$99+ Cheap flights from Portland, ME (PWM) to Chicago (CHI)
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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Aug 10 — Aug 171
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Chicago 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.Cheapflights Tip: The best prices from Portland to Chicago are usually found in September or May, booked 88 days in advance, depart on a Wednesday or Friday and return on a Saturday
Cheap flight deals from Portland to Chicago
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Best
Last-minute
One-way
Cheapest flights from Portland to ChicagoExplore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 11, 2026.
Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 11, 2026.
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Sat 8/155:50 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 7/10![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 7/6. 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 9/27:45 am
PWM
- MDW
Nonstop2h 35m
Southwest
Wed 9/93:05 pm
MDW
- PWM
1 stop5h 05m
Southwest
Deal found 7/6![Southwest logo]()
$317
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:38 pm
PWM
- ORD
Nonstop3h 21m
American Airlines
Mon 9/217:59 pm
ORD
- PWM
Nonstop2h 48m
American Airlines
Deal found 7/11![American Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:40 am
PWM
- MDW
Nonstop2h 30m
Southwest
Mon 9/76:10 pm
MDW
- PWM
Nonstop2h 20m
Southwest
Deal found 7/10![Southwest logo]()
$318
This United Airlines deal was found by Cheapflights users on 7/7. 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.
Tue 8/46:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Wed 8/56:08 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 7/7![United Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 7/9. 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.
Fri 10/233:25 pm
PWM
- MDW
2 stops8h 45m
Southwest
Mon 10/268:00 am
MDW
- PWM
2 stops7h 55m
Southwest
Deal found 7/9![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/84:45 pm
PWM
- ORD
1 stop4h 45m
Delta
Sat 9/1211:17 am
ORD
- PWM
2 stops9h 08m
Delta
Deal found 7/11![Delta logo]()
$322
This United Airlines deal was found by Cheapflights users on 7/8. 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.
Sat 8/16:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Wed 8/53:53 pm
ORD
- PWM
1 stop6h 58m
United Airlines
Deal found 7/8![United Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 7/9. 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 9/55:40 am
PWM
- MDW
1 stop6h 00m
Southwest
Mon 9/78:15 am
MDW
- PWM
2 stops5h 45m
Southwest
Deal found 7/9![Southwest logo]()
$323
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:38 pm
PWM
- ORD
Nonstop3h 21m
American Airlines
Tue 9/295:54 pm
ORD
- PWM
1 stop5h 05m
American Airlines
Deal found 7/11![American Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:45 am
PWM
- MDW
2 stops7h 05m
Southwest
Sun 8/303:10 pm
MDW
- PWM
1 stop6h 45m
Southwest
Deal found 7/10![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 7/8. 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 8/116:05 am
PWM
- ORD
1 stop7h 11m
Delta
Fri 8/141:50 pm
ORD
- PWM
1 stop8h 23m
Delta
Deal found 7/8![Delta logo]()
$325
Best flights from Portland to ChicagoDiscover carefully curated flight deals from Portland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 11, 2026.
Discover carefully curated flight deals from Portland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 11, 2026.
This Southwest deal was found by Cheapflights users on 7/6. 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 9/27:45 am
PWM
- MDW
Nonstop2h 35m
Southwest
Wed 9/93:05 pm
MDW
- PWM
1 stop5h 05m
Southwest
Deal found 7/6![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:52 pm
PWM
- ORD
1 stop4h 32m
Delta
Sun 10/253:40 pm
ORD
- PWM
1 stop6h 56m
Delta
Deal found 7/10![Delta logo]()
$318
This United Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:03 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Thu 9/35:50 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 7/11![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 7/9. 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 10/109:25 am
PWM
- MDW
2 stops8h 55m
Southwest
Tue 10/133:05 pm
MDW
- PWM
2 stops6h 30m
Southwest
Deal found 7/9![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:52 pm
PWM
- ORD
2 stops9h 08m
Delta
Sun 11/85:30 am
ORD
- PWM
2 stops10h 29m
Delta
Deal found 7/9![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:50 am
PWM
- ORD
1 stop8h 43m
Delta
Tue 9/229:30 am
ORD
- PWM
1 stop6h 19m
Delta
Deal found 7/11![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 7/8. 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.
