$82+ Cheap flights from Portland (PDX) to Illinois
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Apr 8 — Apr 151
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Illinois
Cheapest
Best
Last-minute
One-way
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 March 9, 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 March 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Fri 4/1011:58 am
PDX
- STL
1 stop19h 50m
Frontier
Mon 4/138:19 pm
STL
- PDX
1 stop18h 43m
Frontier
Deal found 3/6![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 3/4. 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.
Thu 4/3011:58 am
PDX
- STL
1 stop29h 23m
Frontier
Mon 5/48:17 pm
STL
- PDX
1 stop18h 45m
Frontier
Deal found 3/4![Frontier logo]()
$179
This Travelocity deal was found by Cheapflights users on 3/5. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:37 am
PDX
- STL
Nonstop4h 00m
Alaska Airlines
Sat 5/165:33 pm
STL
- PDX
Nonstop4h 17m
Alaska Airlines
Deal found 3/5![Alaska Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Wed 5/61:48 pm
PDX
- STL
1 stop27h 24m
Frontier
Mon 5/118:12 pm
STL
- PDX
1 stop18h 50m
Frontier
Deal found 3/8![Frontier logo]()
$199
This CheapOair deal was found by Cheapflights users on 3/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:48 am
PDX
- STL
1 stop5h 33m
Frontier
Sat 4/188:17 pm
STL
- PDX
1 stop16h 03m
Frontier
Deal found 3/9![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Wed 4/1512:28 pm
PDX
- ORD
1 stop19h 22m
Frontier
Thu 4/164:28 pm
ORD
- PDX
2 stops20h 35m
Frontier
Deal found 3/6![Frontier logo]()
$217
This American Airlines deal was found by Cheapflights users on 3/4. 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.
Tue 4/147:00 am
PDX
- STL
1 stop8h 21m
American Airlines
Tue 4/214:30 pm
STL
- PDX
1 stop8h 26m
American Airlines
Deal found 3/4![American Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 3/5. 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.
Wed 4/1512:28 pm
PDX
- ORD
1 stop19h 22m
Frontier
Tue 4/2110:45 am
ORD
- PDX
2 stops27h 07m
Frontier
Deal found 3/5![Frontier logo]()
$218
This Travelocity deal was found by Cheapflights users on 3/8. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:35 pm
PDX
- ORD
1 stop8h 24m
Multiple Airlines
Wed 4/157:21 pm
ORD
- PDX
1 stop18h 29m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$220
This CheapOair deal was found by Cheapflights users on 3/8. 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.
Mon 4/209:54 am
PDX
- ORD
1 stop17h 56m
Frontier
Wed 4/297:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Deal found 3/8![Frontier logo]()
$221
This CheapOair deal was found by Cheapflights users on 3/4. 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.
Thu 4/303:05 pm
PDX
- ORD
1 stop13h 15m
Frontier
Sat 5/27:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Deal found 3/4![Frontier logo]()
$222
This Alaska Airlines deal was found by Cheapflights users on 3/8. 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.
Tue 4/147:03 am
PDX
- ORD
Nonstop4h 10m
Alaska Airlines
Wed 4/156:00 am
ORD
- PDX
1 stop6h 36m
Alaska Airlines
Deal found 3/8![Alaska Airlines logo]()
$223
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 March 9, 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 March 9, 2026.
This Delta deal was found by Cheapflights users on 3/6. 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.
Wed 4/226:00 am
PDX
- STL
1 stop6h 29m
Delta
Wed 4/292:20 pm
STL
- PDX
1 stop5h 48m
Delta
Deal found 3/6![Delta logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 3/8. 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.
Wed 5/2010:37 am
PDX
- STL
Nonstop4h 00m
Alaska Airlines
Fri 5/295:33 pm
STL
- PDX
Nonstop4h 17m
Alaska Airlines
Deal found 3/8![Alaska Airlines logo]()
$243
This Southwest deal was found by Cheapflights users on 3/8. 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.
