$135+ Cheap flights from Portland, ME (PWM) to O'Hare Intl (ORD)
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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Sep 28 — Oct 51
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Portland to O'Hare Intl with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Portland to Chicago O'Hare Intl are usually found in January or April, booked 84 days in advance, depart on a Wednesday or Saturday and return on a Saturday
Cheap flight deals from Portland to O'Hare Intl
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to O'Hare IntlExplore the most affordable flight options available from Portland to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
Explore the most affordable flight options available from Portland to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:35 am -
Nonstop3h 02m
Sat 10/316:18 pm -
Nonstop2h 33m
Deal found 8/24![United Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:28 am -
1 stop5h 42m
Tue 10/278:00 pm -
Nonstop2h 40m
Deal found 8/27![American Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:50 pm -
Nonstop3h 10m
Mon 11/168:25 am -
Nonstop2h 28m
Deal found 8/27![American Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:33 pm -
1 stop8h 10m
Sat 10/3110:05 am -
1 stop4h 50m
Deal found 8/26![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:04 am -
1 stop7h 42m
Tue 10/271:55 pm -
2 stops8h 40m
Deal found 8/27![Delta logo]()
$322
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:25 pm -
1 stop5h 06m
Mon 10/127:00 am -
Nonstop2h 41m
Deal found 8/25![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:30 am -
2 stops7h 29m
Tue 9/221:55 pm -
2 stops8h 22m
Deal found 8/25![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:18 pm -
1 stop6h 00m
Mon 11/165:30 am -
1 stop6h 31m
Deal found 8/27![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
Nonstop2h 57m
Thu 10/16:59 am -
Nonstop2h 41m
Deal found 8/25![United Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:15 am -
1 stop7h 33m
Thu 10/156:10 pm -
Nonstop2h 36m
Deal found 8/26![United Airlines logo]()
$335
Best flights from Portland to O'Hare IntlDiscover carefully curated flight deals from Portland to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
Discover carefully curated flight deals from Portland to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:47 pm -
2 stops8h 10m
Wed 11/45:27 am -
2 stops9h 35m
Deal found 8/25![Delta logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am -
Nonstop2h 57m
Thu 10/84:00 pm -
1 stop6h 59m
Deal found 8/25![United Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:28 am -
2 stops7h 31m
Mon 11/92:44 pm -
2 stops8h 35m
Deal found 8/24![Delta logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:08 pm -
Nonstop2h 57m
Sun 11/810:32 am -
1 stop7h 30m
Deal found 8/27![United Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:42 pm -
1 stop6h 47m
Sat 10/245:27 am -
2 stops9h 35m
Deal found 8/25![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
Nonstop2h 57m
Thu 10/16:10 pm -
Nonstop2h 36m
Deal found 8/29![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:00 am -
Nonstop2h 57m
Wed 10/76:18 pm -
Nonstop2h 36m
Deal found 8/27![United Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 8/28. 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 10/302:09 pm -
1 stop7h 29m
Mon 11/95:05 pm -
2 stops6h 14m
Deal found 8/28![Delta logo]()
$434
This United Airlines deal was found by Cheapflights users on 8/29. 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 11/55:08 pm -
Nonstop2h 57m
Mon 11/94:40 pm -
1 stop5h 41m
Deal found 8/29![United Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:28 am -
2 stops7h 31m
Fri 10/161:55 pm -
2 stops8h 40m
Deal found 8/26![Delta logo]()
$435
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:15 am -
1 stop7h 33m
Mon 10/126:10 pm -
Nonstop2h 36m
Deal found 8/25![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:02 am -
2 stops9h 27m
Sun 9/137:05 am -
1 stop4h 05m
Deal found 8/26![Delta logo]()
$442
Last-minute flights from Portland to O'Hare IntlDiscover last-minute flight deals from Portland to O'Hare Intl. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to O'Hare Intl. Data last updated August 29, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am -
Nonstop2h 57m
Sat 9/125:50 pm -
Nonstop2h 33m
Deal found 8/25![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:59 pm -
2 stops7h 31m
Wed 9/161:55 pm -
2 stops9h 01m
Deal found 8/25![Delta logo]()
$347
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/122:10 pm -
1 stop7h 46m
Tue 9/221:55 pm -
2 stops9h 01m
Deal found 8/25![Delta logo]()
$342
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:38 pm -
Nonstop3h 21m
Fri 9/187:59 pm -
Nonstop2h 48m
Deal found 8/24![American Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:30 am -
1 stop7h 29m
Sat 9/196:10 am -
2 stops8h 51m
Deal found 8/25![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:30 am -
2 stops7h 29m
Tue 9/221:55 pm -
2 stops8h 22m
Deal found 8/25![Delta logo]()
$327
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:06 pm -
1 stop5h 54m
Mon 9/217:59 pm -
Nonstop2h 48m
Deal found 8/27![American Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:08 pm -
Nonstop2h 57m
Thu 10/16:59 am -
Nonstop2h 41m
Deal found 8/27![United Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:30 am -
Nonstop3h 08m
Tue 9/291:10 pm -
Nonstop2h 44m
Deal found 8/27![American Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
Nonstop2h 57m
Thu 10/16:59 am -
Nonstop2h 41m
Deal found 8/25![United Airlines logo]()
$334
One-way flights from Portland to O'Hare IntlSearch for one-way flight options from Portland to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
Search for one-way flight options from Portland to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
This JetBlue deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop6h 24m
Deal found 8/24![JetBlue logo]()
$135
This JetBlue deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am -
1 stop4h 58m
Deal found 8/25![JetBlue logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:31 pm -
2 stops22h 06m
Deal found 8/26![Multiple Airlines logo]()
$148
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:00 am -
Nonstop2h 57m
Deal found 8/27![United Airlines logo]()
$149
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Tue 9/295:38 pm -
Nonstop3h 21m
Deal found 8/27![American Airlines logo]()
$152
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:00 am -
Nonstop2h 57m
Deal found 8/26![United Airlines logo]()
$160
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:30 am -
2 stops8h 59m
Deal found 8/27![Delta logo]()
$164
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:57 pm -
Nonstop2h 57m
Deal found 8/27![United Airlines logo]()
$169
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:09 pm -
1 stop7h 29m
Deal found 8/27![Delta logo]()
$170
Find flight deals from Portland to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to O'Hare Intl (ORD). 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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $297 (United Airlines) |
One-way from | $135 (JetBlue) |
Popular in | December |
Cheapest in | January |
Average price | $393 |
Good round-trip deal | $381 or less |
Good one-way deal | $237 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to O'Hare Intl 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 29, 2026.
