$128+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Sep 11 — Sep 181
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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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 August 12, 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 August 12, 2026.
This Delta deal was found by Cheapflights users on 8/10. 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.
Fri 9/114:45 pm -
1 stop4h 45m
Tue 9/223:40 pm -
1 stop6h 48m
Deal found 8/10![Delta logo]()
$238
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:03 pm -
Nonstop2h 56m
Wed 9/165:54 pm -
1 stop4h 51m
Deal found 8/10![American Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 10/265:20 am -
1 stop5h 40m
Wed 10/287:45 am -
Nonstop2h 10m
Deal found 8/10![Southwest logo]()
$240
This American Airlines deal was found by Cheapflights users on 8/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:24 pm -
1 stop4h 44m
Sun 9/61:59 pm -
Nonstop2h 33m
Deal found 8/7![American Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 8/7. 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 9/510:30 am -
1 stop7h 10m
Sun 9/66:30 pm -
Nonstop2h 15m
Deal found 8/7![Southwest logo]()
$245
This United Airlines deal was found by Cheapflights users on 8/11. 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 10/15:15 am -
1 stop5h 23m
Sat 10/36:06 pm -
1 stop4h 53m
Deal found 8/11![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/195:38 pm -
Nonstop3h 21m
Tue 9/227:59 pm -
Nonstop2h 48m
Deal found 8/11![American Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 8/10. 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 -
Nonstop2h 30m
Tue 9/86:50 pm -
Nonstop2h 20m
Deal found 8/10![Southwest logo]()
$251
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:20 pm -
1 stop6h 17m
Tue 9/157:05 am -
1 stop4h 05m
Deal found 8/11![Delta logo]()
$253
This United Airlines deal was found by Cheapflights users on 8/11. 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 10/15:08 pm -
Nonstop2h 57m
Mon 10/53:00 pm -
Nonstop2h 43m
Deal found 8/11![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:30 am -
Nonstop2h 35m
Mon 10/56:40 pm -
Nonstop2h 10m
Deal found 8/11![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 8/11. 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.
Sat 10/246:25 am -
2 stops11h 16m
Tue 10/276:00 am -
1 stop6h 12m
Deal found 8/11![Delta logo]()
$258
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 August 12, 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 August 12, 2026.
This Delta deal was found by Cheapflights users on 8/11. 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.
Sat 10/246:25 am -
2 stops11h 22m
Tue 10/276:04 am -
2 stops8h 31m
Deal found 8/11![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:30 am -
1 stop6h 20m
Wed 9/306:50 pm -
Nonstop2h 20m
Deal found 8/11![Southwest logo]()
$269
This United Airlines deal was found by Cheapflights users on 8/10. 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.
Wed 9/96:53 pm -
1 stop6h 35m
Fri 9/112:10 pm -
Nonstop2h 44m
Deal found 8/10![United Airlines logo]()
$286
This JetBlue deal was found by Cheapflights users on 8/8. 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.
Mon 8/242:40 pm -
1 stop8h 18m
Fri 8/285:27 pm -
1 stop5h 58m
Deal found 8/8![JetBlue logo]()
$481
This Delta deal was found by Cheapflights users on 8/11. 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.
Thu 10/296:01 am -
1 stop6h 49m
Mon 11/26:04 am -
1 stop5h 58m
Deal found 8/11![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 8/10. 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 9/15:45 am -
1 stop6h 50m
Wed 9/96:50 pm -
Nonstop2h 20m
Deal found 8/10![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 8/11. 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 9/106:00 am -
Nonstop2h 57m
Wed 9/165:50 pm -
Nonstop2h 33m
Deal found 8/11![United Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 8/11. 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 2/44:48 pm -
Nonstop2h 57m
Sat 2/610:35 am -
Nonstop2h 17m
Deal found 8/11![United Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 8/7. 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.
Tue 10/206:00 pm -
Nonstop2h 35m
Thu 10/226:25 pm -
1 stop4h 30m
Deal found 8/7![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 8/7. 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 10/224:47 pm -
2 stops8h 05m
Sat 10/2410:35 am -
2 stops9h 26m
Deal found 8/7![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/11. 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 10/276:01 am -
2 stops11h 31m
Sun 11/15:27 am -
2 stops9h 08m
Deal found 8/11![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1510:25 am -
1 stop9h 30m
Fri 12/188:50 am -
1 stop6h 50m
Deal found 8/11![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 8/7. 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.
