$135+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Sep 26 — Oct 31
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 May or February, booked 88 days in advance, depart on a Wednesday or Friday and return on a Saturday
Cheap flight deals from Portland to Chicago
Cheapest
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 August 27, 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 27, 2026.
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/2411:35 am -
Nonstop3h 02m
Sat 10/316:18 pm -
Nonstop2h 33m
Deal found 8/24![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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
Wed 10/287:45 am -
Nonstop2h 10m
Deal found 8/26![Southwest logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/26:30 am -
Nonstop3h 08m
Mon 10/58:00 pm -
Nonstop2h 40m
Deal found 8/26![American Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 -
Nonstop2h 35m
Mon 10/56:40 pm -
Nonstop2h 10m
Deal found 8/24![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/242:33 pm -
1 stop8h 10m
Sat 10/3110:05 am -
1 stop4h 50m
Deal found 8/26![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/246:01 am -
1 stop5h 36m
Tue 10/275:09 pm -
1 stop5h 26m
Deal found 8/27![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/26:00 am -
1 stop5h 53m
Mon 10/57:00 am -
Nonstop2h 41m
Deal found 8/24![United Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 -
1 stop6h 40m
Fri 10/236:40 pm -
Nonstop2h 10m
Deal found 8/25![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/265:40 am -
2 stops8h 25m
Mon 9/286:10 pm -
Nonstop2h 25m
Deal found 8/24![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/107:25 pm -
1 stop5h 06m
Mon 10/127:00 am -
Nonstop2h 41m
Deal found 8/25![United Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 8/24![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 11/193:25 pm -
1 stop7h 00m
Mon 11/235:05 am -
1 stop4h 25m
Deal found 8/24![Southwest logo]()
$328
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 27, 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 27, 2026.
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/146:00 am -
Nonstop2h 57m
Wed 10/213:00 pm -
Nonstop2h 43m
Deal found 8/22![United Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/196:00 am -
1 stop7h 50m
Mon 9/215:48 pm -
1 stop4h 48m
Deal found 8/22![American Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 -
1 stop6h 40m
Fri 10/236:40 pm -
Nonstop2h 10m
Deal found 8/25![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/246:01 am -
2 stops11h 25m
Sat 10/315:27 am -
2 stops9h 28m
Deal found 8/23![Delta logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/166:00 am -
Nonstop2h 57m
Tue 9/225:50 pm -
Nonstop2h 33m
Deal found 8/22![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/2412:45 pm -
1 stop4h 25m
Sat 10/318:30 am -
2 stops8h 05m
Deal found 8/23![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 11/24:47 pm -
2 stops8h 10m
Wed 11/45:27 am -
2 stops9h 35m
Deal found 8/25![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/234:47 pm -
2 stops8h 10m
Sat 10/316:30 am -
1 stop5h 33m
Deal found 8/23![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/165:20 am -
1 stop5h 40m
Wed 10/217:45 am -
Nonstop2h 10m
Deal found 8/27![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/66:00 am -
Nonstop2h 57m
Thu 10/84:00 pm -
1 stop6h 59m
Deal found 8/25![United Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:50 pm -
1 stop4h 27m
Mon 11/167:05 am -
2 stops8h 33m
Deal found 8/25![Delta logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/155:08 pm -
Nonstop2h 57m
Sun 10/186:10 pm -
Nonstop2h 36m
Deal found 8/24![United Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/223:25 pm -
2 stops8h 45m
Sun 10/257:50 pm -
Nonstop2h 10m
Deal found 8/22![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/95:29 pm -
1 stop5h 49m
Fri 9/111:51 pm -
2 stops9h 05m
Deal found 8/24![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/155:20 am -
1 stop4h 30m
Sun 10/185:10 am -
1 stop6h 20m
Deal found 8/24![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/196:00 am -
2 stops11h 14m
Mon 9/215:40 pm -
1 stop4h 37m
Deal found 8/22![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/117:40 am -
Nonstop2h 30m
Tue 9/159:00 am -
2 stops7h 15m
Deal found 8/27![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/175:35 am -
2 stops9h 20m
Mon 10/195:00 am -
1 stop6h 25m
Deal found 8/26![Southwest logo]()
$412
Last-minute flights from Portland to ChicagoDiscover last-minute flight deals from Portland to Chicago. Data last updated August 27, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Chicago. Data last updated August 27, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/97:45 am -
Nonstop2h 35m
Sat 9/123:20 pm -
Nonstop2h 20m
Deal found 8/25![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 8/24![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/95:29 pm -
1 stop5h 49m
Wed 9/161:55 pm -
2 stops9h 01m
Deal found 8/24![Delta logo]()
$332
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/96:00 am -
Nonstop2h 57m
Sat 9/125:50 pm -
Nonstop2h 33m
Deal found 8/25![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/117:40 am -
Nonstop2h 30m
Wed 9/166:50 pm -
Nonstop2h 20m
Deal found 8/24![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 -
1 stop7h 29m
Sat 9/196:10 am -
2 stops8h 51m
Deal found 8/25![Delta logo]()
$322
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/186:00 am -
Nonstop2h 57m
Mon 9/215:50 pm -
Nonstop2h 33m
Deal found 8/24![United Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/186:00 am -
1 stop6h 41m
Mon 9/217:59 pm -
Nonstop2h 48m
Deal found 8/24![American Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/266:30 am -
Nonstop3h 08m
Mon 9/287:59 pm -
Nonstop2h 48m
Deal found 8/24![American Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/2610:44 am -
1 stop8h 13m
Tue 9/297:59 pm -
Nonstop2h 48m
Deal found 8/27![American Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/265:40 am -
1 stop6h 00m
Mon 9/286:10 pm -
Nonstop2h 25m
Deal found 8/24![Southwest logo]()
$318
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/286:00 am -
Nonstop2h 57m
Thu 10/16:59 am -
Nonstop2h 41m
Deal found 8/25![United Airlines logo]()
$334
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 27, 2026.
