Title: CA $173 Cheap Flights from Portland (PWM) to Chicago (ORD) - Expedia.ca ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $173 Cheap Flights from Portland (PWM) to Chicago (ORD) [View CA $173 flight on Fri, Oct 31, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:PWM,to:ORD,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:173.00&airProductToken=AQozCjEIwYIBEgQ0MzkxGM9lIK4cKJXo-wIww-n7AjhCQABYAWoFQkFTSUNyCFE3QVdaU0JaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from Portland Intl. Jetport Airport (PWM) to Chicago O'Hare International Airport (ORD) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:pwm,to:ord,departure:27/10/2025TANYT&leg2=from:ord,to:pwm,departure:03/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:pwm,to:ord,departure:27/10/2025TANYT&leg2=from:ord,to:pwm,departure:03/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:pwm,to:ord,departure:27/10/2025TANYT&leg2=from:ord,to:pwm,departure:03/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:pwm,to:ord,departure:27/10/2025TANYT&leg2=from:ord,to:pwm,departure:03/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:pwm,to:ord,departure:27/10/2025TANYT&leg2=from:ord,to:pwm,departure:03/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Portland (PWM) to Chicago (ORD) Prices were available within the past 7 days and start at CA $173 for one-way flights and CA $415 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Nov 11 - Tue, Nov 18 PWM Portland ORD Chicago CA $415 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PWM,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:414.80&airProductToken=AQozCjEIwYIBEgQ2MjE4GM9lIK4cKM3p_AIwjuv8AjhCQABYAWoFQkFTSUNyCE5WQUlLU0JYCjMKMQjBggESBDYyMTgYrhwgz2Uo_Lb9AjCNuP0COEJAAFgBagVCQVNJQ3IITlZBSUtTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Nov 11 - Tue, Nov 18 PWM Portland ORD Chicago CA $426 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PWM,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:425.84&airProductToken=AQpuCjUIxJgBEgQ1NjcwGM9lIMsBKJTk_AIw9OT8AjhFQABYAWoJTUFJTkJBU0lDcghYQVZTQzJCQwo1CMSYARIEMTg3NBjLASCuHCiq5fwCMM3m_AI4RUABWAFqCU1BSU5CQVNJQ3IIWEFWU0MyQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Nov 11 - Tue, Nov 18 PWM Portland ORD Chicago CA $429 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PWM,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:428.40&airProductToken=AQozCjEIwYIBEgQ2MjE4GM9lIK4cKM3p_AIwjuv8AjhCQABYAWoFQkFTSUNyCE5WQUlLU0JYCmUKMAjBggESAzg2MhiuHCDvWSjGtP0CMLy1_QI4QkAAWAFqBUJBU0lDcghOVkFJS1NCWAoxCMGCARIENjEwNRjvWSDPZSjAtv0CMJu3_QI4QkABWAFqBUJBU0lDcghOVkFJS1NCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Nov 11 - Tue, Nov 18 PWM Portland ORD Chicago CA $432 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PWM,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:431.86&airProductToken=AQozCjEIwYIBEgQ2MjE4GM9lIK4cKM3p_AIwjuv8AjhCQABYAWoFQkFTSUNyCE5WQUlLU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Nov 11 - Tue, Nov 18 PWM Portland ORD Chicago CA $439 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PWM,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:438.70&airProductToken=AQpuCjUIxJgBEgQ1Mzk5GM9lIKlRKJLo_AIw7uj8AjhFQABYAWoJTUFJTkJBU0lDcghYQVZTQzJCQwo1CMSYARIENTY3ORipUSCuHCi96vwCMO_r_AI4RUABWAFqCU1BSU5CQVNJQ3IIWEFWU0MyQkMKbgo1CMSYARIEMjc2NxiuHCDLASiws_0CMLu0_QI4RUAAWAFqCU1BSU5CQVNJQ3IIVkZVU0EwQkMKNQjEmAESBDU2NzcYywEgz2Uo-bb9AjDMt_0COEVAAVgBaglNQUlOQkFTSUNyCFZEVk5BMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Nov 11 - Tue, Nov 18 PWM Portland ORD Chicago CA $442 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PWM,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:442.00&airProductToken=AQpkCjAIwYIBEgQyOTczGM9lIEMog-T8AjD25PwCOEJAAFgBagVCQVNJQ3IITlZBSUtTQlgKMAjBggESBDEyMDAYQyCuHCj15fwCMPrm_AI4QkABWAFqBUJBU0lDcghOVkFJS1NCWApjCi8IwYIBEgM2MDMYrhwgQyiEtv0CMOy2_QI4QkAAWAFqBUJBU0lDcghOVkFJS1NCWAowCMGCARIEMjQ4ORhDIM9lKJS3_QIw9bf9AjhCQAFYAWoFQkFTSUNyCE5WQUlLU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Nov 11 - Tue, Nov 18 PWM Portland ORD Chicago CA $446 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PWM,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:445.46&airProductToken=AQpmCjEIwYIBEgQ2MDU0GM9lIO9ZKJTk_AIwhOX8AjhCQABYAWoFQkFTSUNyCE5WQUlLU0JYCjEIwYIBEgQxODU0GO9ZIK4cKL3m_AIw1uf8AjhCQAFYAWoFQkFTSUNyCE5WQUlLU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Nov 11 - Tue, Nov 18 PWM Portland ORD Chicago CA $447 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PWM,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:446.30&airProductToken=AQpuCjUIxJgBEgQ1NjcwGM9lIMsBKJTk_AIw9OT8AjhFQABYAWoJTUFJTkJBU0lDcghYQVZTQzJCQwo1CMSYARIEMTg3NBjLASCuHCiq5fwCMM3m_AI4RUABWAFqCU1BSU5CQVNJQ3IIWEFWU0MyQkMKbgo1CMSYARIEMTA3NBiuHCDLASizt_0CMLq4_QI4RUAAWAFqCU1BSU5CQVNJQ3IIWEZWTkEwQlEKNQjEmAESBDU2NjkYywEgz2Uos7r9AjCDu_0COEVAAVgBaglNQUlOQkFTSUNyCFZEVk5BMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Nov 11 - Tue, Nov 18 PWM Portland ORD Chicago CA $451 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PWM,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:450.46&airProductToken=AQozCjEIwYIBEgQ2MjE4GM9lIK4cKM3p_AIwjuv8AjhCQABYAWoFQkFTSUNyCE5WQUlLU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Oct 