$72+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
may. 8 — may. 151
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 abril 8, 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 abril 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/4. 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.
vie. 5/812:35 pm
PDX
- STL
1 stop28h 48m
Frontier
jue. 5/1412:36 pm
STL
- PDX
2 stops30h 10m
Frontier
Deal found 4/4![Frontier logo]()
$238
This CheapOair deal was found by Cheapflights users on 4/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/118:46 pm
PDX
- STL
1 stop19h 20m
Frontier
mié. 5/136:51 pm
STL
- PDX
1 stop28h 00m
Frontier
Deal found 4/4![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 4/4. 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.
vie. 5/812:35 pm
PDX
- STL
1 stop28h 48m
Frontier
mar. 5/126:51 pm
STL
- PDX
2 stops42h 59m
Frontier
Deal found 4/4![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 4/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/232:54 pm
PDX
- ORD
1 stop13h 26m
Frontier
dom. 4/268:58 pm
ORD
- PDX
1 stop14h 01m
Frontier
Deal found 4/4![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 4/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/2711:48 am
PDX
- STL
1 stop5h 44m
Frontier
jue. 5/1412:36 pm
STL
- PDX
1 stop10h 15m
Frontier
Deal found 4/5![Frontier logo]()
$250
This American Airlines deal was found by Cheapflights users on 4/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/96:22 am
PDX
- ORD
Nonstop4h 10m
American Airlines
mar. 5/129:17 pm
ORD
- PDX
Nonstop4h 31m
American Airlines
Deal found 4/4![American Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 4/6. 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.
sáb. 5/911:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
mié. 5/138:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 4/6![Southwest logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
mié. 4/2212:38 pm
PDX
- STL
2 stops19h 52m
Frontier
sáb. 5/28:17 pm
STL
- PDX
1 stop16h 03m
Frontier
Deal found 4/6![Frontier logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/232:54 pm
PDX
- ORD
1 stop13h 26m
Frontier
lun. 4/276:09 pm
ORD
- PDX
2 stops43h 43m
Frontier
Deal found 4/7![Frontier logo]()
$252
This Expedia deal was found by Cheapflights users on 4/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/1712:45 pm
PDX
- STL
1 stop6h 25m
Frontier
dom. 4/199:55 pm
STL
- PDX
1 stop13h 04m
Frontier
Deal found 4/8![Frontier logo]()
$252
This Travelocity deal was found by Cheapflights users on 4/4. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/303:05 pm
PDX
- ORD
1 stop13h 15m
Frontier
dom. 5/310:50 am
ORD
- PDX
1 stop26h 13m
Frontier
Deal found 4/4![Frontier logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/79:46 pm
PDX
- ORD
2 stops30h 53m
Frontier
jue. 5/149:37 pm
ORD
- PDX
1 stop21h 09m
Frontier
Deal found 4/7![Frontier logo]()
$254
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 abril 8, 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 abril 8, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/51:52 pm
PDX
- STL
1 stop8h 07m
Alaska Airlines
mié. 5/135:33 pm
STL
- PDX
Nonstop4h 17m
Alaska Airlines
Deal found 4/4![Alaska Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 4/6. 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.
sáb. 5/97:10 am
PDX
- ORD
2 stops13h 10m
Southwest
mar. 5/124:50 pm
ORD
- PDX
1 stop8h 20m
Southwest
Deal found 4/6![Southwest logo]()
$276
This United Airlines deal was found by Cheapflights users on 4/6. 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.
sáb. 5/97:45 pm
PDX
- ORD
1 stop7h 55m
United Airlines
mié. 5/139:20 pm
ORD
- PDX
Nonstop4h 35m
United Airlines
Deal found 4/6![United Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 4/6. 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.
mar. 5/56:15 am
PDX
- STL
1 stop8h 35m
Delta
dom. 5/107:00 am
STL
- PDX
1 stop7h 33m
Delta
Deal found 4/6![Delta logo]()
$293
This CheapOair deal was found by Cheapflights users on 4/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/2212:38 pm
PDX
- STL
1 stop28h 43m
Frontier
vie. 4/248:06 pm
STL
- PDX
1 stop17h 36m
Frontier
Deal found 4/8![Frontier logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/77:46 pm
PDX
- RFD
1 stop21h 59m
Multiple Airlines
jue. 5/1412:50 pm
RFD
- PDX
1 stop10h 01m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 4/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/2312:59 am
PDX
- PIA
1 stop8h 43m
American Airlines
dom. 4/265:40 pm
PIA
- PDX
1 stop8h 14m
American Airlines
Deal found 4/4![American Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
dom. 5/317:17 pm
PDX
- RFD
1 stop23h 06m
Allegiant Air
mié. 6/38:50 pm
RFD
- PDX
1 stop23h 37m
Allegiant Air
Deal found 4/6![Allegiant Air logo]()
$452
This Southwest deal was found by Cheapflights users on 4/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/1311:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
mié. 5/2710:10 am
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 4/4![Southwest logo]()
$278
This Alaska Airlines deal was found by Cheapflights users on 4/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/288:45 am
PDX
- ORD
1 stop6h 11m
Alaska Airlines
mié. 4/298:00 am
ORD
- PDX
1 stop6h 52m
Alaska Airlines
Deal found 4/4![Alaska Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 4/4. 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.
