$167+ Cheap flights from Chicago (CHI) to Portland, ME (PWM)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Oct 9 — Oct 161
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Portland 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 Chicago to Portland are usually found in May or April, booked 87 days in advance, depart on a Wednesday or Saturday and return on a Wednesday
Cheap flight deals from Chicago to Portland
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to PortlandExplore the most affordable flight options available from Chicago to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 9, 2026.
Explore the most affordable flight options available from Chicago to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 9, 2026.
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:59 pm -
Nonstop2h 44m
Sat 10/315:45 pm -
Nonstop3h 10m
Deal found 9/5![American Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 9/7. 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 10/244:10 pm -
Nonstop2h 15m
Wed 10/286:00 pm -
Nonstop2h 35m
Deal found 9/7![Southwest logo]()
$337
This United Airlines deal was found by Cheapflights users on 9/8. 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 10/176:59 am -
Nonstop2h 41m
Wed 10/215:15 am -
1 stop7h 33m
Deal found 9/8![United Airlines logo]()
$347
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:59 pm -
Nonstop2h 48m
Mon 10/55:37 pm -
1 stop5h 23m
Deal found 9/8![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Fri 10/26:10 pm -
Nonstop2h 36m
Wed 10/76:00 am -
Nonstop2h 57m
Deal found 9/8![United Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 10/174:10 pm -
Nonstop2h 15m
Wed 10/216:00 pm -
Nonstop2h 35m
Deal found 9/8![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 9/8. 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 10/176:05 pm -
1 stop5h 05m
Tue 10/204:15 pm -
1 stop6h 28m
Deal found 9/8![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 11/147:35 am -
1 stop6h 10m
Tue 11/173:25 pm -
1 stop7h 00m
Deal found 9/8![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 9/9. 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.
Sat 10/176:20 am -
2 stops8h 42m
Sat 10/244:47 pm -
1 stop4h 43m
Deal found 9/9![Delta logo]()
$362
This Southwest deal was found by Cheapflights users on 9/7. 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 10/248:40 am -
1 stop5h 10m
Tue 10/275:40 am -
2 stops9h 45m
Deal found 9/7![Southwest logo]()
$362
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Fri 10/96:10 pm -
Nonstop2h 36m
Sat 10/176:55 pm -
1 stop5h 26m
Deal found 9/8![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 9/7. 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.
Fri 10/236:40 pm -
Nonstop2h 15m
Mon 10/265:20 am -
1 stop4h 30m
Deal found 9/7![Southwest logo]()
$363
Best flights from Chicago to PortlandDiscover carefully curated flight deals from Chicago to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
Discover carefully curated flight deals from Chicago to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:50 am -
Nonstop2h 26m
Sat 11/75:08 pm -
Nonstop2h 57m
Deal found 9/4![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 11/147:35 am -
1 stop6h 10m
Tue 11/173:25 pm -
1 stop7h 00m
Deal found 9/8![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 9/8. 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 10/281:23 pm -
1 stop8h 38m
Sat 10/3112:43 pm -
2 stops9h 44m
Deal found 9/8![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 9/8. 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 10/176:20 am -
2 stops8h 42m
Sat 10/242:09 pm -
1 stop6h 02m
Deal found 9/8![Delta logo]()
$362
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:10 pm -
Nonstop2h 15m
Mon 10/266:30 am -
Nonstop2h 35m
Deal found 9/5![Southwest logo]()
$371
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:10 pm -
Nonstop2h 36m
Wed 10/146:00 am -
Nonstop2h 57m
Deal found 9/6![United Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:40 pm -
Nonstop2h 15m
Mon 10/266:30 am -
Nonstop2h 35m
Deal found 9/4![Southwest logo]()
$405
This Delta deal was found by Cheapflights users on 9/8. 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.
Thu 10/295:27 am -
2 stops9h 35m
Sun 11/14:47 pm -
1 stop4h 43m
Deal found 9/8![Delta logo]()
$419
This Southwest deal was found by Cheapflights users on 9/6. 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.
Mon 9/286:10 pm -
Nonstop2h 25m
Tue 9/296:15 pm -
1 stop5h 10m
Deal found 9/6![Southwest logo]()
$411
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:35 am -
1 stop8h 25m
Tue 9/2911:50 am -
1 stop7h 29m
Deal found 9/4![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 9/7. 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.
Sat 9/262:00 pm -
2 stops8h 56m
Wed 9/306:30 am -
2 stops11h 07m
Deal found 9/7![Delta logo]()
$441
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:51 pm -
1 stop6h 09m
Tue 9/296:30 am -
2 stops7h 29m
Deal found 9/5![Delta logo]()
$442
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:19 pm -
2 stops9h 37m
Wed 9/306:02 am -
2 stops11h 13m
Deal found 9/4![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:33 am -
1 stop8h 27m
Wed 10/146:28 am -
2 stops7h 19m
Deal found 9/5![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:09 am -
2 stops8h 52m
Thu 10/226:28 am -
1 stop7h 40m
Deal found 9/6![Delta logo]()
$462
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:30 am -
1 stop6h 31m
Mon 11/164:50 pm -
2 stops8h 04m
Deal found 9/4![Delta logo]()
$463
This Delta deal was found by Cheapflights users on 9/8. 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 10/179:29 am -
1 stop5h 33m
Thu 10/226:01 am -
1 stop6h 53m
Deal found 9/8![Delta logo]()
$508
Last-minute flights from Chicago to PortlandDiscover last-minute flight deals from Chicago to Portland. Data last updated September 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Portland. Data last updated September 9, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:59 pm -
Nonstop2h 48m
Wed 10/285:45 pm -
Nonstop3h 10m
Deal found 9/8![American Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Fri 10/26:10 pm -
Nonstop2h 36m
Wed 10/76:00 am -
Nonstop2h 57m
Deal found 9/8![United Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:59 pm -
Nonstop2h 48m
Mon 10/55:37 pm -
1 stop5h 23m
Deal found 9/8![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Fri 10/96:10 pm -
Nonstop2h 36m
Sat 10/176:55 pm -
1 stop5h 26m
Deal found 9/8![United Airlines logo]()
$363
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:59 pm -
Nonstop2h 44m
Sat 10/315:45 pm -
Nonstop3h 10m
Deal found 9/5![American Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 9/8. 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 10/176:59 am -
Nonstop2h 41m
Wed 10/215:15 am -
1 stop7h 33m
Deal found 9/8![United Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 10/174:10 pm -
Nonstop2h 15m
Wed 10/216:00 pm -
Nonstop2h 35m
Deal found 9/8![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 9/8. 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 10/176:05 pm -
1 stop5h 05m
Tue 10/204:15 pm -
1 stop6h 28m
Deal found 9/8![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 9/9. 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.
