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O'Hare Intl

$99+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Mar 21 — Mar 281
Sat 3/21
Sat 3/28
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chicago O'Hare Intl are usually found in September or January, booked 52 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap flight deals from Portland to O'Hare Intl

Cheapest flights from Portland to O'Hare Intl
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 February 19, 2026.

This United Airlines deal was found by Cheapflights users on 2/17. 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 3/285:45 am
PWM
-
ORD
Nonstop3h 12m
United Airlines
Tue 3/3111:53 am
ORD
-
PWM
Nonstop2h 29m
United Airlines
Deal found 2/17$209
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Thu 4/97:36 pm
PWM
-
ORD
1 stop5h 07m
United Airlines
Sun 4/126:10 pm
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 2/18$219
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:37 pm
PWM
-
ORD
Nonstop3h 13m
American Airlines
Sun 11/81:42 pm
ORD
-
PWM
Nonstop2h 25m
American Airlines
Deal found 2/19$229
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:17 am
PWM
-
ORD
Nonstop3h 17m
American Airlines
Tue 3/316:40 am
ORD
-
PWM
1 stop4h 34m
American Airlines
Deal found 2/18$230
This United Airlines deal was found by Cheapflights users on 2/16. 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.
Tue 5/124:45 pm
PWM
-
ORD
Nonstop2h 58m
United Airlines
Wed 5/135:56 pm
ORD
-
PWM
Nonstop2h 23m
United Airlines
Deal found 2/16$231
This Delta deal was found by Cheapflights users on 2/17. 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 7/226:50 pm
PWM
-
ORD
1 stop6h 05m
Delta
Tue 7/281:15 pm
ORD
-
PWM
2 stops9h 44m
Delta
Deal found 2/17$234
This American Airlines deal was found by Cheapflights users on 2/17. 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 4/35:40 pm
PWM
-
ORD
Nonstop3h 10m
American Airlines
Mon 4/63:16 pm
ORD
-
PWM
1 stop6h 34m
American Airlines
Deal found 2/17$239
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 6/256:25 pm
PWM
-
ORD
Nonstop3h 09m
United Airlines
Sun 6/286:25 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Deal found 2/19$242
This American Airlines deal was found by Cheapflights users on 2/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/195:40 pm
PWM
-
ORD
Nonstop3h 10m
American Airlines
Mon 3/238:02 pm
ORD
-
PWM
Nonstop2h 32m
American Airlines
Deal found 2/15$248
This Delta deal was found by Cheapflights users on 2/17. 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 5/124:48 pm
PWM
-
ORD
1 stop4h 31m
Delta
Sat 5/167:00 am
ORD
-
PWM
1 stop3h 57m
Delta
Deal found 2/17$249
This American Airlines deal was found by Cheapflights users on 2/16. 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.
Wed 3/117:10 am
PWM
-
ORD
1 stop6h 27m
American Airlines
Sat 3/148:02 pm
ORD
-
PWM
Nonstop2h 32m
American Airlines
Deal found 2/16$250

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 February 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$99
(Delta)

Popular in

December

Cheapest in

September

Average price

$370

Good round-trip deal

$371 or less

Good one-way deal

$178 or less
Provider with most accurate pricing for Portland-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago O'Hare Intl flights.
Search Deals
From Portland to Chicago O'Hare Intl
Search Deals
One-way flight from Portland to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Portland to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Portland to Chicago O'Hare Intl.
Search Deals

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 2,558,603 searches. Data last updated February 19, 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