mié. 5/1311:12 pm
PDX
- ORD
1 stop7h 33m
Delta
mié. 5/2712:47 pm
ORD
- PDX
1 stop6h 24m
Delta
Deal found 4/4![Delta logo]()
$298
This United Airlines deal was found by Cheapflights users on 4/5. 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.
mié. 7/225:00 pm
PDX
- ORD
Nonstop4h 13m
United Airlines
mar. 7/284:15 pm
ORD
- PDX
Nonstop4h 32m
United Airlines
Deal found 4/5![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 4/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/55:40 am
PDX
- MDW
Nonstop3h 55m
Southwest
dom. 5/109:45 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 4/4![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 4/5. 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.
jue. 5/711:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
mar. 5/128:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 4/5![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 4/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/2210:53 am
PDX
- ORD
1 stop10h 25m
Delta
mar. 7/286:55 am
ORD
- PDX
1 stop6h 48m
Delta
Deal found 4/5![Delta logo]()
$325
This Alaska Airlines deal was found by Cheapflights users on 4/8. 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.
mié. 8/261:59 pm
PDX
- ORD
1 stop8h 00m
Alaska Airlines
vie. 8/282:22 pm
ORD
- PDX
Nonstop4h 28m
Alaska Airlines
Deal found 4/8![Alaska Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/4. 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.
jue. 5/2110:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
lun. 5/255:00 am
ORD
- PDX
1 stop6h 47m
United Airlines
Deal found 4/4![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 4/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/2112:35 am
PDX
- MDW
1 stop6h 02m
Delta
mar. 7/281:49 pm
MDW
- PDX
1 stop8h 26m
Delta
Deal found 4/5![Delta logo]()
$325
This Alaska Airlines deal was found by Cheapflights users on 4/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/810:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
mié. 7/156:20 am
ORD
- PDX
1 stop9h 23m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 4/5. 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.
mié. 7/2211:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
mar. 7/285:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 4/5![Southwest logo]()
$305
This American Airlines deal was found by Cheapflights users on 4/5. 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.
jue. 5/711:56 am
PDX
- CMI
1 stop6h 43m
American Airlines
dom. 5/106:55 pm
CMI
- PDX
1 stop6h 53m
American Airlines
Deal found 4/5![American Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 4/6. 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.
sáb. 9/55:05 pm
PDX
- STL
1 stop5h 31m
Delta
mié. 9/96:30 am
STL
- PDX
1 stop8h 24m
Delta
Deal found 4/6![Delta logo]()
$329
This United Airlines deal was found by Cheapflights users on 4/5. 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.
mar. 7/710:40 pm
PDX
- DEC
1 stop8h 17m
United Airlines
jue. 7/167:20 pm
DEC
- PDX
1 stop6h 42m
United Airlines
Deal found 4/5![United Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 4/5. 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.
mar. 4/282:35 pm
PDX
- ORD
1 stop7h 20m
Southwest
jue. 5/78:00 am
ORD
- PDX
1 stop8h 20m
Southwest
Deal found 4/5![Southwest logo]()
$309
This Alaska Airlines deal was found by Cheapflights users on 4/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/112:00 pm
PDX
- ORD
1 stop7h 57m
Alaska Airlines
lun. 9/142:18 pm
ORD
- PDX
1 stop8h 31m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
mié. 7/155:42 pm
PDX
- RFD
2 stops16h 42m
Multiple Airlines
mié. 7/228:49 pm
RFD
- PDX
1 stop22h 59m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 4/4. 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.