Sat 10/1711:09 am -
2 stops8h 52m
Sat 10/316:01 am -
1 stop7h 12m
Deal found 9/9![Delta logo]()
$362
This Southwest deal was found by Cheapflights users on 9/7. 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.
Fri 10/236:40 pm -
Nonstop2h 15m
Mon 10/265:20 am -
1 stop4h 30m
Deal found 9/7![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 9/7. 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 10/244:10 pm -
Nonstop2h 15m
Tue 10/276:00 pm -
Nonstop2h 35m
Deal found 9/7![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/7. 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 10/246:45 am -
1 stop7h 05m
Wed 10/286:00 pm -
Nonstop2h 35m
Deal found 9/7![Southwest logo]()
$347
One-way flights from Chicago to PortlandSearch for one-way flight options from Chicago to Portland. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
Search for one-way flight options from Chicago to Portland. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:11 am -
2 stops33h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$167
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:18 pm -
Nonstop2h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![United Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 9/6. 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.
Tue 10/67:45 am -
Nonstop2h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:41 pm -
2 stops22h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$173
This Delta deal was found by Cheapflights users on 9/9. 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.
Sat 10/106:10 am -
1 stop6h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:28 pm -
2 stops41h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:00 am -
2 stops32h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:04 pm -
2 stops20h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:42 pm -
2 stops22h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$183
This Delta deal was found by Cheapflights users on 9/9. 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.
Tue 11/106:49 am -
2 stops8h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$184
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/308:00 pm -
Nonstop2h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$185
This Southwest deal was found by Cheapflights users on 9/7. 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.
Fri 10/306:40 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$185
Find flight deals from Chicago to Portland
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Portland (PWM). 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 September 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $337 (American Airlines) |
One-way from | $167 (Kiwi.com) |
Popular in | July |
Cheapest in | May |
Average price | $348 |
Good round-trip deal | $321 or less |
Good one-way deal | $196 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Portland 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 September 9, 2026.
Use the filters below to find and compare flights from Chicago to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Thu 12/10
10:05 am-4:39 pm
1 stop5h 34m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
Quickest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Sat 10/10
6:10 pm-9:46 pm
Nonstop2h 36m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Wed 11/4
6:00 am-12:10 pm
1 stop5h 10m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Tue 10/6
6:00 pm-12:10 am
1 stop5h 10m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Sat 12/5
7:00 am-1:07 pm
1 stop5h 07m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Tue 12/8
3:59 pm-11:34 pm
1 stop6h 35m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Tue 11/3
1:20 pm-9:45 pm
2 stops7h 25m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$184
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 3/3
3:00 pm-10:23 pm
1 stop6h 23m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 12/2
2:39 pm-11:20 pm
1 stop7h 41m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 10/7
8:36 am-4:47 pm
1 stop7h 11m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from Chicago to Portland
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 Chicago to Portland in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Portland, Maine flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Portland, Maine 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 Chicago-Portland, Maine 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 Chicago to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Chicago with our price prediction graph.
CHI-PWM
ORD-PWM
MDW-PWM
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 Chicago to Portland
CHI-PWM
ORD-PWM
MDW-PWM
What is the cheapest month to book a flight from Chicago to Portland, Maine?
Currently, May is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $316). Flying from Chicago to Portland, Maine in July is currently the most expensive (average of $438). 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 CHI to PWM?
Find hourly flight availability from Chicago to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 9, 2026.
One of the essential ways to save on airfare from Chicago to Portland, Maine is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 38% on airfare.
How much does it cost to fly round-trip from Chicago to Portland, Maine?
Airfare is typical for this route at the moment.
Chicago to Portland, Maine flights typically cost between $304 and $438 in October.The cheapest round-trip price found within the last 5 days was $337 on American Airlines (Oct 17-Oct 31).
How often are flights from Chicago to Portland delayed?
About 19% of weekly flights between Chicago and Portland have experienced delays in the past year, with the average delay time being 135 minutes.
What is the most punctual flight time for Chicago to Portland flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Portland flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 17% of flights being delayed.
How far ahead should I book a flight from Chicago to Portland, Maine?
The best time to book flights from Chicago to Portland, Maine is 89 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Chicago to Portland, Maine?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Portland. Price data was last updated on July 4, 2026.
Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated September 9, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Portland. 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 Portland?
Book flights to Portland if you plan to visit one of these locationsNorth Conway
Lewiston
Brunswick
Conway
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Chicago and Portland flights
Browse other Chicago and Portland flight options. Last updated on September 9, 2026.
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Top 2 airlines flying from Chicago to Portland
Discover the top 2 airlines that operate flights from Chicago to Portland. 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 September 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$376 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$229 | Average$366 | FlexibilityNo cancel fee | On-time71% |