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O'Hare Intl

$55+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Feb 10 — Feb 171
Mon 2/10
Mon 2/17
1 adult, Economy
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The best prices from Portland to Chicago O'Hare Intl are usually found in September or May, booked 57 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 February 5, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$244
(Delta)

One-way from

$55
(Frontier)

Popular in

April

Cheapest in

September

Average price

$374

Good round-trip deal

$452 or less

Good one-way deal

$223 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. 8% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 5, 2025.

This United Airlines deal was found by Cheapflights users on 2/5. 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 3/89:30 amPWM - ORD
Nonstop3h 05mUnited Airlines
Sat 3/156:00 pmORD - PWM
Nonstop2h 22mUnited Airlines
Deal found 2/5$244
This Southwest deal was found by Cheapflights users on 2/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/204:20 pmPWM - ORD
1 stop6h 10mSouthwest
Tue 2/257:00 amORD - PWM
1 stop4h 30mSouthwest
Deal found 2/5$249
This American Airlines deal was found by Cheapflights users on 2/5. 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 5/201:59 pmPWM - ORD
1 stop6h 17mAmerican Airlines
Tue 5/278:00 amORD - PWM
Nonstop2h 37mAmerican Airlines
Deal found 2/5$268
This Delta deal was found by Cheapflights users on 2/5. 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 9/312:50 pmPWM - ORD
1 stop6h 50mDelta
Sun 9/76:00 amORD - PWM
1 stop7h 24mDelta
Deal found 2/5$269
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2112:06 pmPWM - ORD
2 stops12h 52mMultiple Airlines
Sun 2/237:13 pmORD - PWM
2 stops21h 25mMultiple Airlines
Deal found 2/4$353
This JetBlue Airways deal was found by Cheapflights users on 2/5. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/293:20 pmPWM - ORD
1 stop8h 00mJetBlue
Sun 6/16:20 amORD - PWM
1 stop7h 05mJetBlue
Deal found 2/5$407
This Trip.com deal was found by Cheapflights users on 2/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/910:48 amPWM - ORD
1 stop9h 36mFrontier
Mon 3/175:01 amORD - PWM
1 stop13h 34mFrontier
Deal found 2/5$520

Find flights from Portland to O'Hare Intl within your budget

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 5, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 3/1

4:46 pm-9:15 pm

1 stop5h 29m

Chicago O'Hare Intl

Mon 3/3

1:40 pm-11:55 pm

2 stops9h 15m

$244

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 2/20

4:20 pm-9:30 pm

1 stop6h 10m

Chicago O'Hare Intl

Tue 2/25

7:00 am-12:30 pm

1 stop4h 30m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 2/25

4:04 pm-6:10 pm

Nonstop3h 06m

Chicago O'Hare Intl

Sun 3/2

3:35 pm-11:15 pm

1 stop6h 40m

$250

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/16

9:43 pm-11:32 pm

1 stop26h 49m

Chicago O'Hare Intl

Sun 5/18

4:15 pm-8:43 pm

1 stop27h 28m

$260

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 5/20

1:59 pm-7:16 pm

1 stop6h 17m

Chicago O'Hare Intl

Tue 5/27

8:00 am-11:37 am

Nonstop2h 37m

$268

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 8/1

12:32 pm-7:11 pm

1 stop7h 39m

Chicago O'Hare Intl

Sun 8/3

8:10 pm-11:35 am

1 stop14h 25m

$300

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/9

6:16 pm-7:40 am

2 stops14h 24m

Chicago O'Hare Intl

Mon 5/12

8:35 am-6:36 pm

1 stop9h 01m

$305

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 6/6

3:20 pm-10:20 pm

1 stop8h 00m

Chicago O'Hare Intl

Thu 6/12

6:00 am-1:23 pm

1 stop6h 23m

$319

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 2/22

10:23 am-7:39 pm

1 stop10h 16m

$55

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 4/9

6:10 am-12:27 pm

1 stop7h 17m

$82

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

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

Travel insights for flights from Portland to O'Hare Intl

Get recent, data-driven insights about flights from Portland to O'Hare Intl including ideal travel times, pricing trends, and more.

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 January 31, 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 57 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, August is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $245). Flying from Portland, Maine to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $323). 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 5, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 80% 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 February 2, 2025.

Travelers seeking maximum savings on their Portland, Maine to Chicago O'Hare Intl Airport flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Portland, Maine to Chicago O'Hare Intl Airport

Explore weekly flight availability from Portland to O'Hare Intl. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 5, 2025.

The most flights from PWM to ORD are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 5, 2025.
See what other customers who have flown with Southwest, Delta and JetBlue from Portland to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,553 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,553 reviews
Southwest
8.1
Very good
4,553 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,406 reviews
Southwest
8.1
Very good
4,553 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,131 reviews
Southwest
8.1
Very good
4,553 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,885 reviews
Southwest
8.1
Very good
4,553 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,553 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 4 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

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

    According to our current data, Delta ($244), Southwest ($249), and United Airlines ($254) offers the cheapest pricing from Portland, Maine to Chicago O'Hare Intl Airport. These flights start at 37% 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 Frontier, which is currently one of the cheapest options available, starting at $55. JetBlue flights start at $82 while deals on Delta start at $109 one-way.

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

    Consider Republic Airways (90%), United Airlines (88%) or Air New Zealand (86%) 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 $835, our data indicates the cheapest price to be $160. The most popular route (Portland - Chicago O'Hare Intl), is priced around $163.

  • 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, August is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $245). Flying from Portland, Maine to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $323). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Naperville
Rosemont
Beloit
Racine
Hoffman Estates
Schaumburg
Rockford
Skokie
Tinley Park
Arlington Heights
Northbrook
Evanston
Des Plaines
Joliet
Orland Park
Merrillville
Kenosha
Lake Geneva
New Buffalo
Glenview

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Top 4 airlines flying from Portland to O'Hare Intl

Discover the top 4 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 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$110FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$350FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$204Average$408FlexibilityNo cancel feeOn-time69%
DeltaCheapest$242Average$360FlexibilityNo cancel feeOn-timeN/A
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