Portland

Fly to

O'Hare Intl

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/23

6:25 pm-8:34 pm

Nonstop3h 09m

Chicago O'Hare Intl

Mon 5/25

6:18 pm-9:51 pm

Nonstop2h 33m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 4/3

6:13 pm-8:23 pm

Nonstop3h 10m

Chicago O'Hare Intl

Mon 4/6

6:10 pm-9:40 pm

Nonstop2h 30m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 4/9

7:36 pm-11:43 pm

1 stop5h 07m

Chicago O'Hare Intl

Mon 4/13

6:10 pm-9:40 pm

Nonstop2h 30m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 7/2

7:15 pm-11:21 pm

1 stop5h 06m

Chicago O'Hare Intl

Mon 7/20

6:25 pm-9:58 pm

Nonstop2h 33m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/8

6:00 am-7:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 5/13

6:15 pm-11:59 pm

1 stop4h 44m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 7/11

5:20 am-9:36 am

1 stop5h 16m

Chicago O'Hare Intl

Mon 7/13

6:25 pm-9:58 pm

Nonstop2h 33m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/14

12:52 pm-6:13 pm

1 stop6h 21m

Chicago O'Hare Intl

Mon 5/18

7:00 am-11:57 am

1 stop3h 57m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/22

6:50 pm-11:55 pm

1 stop6h 05m

Chicago O'Hare Intl

Tue 7/28

11:10 am-6:01 pm

1 stop5h 51m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/22

12:52 pm-6:13 pm

1 stop6h 21m

Chicago O'Hare Intl

Mon 5/25

7:00 am-11:57 am

1 stop3h 57m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/16

12:52 pm-8:34 pm

2 stops8h 42m

$104

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/15

Showing 1-10 of 17 results
1
2

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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

How far ahead should I book a flight from Portland, Maine to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Portland to O'Hare Intl. Price data was last updated on February 18, 2026.

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 52 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, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $91). Flying from Portland, Maine to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $134). 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 February 19, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 59% on flights from Portland, Maine to Chicago O'Hare Intl Airport by exploring options for tickets in the afternoon.

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 February 19, 2026.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American 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.
Delta
7.9
Good
8,212 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,212 reviews
Delta
7.9
Good
8,212 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,321 reviews
Delta
7.9
Good
8,212 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,313 reviews
Delta
7.9
Good
8,212 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • What airport do you fly from for flights from Portland to Chicago O'Hare Intl?

    Most people fly from Portland (PWM) if they book a flight from Portland to Chicago O'Hare Intl. On average, Portland has 4 outbound flights to Chicago O'Hare Intl per day from 3 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

  • How long is the flight from Portland, Maine to Chicago O'Hare Intl Airport?

    A quick flight from Portland, Maine to Chicago O'Hare Intl Airport can take about 3h 09m. United Airlines provides one of the quickest options available for as low as $209. There are 897 mi between Portland, Maine and Chicago O'Hare Intl Airport. All flights are typically nonstop.

  • What are the cheapest airlines flying from Portland, Maine to Chicago O'Hare Intl Airport round-trip?

    According to our current data, Delta ($114), American Airlines ($209), and United Airlines ($226) offers the cheapest pricing from Portland, Maine to Chicago O'Hare Intl Airport. These flights start at 67% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Portland, Maine to Chicago O'Hare Intl Airport one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $104. Delta flights start at $114 while deals on United Airlines start at $115 one-way.

  • What are the most reliable airlines from Portland, Maine to Chicago O'Hare Intl Airport?

    Consider American Airlines (100%), Envoy Air (100%) or Republic Airways (97%) when booking your flight. These represent the most reliable airlines when flying from Portland, Maine to Chicago O'Hare Intl Airport.

  • What are the cheapest flights from Portland, Maine to Chicago O'Hare Intl Airport?

    Looking for the cheapest flight from Portland, Maine to Chicago O'Hare Intl Airport? While on average our users pay $877, our data indicates the cheapest price to be $143. The most popular route (Portland - Chicago O'Hare Intl), is priced around $209.

  • Can I find deals for flights from Portland to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Portland to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to O'Hare Intl.

  • Can I find deals for business class flights from Portland to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Portland to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Chicago O'Hare Intl Airport?

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $91). Flying from Portland, Maine to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $134). 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.

See more FAQs

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 locations
Schaumburg
Rosemont
Gurnee
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Elgin
Downers Grove
Elk Grove Village
Skokie
Libertyville
Oakbrook Terrace
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville

Browse thousands of different options on Cheapflights for your next trip

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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 2,558,603 searches. Data last updated February 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$114Average$373FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$307FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$371FlexibilityNo cancel feeOn-time69%

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