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O'Hare Intl

$124+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 August, 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 July 3, 2025.

Round-trip from

$231
(American Airlines)

One-way from

$124
(JetBlue)

Popular in

December

Cheapest in

September

Average price

$341

Good round-trip deal

$352 or less

Good one-way deal

$178 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. 15% potential increase in price ($68 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 July 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 July 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/3. 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 8/1312:08 pmPWM - ORD
Nonstop3h 02mAmerican Airlines
Wed 8/206:45 pmORD - PWM
Nonstop2h 43mAmerican Airlines
Deal found 7/3$231
This Delta deal was found by Cheapflights users on 7/3. 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.
Sat 8/236:00 amPWM - ORD
1 stop7h 17mDelta
Sun 8/317:15 amORD - PWM
1 stop3h 53mDelta
Deal found 7/3$235
This JetBlue deal was found by Cheapflights users on 7/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/66:10 amPWM - ORD
1 stop6h 08mJetBlue
Mon 8/116:15 amORD - PWM
1 stop6h 08mJetBlue
Deal found 7/1$237
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:14 amPWM - ORD
Nonstop2h 51mUnited Airlines
Sat 9/66:00 amORD - PWM
1 stop6h 22mUnited Airlines
Deal found 6/30$239
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/95:50 amPWM - ORD
2 stops13h 05mSouthwest
Sat 9/131:30 pmORD - PWM
1 stop7h 30mSouthwest
Deal found 7/1$262

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 July 3, 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 8/13

12:08 pm-2:10 pm

Nonstop3h 02m

Chicago O'Hare Intl

Wed 8/20

6:45 pm-10:28 pm

Nonstop2h 43m

$231

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/23

6:00 am-12:17 pm

1 stop7h 17m

Chicago O'Hare Intl

Sun 8/31

7:15 am-12:08 pm

1 stop3h 53m

$235

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/6

6:10 am-11:18 am

1 stop6h 08m

Chicago O'Hare Intl

Mon 8/11

6:15 am-1:23 pm

1 stop6h 08m

$237

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 8/31

6:14 am-8:05 am

Nonstop2h 51m

Chicago O'Hare Intl

Sat 9/6

6:00 am-1:22 pm

1 stop6h 22m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 9/9

5:50 am-5:55 pm

2 stops13h 05m

Chicago O'Hare Intl

Sat 9/13

1:30 pm-10:00 pm

1 stop7h 30m

$262

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 8/15

2:19 pm-10:28 pm

1 stop9h 09m

$124

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 9/24

6:00 am-10:05 am

1 stop5h 05m

$126

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 9/5

3:28 pm-5:30 pm

Nonstop3h 02m

$130

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/13

9:05 am-9:30 pm

2 stops13h 25m

$131

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 7/12

6:58 pm-3:43 pm

1 stop21h 45m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 13 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 June 27, 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 $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 July 3, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 75% 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 June 29, 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 July 3, 2025.

The most flights from PWM to ORD are scheduled on a Thursday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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 July 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,916 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 4 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, American Airlines ($231), Delta ($235), and JetBlue ($237) offers the cheapest pricing from Portland, Maine to Chicago O'Hare Intl Airport. These flights start at 38% 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 JetBlue, which is currently one of the cheapest options available, starting at $124. Delta flights start at $126 while deals on United Airlines start at $130 one-way.

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

    Consider SkyWest Airlines (94%), Envoy Air (93%) or American Airlines (90%) 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 $869, our data indicates the cheapest price to be $129. The most popular route (Portland - Chicago O'Hare Intl), is priced around $183.

  • 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Schaumburg
Hoffman Estates
Rosemont
Beloit
Skokie
Des Plaines
Arlington Heights
Elgin
Naperville
Orland Park
Elk Grove Village
Racine
Rockford
Tinley Park
Merrillville
Bridgeview
Glenview
Lake Geneva
Joliet
Waukegan

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$32Average$115FlexibilityNo cancel feeOn-time62%
DeltaCheapest$124Average$378FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$186Average$312FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$374FlexibilityNo cancel feeOn-time69%

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