vie. 6/1912:31 am
PDX
- STL
1 stop7h 57m
Delta
mié. 6/243:57 pm
STL
- PDX
1 stop9h 24m
Delta
Deal found 4/4![Delta logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
dom. 6/147:17 pm
PDX
- RFD
1 stop23h 03m
Allegiant Air
mié. 6/178:50 pm
RFD
- PDX
1 stop23h 37m
Allegiant Air
Deal found 4/6![Allegiant Air logo]()
$503
This American Airlines deal was found by Cheapflights users on 4/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/711:56 am
PDX
- CMI
1 stop6h 43m
American Airlines
jue. 5/146:55 pm
CMI
- PDX
1 stop6h 53m
American Airlines
Deal found 4/8![American Airlines logo]()
$458
This Southwest deal was found by Cheapflights users on 4/5. 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.
sáb. 5/2311:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
mié. 5/275:35 pm
MDW
- PDX
1 stop7h 25m
Southwest
Deal found 4/5![Southwest logo]()
$315
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated abril 8, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated abril 8, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/1712:45 pm
PDX
- STL
1 stop6h 25m
Frontier
dom. 4/199:55 pm
STL
- PDX
1 stop13h 04m
Frontier
Deal found 4/8![Frontier logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
mié. 4/2212:38 pm
PDX
- STL
2 stops19h 52m
Frontier
sáb. 5/28:17 pm
STL
- PDX
1 stop16h 03m
Frontier
Deal found 4/6![Frontier logo]()
$251
This Frontier deal was found by Cheapflights users on 4/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/232:54 pm
PDX
- ORD
1 stop13h 26m
Frontier
dom. 4/268:58 pm
ORD
- PDX
1 stop14h 01m
Frontier
Deal found 4/4![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/232:54 pm
PDX
- ORD
1 stop13h 26m
Frontier
lun. 4/276:09 pm
ORD
- PDX
2 stops43h 43m
Frontier
Deal found 4/7![Frontier logo]()
$252
This Frontier deal was found by Cheapflights users on 4/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/2711:48 am
PDX
- STL
1 stop5h 44m
Frontier
jue. 5/1412:36 pm
STL
- PDX
1 stop10h 15m
Frontier
Deal found 4/5![Frontier logo]()
$250
This Travelocity deal was found by Cheapflights users on 4/4. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/303:05 pm
PDX
- ORD
1 stop13h 15m
Frontier
dom. 5/310:50 am
ORD
- PDX
1 stop26h 13m
Frontier
Deal found 4/4![Frontier logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/79:46 pm
PDX
- ORD
2 stops30h 53m
Frontier
jue. 5/149:37 pm
ORD
- PDX
1 stop21h 09m
Frontier
Deal found 4/7![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 4/4. 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.
vie. 5/812:35 pm
PDX
- STL
1 stop28h 48m
Frontier
jue. 5/1412:36 pm
STL
- PDX
2 stops30h 10m
Frontier
Deal found 4/4![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 4/4. 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.
vie. 5/812:35 pm
PDX
- STL
1 stop28h 48m
Frontier
mar. 5/126:51 pm
STL
- PDX
2 stops42h 59m
Frontier
Deal found 4/4![Frontier logo]()
$249
This American Airlines deal was found by Cheapflights users on 4/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/96:22 am
PDX
- ORD
Nonstop4h 10m
American Airlines
mar. 5/129:17 pm
ORD
- PDX
Nonstop4h 31m
American Airlines
Deal found 4/4![American Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 4/6. 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.
sáb. 5/98:00 am
PDX
- MDW
Nonstop3h 55m
Southwest
sáb. 5/96:05 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 4/6![Southwest logo]()
$251
This CheapOair deal was found by Cheapflights users on 4/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/118:46 pm
PDX
- STL
1 stop19h 20m
Frontier
mié. 5/136:51 pm
STL
- PDX
1 stop28h 00m
Frontier
Deal found 4/4![Frontier logo]()
$241
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 abril 8, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated abril 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/2912:38 pm
PDX
- STL
1 stop28h 43m
Frontier
Deal found 4/8![Frontier logo]()
$72
This Priceline deal was found by Cheapflights users on 4/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/2611:15 am
PDX
- STL
1 stop6h 06m
Frontier
Deal found 4/5![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 4/4. 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.
