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O'Hare Intl

$67+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chicago O'Hare Intl are usually found in October 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 September 11, 2025.

Round-trip from

$222
(Delta)

One-way from

$67
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$319

Good round-trip deal

$309 or less

Good one-way deal

$202 or less
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. 14% potential increase in price ($62 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 September 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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/11. 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 10/225:42 amPWM - ORD
1 stop5h 29mDelta
Wed 10/2910:30 amORD - PWM
2 stops10h 49mDelta
Deal found 9/11$222
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/34:57 pmPWM - ORD
Nonstop2h 51mUnited Airlines
Sun 10/56:10 pmORD - PWM
Nonstop2h 34mUnited Airlines
Deal found 9/11$235
This JetBlue deal was found by Cheapflights users on 9/10. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:30 amPWM - ORD
1 stop5h 40mJetBlue
Mon 10/206:45 amORD - PWM
1 stop5h 37mJetBlue
Deal found 9/10$237
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 10/85:41 pmPWM - ORD
1 stop6h 49mUnited Airlines
Fri 10/2411:05 amORD - PWM
Nonstop2h 28mUnited Airlines
Deal found 9/10$241
This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 10/15:50 amPWM - ORD
1 stop7h 00mSouthwest
Thu 10/21:50 pmORD - PWM
1 stop9h 15mSouthwest
Deal found 9/10$242
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/176:14 amPWM - ORD
Nonstop2h 54mAmerican Airlines
Mon 10/207:58 amORD - PWM
Nonstop2h 30mAmerican Airlines
Deal found 9/10$243
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/34:57 pmPWM - ORD
Nonstop2h 51mUnited Airlines
Sat 10/412:00 pmORD - PWM
1 stop5h 38mUnited Airlines
Deal found 9/11$245
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/410:30 amPWM - ORD
1 stop5h 25mUnited Airlines
Sun 10/56:10 pmORD - PWM
Nonstop2h 34mUnited Airlines
Deal found 9/10$246
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/155:21 pmPWM - ORD
1 stop7h 29mAmerican Airlines
Tue 10/2110:05 amORD - PWM
1 stop9h 09mAmerican Airlines
Deal found 9/10$250
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/76:00 amPWM - ORD
1 stop7h 03mAmerican Airlines
Tue 10/145:00 amORD - PWM
1 stop5h 14mAmerican Airlines
Deal found 9/10$251
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/167:00 amPWM - ORD
1 stop5h 08mAmerican Airlines
Mon 10/207:58 amORD - PWM
Nonstop2h 30mAmerican Airlines
Deal found 9/10$253

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 September 11, 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

Fri 10/3

4:57 pm-6:48 pm

Nonstop2h 51m

Chicago O'Hare Intl

Sun 10/5

6:10 pm-9:44 pm

Nonstop2h 34m

$235

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 11/7

4:48 pm-8:23 pm

1 stop4h 35m

Chicago O'Hare Intl

Tue 11/11

7:00 am-1:50 pm

1 stop5h 50m

$245

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 10/3

7:25 pm-11:15 pm

1 stop4h 50m

Chicago O'Hare Intl

Sat 10/4

5:05 pm-11:20 pm

1 stop5h 15m

$255

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 11/9

4:53 pm-8:29 pm

1 stop4h 36m

Chicago O'Hare Intl

Wed 11/12

5:32 am-12:30 pm

1 stop5h 58m

$258

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 10/31

2:38 pm-9:39 pm

1 stop8h 01m

Chicago O'Hare Intl

Sun 11/2

5:20 am-12:32 pm

1 stop6h 12m

$258

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 10/23

11:30 am-6:14 pm

2 stops7h 44m

Chicago O'Hare Intl

Sun 10/26

7:10 am-12:00 pm

1 stop3h 50m

$273

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 10/18

12:00 pm-4:34 pm

1 stop5h 34m

Chicago O'Hare Intl

Sun 10/19

7:10 am-12:00 pm

1 stop3h 50m

$278

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 9/26

6:25 pm-8:25 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 9/28

6:10 pm-9:44 pm

Nonstop2h 34m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 9/25

6:25 pm-8:25 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sat 9/27

6:10 pm-9:44 pm

Nonstop2h 34m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 10/17

6:14 am-8:05 am

Nonstop2h 51m

Chicago O'Hare Intl

Sun 10/19

11:05 am-2:33 pm

Nonstop2h 28m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 22 results
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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 August 29, 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, 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 $321). 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 September 11, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 57% 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 September 7, 2025.

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

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 September 11, 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
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 8 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 2h 51m. United Airlines provides one of the quickest options available for as low as $235. 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 ($200), and United Airlines ($235) offers the cheapest pricing from Portland, Maine to Chicago O'Hare Intl Airport. These flights start at 67% 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 Envoy Air (100%), American Airlines (85%) or Republic Airways (73%) 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 $858, our data indicates the cheapest price to be $135. The most popular route (Portland - Chicago O'Hare Intl), is priced around $133.

  • 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 $321). 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
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Beloit
Racine
Rockford
Orland Park
Oak Brook
Downers Grove
Naperville
Elk Grove Village
Evanston
Merrillville
Bridgeview
Warrenville

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$378FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$200Average$307FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$235Average$389FlexibilityNo cancel feeOn-time69%

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