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O'Hare Intl

$87+ Cheap flights from Portland (PDX) 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Mar 30 — Apr 61
Sun 3/30
Sun 4/6
1 adult, Economy
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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
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Cheapflights Tip: The best prices from Portland to Chicago O'Hare Intl are usually found in January or August, booked 40 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

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 (PDX) 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 March 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$247
(Alaska Airlines)

One-way from

$87
(Cheapflightsfares)

Popular in

March

Cheapest in

January

Average price

$512

Good round-trip deal

$365 or less

Good one-way deal

$190 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 ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 25, 2025.

This Delta deal was found by Cheapflights users on 3/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/35:26 pmPDX - ORD
1 stop5h 27mDelta
Sat 5/105:15 pmORD - PDX
1 stop7h 00mDelta
Deal found 3/24$247
This United Airlines deal was found by Cheapflights users on 3/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/911:59 pmPDX - ORD
Nonstop3h 57mUnited Airlines
Wed 5/148:45 amORD - PDX
1 stop8h 13mUnited Airlines
Deal found 3/24$248
This Hawaiian Airlines deal was found by Cheapflights users on 3/24. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/25:51 pmPDX - ORD
Nonstop4h 05mHawaiian Airlines
Thu 6/57:00 amORD - PDX
Nonstop4h 23mHawaiian Airlines
Deal found 3/24$249
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/165:40 pmPDX - ORD
1 stop9h 45mSpirit Airlines
Tue 5/2011:50 amORD - PDX
1 stop6h 55mSpirit Airlines
Deal found 3/24$251
This American Airlines deal was found by Cheapflights users on 3/23. 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 4/2311:52 pmPDX - ORD
Nonstop4h 05mAmerican Airlines
Mon 4/288:20 pmORD - PDX
Nonstop4h 42mAmerican Airlines
Deal found 3/23$252
This CheapOair deal was found by Cheapflights users on 3/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/259:38 pmPDX - ORD
1 stop12h 51mMultiple Airlines
Sun 4/277:12 pmORD - PDX
1 stop16h 08mMultiple Airlines
Deal found 3/24$255
This Alaska Airlines deal was found by Cheapflights users on 3/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/169:47 amPDX - ORD
1 stop6h 08mAlaska Airlines
Tue 4/229:00 amORD - PDX
1 stop6h 50mAlaska Airlines
Deal found 3/24$256
This Sun Country Air deal was found by Cheapflights users on 3/24. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/16:30 pmPDX - ORD
1 stop22h 39mSun Country Air
Sun 5/48:05 pmORD - PDX
1 stop14h 32mSun Country Air
Deal found 3/24$300
This CheapOair deal was found by Cheapflights users on 3/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/316:45 amPDX - ORD
1 stop15h 59mFrontier
Wed 4/98:00 amORD - PDX
1 stop8h 22mFrontier
Deal found 3/24$301
This Southwest deal was found by Cheapflights users on 3/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/65:10 amPDX - ORD
2 stops9h 35mSouthwest
Mon 6/95:25 pmORD - PDX
1 stop8h 50mSouthwest
Deal found 3/24$367

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 March 25, 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