Wed 5/66:00 am
PDX
- ORD
2 stops10h 50m
Southwest
Sat 5/97:00 am
ORD
- PDX
2 stops13h 45m
Southwest
Deal found 3/8![Southwest logo]()
$259
This United Airlines deal was found by Cheapflights users on 3/7. 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.
Fri 5/2210:40 pm
PDX
- STL
1 stop8h 01m
United Airlines
Tue 5/265:10 am
STL
- PDX
1 stop6h 37m
United Airlines
Deal found 3/7![United Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/128:39 pm
PDX
- STL
2 stops11h 09m
Frontier
Mon 4/138:19 pm
STL
- PDX
1 stop18h 43m
Frontier
Deal found 3/9![Frontier logo]()
$322
This American Airlines deal was found by Cheapflights users on 3/6. 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.
Wed 4/81:23 pm
PDX
- CMI
1 stop6h 12m
American Airlines
Mon 4/136:58 pm
CMI
- PDX
1 stop6h 59m
American Airlines
Deal found 3/6![American Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Thu 5/217:17 pm
PDX
- RFD
1 stop23h 06m
Allegiant Air
Wed 6/38:50 pm
RFD
- PDX
1 stop23h 37m
Allegiant Air
Deal found 3/9![Allegiant Air logo]()
$467
This Alaska Airlines deal was found by Cheapflights users on 3/7. 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.
Tue 4/141:35 pm
PDX
- STL
1 stop8h 24m
Alaska Airlines
Wed 4/157:00 am
STL
- PDX
1 stop7h 35m
Alaska Airlines
Deal found 3/7![Alaska Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Thu 6/47:17 pm
PDX
- RFD
1 stop23h 03m
Multiple Airlines
Sun 6/71:13 pm
RFD
- PDX
1 stop9h 56m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 3/8. 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.
Wed 4/225:30 am
PDX
- ORD
1 stop5h 53m
Delta
Wed 4/296:00 pm
ORD
- PDX
1 stop7h 56m
Delta
Deal found 3/8![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 3/8. 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.
Wed 4/225:40 am
PDX
- MDW
Nonstop3h 55m
Southwest
Wed 4/294:00 pm
MDW
- PDX
2 stops9h 10m
Southwest
Deal found 3/8![Southwest logo]()
$266
This United Airlines deal was found by Cheapflights users on 3/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/114:07 pm
PDX
- STL
1 stop5h 43m
United Airlines
Tue 8/185:10 am
STL
- PDX
1 stop6h 11m
United Airlines
Deal found 3/8![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 3/8. 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 4/71:55 pm
PDX
- ORD
1 stop8h 45m
Delta
Tue 4/143:53 pm
ORD
- PDX
2 stops10h 03m
Delta
Deal found 3/8![Delta logo]()
$270
This United Airlines deal was found by Cheapflights users on 3/6. 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.
Sat 5/211:55 pm
PDX
- MLI
1 stop8h 09m
United Airlines
Sat 5/93:47 pm
MLI
- PDX
1 stop8h 48m
United Airlines
Deal found 3/6![United Airlines logo]()
$271
This Southwest deal was found by Cheapflights users on 3/9. 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 5/1411:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 5/196:45 am
MDW
- PDX
1 stop9h 05m
Southwest
Deal found 3/9![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 3/8. 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 4/207:32 pm
PDX
- ORD
2 stops11h 06m
Delta
Wed 4/296:00 pm
ORD
- PDX
1 stop7h 56m
Delta
Deal found 3/8![Delta logo]()
$270
This Alaska Airlines deal was found by Cheapflights users on 3/8. 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.
Wed 6/310:45 am
PDX
- STL
1 stop6h 00m
Alaska Airlines
Tue 6/95:33 pm
STL
- PDX
Nonstop4h 17m
Alaska Airlines
Deal found 3/8![Alaska Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 3/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/611:59 pm
PDX
- STL
1 stop6h 26m
United Airlines
Fri 4/107:45 am
STL
- PDX
1 stop9h 24m
United Airlines
Deal found 3/8![United Airlines logo]()
$278
This Southwest deal was found by Cheapflights users on 3/8. 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.
