HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
O'Hare Intl

$96+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
nov. 26 — dic. 31
mié. 11/26
mié. 12/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to O'Hare Intl with Cheapflights

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”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 octubre 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$239
(Delta)

One-way from

$96
(Priceline)

Popular in

December

Cheapest in

September

Average price

$330

Good round-trip deal

$334 or less

Good one-way deal

$188 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. 12% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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

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 octubre 27, 2025.

This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/36:15 amPWM - ORD
2 stops10h 05mDelta
sáb. 12/610:45 amORD - PWM
2 stops9h 06mDelta
Deal found 10/27$239
This United Airlines deal was found by Cheapflights users on 10/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/246:00 amPWM - ORD
1 stop5h 45mUnited Airlines
jue. 11/2710:53 amORD - PWM
Nonstop2h 19mUnited Airlines
Deal found 10/25$243
This Delta deal was found by Cheapflights users on 10/25. 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.
vie. 11/144:53 pmPWM - ORD
1 stop4h 36mDelta
lun. 11/1711:19 amORD - PWM
2 stops11h 00mDelta
Deal found 10/25$244
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/52:34 pmPWM - ORD
1 stop8h 05mDelta
lun. 12/81:01 pmORD - PWM
1 stop8h 22mDelta
Deal found 10/26$249
This Delta deal was found by Cheapflights users on 10/25. 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.
dom. 11/96:00 amPWM - ORD
1 stop5h 13mDelta
jue. 11/136:00 amORD - PWM
2 stops9h 07mDelta
Deal found 10/25$254
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/65:00 pmPWM - ORD
Nonstop2h 55mUnited Airlines
lun. 11/1010:53 amORD - PWM
Nonstop2h 19mUnited Airlines
Deal found 10/26$259
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/66:00 amPWM - ORD
1 stop7h 16mDelta
mar. 11/186:45 amORD - PWM
1 stop4h 23mDelta
Deal found 10/26$269
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/212:46 pmPWM - ORD
2 stops12h 12mDelta
dom. 11/166:45 amORD - PWM
1 stop4h 23mDelta
Deal found 10/26$274
This United Airlines deal was found by Cheapflights users on 10/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/66:00 amPWM - ORD
1 stop8h 09mUnited Airlines
mar. 12/95:50 pmORD - PWM
Nonstop2h 27mUnited Airlines
Deal found 10/25$278
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/55:00 pmPWM - ORD
1 stop6h 26mDelta
dom. 11/96:45 amORD - PWM
1 stop4h 23mDelta
Deal found 10/26$279
This American Airlines deal was found by Cheapflights users on 10/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/316:00 amPWM - ORD
1 stop7h 03mAmerican Airlines
lun. 11/31:40 pmORD - PWM
Nonstop2h 25mAmerican Airlines
Deal found 10/24$283
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/66:01 amPWM - ORD
2 stops7h 39mDelta
dom. 11/96:45 amORD - PWM
1 stop4h 23mDelta
Deal found 10/26$284

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 octubre 27, 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

jue. 3/19

4:50 pm-8:38 pm

1 stop4h 48m

Chicago O'Hare Intl

mar. 3/24

10:35 am-4:15 pm

1 stop4h 40m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

vie. 11/14

4:53 pm-8:29 pm

1 stop4h 36m

Chicago O'Hare Intl

lun. 11/17

8:55 am-4:07 pm

1 stop6h 12m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

sáb. 12/13

6:00 am-3:20 pm

2 stops10h 20m

Chicago O'Hare Intl

lun. 12/15

2:30 pm-11:21 pm

2 stops7h 51m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

mié. 12/3

6:15 am-4:42 pm

2 stops11h 27m

Chicago O'Hare Intl

sáb. 12/6

6:45 am-4:00 pm

2 stops8h 15m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

jue. 2/5

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

dom. 2/8

8:52 am-2:31 pm

1 stop4h 39m

$247

PortlandChicago

PWM - ORD

PWMORD

Portland

vie. 12/5

2:34 pm-12:01 am

2 stops10h 27m

Chicago O'Hare Intl

lun. 12/8

11:15 am-11:59 pm

2 stops11h 44m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

mié. 3/18

2:35 pm-8:38 pm

2 stops7h 03m

Chicago O'Hare Intl

mar. 3/24

10:35 am-9:59 pm

2 stops10h 24m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

dom. 11/9

6:00 am-10:13 am

1 stop5h 13m

Chicago O'Hare Intl

jue. 11/13

6:00 am-4:07 pm

2 stops9h 07m

$254

PortlandChicago

PWM - ORD

PWMORD

Portland

lun. 11/10

4:53 pm-12:01 am

2 stops8h 08m

Chicago O'Hare Intl

vie. 11/14

10:46 am-11:54 pm

2 stops12h 08m

$259

PortlandChicago

PWM - ORD

PWMORD

Portland

jue. 11/6

1:27 pm-6:49 pm

1 stop6h 22m

Chicago O'Hare Intl

lun. 11/17

5:23 am-12:30 pm

1 stop6h 07m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 23 results
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 October.
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 October 24, 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, November is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $88). Flying from Portland, Maine to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $135). 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 octubre 27, 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 October 19, 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 octubre 27, 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
7,996 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,996 reviews
Delta
7.9
Good
7,996 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,997 reviews
Delta
7.9
Good
7,996 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,033 reviews
Delta
7.9
Good
7,996 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 6 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. Delta provides one of the quickest options available for as low as $247. 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 ($204), and United Airlines ($229) offers the cheapest pricing from Portland, Maine to Chicago O'Hare Intl Airport. These flights start at 66% 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 Air New Zealand (74%), American Airlines (70%) or Republic Airways (60%) 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 $1,077, our data indicates the cheapest price to be $137. 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, November is the cheapest month in which you can book a flight from Portland, Maine to Chicago O'Hare Intl Airport (average of $88). Flying from Portland, Maine to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $135). 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
Skokie
Des Plaines
Gurnee
Hoffman Estates
Elgin
Oak Brook
Elk Grove Village
Beloit
Rockford
Naperville
Racine
Downers Grove
Orland Park
Merrillville
Bridgeview
Warrenville
Joliet
Waukegan

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 octubre 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$377FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$204Average$305FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$377FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.