$145+ Cheap flights from O'Hare Intl (ORD) 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Nov 18 — Nov 251
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 May or April, booked 47 days in advance, depart on a Wednesday or Saturday 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 October 19, 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 October 19, 2026.
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/112:34 pm -
2 stops9h 59m
Sat 12/122:00 pm -
1 stop6h 25m
Deal found 10/14![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/112:34 pm -
2 stops9h 59m
Wed 12/911:40 am -
2 stops7h 46m
Deal found 10/14![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/103:36 pm -
1 stop6h 45m
Tue 11/175:08 pm -
Nonstop2h 57m
Deal found 10/14![United Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Wed 11/186:18 pm -
Nonstop2h 33m
Sat 11/218:45 am -
Nonstop3h 01m
Deal found 10/18![United Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/236:00 pm -
1 stop5h 19m
Wed 12/26:12 am -
1 stop7h 57m
Deal found 10/14![Delta logo]()
$341
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/105:30 am -
1 stop6h 31m
Tue 11/1711:39 am -
2 stops8h 26m
Deal found 10/14![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/136:18 pm -
Nonstop2h 34m
Sun 11/155:08 pm -
Nonstop2h 57m
Deal found 10/14![United Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 10/18. 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.
Wed 11/185:30 am -
2 stops10h 08m
Sat 11/214:50 pm -
1 stop4h 27m
Deal found 10/18![Delta logo]()
$358
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 October 19, 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 October 19, 2026.
This Delta deal was found by Cheapflights users on 10/16. 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 11/143:00 pm -
1 stop7h 31m
Tue 11/175:18 pm -
1 stop6h 00m
Deal found 10/16![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Wed 11/2510:50 am -
Nonstop2h 26m
Fri 12/44:47 pm -
Nonstop3h 13m
Deal found 10/18![United Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:30 am -
1 stop5h 32m
Mon 11/95:18 pm -
1 stop6h 00m
Deal found 10/14![Delta logo]()
$391
This Delta deal was found by Cheapflights users on 10/16. 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.
Wed 12/211:39 am -
2 stops10h 41m
Sat 12/126:00 am -
2 stops11h 43m
Deal found 10/16![Delta logo]()
$407
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Sun 11/156:18 pm -
Nonstop2h 33m
Sat 11/215:08 pm -
Nonstop2h 57m
Deal found 10/18![United Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:30 am -
1 stop6h 31m
Mon 11/236:00 am -
2 stops11h 41m
Deal found 10/15![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 10/18. 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.
Wed 11/255:30 am -
1 stop6h 31m
Fri 12/412:49 pm -
1 stop6h 37m
Deal found 10/18![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 10/16. 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 11/75:27 am -
2 stops9h 35m
Wed 11/1112:45 pm -
1 stop6h 45m
Deal found 10/16![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 10/249:59 am -
2 stops10h 02m
Sat 11/72:09 pm -
1 stop6h 02m
Deal found 10/15![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 10/17. 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 11/2512:38 pm -
2 stops9h 53m
Wed 12/212:49 pm -
1 stop6h 37m
Deal found 10/17![Delta logo]()
$469
Last-minute flights from O'Hare Intl to PortlandDiscover last-minute flight deals from O'Hare Intl to Portland. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Portland. Data last updated October 19, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/18. 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 11/710:50 am -
Nonstop2h 26m
Tue 11/175:08 pm -
Nonstop2h 57m
Deal found 10/18![United Airlines logo]()
$361
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/103:36 pm -
1 stop6h 45m
Tue 11/175:08 pm -
Nonstop2h 57m
Deal found 10/14![United Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/105:30 am -
1 stop6h 31m
Tue 11/1711:39 am -
2 stops8h 26m
Deal found 10/14![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/136:18 pm -
Nonstop2h 34m
Sun 11/155:08 pm -
Nonstop2h 57m
Deal found 10/14![United Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Wed 11/186:18 pm -
Nonstop2h 33m
Sat 11/218:45 am -
Nonstop3h 01m
Deal found 10/18![United Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 10/18. 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.
