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O'Hare Intl

$100+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Dec 25 — Jan 11
Thu 12/25
Thu 1/1
1 adult, Economy
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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”

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Cheapflights Tip: The best prices from Portland to Chicago O'Hare Intl are usually found in September or August, booked 83 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap 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 November 25, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$278
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$353

Good round-trip deal

$374 or less

Good one-way deal

$233 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
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Highest demand for flights based on searches. 5% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Portland to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Portland to Chicago O'Hare Intl.
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Find 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 November 25, 2025.

This Delta deal was found by Cheapflights users on 11/24. 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.
Tue 12/96:00 amPWM - ORD
2 stops8h 50mDelta
Sat 12/1310:45 amORD - PWM
2 stops10h 38mDelta
Deal found 11/24$279
This United Airlines deal was found by Cheapflights users on 11/23. 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 12/53:20 pmPWM - ORD
1 stop5h 47mUnited Airlines
Mon 12/85:50 pmORD - PWM
Nonstop2h 27mUnited Airlines
Deal found 11/23$289
This Delta deal was found by Cheapflights users on 11/25. 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 12/34:43 pmPWM - ORD
1 stop6h 47mDelta
Mon 12/87:00 amORD - PWM
1 stop5h 54mDelta
Deal found 11/25$299
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:16 amPWM - ORD
2 stops11h 55mMultiple Airlines
Sun 12/146:00 amORD - PWM
1 stop27h 41mMultiple Airlines
Deal found 11/24$300
This United Airlines deal was found by Cheapflights users on 11/24. 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.
Fri 12/124:25 pmPWM - ORD
Nonstop3h 10mUnited Airlines
Sun 12/148:50 amORD - PWM
1 stop4h 29mUnited Airlines
Deal found 11/24$301
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:21 amPWM - ORD
2 stops26h 55mMultiple Airlines
Sun 12/1412:09 pmORD - PWM
1 stop19h 57mMultiple Airlines
Deal found 11/24$316
This American Airlines deal was found by Cheapflights users on 11/23. 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 12/35:17 pmPWM - ORD
1 stop5h 02mAmerican Airlines
Sun 12/76:05 amORD - PWM
1 stop4h 32mAmerican Airlines
Deal found 11/23$324
This Kiwi.com deal was found by Cheapflights users on 11/23. 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 12/2411:16 amPWM - ORD
2 stops28h 46mMultiple Airlines
Wed 1/79:19 amORD - PWM
1 stop24h 02mMultiple Airlines
Deal found 11/23$327
This Delta deal was found by Cheapflights users on 11/24. 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 12/34:43 pmPWM - ORD
1 stop4h 55mDelta
Thu 12/47:00 amORD - PWM
1 stop5h 54mDelta
Deal found 11/24$329

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 November 25, 2025.
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

Wed 1/28

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sat 1/31

11:00 am-2:39 pm

Nonstop2h 39m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/14

6:00 am-1:08 pm

2 stops8h 08m

Chicago O'Hare Intl

Wed 1/14

6:25 pm-12:20 am

1 stop4h 55m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 2/27

5:45 am-7:57 am

Nonstop3h 12m

Chicago O'Hare Intl

Sun 3/8

4:30 pm-10:51 pm

1 stop5h 21m

$288

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 1/8

6:00 am-10:53 am

1 stop5h 53m

Chicago O'Hare Intl

Sun 1/11

11:00 am-2:39 pm

Nonstop2h 39m

$288

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 1/8

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Thu 1/15

8:52 am-2:31 pm

1 stop4h 39m

$289

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 12/6

6:00 am-1:09 pm

1 stop8h 09m

Chicago O'Hare Intl

Mon 12/8

5:50 pm-9:17 pm

Nonstop2h 27m

$289

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/2

7:30 pm-11:44 pm

1 stop5h 14m

Chicago O'Hare Intl

Mon 1/5

6:00 am-2:40 pm

1 stop7h 40m

$295

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/14

5:57 pm-10:34 pm

1 stop5h 37m

Chicago O'Hare Intl

Thu 1/15

7:01 am-1:45 pm

1 stop5h 44m

$296

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 3/6

5:59 pm-10:05 pm

1 stop5h 06m

Chicago O'Hare Intl

Sun 3/8

6:30 am-12:00 pm

1 stop4h 30m

$299

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 1/26

2:35 pm-9:35 pm

1 stop8h 00m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 16 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland, Maine-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 November 21, 2025.

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, April is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $89). 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 November 25, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 55% on flights from Portland, Maine to Chicago O'Hare Intl Airport by exploring options for tickets in the evening.

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 November 25, 2025.

Travelers seeking maximum savings on their Portland, Maine to Chicago O'Hare Intl Airport flight should consider departing on Saturday evenings when fares are most often at their lowest. Tuesday at noon 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 November 25, 2025.
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
7,998 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

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
7,998 reviews
Delta
7.9
Good
7,998 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

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
9,046 reviews
Delta
7.9
Good
7,998 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

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
11,038 reviews
Delta
7.9
Good
7,998 reviews

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

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 2 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 08m. United Airlines provides one of the quickest options available for as low as $279. 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, Delta ($124), American Airlines ($209), and United Airlines ($228) offers the cheapest pricing from Portland, Maine to Chicago O'Hare Intl Airport. These flights start at 65% lower than the current average price 3 months from now.

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

    Consider Republic Airways (85%), United Airlines (79%) or Air New Zealand (68%) 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 $964, our data indicates the cheapest price to be $125. 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, April is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $89). 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
Elgin
Skokie
Delavan
Oak Brook
Des Plaines
Elk Grove Village
Lake Geneva
Downers Grove
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

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 November 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$373FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$305FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$228Average$374FlexibilityNo cancel feeOn-time69%

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