Wed 4/2212:45 pm
PDX
- ORD
2 stops9h 10m
Southwest
Wed 4/2911:55 am
ORD
- PDX
2 stops11h 05m
Southwest
Deal found 3/8![Southwest logo]()
$281
This Delta deal was found by Cheapflights users on 3/8. 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 4/1312:30 am
PDX
- MDW
1 stop6h 16m
Delta
Tue 4/2110:41 am
MDW
- PDX
1 stop10h 24m
Delta
Deal found 3/8![Delta logo]()
$271
This United Airlines deal was found by Cheapflights users on 3/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/134:15 pm
PDX
- ORD
1 stop6h 43m
United Airlines
Fri 5/154:15 pm
ORD
- PDX
Nonstop4h 30m
United Airlines
Deal found 3/8![United Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 3/8. 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.
Wed 5/1311:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Fri 5/152:30 pm
MDW
- PDX
2 stops9h 10m
Southwest
Deal found 3/8![Southwest logo]()
$284
This Alaska Airlines deal was found by Cheapflights users on 3/6. 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 6/2810:45 am
PDX
- STL
Nonstop3h 48m
Alaska Airlines
Wed 7/15:33 pm
STL
- PDX
Nonstop4h 10m
Alaska Airlines
Deal found 3/6![Alaska Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 3/6. 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.
Sat 5/306:00 am
PDX
- ORD
1 stop8h 51m
Delta
Sat 6/612:47 pm
ORD
- PDX
1 stop6h 22m
Delta
Deal found 3/6![Delta logo]()
$285
This Southwest deal was found by Cheapflights users on 3/6. 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.
Fri 5/295:10 am
PDX
- MDW
Nonstop3h 55m
Southwest
Sun 5/319:45 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 3/6![Southwest logo]()
$287
This Alaska Airlines deal was found by Cheapflights users on 3/4. 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.
Mon 4/135:32 pm
PDX
- ORD
1 stop23h 08m
Alaska Airlines
Thu 4/164:10 pm
ORD
- PDX
1 stop9h 49m
Alaska Airlines
Deal found 3/4![Alaska Airlines logo]()
$335
This United Airlines deal was found by Cheapflights users on 3/4. 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.
Wed 4/84:15 pm
PDX
- ORD
1 stop6h 15m
United Airlines
Fri 4/108:00 pm
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 3/4![United Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 3/6. 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.
Wed 4/81:23 pm
PDX
- BMI
1 stop19h 23m
American Airlines
Mon 4/1311:16 am
BMI
- PDX
1 stop14h 41m
American Airlines
Deal found 3/6![American Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 3/5. 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.
Tue 6/2312:40 am
PDX
- STL
1 stop6h 00m
Delta
Tue 6/305:30 pm
STL
- PDX
1 stop8h 04m
Delta
Deal found 3/5![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 3/5. 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.
Thu 5/711:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Mon 5/112:30 pm
MDW
- PDX
2 stops9h 10m
Southwest
Deal found 3/5![Southwest logo]()
$302
Last-minute flights from Portland to IllinoisDiscover last-minute flight deals from Portland to Illinois. Data last updated March 9, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Illinois. Data last updated March 9, 2026 and is based on user searches.
This Travelocity deal was found by Cheapflights users on 3/8. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:35 pm
PDX
- ORD
1 stop8h 24m
Multiple Airlines
Wed 4/157:21 pm
ORD
- PDX
1 stop18h 29m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Fri 4/1011:58 am
PDX
- STL
1 stop19h 50m
Frontier
Mon 4/138:19 pm
STL
- PDX
1 stop18h 43m
Frontier
Deal found 3/6![Frontier logo]()
$177
This Alaska Airlines deal was found by Cheapflights users on 3/8. 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.