Wed 11/185:30 am -
2 stops10h 08m
Sat 11/214:50 pm -
1 stop4h 27m
Deal found 10/18![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/236:00 pm -
1 stop5h 19m
Wed 12/26:12 am -
1 stop7h 57m
Deal found 10/14![Delta logo]()
$341
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 October 19, 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 October 19, 2026.
This American Airlines deal was found by Cheapflights users on 10/16. 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.
Mon 11/168:25 am -
Nonstop2h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![American Airlines logo]()
$145
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Mon 11/163:36 pm -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![United Airlines logo]()
$155
This Delta deal was found by Cheapflights users on 10/17. 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.
Mon 11/1611:35 am -
2 stops10h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Delta logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Mon 11/167:50 pm -
2 stops36h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Multiple Airlines logo]()
$175
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/510:50 am -
Nonstop2h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/117:35 pm -
2 stops41h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:27 am -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$187
This United Airlines deal was found by Cheapflights users on 10/17. 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 1/211:59 am -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![United Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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.
Thu 11/57:50 pm -
2 stops43h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Sun 12/133:30 pm -
2 stops24h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Multiple Airlines logo]()
$191
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/76:20 am -
2 stops8h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$192
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 1/1411:00 am -
Nonstop2h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$193
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 October 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $331 (United Airlines) |
One-way from | $145 (American Airlines) |
Popular in | November |
Cheapest in | May |
Average price | $451 |
Good round-trip deal | $462 or less |
Good one-way deal | $225 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 October 19, 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 11/14
6:15 pm-9:48 pm
Nonstop2h 33m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$145
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Thu 1/7
11:00 am-2:44 pm
Nonstop2h 44m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$145
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Tue 11/17
5:30 am-1:01 pm
1 stop6h 31m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Thu 1/7
2:30 pm-11:06 pm
1 stop7h 36m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Mon 11/16
11:19 am-11:31 pm
2 stops11h 12m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$160
Quickest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Thu 11/5
10:50 am-2:16 pm
Nonstop2h 26m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 11/13
6:18 pm-9:52 pm
Nonstop2h 34m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$195
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 11/4
6:18 pm-9:51 pm
Nonstop2h 33m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$218
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 11/4
8:36 am-4:47 pm
1 stop7h 11m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$227
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Sat 10/24
2:00 pm-9:01 pm
1 stop6h 01m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$228
Showing 1-10 of 20 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 October.
| 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 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, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $319). Flying from Chicago O'Hare Intl Airport to Portland, Maine in November is currently the most expensive (average of $495). 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 October 19, 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 in the evening, which can drop the price by up to 26% 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 October 10, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland, Maine flight should consider departing on Saturday at noon 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.
How often are flights from Chicago to Portland delayed?
About 18% of weekly flights between Chicago and Portland have experienced delays in the past year, with the average delay time being 139 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 October 19, 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.
Food
6.7
Overall
7.3
Boarding
7.7
Entertainment
7.1
Crew
8.1
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Overall
7.3
Boarding
7.7
Entertainment
7.1
Crew
8.1
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Overall
7.3
Boarding
7.7
Entertainment
7.1
Crew
8.1
Comfort
7.3
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 locationsLewiston
North Conway
Brunswick
Conway
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from O'Hare Intl
Popular flights
Portland flight routes
Alternative routes for O'Hare Intl to Portland
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Portland by cabin class
Find flights from O'Hare Intl to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Portland flights
Browse other O'Hare Intl and Portland flight options. Last updated on October 19, 2026.
Other flights from O'Hare Intl
Browse through other flights departing from O'Hare Intl. Flights are based on user searches made on Cheapflights and were last updated on October 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 19, 2026.
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 October 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$370 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$389 | FlexibilityNo cancel fee | On-time69% |