$139+ Cheap flights from O'Hare Intl (ORD) to Portland, ME (PWM)
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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl 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 O'Hare Intl to Portland are usually found in March or May, booked 47 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
Cheap flight deals from O'Hare Intl to Portland
Cheapest
Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to PortlandExplore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/266:10 pm -
Nonstop2h 36m
Wed 9/306:00 am -
Nonstop2h 57m
Deal found 8/17![United Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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
Tue 10/67:58 am -
Nonstop3h 02m
Deal found 8/19![United Airlines logo]()
$308
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/266:06 pm -
1 stop4h 53m
Sat 10/35:15 am -
1 stop5h 23m
Deal found 8/18![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/257:59 pm -
Nonstop2h 48m
Mon 9/285:29 pm -
1 stop6h 46m
Deal found 8/17![American Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/185:50 pm -
Nonstop2h 33m
Fri 9/256:00 am -
Nonstop2h 57m
Deal found 8/21![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 12/18:45 am -
1 stop7h 00m
Sat 12/126:00 am -
2 stops11h 24m
Deal found 8/17![Delta logo]()
$322
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/196:22 pm -
1 stop4h 37m
Mon 9/216:00 am -
Nonstop2h 57m
Deal found 8/19![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/178:29 am -
2 stops11h 31m
Sat 10/314:47 pm -
2 stops8h 10m
Deal found 8/17![Delta logo]()
$327
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:00 pm -
1 stop5h 45m
Fri 9/252:03 pm -
Nonstop2h 56m
Deal found 8/21![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/102:10 pm -
Nonstop2h 44m
Sat 9/196:00 am -
Nonstop2h 57m
Deal found 8/16![United Airlines logo]()
$331
Best flights from O'Hare Intl to PortlandDiscover carefully curated flight deals from O'Hare Intl to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from O'Hare Intl to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/2410:05 am -
1 stop4h 50m
Sat 11/72:09 pm -
1 stop6h 02m
Deal found 8/16![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/196:22 pm -
1 stop4h 37m
Mon 9/216:00 am -
Nonstop2h 57m
Deal found 8/19![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/196:30 am -
1 stop5h 32m
Thu 10/2212:42 pm -
2 stops12h 15m
Deal found 8/18![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/31:51 pm -
2 stops9h 05m
Wed 10/76:04 am -
2 stops11h 54m
Deal found 8/20![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/113:40 pm -
1 stop6h 49m
Tue 9/1511:35 am -
2 stops9h 55m
Deal found 8/21![Delta logo]()
$332
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/115:50 pm -
Nonstop2h 33m
Tue 9/154:57 pm -
Nonstop2h 57m
Deal found 8/21![United Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/163:00 pm -
Nonstop2h 43m
Sun 10/186:00 am -
Nonstop2h 57m
Deal found 8/20![United Airlines logo]()
$445
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/115:30 am -
1 stop6h 34m
Sat 9/196:30 am -
2 stops11h 07m
Deal found 8/20![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/16:40 am -
1 stop5h 27m
Sat 9/54:47 pm -
2 stops8h 10m
Deal found 8/20![Delta logo]()
$372
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/175:50 pm -
Nonstop2h 33m
Mon 9/216:00 am -
Nonstop2h 57m
Deal found 8/17![United Airlines logo]()
$471
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/21:55 pm -
2 stops9h 01m
Tue 10/64:15 pm -
1 stop6h 28m
Deal found 8/20![Delta logo]()
$379
Last-minute flights from O'Hare Intl to PortlandDiscover last-minute flight deals from O'Hare Intl to Portland. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Portland. Data last updated August 21, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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.
Sun 9/69:56 am -
1 stop5h 37m
Thu 9/1012:24 pm -
1 stop6h 04m
Deal found 8/17![American Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/102:10 pm -
Nonstop2h 44m
Sat 9/196:00 am -
Nonstop2h 57m
Deal found 8/16![United Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/185:50 pm -
Nonstop2h 33m
Fri 9/256:00 am -
Nonstop2h 57m
Deal found 8/21![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:00 pm -
1 stop5h 45m
Fri 9/252:03 pm -
Nonstop2h 56m
Deal found 8/21![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/196:22 pm -
1 stop4h 37m
Mon 9/216:00 am -
Nonstop2h 57m
Deal found 8/19![United Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/257:59 pm -
Nonstop2h 48m
Mon 9/286:00 pm -
1 stop5h 35m
Deal found 8/16![American Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/266:10 pm -
Nonstop2h 36m
Wed 9/306:00 am -
Nonstop2h 57m
Deal found 8/17![United Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/266:06 pm -
1 stop4h 53m
Sat 10/35:15 am -
1 stop5h 23m
Deal found 8/18![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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.