Sat 8/16:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Wed 8/56:08 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 7/8![United Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:30 am
PWM
- MDW
2 stops10h 10m
Southwest
Sun 9/205:00 am
MDW
- PWM
1 stop4h 35m
Southwest
Deal found 7/10![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 7/8. 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 8/56:30 am
PWM
- ORD
2 stops11h 21m
Delta
Sat 8/81:50 pm
ORD
- PWM
2 stops10h 09m
Delta
Deal found 7/8![Delta logo]()
$343
This Southwest deal was found by Cheapflights users on 7/9. 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.
Fri 9/257:40 am
PWM
- MDW
Nonstop2h 30m
Southwest
Fri 9/252:35 pm
MDW
- PWM
2 stops6h 50m
Southwest
Deal found 7/9![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 7/8. 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.
Fri 9/251:59 pm
PWM
- ORD
1 stop7h 32m
Delta
Sun 9/275:30 am
ORD
- PWM
2 stops10h 19m
Delta
Deal found 7/8![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/95:15 am
PWM
- ORD
1 stop5h 21m
United Airlines
Sun 8/168:45 am
ORD
- PWM
1 stop4h 53m
United Airlines
Deal found 7/10![United Airlines logo]()
$440
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:30 am
PWM
- MDW
Nonstop2h 35m
Southwest
Sun 10/41:15 pm
MDW
- PWM
2 stops9h 40m
Southwest
Deal found 7/8![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 7/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:30 pm
PWM
- ORD
1 stop5h 54m
Delta
Wed 8/55:30 am
ORD
- PWM
2 stops10h 20m
Delta
Deal found 7/7![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 7/6. 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 8/225:40 am
PWM
- MDW
2 stops9h 30m
Southwest
Sun 8/235:00 am
MDW
- PWM
1 stop4h 35m
Southwest
Deal found 7/6![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 7/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:52 pm
PWM
- ORD
1 stop4h 32m
Delta
Sat 10/248:05 am
ORD
- PWM
2 stops11h 57m
Delta
Deal found 7/7![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:05 pm
PWM
- MDW
2 stops9h 25m
Southwest
Sun 9/2710:45 am
MDW
- PWM
1 stop3h 55m
Southwest
Deal found 7/8![Southwest logo]()
$422
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:30 am
PWM
- ORD
2 stops8h 59m
Delta
Sun 10/47:00 am
ORD
- PWM
1 stop5h 16m
Delta
Deal found 7/11![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/611:01 am
PWM
- ORD
2 stops10h 29m
Delta
Tue 8/111:59 pm
ORD
- PWM
2 stops8h 31m
Delta
Deal found 7/10![Delta logo]()
$432
Last-minute flights from Portland to ChicagoDiscover last-minute flight deals from Portland to Chicago. Data last updated July 11, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Chicago. Data last updated July 11, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 7/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:15 pm
PWM
- ORD
1 stop8h 43m
JetBlue
Fri 7/245:27 pm
ORD
- PWM
1 stop5h 49m
JetBlue
Deal found 7/8![JetBlue logo]()
$393
This JetBlue deal was found by Cheapflights users on 7/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:15 pm
PWM
- ORD
1 stop8h 43m
JetBlue
Sun 7/266:00 am
ORD
- PWM
1 stop5h 30m
JetBlue
Deal found 7/8![JetBlue logo]()
$437
This JetBlue deal was found by Cheapflights users on 7/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:15 pm
PWM
- ORD
1 stop8h 43m
JetBlue
Sun 7/196:00 am
ORD
- PWM
1 stop5h 30m
JetBlue
Deal found 7/8![JetBlue logo]()
$459
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:19 am
PWM
- ORD
Nonstop3h 11m
American Airlines
Sat 8/17:59 pm
ORD
- PWM
Nonstop2h 35m
American Airlines
Deal found 7/9![American Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/182:51 pm
PWM
- ORD
1 stop8h 01m
Delta
Sat 8/13:35 pm
ORD
- PWM
1 stop6h 39m
Delta
Deal found 7/10![Delta logo]()
$451
This United Airlines deal was found by Cheapflights users on 7/8. 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.