Use the filters below to find and compare flights from Portland to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Mon 11/2
4:47 pm-11:57 pm
2 stops8h 10m
Chicago O'Hare Intl
Wed 11/4
5:27 am-4:02 pm
2 stops9h 35m
$327
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 11/4
6:28 am-12:59 pm
2 stops7h 31m
Chicago O'Hare Intl
Mon 11/9
2:44 pm-12:19 am
2 stops8h 35m
$327
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Tue 10/6
6:00 am-7:57 am
Nonstop2h 57m
Chicago O'Hare Intl
Thu 10/8
4:00 pm-11:59 pm
1 stop6h 59m
$354
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 10/22
12:42 pm-6:29 pm
1 stop6h 47m
Chicago O'Hare Intl
Sat 10/24
5:27 am-4:02 pm
2 stops9h 35m
$363
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Fri 11/6
5:08 pm-7:05 pm
Nonstop2h 57m
Chicago O'Hare Intl
Sun 11/8
10:32 am-7:02 pm
1 stop7h 30m
$385
Quickest round-trip
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Mon 9/28
6:00 am-7:57 am
Nonstop2h 57m
Chicago O'Hare Intl
Thu 10/1
6:10 pm-9:46 pm
Nonstop2h 36m
$409
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Mon 10/5
6:00 am-7:57 am
Nonstop2h 57m
Chicago O'Hare Intl
Wed 10/7
6:18 pm-9:54 pm
Nonstop2h 36m
$414
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 11/5
5:08 pm-7:05 pm
Nonstop2h 57m
Chicago O'Hare Intl
Mon 11/9
4:40 pm-11:21 pm
1 stop5h 41m
$419
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 10/8
5:15 am-11:48 am
1 stop7h 33m
Chicago O'Hare Intl
Mon 10/12
6:10 pm-9:46 pm
Nonstop2h 36m
$424
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Fri 10/30
2:09 pm-8:38 pm
1 stop7h 29m
Chicago O'Hare Intl
Mon 11/9
5:05 pm-12:19 am
2 stops6h 14m
$434
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Portland to O'Hare Intl
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to O'Hare Intl 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 Portland, Maine-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland, Maine-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland, Maine-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Portland with our price prediction graph.
PWM-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Chicago O'Hare Intl Airport
Prices
Airlines
How far ahead should I book a flight from Portland, Maine to Chicago O'Hare Intl Airport?
To ensure you get the cheapest price possible for a flight from Portland, Maine to Chicago O'Hare Intl Airport, you should look to book at least 83 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 Portland, Maine to Chicago O'Hare Intl Airport?
Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $293). Flying from Portland, Maine to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $509). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from PWM to ORD?
Find hourly flight availability from Portland to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 29, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 22% on flights from Portland, Maine to Chicago O'Hare Intl Airport by exploring options for tickets at noon.
What is the cheapest day to fly from Portland, Maine to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from Portland to O'Hare Intl. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Portland, Maine to Chicago O'Hare Intl Airport flight should consider departing on Friday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated August 29, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican Airlines from Portland to Chicago O'Hare Intl Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Related info for your journey
Find useful and relevant information for your journey from Portland to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBenton Harbor
Rosemont
Naperville
Lake Geneva
Schaumburg
Oak Brook
Oakbrook Terrace
Delavan
South Holland
Libertyville
Glenview
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
Racine
Great Lakes
Janesville
Gurnee
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
O'Hare Intl flight routes
Other flight options
Other flights from Portland
Popular flights
Alternative routes for Portland to O'Hare Intl
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to O'Hare Intl by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to O'Hare Intl by cabin class
Find flights from Portland to O'Hare Intl, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 29, 2026.
Portland and O'Hare Intl flights
Browse other Portland and O'Hare Intl flight options. Last updated on August 29, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on August 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Portland to O'Hare Intl
Discover the top 3 airlines that operate flights from Portland to O'Hare Intl. 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 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$335 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$374 | FlexibilityNo cancel fee | On-time69% |