/2
2:27 pm-10:59 pm
1 stop6h 32m
Lambert-St Louis
Tue 10/6
1:29 pm-6:51 pm
1 stop7h 22m
$319
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Thu 9/10
3:25 pm-11:50 pm
1 stop6h 25m
Lambert-St Louis
Mon 9/14
11:55 am-7:15 pm
1 stop9h 20m
$319
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Fri 8/28
7:16 am-3:38 pm
1 stop6h 22m
Lambert-St Louis
Mon 8/31
5:30 pm-10:52 pm
1 stop7h 22m
$319
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Thu 7/9
4:15 pm-11:57 pm
1 stop5h 42m
Lambert-St Louis
Mon 7/13
7:23 pm-12:50 am
1 stop7h 27m
$319
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 7/4
12:50 pm-9:39 pm
1 stop6h 49m
Chicago O'Hare Intl
Sat 7/11
4:15 pm-6:47 pm
Nonstop4h 32m
$321
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Sat 8/15
6:20 am-3:25 pm
1 stop7h 05m
Lambert-St Louis
Thu 8/20
11:55 am-7:20 pm
2 stops9h 25m
$324
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 9/30
8:00 am-5:05 pm
1 stop7h 05m
Chicago Midway
Wed 9/30
8:55 pm-11:10 pm
Nonstop4h 15m
$325
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 7/22
11:30 pm-5:20 am
Nonstop3h 50m
Chicago Midway
Tue 7/28
6:40 pm-11:55 pm
1 stop7h 15m
$325
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 7/12
10:59 pm-5:00 am
Nonstop4h 01m
Chicago O'Hare Intl
Wed 7/15
7:20 am-9:45 am
Nonstop4h 25m
$326
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 7/21
11:30 pm-5:20 am
Nonstop3h 50m
Chicago Midway
Sun 7/26
9:50 pm-12:15 am
Nonstop4h 25m
$326
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-ORD
PDX-STL
PDX-MDW
PDX-RFD
PDX-BMI
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Illinois
PDX-USIL
PDX-ORD
PDX-STL
PDX-MDW
PDX-RFD
What is the cheapest month to book a flight from Portland to Illinois?
Currently, November is the cheapest month in which you can book a flight from Portland to Illinois (average of $103). Flying from Portland to Illinois in September is currently the most expensive (average of $746). 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 June 7, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 15% 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 June 7, 2026.
The most flights from PDX to USIL are scheduled on a Friday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).
How much does it cost to fly round-trip from Portland to Illinois?
How far ahead should I book a flight from Portland to Illinois?
To ensure you get the cheapest price possible for a flight from Portland to Illinois, you should look to book at least 89 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Portland to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Portland to Illinois. Price data was last updated on May 30, 2026.
Travelers seeking maximum savings on their Portland to Illinois flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 June 7, 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.
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 7, 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 June 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$249 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$96 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$433 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$172 | Average$440 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$209 | Average$341 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$217 | Average$450 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$217 | Average$357 | FlexibilityNo cancel fee | On-time63% |