PDX - ORD

PDXORD

Portland

Sat 5/3

5:26 pm-12:53 am

1 stop5h 27m

Chicago O'Hare Intl

Sat 5/10

5:15 pm-10:15 pm

1 stop7h 00m

$247

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 5/9

11:59 pm-5:56 am

Nonstop3h 57m

Chicago O'Hare Intl

Wed 5/14

8:45 am-2:58 pm

1 stop8h 13m

$248

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 6/2

5:51 pm-11:56 pm

Nonstop4h 05m

Chicago O'Hare Intl

Thu 6/5

7:00 am-9:23 am

Nonstop4h 23m

$249

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 5/16

5:40 pm-5:25 am

1 stop9h 45m

Chicago O'Hare Intl

Tue 5/20

11:50 am-4:45 pm

1 stop6h 55m

$251

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 4/23

11:52 pm-5:57 am

Nonstop4h 05m

Chicago O'Hare Intl

Mon 4/28

8:20 pm-11:02 pm

Nonstop4h 42m

$252

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 7/2

5:35 pm-11:39 pm

Nonstop4h 04m

Chicago O'Hare Intl

Fri 7/11

7:00 am-9:25 am

Nonstop4h 25m

$254

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 4/25

9:38 pm-12:29 pm

1 stop12h 51m

Chicago O'Hare Intl

Sun 4/27

7:12 pm-9:20 am

1 stop16h 08m

$255

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 5/1

6:30 pm-7:09 pm

1 stop22h 39m

Chicago O'Hare Intl

Sun 5/4

8:05 pm-8:37 am

1 stop14h 32m

$300

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 5/23

5:50 pm-11:52 pm

1 stop28h 02m

Chicago O'Hare Intl

Mon 5/26

6:00 am-12:17 am

1 stop20h 17m

$361

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 6/6

5:10 am-4:45 pm

2 stops9h 35m

Chicago O'Hare Intl

Mon 6/9

5:25 pm-12:15 am

1 stop8h 50m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 20 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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
MytripPrice Accuracy3 starsTrust 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-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-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-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-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-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Portland to Chicago O'Hare Intl Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Portland to Chicago O'Hare Intl Airport trip
Airlines
United Airlines

Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.


Prepay checked bags 24 hours before to save on fees.

Read more about United Airlinesby Harriet Baskas
Alaska Airlines

Saver Fare allows a carry-on; seat selection is restricted.


Alaska offers Wi-Fi for a flat fee, ideal for business travelers.

Read more about Alaska Airlinesby Robert Schrader
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom.


Add bags during purchase for best prices; use Spirit's Bag-O-Tron tool.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
PDX

Security wait times at PDX can be up to 30 minutes during rush hours. Consider arriving early to avoid delays.

Read more about PDXby Brandon Schultz
ORD

For a quick city transfer, take the 'L' train from ORD to downtown Chicago, avoiding potential traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Robert Schrader

Robert Schrader

Expert on Alaska Airlines

Robert Schrader

Robert Schrader

One of the web's original travel bloggers, Robert launched his first site Leave Your Daily Hell in 2009. Since then, he's expanded into destination niche sites (one each for Japan, Thailand and Taiwan), in addition to having written for the inflight magazines of Singapore Airlines and Korean Air. Overall, he's visited nearly 100 countries, and flies business as often as possible.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on PDX

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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 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 March 21, 2025.

Booking 40 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Portland to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $245). Flying from Portland 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 PDX 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 March 25, 2025.

When flying from Portland to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 36% versus a flight in the morning.

What is the cheapest day to fly from Portland 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 March 16, 2025.

Travelers seeking maximum savings on their Portland to Chicago O'Hare Intl Airport flight should consider departing on Saturday afternoons 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 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 March 25, 2025.

The most flights from PDX to ORD are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 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 March 25, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Portland to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,782 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,782 reviews
Alaska Airlines
8.0
Very good
9,782 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,272 reviews
Alaska Airlines
8.0
Very good
9,782 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,890 reviews
Alaska Airlines
8.0
Very good
9,782 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,330 reviews
Alaska Airlines
8.0
Very good
9,782 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,605 reviews
Alaska Airlines
8.0
Very good
9,782 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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?

    For a flight from Portland to Chicago O'Hare Intl, you will be flying from Portland. Portland (PDX) is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 11 outbound flights to Chicago O'Hare Intl per day. 7 airlines have flights to Chicago O'Hare Intl from Portland on a regular basis.

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

    Our cheapest airline available from Portland to Chicago O'Hare Intl Airport is Alaska Airlines. Our recent data shows that you can find tickets from as low as $247 on this airline. Additional options worth looking into are Hawaiian Airlines and Spirit Airlines, starting at $248 and $249 round-trip. Alaska Airlines is currently priced 30% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Portland to Chicago O'Hare Intl Airport one-way?

    One-way options have recently been found by users for as low as $87 on Spirit Airlines. Other airlines that offer cheap prices include United Airlines from $90 and Delta from $100 one-way.

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

    No one likes to see their flight delayed. When booking a flight from Portland to Chicago O'Hare Intl Airport consider choosing Lufthansa (96%), United Airlines (94%) or Air Canada (94%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Portland to Chicago O'Hare Intl Airport?

    The cheapest flight price from Portland to Chicago O'Hare Intl Airport is $124. On average you can expect to pay $1,439. The most popular route, (Portland - Chicago O'Hare Intl), can usually be booked for $176.

  • 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 to Chicago O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $245). Flying from Portland 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
Rosemont
Beloit
Naperville
Schaumburg
Racine
Hoffman Estates
Rockford
Tinley Park
Skokie
Kenosha
Arlington Heights
Joliet
Orland Park
Merrillville
Northbrook
Evanston
New Buffalo
Elgin
Glenview
Lake Geneva

Browse thousands of different options on Cheapflights for your next trip

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Top 7 airlines flying from Portland to O'Hare Intl

Discover the top 7 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 March 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$135FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$193FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$288FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$184Average$340FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$189Average$335FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$202Average$392FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$217Average$406FlexibilityNo cancel feeOn-time69%
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