Fri 10/3012:42 pm -
2 stops12h 10m
Sun 11/16:15 am -
1 stop5h 57m
Deal found 8/7![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 8/9. 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 10/165:30 pm -
2 stops8h 35m
Mon 10/196:25 pm -
1 stop4h 30m
Deal found 8/9![Southwest logo]()
$360
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:00 am -
2 stops11h 39m
Thu 11/266:00 am -
1 stop6h 03m
Deal found 8/11![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:40 am -
1 stop6h 00m
Sat 9/269:05 am -
1 stop4h 55m
Deal found 8/11![Southwest logo]()
$363
This Delta deal was found by Cheapflights users on 8/7. 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 9/101:59 pm -
1 stop5h 05m
Mon 9/145:40 pm -
1 stop4h 37m
Deal found 8/7![Delta logo]()
$352
This United Airlines deal was found by Cheapflights users on 8/10. 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.
Fri 10/96:00 am -
Nonstop2h 57m
Mon 10/126:10 pm -
Nonstop2h 36m
Deal found 8/10![United Airlines logo]()
$491
This Southwest deal was found by Cheapflights users on 8/9. 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 11/265:15 am -
1 stop7h 40m
Tue 12/18:50 am -
1 stop4h 55m
Deal found 8/9![Southwest logo]()
$384
This Delta deal was found by Cheapflights users on 8/11. 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 12/1112:50 pm -
1 stop6h 14m
Sun 12/131:00 pm -
1 stop8h 23m
Deal found 8/11![Delta logo]()
$376
This Delta deal was found by Cheapflights users on 8/8. 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.
Sat 9/266:02 am -
2 stops9h 27m
Tue 9/2910:30 am -
1 stop5h 19m
Deal found 8/8![Delta logo]()
$448
Last-minute flights from Portland to ChicagoDiscover last-minute flight deals from Portland to Chicago. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Chicago. Data last updated August 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:45 am -
Nonstop2h 35m
Wed 9/306:50 pm -
Nonstop2h 20m
Deal found 8/11![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 8/10. 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 -
Nonstop2h 30m
Tue 9/86:50 pm -
Nonstop2h 20m
Deal found 8/10![Southwest logo]()
$251
This United Airlines deal was found by Cheapflights users on 8/10. 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.
Fri 9/46:00 am -
1 stop5h 58m
Tue 9/85:50 pm -
Nonstop2h 33m
Deal found 8/10![United Airlines logo]()
$261
This American Airlines deal was found by Cheapflights users on 8/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:24 pm -
1 stop4h 44m
Sun 9/61:59 pm -
Nonstop2h 33m
Deal found 8/7![American Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 8/7. 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 9/510:30 am -
1 stop7h 10m
Sun 9/66:30 pm -
Nonstop2h 15m
Deal found 8/7![Southwest logo]()
$245
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:03 pm -
Nonstop2h 56m
Wed 9/165:54 pm -
1 stop4h 51m
Deal found 8/10![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:20 pm -
1 stop6h 17m
Tue 9/157:05 am -
1 stop4h 05m
Deal found 8/11![Delta logo]()
$253
This Delta deal was found by Cheapflights users on 8/10. 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.
Fri 9/114:45 pm -
1 stop4h 45m
Tue 9/223:40 pm -
1 stop6h 48m
Deal found 8/10![Delta logo]()
$238
This American Airlines deal was found by Cheapflights users on 8/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:03 pm -
Nonstop2h 56m
Mon 9/149:29 am -
Nonstop2h 36m
Deal found 8/7![American Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:20 pm -
1 stop6h 17m
Tue 9/221:55 pm -
2 stops8h 22m
Deal found 8/10![Delta logo]()
$258
This United Airlines deal was found by Cheapflights users on 8/11. 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.
Sat 9/196:53 pm -
1 stop6h 35m
Tue 9/2212:16 pm -
1 stop5h 13m
Deal found 8/11![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/195:38 pm -
Nonstop3h 21m
Sat 9/269:29 am -
Nonstop2h 36m
Deal found 8/11![American Airlines logo]()
$251
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 August 12, 2026.
Search for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Delta deal was found by Cheapflights users on 8/10. 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.
Fri 9/115:29 pm -
1 stop5h 49m
Deal found 8/10![Delta logo]()
$128
This American Airlines deal was found by Cheapflights users on 8/11. 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.
Thu 9/39:08 am -
Nonstop2h 59m
Deal found 8/11![American Airlines logo]()
$129
This United Airlines deal was found by Cheapflights users on 8/10. 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.
Mon 9/216:00 am -
Nonstop2h 57m
Deal found 8/10![United Airlines logo]()
$133
This JetBlue deal was found by Cheapflights users on 8/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am -
1 stop4h 58m
Deal found 8/10![JetBlue logo]()
$135
This Delta deal was found by Cheapflights users on 8/11. 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.
