O'Hare Intl

$110+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Oct 16 — Oct 231
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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 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 September 16, 2025.

Round-trip from

$195
(Frontier)

One-way from

$110
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$315

Good round-trip deal

$324 or less

Good one-way deal

$169 or less
From Portland to Chicago O'Hare Intl
One-way flight from Portland to Chicago O'Hare Intl
Highest demand for flights based on searches. 5% potential increase in price ($21 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in September 2025
Price to beat on a round-trip flight from Portland to Chicago O'Hare Intl.
Price to beat on a one-way flight from Portland to Chicago O'Hare Intl.

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 September 16, 2025.

This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/308:06 amPDX - ORD
1 stop11h 22mFrontier
Sat 10/412:22 pmORD - PDX
2 stops12h 12mFrontier
Deal found 9/15$195
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/212:07 pmPDX - ORD
1 stop7h 29mMultiple Airlines
Mon 10/610:32 amORD - PDX
1 stop27h 16mMultiple Airlines
Deal found 9/15$196
This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2612:43 pmPDX - ORD
1 stop18h 53mFrontier
Fri 10/316:00 amORD - PDX
1 stop7h 56mFrontier
Deal found 9/15$198
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1412:43 pmPDX - ORD
1 stop9h 10mFrontier
Tue 10/217:15 amORD - PDX
1 stop6h 33mFrontier
Deal found 9/14$199
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/313:26 pmPDX - ORD
1 stop6h 50mFrontier
Wed 11/57:20 amORD - PDX
1 stop30h 36mFrontier
Deal found 9/15$200
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:05 amPDX - ORD
2 stops15h 15mFrontier
Wed 10/87:15 amORD - PDX
1 stop6h 33mFrontier
Deal found 9/15$202
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Wed 10/112:07 pmPDX - ORD
1 stop7h 25mSpirit Airlines
Fri 10/36:15 amORD - PDX
1 stop6h 56mSpirit Airlines
Deal found 9/14$203
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:43 pmPDX - ORD
1 stop10h 16mFrontier
Mon 10/206:50 amORD - PDX
1 stop6h 58mFrontier
Deal found 9/14$204
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2012:43 pmPDX - ORD
1 stop10h 16mFrontier
Mon 10/276:50 amORD - PDX
1 stop6h 58mFrontier
Deal found 9/13$205
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/169:08 amPDX - ORD
1 stop10h 02mFrontier
Fri 10/176:50 amORD - PDX
1 stop6h 58mFrontier
Deal found 9/15$206
This Expedia deal was found by Cheapflights users on 9/13. 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 10/811:00 pmPDX - ORD
Nonstop4h 01mMultiple Airlines
Wed 10/157:15 amORD - PDX
1 stop6h 33mMultiple Airlines
Deal found 9/13$207
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:58 pmPDX - ORD
Nonstop3h 55mAmerican Airlines
Wed 11/58:14 amORD - PDX
Nonstop4h 34mAmerican Airlines
Deal found 9/15$209

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 September 16, 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 10/28

7:00 am-1:09 pm

Nonstop4h 09m

Chicago O'Hare Intl

Tue 11/4

2:05 pm-4:41 pm

Nonstop4h 36m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 10/22

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Wed 10/29

2:54 pm-8:46 pm

1 stop7h 52m

$241

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 10/28

7:00 am-1:09 pm

Nonstop4h 09m

Chicago O'Hare Intl

Tue 11/4

2:54 pm-8:46 pm

1 stop7h 52m

$241

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/10

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Tue 10/14

7:59 pm-9:44 am

1 stop15h 45m

$254

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 2/5

10:47 am-4:48 pm

Nonstop4h 01m

Chicago O'Hare Intl

Sun 2/8

9:10 am-11:57 am

Nonstop4h 47m

$257

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 11/23

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Fri 11/28

7:00 am-9:39 am

Nonstop4h 39m

$257

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 3/10

8:45 pm-5:04 am

1 stop6h 19m

Chicago O'Hare Intl

Wed 3/11

7:45 am-1:46 pm

1 stop8h 01m

$261

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 12/9

12:32 am-8:40 am

1 stop6h 08m

Chicago O'Hare Intl

Mon 12/15

5:03 pm-10:09 pm

1 stop7h 06m

$264

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/17

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Mon 10/20

7:59 pm-9:44 am

1 stop15h 45m

$267

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/10

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Wed 10/15

8:20 am-4:50 pm

1 stop10h 30m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 22 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.

Alaska Airlines

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


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

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.

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 September 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 $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 September 16, 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 41% 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 September 14, 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.

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 September 16, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Hawaiian Airlines, and United 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.

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2025

SEA - MKE

The crew were excellent, flight good, but the actual space for a person to occupy for 4 hours seems to get smaller and smaller 🤣. I am not overweight, and average height….very uncomfortable,, especially when I couldn’t recliner the seat at all, and the pocket in front doesn’t accommodate a water bottle.

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2025

SEA - MKE

The crew were excellent, flight good, but the actual space for a person to occupy for 4 hours seems to get smaller and smaller 🤣. I am not overweight, and average height….very uncomfortable,, especially when I couldn’t recliner the seat at all, and the pocket in front doesn’t accommodate a water bottle.

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2025

SEA - MKE

The crew were excellent, flight good, but the actual space for a person to occupy for 4 hours seems to get smaller and smaller 🤣. I am not overweight, and average height….very uncomfortable,, especially when I couldn’t recliner the seat at all, and the pocket in front doesn’t accommodate a water bottle.

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2025

SEA - MKE

The crew were excellent, flight good, but the actual space for a person to occupy for 4 hours seems to get smaller and smaller 🤣. I am not overweight, and average height….very uncomfortable,, especially when I couldn’t recliner the seat at all, and the pocket in front doesn’t accommodate a water bottle.

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2025

SEA - MKE

The crew were excellent, flight good, but the actual space for a person to occupy for 4 hours seems to get smaller and smaller 🤣. I am not overweight, and average height….very uncomfortable,, especially when I couldn’t recliner the seat at all, and the pocket in front doesn’t accommodate a water bottle.

Comfort

7.8

Overall

8.0

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2025

SEA - MKE

The crew were excellent, flight good, but the actual space for a person to occupy for 4 hours seems to get smaller and smaller 🤣. I am not overweight, and average height….very uncomfortable,, especially when I couldn’t recliner the seat at all, and the pocket in front doesn’t accommodate a water bottle.

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 23 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 4h 01m. Alaska Airlines provides one of the quickest options available for as low as $241. The distance from Portland to Chicago O'Hare Intl Airport is about 1733 mi. All flights are typically nonstop.

  • 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 $93 on this airline. Additional options worth looking into are Frontier and Delta, starting at $108 and $123 round-trip. Spirit Airlines is currently priced 74% 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 $114 on Southwest. Other airlines that offer cheap prices include Alaska Airlines from $116 and Hawaiian Airlines from $116 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 Brussels Airlines (89%), Qatar Airways (87%) or Air Canada (84%) 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 $115. On average you can expect to pay $814. The most popular route, (Portland - Chicago O'Hare Intl), can usually be booked for $175.

  • 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 Chicago O'Hare Intl Airport?

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

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$200FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$212FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$288FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$286FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$195Average$316FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$200Average$348FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$226Average$393FlexibilityNo cancel feeOn-time69%

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