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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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chicago O'Hare Intl are usually found in August or September, 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 29, 2025.

Round-trip from

$257
(Priceline)

One-way from

$124
(Delta)

Popular in

December

Cheapest in

August

Average price

$353

Good round-trip deal

$329 or less

Good one-way deal

$216 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 ($64 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 29, 2025.

This Priceline deal was found by Cheapflights users on 7/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/22:19 pmPWM - ORD
1 stop9h 09mJetBlue
Fri 9/51:36 pmORD - PWM
1 stop7h 26mJetBlue
Deal found 7/27$257
This Delta deal was found by Cheapflights users on 7/29. 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 8/202:36 pmPWM - ORD
1 stop8h 17mDelta
Mon 8/2511:05 amORD - PWM
1 stop5h 43mDelta
Deal found 7/29$258
This American Airlines deal was found by Cheapflights users on 7/29. 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 10/33:28 pmPWM - ORD
Nonstop3h 02mAmerican Airlines
Sun 10/58:24 pmORD - PWM
Nonstop2h 35mAmerican Airlines
Deal found 7/29$259
This United Airlines deal was found by Cheapflights users on 7/28. 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 8/166:10 amPWM - ORD
Nonstop2h 55mUnited Airlines
Tue 8/1910:58 amORD - PWM
Nonstop2h 28mUnited Airlines
Deal found 7/28$267
This Southwest deal was found by Cheapflights users on 7/28. 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 8/269:05 amPWM - ORD
2 stops9h 50mSouthwest
Tue 9/21:50 pmORD - PWM
1 stop7h 35mSouthwest
Deal found 7/28$277

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 29, 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

Tue 9/2

2:19 pm-10:28 pm

1 stop9h 09m

Chicago O'Hare Intl

Fri 9/5

1:36 pm-10:02 pm

1 stop7h 26m

$257

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/20

2:36 pm-9:53 pm

1 stop8h 17m

Chicago O'Hare Intl

Mon 8/25

11:05 am-5:48 pm

1 stop5h 43m

$258

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 10/3

3:28 pm-5:30 pm

Nonstop3h 02m

Chicago O'Hare Intl

Sun 10/5

8:24 pm-11:59 pm

Nonstop2h 35m

$259

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/16

6:10 am-8:05 am

Nonstop2h 55m

Chicago O'Hare Intl

Tue 8/19

10:58 am-2:26 pm

Nonstop2h 28m

$267

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 8/26

9:05 am-5:55 pm

2 stops9h 50m

Chicago O'Hare Intl

Tue 9/2

1:50 pm-10:25 pm

1 stop7h 35m

$277

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 8/26

11:48 am-8:23 pm

2 stops9h 35m

$124

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 12/13

9:45 am-11:55 am

Nonstop3h 10m

$127

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/23

5:45 am-4:25 pm

2 stops11h 40m

$129

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 8/31

6:10 am-10:47 am

1 stop5h 37m

$142

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 9/27

6:15 am-8:11 am

Nonstop2h 56m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 12 results
1
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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 July 25, 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 29, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 58% 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 July 27, 2025.

Travelers seeking maximum savings on their Portland, Maine to Chicago O'Hare Intl Airport flight should consider departing on Thursday 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 29, 2025.

The most flights from PWM to ORD are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 29, 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
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 5 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.

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

    According to our current data, JetBlue ($257), Delta ($258), and American Airlines ($259) offers the cheapest pricing from Portland, Maine to Chicago O'Hare Intl Airport. These flights start at 31% 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 Delta, which is currently one of the cheapest options available, starting at $124. United Airlines flights start at $127 while deals on Southwest start at $129 one-way.

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

    Consider Envoy Air (95%), American Airlines (92%) or SkyWest 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 $689, our data indicates the cheapest price to be $118. 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 Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Beloit
Hoffman Estates
Skokie
Naperville
Des Plaines
Elgin
Arlington Heights
Elk Grove Village
Racine
Rockford
Tinley Park
Orland Park
Merrillville
Downers Grove
Evanston
Lake Geneva
Gurnee
Joliet

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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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$378FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$204Average$316FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$385FlexibilityNo cancel feeOn-time69%

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