Sat 7/185:15 am
PWM
- ORD
1 stop27h 12m
United Airlines
Sun 7/1910:59 am
ORD
- PWM
Nonstop2h 31m
United Airlines
Deal found 7/8![United Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 7/7. 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.
Tue 7/216:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Wed 7/226:12 pm
ORD
- PWM
1 stop4h 39m
United Airlines
Deal found 7/7![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 7/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:05 am
PWM
- MDW
1 stop6h 46m
Delta
Wed 8/59:24 am
MDW
- PWM
1 stop5h 37m
Delta
Deal found 7/7![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 7/8. 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 8/197:45 am
PWM
- MDW
Nonstop2h 35m
Southwest
Wed 8/266:50 pm
MDW
- PWM
Nonstop2h 15m
Southwest
Deal found 7/8![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 7/6. 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 8/225:40 am
PWM
- MDW
1 stop6h 00m
Southwest
Sun 8/236:10 pm
MDW
- PWM
Nonstop2h 20m
Southwest
Deal found 7/6![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:45 am
PWM
- MDW
2 stops7h 05m
Southwest
Sun 8/303:10 pm
MDW
- PWM
1 stop6h 45m
Southwest
Deal found 7/10![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:40 am
PWM
- MDW
Nonstop2h 30m
Southwest
Sun 8/306:10 pm
MDW
- PWM
Nonstop2h 20m
Southwest
Deal found 7/10![Southwest logo]()
$326
One-way flights from Portland to ChicagoSearch for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Data last updated July 11, 2026.
Search for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Data last updated July 11, 2026.
This Southwest deal was found by Cheapflights users on 7/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:40 pm
PWM
- MDW
Nonstop2h 35m
Southwest
Deal found 7/7![Southwest logo]()
$99
This JetBlue deal was found by Cheapflights users on 7/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:25 pm
PWM
- ORD
1 stop5h 10m
JetBlue
Deal found 7/6![JetBlue logo]()
$101
This JetBlue deal was found by Cheapflights users on 7/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:40 pm
PWM
- ORD
1 stop8h 18m
JetBlue
Deal found 7/6![JetBlue logo]()
$106
This Southwest deal was found by Cheapflights users on 7/6. 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 10/215:40 am
PWM
- MDW
1 stop6h 40m
Southwest
Deal found 7/6![Southwest logo]()
$108
This JetBlue deal was found by Cheapflights users on 7/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/52:49 pm
PWM
- ORD
1 stop8h 09m
JetBlue
Deal found 7/6![JetBlue logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 8/188:00 am
PWM
- ORD
2 stops29h 50m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$156
This United Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Deal found 7/11![United Airlines logo]()
$158
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:03 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Deal found 7/9![United Airlines logo]()
$160
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am
PWM
- MDW
1 stop5h 37m
Delta
Deal found 7/9![Delta logo]()
$161
This United Airlines deal was found by Cheapflights users on 7/8. 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 8/105:15 am
PWM
- ORD
1 stop7h 33m
United Airlines
Deal found 7/8![United Airlines logo]()
$162
This United Airlines deal was found by Cheapflights users on 7/8. 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.