vie. 5/812:35 pm
PDX
- STL
1 stop28h 48m
Frontier
Deal found 4/4![Frontier logo]()
$88
This CheapOair deal was found by Cheapflights users on 4/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/118:46 pm
PDX
- STL
1 stop19h 20m
Frontier
Deal found 4/5![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
mar. 6/25:46 pm
PDX
- STL
1 stop23h 37m
Frontier
Deal found 4/6![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
dom. 5/1012:35 pm
PDX
- STL
1 stop28h 48m
Frontier
Deal found 4/6![Frontier logo]()
$101
This Priceline deal was found by Cheapflights users on 4/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/2711:48 am
PDX
- STL
1 stop5h 44m
Frontier
Deal found 4/6![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
mié. 4/2912:38 pm
PDX
- ORD
2 stops21h 35m
Frontier
Deal found 4/6![Frontier logo]()
$117
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/2312:35 pm
PDX
- STL
1 stop28h 48m
Frontier
Deal found 4/6![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/212:27 pm
PDX
- ORD
1 stop19h 18m
Frontier
Deal found 4/7![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
lun. 4/2711:48 am
PDX
- ORD
2 stops40h 02m
Frontier
Deal found 4/6![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 4/4. 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.
dom. 5/315:31 pm
PDX
- ORD
1 stop11h 03m
Frontier
Deal found 4/4![Frontier logo]()
$124
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 abril 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $238 (Kiwi.com) |
One-way from | $72 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $363 |
Good round-trip deal | $367 or less |
Good one-way deal | $191 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 abril 8, 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
mar. 5/5
1:52 pm-11:59 pm
1 stop8h 07m
Lambert-St Louis
mié. 5/13
5:33 pm-7:50 pm
Nonstop4h 17m
$267
PortlandChicago
PDX - ORD
PDXORD
Portland
sáb. 5/9
7:10 am-10:20 pm
2 stops13h 10m
Chicago O'Hare Intl
mar. 5/12
4:50 pm-11:10 pm
1 stop8h 20m
$276
PortlandChicago
PDX - MDW
PDXMDW
Portland
mié. 5/13
11:55 pm-5:50 am
Nonstop3h 55m
Chicago Midway
mié. 5/27
10:10 am-12:30 pm
Nonstop4h 20m
$278
PortlandChicago
PDX - ORD
PDXORD
Portland
sáb. 5/9
7:45 pm-5:40 am
1 stop7h 55m
Chicago O'Hare Intl
mié. 5/13
9:20 pm-11:55 pm
Nonstop4h 35m
$281
PortlandChicago
PDX - MDW
PDXMDW
Portland
mar. 5/5
5:40 am-11:35 am
Nonstop3h 55m
Chicago Midway
dom. 5/10
9:45 pm-12:05 am
Nonstop4h 20m
$289
PortlandChicago
PDX - MDW
PDXMDW
Portland
jue. 5/7
11:55 pm-5:50 am
Nonstop3h 55m
Chicago Midway
mar. 5/12
8:50 pm-11:10 pm
Nonstop4h 20m
$289
PortlandChicago
PDX - ORD
PDXORD
Portland
mar. 4/28
8:45 am-4:56 pm
1 stop6h 11m
Chicago O'Hare Intl
mié. 4/29
8:00 am-12:52 pm
1 stop6h 52m
$291
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
mar. 5/5
6:15 am-4:50 pm
1 stop8h 35m
Lambert-St Louis
dom. 5/10
7:00 am-12:33 pm
1 stop7h 33m
$293
PortlandChicago
PDX - ORD
PDXORD
Portland
mié. 5/13
11:12 pm-8:45 am
1 stop7h 33m
Chicago O'Hare Intl
mié. 5/27
12:47 pm-5:11 pm
1 stop6h 24m
$298
PortlandChicago
PDX - ORD
PDXORD
Portland
mié. 7/22
5:00 pm-11:13 pm
Nonstop4h 13m
Chicago O'Hare Intl
mar. 7/28
4:15 pm-6:47 pm
Nonstop4h 32m
$305
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Portland to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Portland with our price prediction graph.
PDX-STL
PDX-ORD
PDX-RFD
PDX-MDW
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-STL
PDX-ORD
PDX-RFD
PDX-MDW
What is the cheapest month to book a flight from Portland to Illinois?
Currently, September is the cheapest month in which you can book a flight from Portland to Illinois (average of $125). 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 abril 8, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 17% 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 April 4, 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 abril 8, 2026.
The most flights from PDX to USIL are scheduled on a Wednesday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).
How much does it cost to fly round-trip from Portland to Illinois?
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 abril 8, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andHawaiian Airlines from Portland to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 abril 8, 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 abril 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$184 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$96 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$288 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$271 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$169 | Average$447 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$205 | Average$447 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$208 | Average$334 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$217 | Average$365 | FlexibilityNo cancel fee | On-time63% |