Tue 4/147:03 am
PDX
- ORD
Nonstop4h 10m
Alaska Airlines
Wed 4/156:00 am
ORD
- PDX
1 stop6h 36m
Alaska Airlines
Deal found 3/8![Alaska Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Tue 4/148:00 am
PDX
- ORD
Nonstop4h 10m
American Airlines
Sat 4/188:20 pm
ORD
- PDX
Nonstop4h 37m
American Airlines
Deal found 3/8![American Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Wed 4/1512:28 pm
PDX
- ORD
1 stop19h 22m
Frontier
Thu 4/164:28 pm
ORD
- PDX
2 stops20h 35m
Frontier
Deal found 3/6![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 3/5. 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.
Wed 4/1512:28 pm
PDX
- ORD
1 stop19h 22m
Frontier
Tue 4/2110:45 am
ORD
- PDX
2 stops27h 07m
Frontier
Deal found 3/5![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 3/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:48 am
PDX
- STL
1 stop5h 33m
Frontier
Sat 4/188:17 pm
STL
- PDX
1 stop16h 03m
Frontier
Deal found 3/9![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Thu 4/1611:48 am
PDX
- ORD
1 stop20h 02m
Frontier
Fri 4/177:21 pm
ORD
- PDX
2 stops40h 59m
Frontier
Deal found 3/9![Frontier logo]()
$226
This CheapOair deal was found by Cheapflights users on 3/8. 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.
Mon 4/209:54 am
PDX
- ORD
1 stop17h 56m
Frontier
Wed 4/297:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Deal found 3/8![Frontier logo]()
$221
This Delta deal was found by Cheapflights users on 3/6. 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.
Wed 4/226:00 am
PDX
- STL
1 stop6h 29m
Delta
Wed 4/292:20 pm
STL
- PDX
1 stop5h 48m
Delta
Deal found 3/6![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 3/9. 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 4/2511:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 4/2810:10 am
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 3/9![Southwest logo]()
$229
This CheapOair deal was found by Cheapflights users on 3/4. 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.
Thu 4/303:05 pm
PDX
- ORD
1 stop13h 15m
Frontier
Sat 5/27:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Deal found 3/4![Frontier logo]()
$222
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 March 9, 2026.
Search for one-way flight options from Portland to Illinois. Find affordable one-way fares based on user searches. Data last updated March 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/5. 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.
Wed 4/1512:28 pm
PDX
- STL
1 stop28h 53m
Frontier
Deal found 3/5![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Wed 5/61:48 pm
PDX
- STL
1 stop27h 24m
Frontier
Deal found 3/6![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 3/5. 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.
Fri 5/811:48 am
PDX
- STL
1 stop29h 24m
Frontier
Deal found 3/5![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Thu 4/3011:58 am
PDX
- STL
1 stop29h 23m
Frontier
Deal found 3/6![Frontier logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
Fri 4/311:58 am
PDX
- STL
1 stop19h 50m
Frontier
Deal found 3/7![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 3/5. 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.
Sat 5/212:27 pm
PDX
- STL
1 stop28h 54m
Frontier
Deal found 3/5![Frontier logo]()
$93
This Priceline deal was found by Cheapflights users on 3/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2011:48 am
PDX
- STL
1 stop5h 44m
Frontier
Deal found 3/9![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 3/5. 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.
Mon 5/1112:52 pm
PDX
- ORD
1 stop15h 55m
Frontier
Deal found 3/5![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 4/141:48 pm
PDX
- MDW
2 stops27h 43m
Frontier
Deal found 3/6![Frontier logo]()
$99
This Alaska Airlines deal was found by Cheapflights users on 3/5. 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.
