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O'Hare Intl

$107+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
May 4 — May 111
Mon 5/4
Mon 5/11
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 Thursday 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 April 4, 2026.

This Expedia deal was found by Cheapflights users on 4/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/132:30 pm
PWM
-
ORD
1 stop8h 00m
JetBlue
Tue 6/166:00 am
ORD
-
PWM
1 stop5h 30m
JetBlue
Deal found 4/1$239
This KAYAK deal was found by Cheapflights users on 4/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/132:30 pm
PWM
-
ORD
1 stop8h 00m
JetBlue
Wed 6/176:00 am
ORD
-
PWM
1 stop6h 35m
JetBlue
Deal found 4/1$251
This Expedia deal was found by Cheapflights users on 4/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:30 pm
PWM
-
ORD
1 stop8h 00m
JetBlue
Tue 6/306:00 am
ORD
-
PWM
1 stop5h 30m
JetBlue
Deal found 4/1$268
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/227:19 pm
PWM
-
ORD
Nonstop3h 26m
American Airlines
Mon 5/258:11 am
ORD
-
PWM
Nonstop2h 35m
American Airlines
Deal found 3/31$269
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/16:01 pm
PWM
-
ORD
Nonstop3h 13m
American Airlines
Fri 5/87:44 pm
ORD
-
PWM
Nonstop2h 38m
American Airlines
Deal found 4/2$272
This American Airlines deal was found by Cheapflights users on 4/4. 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 8/216:15 am
PWM
-
ORD
Nonstop3h 01m
American Airlines
Wed 8/268:02 am
ORD
-
PWM
Nonstop2h 32m
American Airlines
Deal found 4/4$278
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/226:54 pm
PWM
-
ORD
1 stop6h 44m
American Airlines
Sun 5/243:15 pm
ORD
-
PWM
Nonstop2h 34m
American Airlines
Deal found 3/31$279
This KAYAK deal was found by Cheapflights users on 3/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/222:40 pm
PWM
-
ORD
1 stop8h 15m
JetBlue
Tue 7/286:00 am
ORD
-
PWM
1 stop5h 21m
JetBlue
Deal found 3/30$284
This Delta deal was found by Cheapflights users on 3/31. 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 7/226:57 pm
PWM
-
ORD
1 stop5h 56m
Delta
Tue 7/282:07 pm
ORD
-
PWM
2 stops9h 52m
Delta
Deal found 3/31$294

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 April 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(Expedia)

One-way from

$107
(KAYAK)

Popular in

December

Cheapest in

September

Average price

$343

Good round-trip deal

$353 or less

Good one-way deal

$186 or less
Provider with most accurate pricing for Portland-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago O'Hare Intl flights.
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From Portland to Chicago O'Hare Intl
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One-way flight from Portland to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 4, 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
Quickest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/1

9:00 am-10:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Fri 5/8

5:56 pm-9:19 pm

Nonstop2h 23m

$269

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 9/11

7:35 pm-11:21 pm

1 stop4h 46m

Chicago O'Hare Intl

Sun 9/13

6:25 pm-10:01 pm

Nonstop2h 36m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/14

12:55 pm-4:29 pm

1 stop4h 34m

Chicago O'Hare Intl

Tue 5/19

7:00 am-12:00 pm

1 stop4h 00m

$289

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/1

11:35 am-9:25 pm

2 stops10h 50m

Chicago O'Hare Intl

Fri 5/8

6:31 pm-12:43 am

1 stop5h 12m

$294

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 5/5

11:35 am-10:21 pm

2 stops11h 46m

Chicago O'Hare Intl

Fri 5/8

6:31 pm-12:43 am

1 stop5h 12m

$294

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/16

2:38 pm-9:56 pm

1 stop8h 18m

Chicago O'Hare Intl

Tue 5/19

2:00 pm-12:43 am

2 stops9h 43m

$294

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 5/19

6:25 am-4:55 pm

2 stops11h 30m

Chicago O'Hare Intl

Sat 5/23

1:44 pm-12:43 am

2 stops9h 59m

$300

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 4/26

4:43 pm-8:40 pm

1 stop4h 57m

Chicago O'Hare Intl

Wed 4/29

6:21 pm-12:46 am

1 stop5h 25m

$309

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/8

1:12 pm-7:10 pm

1 stop6h 58m

Chicago O'Hare Intl

Sun 7/12

8:52 am-4:01 pm

1 stop6h 09m

$345

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 6/2

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Wed 6/3

6:18 pm-9:51 pm

Nonstop2h 33m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

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 April.
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 April 2, 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 84 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 January is currently the most expensive (average of $123). 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 April 4, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 37% on flights from Portland, Maine to Chicago O'Hare Intl Airport by exploring options for tickets in the afternoon.

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 April 4, 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
9,542 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,542 reviews
United Airlines
7.4
Good
9,542 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,559 reviews
United Airlines
7.4
Good
9,542 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 2h 56m. United Airlines provides one of the quickest options available for as low as $269. 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 ($224) 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 $115 one-way.

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

    Consider Qatar Airways (87%), Republic Airways (84%) or United Airlines (79%) 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 $1,071, our data indicates the cheapest price to be $124. The most popular route (Portland - Chicago O'Hare Intl), is priced around $269.

  • 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 January is currently the most expensive (average of $123). 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
Lake Geneva
Hoffman Estates
Delavan
Downers Grove
Des Plaines
Elgin
Oakbrook Terrace
South Holland
Elk Grove Village
Libertyville
Warrenville
Oak Brook
Bridgeview
Beloit
Great Lakes
Lansing

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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
Boston to Rockford flights
Portland to Midway 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 April 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$304FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$224Average$354FlexibilityNo cancel feeOn-time69%

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