Mon 11/95:29 pm -
1 stop5h 54m
Deal found 8/11![Delta logo]()
$139
This Southwest deal was found by Cheapflights users on 8/10. 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 9/103:40 pm -
1 stop6h 20m
Deal found 8/10![Southwest logo]()
$139
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 11/95:10 pm -
1 stop6h 55m
Deal found 8/10![Southwest logo]()
$140
This United Airlines deal was found by Cheapflights users on 8/11. 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.
Sat 9/196:00 am -
Nonstop2h 57m
Deal found 8/11![United Airlines logo]()
$141
This American Airlines deal was found by Cheapflights users on 8/11. 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 10/107:00 am -
1 stop8h 14m
Deal found 8/11![American Airlines logo]()
$143
This American Airlines deal was found by Cheapflights users on 8/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:46 am -
Nonstop3h 14m
Deal found 8/7![American Airlines logo]()
$145
This Southwest deal was found by Cheapflights users on 8/7. 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 10/244:35 pm -
Nonstop2h 35m
Deal found 8/7![Southwest logo]()
$145
This Delta deal was found by Cheapflights users on 8/10. 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.
Wed 9/166:30 am -
2 stops11h 07m
Deal found 8/10![Delta logo]()
$148
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 August 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $238 (Delta) |
One-way from | $128 (Delta) |
Popular in | July |
Cheapest in | September |
Average price | $340 |
Good round-trip deal | $366 or less |
Good one-way deal | $236 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 August 12, 2026.
Use the filters below to find and compare flights from Portland to Chicago that are best for you.
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Cheapest round-trip
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Sat 10/24
6:25 am-4:47 pm
2 stops11h 22m
Chicago Midway
Tue 10/27
6:04 am-3:35 pm
2 stops8h 31m
$263
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 9/2
10:30 am-3:50 pm
1 stop6h 20m
Chicago Midway
Wed 9/30
6:50 pm-10:10 pm
Nonstop2h 20m
$269
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Thu 10/29
6:01 am-11:50 am
1 stop6h 49m
Chicago Midway
Mon 11/2
6:04 am-1:02 pm
1 stop5h 58m
$277
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 9/9
6:53 pm-12:28 am
1 stop6h 35m
Chicago O'Hare Intl
Fri 9/11
2:10 pm-5:54 pm
Nonstop2h 44m
$286
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Tue 9/1
5:45 am-11:35 am
1 stop6h 50m
Chicago Midway
Wed 9/9
6:50 pm-10:10 pm
Nonstop2h 20m
$295
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 9/10
6:00 am-7:57 am
Nonstop2h 57m
Chicago O'Hare Intl
Wed 9/16
5:50 pm-9:23 pm
Nonstop2h 33m
$309
Quickest round-trip
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 2/4
4:48 pm-6:45 pm
Nonstop2h 57m
Chicago O'Hare Intl
Sat 2/6
10:35 am-1:52 pm
Nonstop2h 17m
$309
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Tue 10/20
6:00 pm-7:35 pm
Nonstop2h 35m
Chicago Midway
Thu 10/22
6:25 pm-11:55 pm
1 stop4h 30m
$313
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 10/22
4:47 pm-11:52 pm
2 stops8h 05m
Chicago O'Hare Intl
Sat 10/24
10:35 am-9:01 pm
2 stops9h 26m
$319
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Tue 10/27
6:01 am-4:32 pm
2 stops11h 31m
Chicago O'Hare Intl
Sun 11/1
5:27 am-3:35 pm
2 stops9h 08m
$336
Showing 1-10 of 42 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 August.
| 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-ORD
PWM-MDW
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-ORD
PWM-MDW
What is the cheapest month to book a flight from Portland, Maine to Chicago?
Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $324). Flying from Portland, Maine to Chicago in December is currently the most expensive (average of $460). 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 August 12, 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 in the evening could potentially save you up to 28% on airfare.
How much does it cost to fly round-trip from Portland, Maine to Chicago?
Airfare is below average for this route at the moment.
Portland, Maine to Chicago flights typically cost between $269 and $401 in September.The cheapest round-trip price found within the last 5 days was $238 on Delta (Sep 11-Sep 22).
How far ahead should I book a flight from Portland, Maine to Chicago?
Booking 82 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 August 12, 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.
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Portland to Chicago
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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 August 12, 2026.
Complete your trip
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Search flights from Portland to Chicago by cabin class
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Portland and Chicago flights
Browse other Portland and Chicago flight options. Last updated on August 12, 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 August 12, 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 August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$327 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$369 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$234 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$267 | Average$378 | FlexibilityNo cancel fee | On-time63% |