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O'Hare Intl

$91+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
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 January, booked 88 days in advance, depart on a Friday 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 July 2, 2025.

Round-trip from

$216
(CheapOair)

One-way from

$91
(FlightHub)

Popular in

December

Cheapest in

August

Average price

$337

Good round-trip deal

$341 or less

Good one-way deal

$182 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. 9% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 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 2, 2025.

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/3011:00 amPDX - ORD
1 stop7h 56mFrontier
Thu 7/35:40 amORD - PDX
1 stop6h 38mFrontier
Deal found 6/30$215
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/153:10 pmPDX - ORD
1 stop12h 53mSpirit Airlines
Sat 7/197:49 pmORD - PDX
1 stop15h 29mSpirit Airlines
Deal found 7/1$216
This Expedia deal was found by Cheapflights users on 6/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/3012:25 pmPDX - ORD
1 stop9h 45mMultiple Airlines
Tue 8/57:00 amORD - PDX
Nonstop4h 25mMultiple Airlines
Deal found 6/29$217
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/287:35 pmPDX - ORD
1 stop7h 48mUnited Airlines
Sun 8/311:05 pmORD - PDX
Nonstop4h 20mUnited Airlines
Deal found 7/1$224
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/271:20 pmPDX - ORD
Nonstop3h 58mAmerican Airlines
Tue 9/212:10 pmORD - PDX
Nonstop4h 19mAmerican Airlines
Deal found 6/30$225
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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.
Fri 10/3110:00 pmPDX - ORD
1 stop6h 22mAlaska Airlines
Mon 11/36:00 amORD - PDX
1 stop8h 29mAlaska Airlines
Deal found 7/2$234
This Hawaiian 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/55:35 pmPDX - ORD
Nonstop4h 04mHawaiian Airlines
Sun 8/107:00 amORD - PDX
Nonstop4h 25mHawaiian Airlines
Deal found 6/30$238

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 2, 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

Tue 7/15

3:10 pm-6:03 am

1 stop12h 53m

Chicago O'Hare Intl

Sat 7/19

7:49 pm-9:18 am

1 stop15h 29m

$216

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 7/30

12:25 pm-12:10 am

1 stop9h 45m

Chicago O'Hare Intl

Tue 8/5

7:00 am-9:25 am

Nonstop4h 25m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 8/2

6:35 am-12:32 am

1 stop15h 57m

Chicago O'Hare Intl

Sun 8/3

9:56 pm-12:51 pm

1 stop16h 55m

$218

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 8/28

7:35 pm-5:23 am

1 stop7h 48m

Chicago O'Hare Intl

Sun 8/31

1:05 pm-3:25 pm

Nonstop4h 20m

$224

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 8/27

1:20 pm-7:18 pm

Nonstop3h 58m

Chicago O'Hare Intl

Tue 9/2

12:10 pm-2:29 pm

Nonstop4h 19m

$225

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

10:15 am-8:58 pm

1 stop8h 43m

Chicago O'Hare Intl

Mon 11/3

7:30 am-2:39 pm

1 stop9h 09m

$234

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 8/13

5:35 pm-11:39 pm

Nonstop4h 04m

Chicago O'Hare Intl

Tue 8/26

6:20 am-12:24 pm

1 stop8h 04m

$235

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 8/5

5:35 pm-11:39 pm

Nonstop4h 04m

Chicago O'Hare Intl

Sun 8/10

7:00 am-9:25 am

Nonstop4h 25m

$238

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 9/26

7:59 pm-4:46 am

1 stop6h 47m

$91

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 11/13

11:28 am-11:03 pm

1 stop9h 35m

$95

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

Showing 1-10 of 16 results
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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

Expect security wait times up to 30 minutes during peak hours. Consider using Express Lanes if eligible for faster processing.

Read more about PDXby Brandon Schultz
ORD

For a quick city transfer, take the “L” train from ORD to downtown Chicago, avoiding traffic delays common with taxis or rideshares.

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 June 27, 2025.

Booking 88 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 $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 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 July 2, 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 43% 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 June 29, 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 at noon 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 July 2, 2025.

The most flights from PDX to ORD are scheduled on a Monday (28 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (9 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 2, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta from Portland to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,272 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,975 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,542 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 19 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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $216 on this airline. Additional options worth looking into are Frontier and United Airlines, starting at $218 and $224 round-trip. Spirit Airlines is currently priced 39% 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 $91 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $100 and Alaska Airlines from $112 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 United Airlines (83%), SWISS (83%) or Brussels Airlines (82%) 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 $1,168. The most popular route, (Portland - Chicago O'Hare Intl), can usually be booked for $162.

  • 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 $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

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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$87Average$146FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$178FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$288FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$187Average$334FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$202Average$293FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$217Average$398FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$333FlexibilityNo cancel feeOn-time71%

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