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O'Hare Intl

$108+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Jun 30 — Jul 71
Tue 6/30
Tue 7/7
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 84 days in advance, depart on a Wednesday or Friday and return on a Saturday

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 May 31, 2026.

This American Airlines deal was found by Cheapflights users on 5/27. 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 9/54:07 pm
PWM
-
ORD
Nonstop3h 07m
American Airlines
Wed 9/97:59 pm
ORD
-
PWM
Nonstop2h 48m
American Airlines
Deal found 5/27$292
This American Airlines deal was found by Cheapflights users on 5/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:10 am
PWM
-
ORD
Nonstop3h 11m
American Airlines
Tue 7/289:09 pm
ORD
-
PWM
Nonstop2h 34m
American Airlines
Deal found 5/28$297
This United Airlines deal was found by Cheapflights users on 5/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:16 pm
PWM
-
ORD
1 stop5h 10m
United Airlines
Tue 6/306:08 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Deal found 5/28$302
This American Airlines deal was found by Cheapflights users on 5/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:28 pm
PWM
-
ORD
Nonstop3h 09m
American Airlines
Tue 6/308:00 am
ORD
-
PWM
Nonstop2h 29m
American Airlines
Deal found 5/29$312
This American Airlines deal was found by Cheapflights users on 5/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:07 pm
PWM
-
ORD
Nonstop3h 07m
American Airlines
Mon 9/77:13 pm
ORD
-
PWM
Nonstop2h 35m
American Airlines
Deal found 5/26$313
This Delta deal was found by Cheapflights users on 5/28. 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.
Wed 7/221:12 pm
PWM
-
ORD
1 stop6h 58m
Delta
Tue 7/281:44 pm
ORD
-
PWM
1 stop8h 30m
Delta
Deal found 5/28$317
This United Airlines deal was found by Cheapflights users on 5/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
PWM
-
ORD
Nonstop2h 57m
United Airlines
Tue 8/182:10 pm
ORD
-
PWM
Nonstop2h 44m
United Airlines
Deal found 5/28$318
This United Airlines deal was found by Cheapflights users on 5/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:15 am
PWM
-
ORD
1 stop5h 21m
United Airlines
Sat 6/276:12 pm
ORD
-
PWM
1 stop4h 39m
United Airlines
Deal found 5/28$322
This Delta deal was found by Cheapflights users on 5/30. 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 8/66:30 am
PWM
-
ORD
1 stop7h 28m
Delta
Tue 8/1110:33 am
ORD
-
PWM
2 stops11h 57m
Delta
Deal found 5/30$323
This American Airlines deal was found by Cheapflights users on 5/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:19 pm
PWM
-
ORD
Nonstop3h 26m
American Airlines
Sat 5/307:28 am
ORD
-
PWM
Nonstop2h 35m
American Airlines
Deal found 5/26$324
This Delta deal was found by Cheapflights users on 5/28. 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.
Wed 7/156:25 am
PWM
-
ORD
2 stops8h 49m
Delta
Wed 7/222:07 pm
ORD
-
PWM
2 stops9h 52m
Delta
Deal found 5/28$327

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 May 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$292
(American Airlines)

One-way from

$108
(Delta)

Popular in

December

Cheapest in

September

Average price

$349

Good round-trip deal

$394 or less

Good one-way deal

$225 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. 9% potential increase in price ($38 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 May 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 May 31, 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

Price

Cheapest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 8/6

12:47 pm-6:28 pm

1 stop6h 41m

Chicago O'Hare Intl

Tue 8/11

6:00 pm-12:59 am

1 stop5h 59m

$318

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 10/21

7:25 pm-11:31 pm

1 stop5h 06m

Chicago O'Hare Intl

Sat 10/24

6:06 pm-11:59 pm

1 stop4h 53m

$322

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 9/23

11:35 am-4:30 pm

1 stop5h 55m

Chicago O'Hare Intl

Sat 9/26

1:50 pm-8:51 pm

1 stop6h 01m

$338

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 6/13

2:59 pm-9:48 pm

1 stop7h 49m

Chicago O'Hare Intl

Tue 6/16

11:23 am-5:52 pm

1 stop5h 29m

$349

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 10/14

2:35 pm-9:33 pm

1 stop7h 58m

Chicago O'Hare Intl

Thu 10/15

7:05 am-11:53 am

1 stop3h 48m

$357

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 9/24

11:50 am-4:52 pm

1 stop6h 02m

Chicago O'Hare Intl

Sat 9/26

11:17 am-8:51 pm

2 stops8h 34m

$364

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 8/13

4:47 pm-12:02 am

2 stops8h 15m

Chicago O'Hare Intl

Sat 8/15

1:50 pm-12:59 am

2 stops10h 09m

$370

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/22

6:25 am-1:03 pm

2 stops7h 38m

Chicago O'Hare Intl

Tue 7/28

1:44 pm-11:30 pm

2 stops8h 46m

$382
Quickest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/15

6:00 am-11:04 am

1 stop6h 04m

Chicago O'Hare Intl

Tue 7/21

6:08 pm-9:41 pm

Nonstop2h 33m

$387

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 9/18

12:55 pm-8:55 pm

2 stops9h 00m

Chicago O'Hare Intl

Mon 9/21

12:40 pm-11:17 pm

2 stops9h 37m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/27

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 May.
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?

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, September is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $281). 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 May 31, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 26% on flights from Portland, Maine to Chicago O'Hare Intl Airport by exploring options for tickets at noon.

How much does it cost to fly round-trip from Portland, Maine to Chicago O'Hare Intl Airport?

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 May 31, 2026.
Peruse reviews from past customers who have flown with 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.
United Airlines
7.4
Good
9,768 reviews

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,768 reviews
United Airlines
7.4
Good
9,768 reviews

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
American Airlines
7.1
Good
11,642 reviews
United Airlines
7.4
Good
9,768 reviews

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 5 outbound flights to Chicago O'Hare Intl per day from 2 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 5h 06m. Delta provides one of the quickest options available for as low as $322. There are 897 mi between Portland, Maine and Chicago O'Hare Intl Airport. This flight may include one or multiple stops.

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

    According to our current data, American Airlines ($209), and United Airlines ($229) offers the cheapest pricing from Portland, Maine to Chicago O'Hare Intl Airport. These flights start at 39% 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 Delta, which is currently one of the cheapest options available, starting at $114. American Airlines flights start at $115 while deals on United Airlines start at $134 one-way.

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

    Consider United Airlines (88%), American Airlines (85%) or Envoy Air (85%) 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 $967, our data indicates the cheapest price to be $137. The most popular route (Portland - Chicago O'Hare Intl), is priced around $297.

  • 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 $281). 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.

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
Rosemont
Schaumburg
Benton Harbor
Naperville
Lake Geneva
Delavan
Oakbrook Terrace
Gurnee
Downers Grove
Des Plaines
Hoffman Estates
Oak Brook
South Holland
Libertyville
Warrenville
Rockford
Great Lakes
Northbrook
Waukegan
Willowbrook

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Alternative routes for Portland to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Boston to O'Hare Intl flights
Boston to Midway flights
Bangor to O'Hare Intl flights
Portland to Midway flights
Boston to Rockford flights

Top 2 airlines flying from Portland to O'Hare Intl

Discover the top 2 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 May 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$311FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$360FlexibilityNo cancel feeOn-time69%

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