30 - Mon, Nov 3 PWM Portland ORD Chicago CA $452 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:30/10/2025TANYT&leg2=from:ORD,to:PWM,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:451.44&airProductToken=AQozCjEIwYIBEgQ0OTY3GM9lIK4cKJDh-wIwwOL7AjhCQABYAWoFQkFTSUNyCE5WQUlWU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ## Find the cheapest month to fly from Portland (PWM) to Chicago (ORD) ### August is typically the cheapest month to fly From CA $202 - CA $494 per traveller. ## Frequently asked questions ### How much is a flight from Portland Intl. Jetport to ORD? > Round-trip tickets between PWM and O'Hare Intl. Airport (ORD) start from CA $415. This figure is based on fares advertised within the last 7 days on Expedia for flights departing within the next year — book ASAP so you don't miss out. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Portland Intl. Jetport to O'Hare Airport? > Every air carrier has its own terms and conditions. If you do decide to cancel, follow the instructions on our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from PWM to ORD that have flexible change policies? > Flights from Portland Intl. Jetport Airport (PWM) to O'Hare Airport offering flexible change policies are available with many carriers. Simply use our "No change fees" filter during your search. You'll only need to cover the cost difference between the two flights, with no extra fees to worry about. ### How many hours is the flight from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)? > There are plenty of ways to make the 4 hours and 52 minutes between Portland Intl. Jetport and O'Hare Intl. Airport (ORD) go by faster. If you want to be productive, organize your camera roll or delete all those backed-up emails. A snooze also helps pass the time! ### How far is the flight from Portland Intl. Jetport to ORD? > That movie you've been desperate to see will just have to wait — the flight distance between Portland Intl. Jetport Airport (PWM) and O'Hare Intl. Airport (ORD) is only 1,450 kilometres. The captain will be asking you to put your seat upright for touchdown before you know it. ### Which airlines fly direct from PWM to O'Hare Intl. Airport (ORD)? > A popular option with many travellers, United Airlines (UA) offers 30 monthly flights from PWM to O'Hare Airport. Pick the one that suits your travel plans and book your ticket today. ### Are Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute? > Booking last minute from Portland Intl. Jetport to O'Hare Intl. Airport (ORD) can be hit-or-miss. You may be able to score a bargain, but then again, you could miss out altogether! If you'd rather start planning your trip early on, Expedia compares flight deals up to a year in advance. Just keep in mind that not all airlines advertise their prices so far in advance. Our top tip? Check back often as updates are made frequently. ## Travel information | Origin airport | Portland Intl. Jetport | | --- | --- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $415 | | Distance | 1435 km | | Average flight time | 2 hours 7 mins | ## Book with confidence ### Portland to Chicago Flights **The easy way to book your flights from Portland to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Portland whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.   Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Portland to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Portland Intl. Jetport, PWM to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Portland to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Portland currently is just CA $415 rising to CA $452.   Here are more money-saving tips:  - Fly in November when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to Chicago   - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times  - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!  **Reasons to choose Expedia for your flight to Chicago from Portland**  Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today. ## Explore a world of travel with Expedia - Flights - [Flights from Calgary to Rosemont](https://www.expedia.ca/lp/flights/178245/7581/calgary-to-rosemont) - [Flights from Denver to Northwest Chicago](https://www.expedia.ca/lp/flights/178254/6350697/denver-to-northwest-chicago) - [Flights from Los Angeles to Evanston](https://www.expedia.ca/lp/flights/178280/8049/los-angeles-to-evanston) - [Flights from Mexico City to Northwest Chicago](https://www.expedia.ca/lp/flights/178285/6350697/mexico-city-to-northwest-chicago) - [Flights from New York to Evanston](https://www.expedia.ca/lp/flights/178293/8049/new-york-to-evanston) - [Flights from Ottawa to Evanston](https://www.expedia.ca/lp/flights/178296/8049/ottawa-to-evanston) - [Flights from Philadelphia to Rosemont](https://www.expedia.ca/lp/flights/178297/7581/philadelphia-to-rosemont) - [Flights from Portland to Rosemont](https://www.expedia.ca/lp/flights/178299/7581/portland-to-rosemont) - 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