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O'Hare Intl

$109+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Find cheap flights from Portland to O'Hare Intl with Cheapflights

1. Tell us where you want to go

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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 Wednesday and return on a Wednesday

Cheap 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 December 18, 2025.

This Alaska Airlines deal was found by Cheapflights users on 12/15. 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.
Thu 12/2511:00 pmPDX - ORD
Nonstop4h 02mAlaska Airlines
Thu 1/223:35 pmORD - PDX
1 stop7h 12mAlaska Airlines
Deal found 12/15$237
This Delta deal was found by Cheapflights users on 12/15. 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.
Thu 12/251:45 pmPDX - ORD
1 stop5h 51mDelta
Thu 1/222:20 pmORD - PDX
1 stop6h 30mDelta
Deal found 12/15$247
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:59 pmPDX - ORD
2 stops20h 18mFrontier
Sun 1/259:38 pmORD - PDX
1 stop15h 40mFrontier
Deal found 12/15$249
This Alaska Airlines deal was found by Cheapflights users on 12/15. 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.
Thu 12/2511:00 pmPDX - ORD
Nonstop4h 02mAlaska Airlines
Fri 1/239:00 amORD - PDX
1 stop9h 44mAlaska Airlines
Deal found 12/15$253
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:39 pmPDX - ORD
1 stop15h 26mMultiple Airlines
Wed 1/212:18 pmORD - PDX
2 stops22h 15mMultiple Airlines
Deal found 12/15$289
This Expedia deal was found by Cheapflights users on 12/17. 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 12/317:00 amPDX - ORD
Nonstop4h 09mMultiple Airlines
Mon 1/51:32 pmORD - PDX
1 stop8h 18mMultiple Airlines
Deal found 12/17$302
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/2511:55 pmPDX - ORD
Nonstop4h 01mUnited Airlines
Wed 1/219:10 amORD - PDX
Nonstop4h 47mUnited Airlines
Deal found 12/15$307
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:29 pmPDX - ORD
2 stops31h 43mFrontier
Sun 1/259:38 pmORD - PDX
1 stop15h 40mFrontier
Deal found 12/15$313
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:39 pmPDX - ORD
1 stop15h 26mMultiple Airlines
Mon 1/265:40 amORD - PDX
2 stops16h 47mMultiple Airlines
Deal found 12/15$316
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:59 pmPDX - ORD
1 stop26h 24mMultiple Airlines
Wed 1/212:18 pmORD - PDX
2 stops22h 15mMultiple Airlines
Deal found 12/15$334
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:00 pmPDX - ORD
Nonstop4h 02mAlaska Airlines
Tue 1/272:06 pmORD - PDX
Nonstop4h 42mAlaska Airlines
Deal found 12/15$335

Find 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 December 18, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$232
(United Airlines)

One-way from

$109
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$452

Good round-trip deal

$368 or less

Good one-way deal

$175 or less
Provider with most accurate pricing for Portland-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago O'Hare Intl flights.
Search Deals
From Portland to Chicago O'Hare Intl
Search Deals
One-way flight from Portland to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Portland to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Portland to Chicago O'Hare Intl.
Search Deals

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 December 18, 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 1/27

1:24 pm-9:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Sat 1/31

12:45 pm-6:55 pm

1 stop8h 10m

$232

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 2/14

1:36 pm-11:56 pm

1 stop8h 20m

Chicago O'Hare Intl

Tue 2/17

3:54 pm-10:41 pm

1 stop8h 47m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 1/24

1:38 pm-11:50 pm

1 stop8h 12m

Chicago O'Hare Intl

Tue 1/27

6:06 pm-10:46 pm

1 stop6h 40m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 1/13

1:38 pm-11:50 pm

1 stop8h 12m

Chicago O'Hare Intl

Sat 1/17

8:00 am-12:38 pm

1 stop6h 38m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 1/10

5:00 am-1:22 pm

1 stop6h 22m

Chicago O'Hare Intl

Sat 1/17

4:16 pm-11:06 pm

1 stop8h 50m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 1/9

7:00 am-1:05 pm

Nonstop4h 05m

Chicago O'Hare Intl

Mon 1/12

7:50 pm-10:32 pm

Nonstop4h 42m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 1/9

7:05 am-1:10 pm

Nonstop4h 05m

Chicago O'Hare Intl

Sun 1/18

8:00 am-12:38 pm

1 stop6h 38m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 1/15

7:00 am-1:05 pm

Nonstop4h 05m

Chicago O'Hare Intl

Thu 1/22

9:10 am-11:57 am

Nonstop4h 47m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 2/15

6:00 am-4:33 pm

1 stop8h 33m

Chicago O'Hare Intl

Sat 2/21

2:07 pm-4:50 pm

Nonstop4h 43m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 3/5

11:59 pm-5:53 am

Nonstop3h 54m

Chicago O'Hare Intl

Mon 3/9

8:04 pm-10:45 pm

Nonstop4h 41m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 22 results
1
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice 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 Justfly.com to be most consistent on Cheapflights vs. Justfly.com Users can find the same prices on Portland-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. Justfly.com >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 Justfly.com the most. Justfly.com 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.

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 December 12, 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 $120). Flying from Portland to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $242). 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 December 18, 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 37% 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 December 13, 2025.

Travelers seeking maximum savings on their Portland to Chicago O'Hare Intl Airport flight should consider departing on Wednesday 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.

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

AI-powered summary based on content written by travel experts. AI can make mistakes.
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

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 December 18, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and Hawaiian Airlines 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
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,477 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,005 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Hawaiian Airlines
7.8
Good
2,820 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,091 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,054 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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 7 outbound flights to Chicago O'Hare Intl per day. 7 airlines have flights to Chicago O'Hare Intl from Portland on a regular basis.

  • How long is the flight from Portland to Chicago O'Hare Intl Airport?

    A quick flight from Portland to Chicago O'Hare Intl Airport can take about 5h 51m. United Airlines provides one of the quickest options available for as low as $232. The distance from Portland to Chicago O'Hare Intl Airport is about 1733 mi. This flight may include one or multiple stops.

  • 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 Frontier. Our recent data shows that you can find tickets from as low as $86 on this airline. Additional options worth looking into are Delta and Spirit Airlines, starting at $104 and $119 round-trip. Frontier is currently priced 75% 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 $72 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $80 and Hawaiian Airlines from $98 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 SWISS (89%), Air Canada (87%) or Gulf Air (87%) 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 $108. On average you can expect to pay $966. The most popular route, (Portland - Chicago O'Hare Intl), can usually be booked for $217.

  • 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 $120). Flying from Portland to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $242). 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
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$96Average$243FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$119Average$184FlexibilityNo cancel feeOn-time65%
DeltaCheapest$123Average$288FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$286FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$194Average$322FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$217Average$347FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$223Average$378FlexibilityNo cancel feeOn-time69%

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