Sun 9/65:51 am
PWM
- ORD
1 stop4h 47m
United Airlines
Deal found 7/8![United Airlines logo]()
$164
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/612:47 pm
PWM
- MDW
1 stop5h 12m
Delta
Deal found 7/9![Delta logo]()
$164
Find flight deals from Portland to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (United Airlines) |
One-way from | $99 (Southwest) |
Popular in | July |
Cheapest in | September |
Average price | $431 |
Good round-trip deal | $399 or less |
Good one-way deal | $232 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Chicago 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 July 11, 2026.
Use the filters below to find and compare flights from Portland to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PWM - MDW
PWMMDW
Portland
Wed 9/2
7:45 am-9:20 am
Nonstop2h 35m
Chicago Midway
Wed 9/9
3:05 pm-9:10 pm
1 stop5h 05m
$317
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 10/22
12:52 pm-4:24 pm
1 stop4h 32m
Chicago O'Hare Intl
Sun 10/25
3:40 pm-11:36 pm
1 stop6h 56m
$318
PortlandChicago
PWM - MDW
PWMMDW
Portland
Sat 10/10
9:25 am-5:20 pm
2 stops8h 55m
Chicago Midway
Tue 10/13
3:05 pm-10:35 pm
2 stops6h 30m
$326
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 11/5
12:52 pm-9:00 pm
2 stops9h 08m
Chicago O'Hare Intl
Sun 11/8
5:30 am-4:59 pm
2 stops10h 29m
$328
Quickest round-trip
PortlandChicago
PWM - ORD
PWMORD
Portland
Mon 8/31
6:03 am-8:00 am
Nonstop2h 57m
Chicago O'Hare Intl
Thu 9/3
5:50 pm-9:23 pm
Nonstop2h 33m
$337
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 9/18
11:50 am-7:33 pm
1 stop8h 43m
Chicago O'Hare Intl
Tue 9/22
9:30 am-4:49 pm
1 stop6h 19m
$338
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 8/5
6:30 am-4:51 pm
2 stops11h 21m
Chicago O'Hare Intl
Sat 8/8
1:50 pm-12:59 am
2 stops10h 09m
$343
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 9/25
1:59 pm-8:31 pm
1 stop7h 32m
Chicago O'Hare Intl
Sun 9/27
5:30 am-4:49 pm
2 stops10h 19m
$351
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 8/4
5:30 pm-10:24 pm
1 stop5h 54m
Chicago O'Hare Intl
Wed 8/5
5:30 am-4:50 pm
2 stops10h 20m
$352
PortlandChicago
PWM - MDW
PWMMDW
Portland
Thu 9/17
10:30 am-7:40 pm
2 stops10h 10m
Chicago Midway
Sun 9/20
5:00 am-10:35 am
1 stop4h 35m
$358
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from Portland to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Chicago in July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland, Maine-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland, Maine-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland, Maine-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Portland with our price prediction graph.
PWM-CHI
PWM-MDW
PWM-ORD
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 Chicago
PWM-CHI
PWM-MDW
PWM-ORD
What is the cheapest month to book a flight from Portland, Maine to Chicago?
Currently, July is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $100). Flying from Portland, Maine to Chicago in January is currently the most expensive (average of $209). 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 PWM to CHI?
Find hourly flight availability from Portland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 11, 2026.
One of the essential ways to save on airfare from Portland, Maine to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 20% on airfare.
Weekly flight availability from Portland, Maine to Chicago
Explore weekly flight availability from Portland to Chicago. 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 July 11, 2026.
The most flights from PWM to CHI are scheduled on a Friday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Portland, Maine to Chicago?
How far ahead should I book a flight from Portland, Maine to Chicago?
Booking 83 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland, Maine to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 11, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Portland to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Portland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 11, 2026.
Complete your trip
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Search flights from Portland to Chicago by cabin class
Find flights from Portland to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Chicago flights
Browse other Portland and Chicago flight options. Last updated on July 11, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on July 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Portland to Chicago
Discover the top 4 airlines that operate flights from Portland to Chicago. 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 July 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$325 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$360 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$234 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$267 | Average$397 | FlexibilityNo cancel fee | On-time63% |