Search for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Data last updated August 27, 2026.
This JetBlue deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 8/24![JetBlue logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/286:31 pm -
2 stops22h 06m
Deal found 8/26![Multiple Airlines logo]()
$148
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/266:00 am -
Nonstop2h 57m
Deal found 8/27![United Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/237:45 am -
Nonstop2h 35m
Deal found 8/23![Southwest logo]()
$149
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/295:38 pm -
Nonstop3h 21m
Deal found 8/24![American Airlines logo]()
$151
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/292:10 pm -
1 stop7h 46m
Deal found 8/27![Delta logo]()
$159
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/246:01 am -
1 stop5h 36m
Deal found 8/27![Delta logo]()
$159
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/256:00 am -
Nonstop2h 57m
Deal found 8/26![United Airlines logo]()
$160
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/236:30 am -
Nonstop2h 35m
Deal found 8/26![Southwest logo]()
$160
This Priceline deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Sun 9/206:00 am -
1 stop4h 58m
Deal found 8/23![JetBlue logo]()
$162
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/306:30 am -
2 stops8h 59m
Deal found 8/27![Delta logo]()
$164
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/224:57 pm -
Nonstop2h 57m
Deal found 8/23![United Airlines logo]()
$168
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 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $297 (United Airlines) |
One-way from | $135 (JetBlue) |
Popular in | July |
Cheapest in | May |
Average price | $351 |
Good round-trip deal | $353 or less |
Good one-way deal | $233 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 7,457,451 searches. Data last updated August 27, 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 Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 10/14
6:00 am-7:57 am
Nonstop2h 57m
Chicago O'Hare Intl
Wed 10/21
3:00 pm-6:43 pm
Nonstop2h 43m
$297
Quickest round-trip
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 9/16
6:00 am-7:57 am
Nonstop2h 57m
Chicago O'Hare Intl
Tue 9/22
5:50 pm-9:23 pm
Nonstop2h 33m
$297
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Sat 9/19
6:00 am-12:50 pm
1 stop7h 50m
Chicago O'Hare Intl
Mon 9/21
5:48 pm-11:36 pm
1 stop4h 48m
$317
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 10/21
5:40 am-11:20 am
1 stop6h 40m
Chicago Midway
Fri 10/23
6:40 pm-9:50 pm
Nonstop2h 10m
$318
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Sat 10/24
12:45 pm-4:10 pm
1 stop4h 25m
Chicago Midway
Sat 10/31
8:30 am-5:35 pm
2 stops8h 05m
$322
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Sat 10/24
6:01 am-4:26 pm
2 stops11h 25m
Chicago O'Hare Intl
Sat 10/31
5:27 am-3:55 pm
2 stops9h 28m
$327
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Mon 11/2
4:47 pm-11:57 pm
2 stops8h 10m
Chicago O'Hare Intl
Wed 11/4
5:27 am-4:02 pm
2 stops9h 35m
$327
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Fri 10/23
4:47 pm-11:57 pm
2 stops8h 10m
Chicago O'Hare Intl
Sat 10/31
6:30 am-1:03 pm
1 stop5h 33m
$333
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Fri 11/13
4:50 pm-8:17 pm
1 stop4h 27m
Chicago O'Hare Intl
Mon 11/16
7:05 am-4:38 pm
2 stops8h 33m
$333
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 9/9
5:29 pm-10:18 pm
1 stop5h 49m
Chicago O'Hare Intl
Fri 9/11
1:51 pm-11:56 pm
2 stops9h 05m
$342
Showing 1-10 of 34 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, January is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $329). Flying from Portland, Maine to Chicago in December is currently the most expensive (average of $447). 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 27, 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.
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 August 27, 2026.
The most flights from PWM to CHI are scheduled on a Wednesday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Portland, Maine to Chicago?
Airfare is typical for this route at the moment.
Portland, Maine to Chicago flights typically cost between $279 and $401 in October.The cheapest round-trip price found within the last 5 days was $297 on United Airlines (Oct 24-Oct 31).
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.
What is the cheapest day to fly from Portland, Maine to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Portland to Chicago. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Portland, Maine to Chicago flight should consider departing on Friday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 27, 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.
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
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
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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 27, 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 27, 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 27, 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 7,457,451 searches. Data last updated August 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$335 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$374 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$267 | Average$378 | FlexibilityNo cancel fee | On-time63% |