Mon 9/287:59 pm -
Nonstop2h 48m
Fri 10/26:30 am -
Nonstop3h 08m
Deal found 8/17![American Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/295:30 am -
2 stops9h 09m
Tue 10/66:28 am -
1 stop7h 40m
Deal found 8/18![Delta logo]()
$322
One-way flights from O'Hare Intl to PortlandSearch for one-way flight options from O'Hare Intl to Portland. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from O'Hare Intl to Portland. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/274:44 pm -
1 stop15h 24m
Deal found 8/16![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/156:20 am -
2 stops37h 59m
Deal found 8/16![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/176:30 am -
2 stops32h 54m
Deal found 8/17![Multiple Airlines logo]()
$148
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/306:18 pm -
Nonstop2h 36m
Deal found 8/17![United Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/136:00 am -
2 stops26h 08m
Deal found 8/16![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/208:04 am -
2 stops32h 47m
Deal found 8/18![Multiple Airlines logo]()
$154
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/156:30 am -
1 stop7h 08m
Deal found 8/18![United Airlines logo]()
$159
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/166:10 pm -
Nonstop2h 36m
Deal found 8/16![United Airlines logo]()
$160
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/186:45 am -
2 stops8h 13m
Deal found 8/17![Delta logo]()
$164
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/64:00 pm -
1 stop6h 59m
Deal found 8/19![United Airlines logo]()
$169
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/168:29 am -
1 stop6h 33m
Deal found 8/18![Delta logo]()
$170
Find flight deals from O'Hare Intl to Portland
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) 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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $297 (United Airlines) |
One-way from | $139 (Kiwi.com) |
Popular in | December |
Cheapest in | March |
Average price | $385 |
Good round-trip deal | $299 or less |
Good one-way deal | $215 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 August 21, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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
Sat 10/24
10:05 am-3:55 pm
1 stop4h 50m
Portland
Sat 11/7
2:09 pm-7:11 pm
1 stop6h 02m
$317
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Mon 10/19
6:30 am-1:02 pm
1 stop5h 32m
Portland
Thu 10/22
12:42 pm-11:57 pm
2 stops12h 15m
$322
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Sat 9/19
6:22 pm-11:59 pm
1 stop4h 37m
Portland
Mon 9/21
6:00 am-7:57 am
Nonstop2h 57m
$326
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Sat 10/3
1:51 pm-11:56 pm
2 stops9h 05m
Portland
Wed 10/7
6:04 am-4:58 pm
2 stops11h 54m
$327
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 9/11
3:40 pm-11:29 pm
1 stop6h 49m
Portland
Tue 9/15
11:35 am-8:30 pm
2 stops9h 55m
$332
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 9/11
5:30 am-1:04 pm
1 stop6h 34m
Portland
Sat 9/19
6:30 am-4:37 pm
2 stops11h 07m
$368
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Tue 9/1
6:40 am-1:07 pm
1 stop5h 27m
Portland
Sat 9/5
4:47 pm-11:57 pm
2 stops8h 10m
$372
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 10/2
1:55 pm-11:56 pm
2 stops9h 01m
Portland
Tue 10/6
4:15 pm-9:43 pm
1 stop6h 28m
$379
Quickest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 9/11
5:50 pm-9:23 pm
Nonstop2h 33m
Portland
Tue 9/15
4:57 pm-6:54 pm
Nonstop2h 57m
$424
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 10/16
3:00 pm-6:43 pm
Nonstop2h 43m
Portland
Sun 10/18
6:00 am-7:57 am
Nonstop2h 57m
$445
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from O'Hare Intl 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 O'Hare Intl to Portland in August.
| 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 O'Hare Intl Airport-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 O'Hare Intl Airport-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Portland, Maine flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-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 O'Hare Intl Airport-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 O'Hare Intl to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from O'Hare Intl with our price prediction graph.
ORD-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 O'Hare Intl Airport to Portland
Prices
Airlines
Delays
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Portland, Maine?
To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Portland, Maine, you should look to book at least 46 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?
Currently, March is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $300). Flying from Chicago O'Hare Intl Airport to Portland, Maine in December is currently the most expensive (average of $501). 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 ORD to PWM?
Find hourly flight availability from O'Hare Intl 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 August 21, 2026.
When flying from Chicago O'Hare Intl Airport to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 20% versus a flight in the afternoon.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Portland, Maine?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Portland. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland, Maine flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 138 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?
Tuesday 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.
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 August 21, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Portland, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Food
6.7
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Crew
8.1
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Food
6.7
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Crew
8.1
Comfort
7.3
Boarding
7.7
Entertainment
7.1
Food
6.7
Overall
7.4
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl 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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Top 2 airlines flying from O'Hare Intl to Portland
Discover the top 2 airlines that operate flights from O'Hare Intl 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 August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$368 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$368 | FlexibilityNo cancel fee | On-time69% |