Wed 5/2010:37 am
PDX
- STL
Nonstop4h 00m
Alaska Airlines
Deal found 3/5![Alaska Airlines logo]()
$99
This Super.com deal was found by Cheapflights users on 3/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:54 am
PDX
- ORD
1 stop17h 56m
Frontier
Deal found 3/5![Frontier logo]()
$100
This Booking.com deal was found by Cheapflights users on 3/6. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:27 pm
PDX
- ORD
1 stop19h 18m
Frontier
Deal found 3/6![Frontier logo]()
$101
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 March 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Kiwi.com) |
One-way from | $82 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $385 |
Good round-trip deal | $336 or less |
Good one-way deal | $168 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 9, 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
Wed 4/22
6:00 am-2:29 pm
1 stop6h 29m
Lambert-St Louis
Wed 4/29
2:20 pm-6:08 pm
1 stop5h 48m
$217
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Wed 5/20
10:37 am-4:37 pm
Nonstop4h 00m
Lambert-St Louis
Fri 5/29
5:33 pm-7:50 pm
Nonstop4h 17m
$243
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Tue 4/14
1:35 pm-11:59 pm
1 stop8h 24m
Lambert-St Louis
Wed 4/15
7:00 am-12:35 pm
1 stop7h 35m
$257
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 5/6
6:00 am-6:50 pm
2 stops10h 50m
Chicago O'Hare Intl
Sat 5/9
7:00 am-6:45 pm
2 stops13h 45m
$259
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 4/22
5:30 am-1:23 pm
1 stop5h 53m
Chicago O'Hare Intl
Wed 4/29
6:00 pm-11:56 pm
1 stop7h 56m
$265
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 4/22
5:40 am-11:35 am
Nonstop3h 55m
Chicago Midway
Wed 4/29
4:00 pm-11:10 pm
2 stops9h 10m
$266
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Fri 5/22
10:40 pm-8:41 am
1 stop8h 01m
Lambert-St Louis
Tue 5/26
5:10 am-9:47 am
1 stop6h 37m
$269
PortlandSt. Louis
PDX - STL
PDXSTL
Portland
Tue 8/11
4:07 pm-11:50 pm
1 stop5h 43m
Lambert-St Louis
Tue 8/18
5:10 am-9:21 am
1 stop6h 11m
$269
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 4/7
1:55 pm-12:40 am
1 stop8h 45m
Chicago O'Hare Intl
Tue 4/14
3:53 pm-11:56 pm
2 stops10h 03m
$270
PortlandChicago
PDX - ORD
PDXORD
Portland
Mon 4/20
7:32 pm-8:38 am
2 stops11h 06m
Chicago O'Hare Intl
Wed 4/29
6:00 pm-11:56 pm
1 stop7h 56m
$270
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Portland to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Portland with our price prediction graph.
PDX-STL
PDX-ORD
PDX-MDW
PDX-RFD
PDX-CMI
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Illinois
PDX-USIL
PDX-STL
PDX-ORD
PDX-MDW
PDX-RFD
What is the cheapest month to book a flight from Portland to Illinois?
Currently, August is the cheapest month in which you can book a flight from Portland to Illinois (average of $122). 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 March 9, 2026.
It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 18% on the flight price compared to flying in the morning, which is usually more expensive.
What is the cheapest day to fly from Portland to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Portland to Illinois. Price data was last updated on February 21, 2026.
Travelers seeking maximum savings on their Portland to Illinois flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Portland to Illinois
Explore weekly flight availability from Portland to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 9, 2026.
The most flights from PDX to USIL are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 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 March 9, 2026.
Read reviews from past customers who have flown Alaska Airlines,Southwest, andHawaiian Airlines from Portland to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.5
Food
7.1
Overall
8.0
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Crew
8.5
Food
7.1
Overall
8.0
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Crew
8.5
Food
7.1
Overall
8.0
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Crew
8.5
Food
7.1
Overall
8.0
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Crew
8.5
Food
7.1
Overall
8.0
Entertainment
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Crew
8.5
Food
7.1
Overall
8.0
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 March 9, 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 March 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$194 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$96 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$333 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$278 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$176 | Average$453 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$202 | Average$453 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$338 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$217 | Average$368 | FlexibilityNo cancel fee | On-time63% |