Title: £95 Cheap Flights from Chicago to Portland (CHI to PDX) - Expedia.co.uk ![View of Portland, Oregon overlooking the willamette river on a Fall Afternoon](https://images.trvl-media.com/place/178299/b61662af-dec4-42f2-b3cd-9aa834264b40.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178299/b61662af-dec4-42f2-b3cd-9aa834264b40.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # £95 Cheap Flights from Chicago (CHI) to Portland (PDX) [View £95 flight on Wed, 29 Apr 2026](https://expedia.co.uk/Flights-Search?trip=oneway&leg1=from:ORD,to:PDX,departure:29/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:94.40&airProductToken=AQowCi4IwaYBEgMzMjUYrhwg77gBKKHViwMwtteLAzhYQABYAWoCU1ZyCEdIMk9YVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ## Popular airlines from Chicago to Portland, OR (PDX-Portland Intl.) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:CHI,to:PDX,departure:18/04/2026TANYT&leg2=from:PDX,to:CHI,departure:25/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.co.uk/Flights-Search?leg1=from:CHI,to:PDX,departure:18/04/2026TANYT&leg2=from:PDX,to:CHI,departure:25/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:CHI,to:PDX,departure:18/04/2026TANYT&leg2=from:PDX,to:CHI,departure:25/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.co.uk/Flights-Search?leg1=from:CHI,to:PDX,departure:18/04/2026TANYT&leg2=from:PDX,to:CHI,departure:25/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:CHI,to:PDX,departure:18/04/2026TANYT&leg2=from:PDX,to:CHI,departure:25/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://a.travel-assets.com/air/airlines/sy_sq.svg) Sun Country Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:CHI,to:PDX,departure:18/04/2026TANYT&leg2=from:PDX,to:CHI,departure:25/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"SY"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:CHI,to:PDX,departure:18/04/2026TANYT&leg2=from:PDX,to:CHI,departure:25/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) ## Cheap Flights from Chicago (CHI) to Portland (PDX) Prices were available within the past 7 days and start at £95 for one-way flights and £197 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, 29 Apr - Sat, 2 May ORD Chicago PDX Portland £197 Return found 21 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:29/04/2026TANYT&leg2=from:PDX,to:ORD,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:196.20&airProductToken=AQowCi4IwaYBEgMzMjUYrhwg77gBKKHViwMwtteLAzhYQABYAWoCU1ZyCEdIMk9YVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, 29 Apr - Sat, 2 May ORD Chicago PDX Portland £197 Return found 21 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:29/04/2026TANYT&leg2=from:PDX,to:ORD,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:196.30&airProductToken=AQowCi4IwaYBEgMzMjUYrhwg77gBKKHViwMwtteLAzhYQABYAWoCU1ZyCEdIMk9YVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, 11 Jun - Tue, 16 Jun ORD Chicago PDX Portland £236 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:11/06/2026TANYT&leg2=from:PDX,to:ORD,departure:16/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:236.00&airProductToken=AQo0CjIIwYIBEgQxMzE3GK4cIO-4ASi1vI8DMMC-jwM4QkAAWAFqBUJBU0lDcghTV0FaWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, 11 Jun - Tue, 16 Jun ORD Chicago PDX Portland £238 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:11/06/2026TANYT&leg2=from:PDX,to:ORD,departure:16/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:237.10&airProductToken=AQo0CjIIwYIBEgQxMzE3GK4cIO-4ASi1vI8DMMC-jwM4QkAAWAFqBUJBU0lDcghTV0FaWk5CWAo0CjIIwYIBEgQyOTc3GO-4ASCuHCin9o8DMJr4jwM4QkAAWAFqBUJBU0lDcghTV0FLVU5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, 11 Jun - Tue, 16 Jun ORD Chicago PDX Portland £244 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:11/06/2026TANYT&leg2=from:PDX,to:ORD,departure:16/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:243.40&airProductToken=AQo0CjIIwYIBEgQxMzE3GK4cIO-4ASi1vI8DMMC-jwM4QkAAWAFqBUJBU0lDcghTV0FaWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, 29 Apr - Sat, 2 May ORD Chicago PDX Portland £245 Return found 21 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:29/04/2026TANYT&leg2=from:PDX,to:ORD,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:244.60&airProductToken=AQowCi4IwaYBEgMzMjUYrhwg77gBKKHViwMwtteLAzhYQABYAWoCU1ZyCEdIMk9YVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, 29 Apr - Sat, 2 May ORD Chicago PDX Portland £252 Return found 21 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:29/04/2026TANYT&leg2=from:PDX,to:ORD,departure:02/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:252.00&airProductToken=AQpfCi0IwaYBEgM1ODcYrhwgkgEorNKLAzDE1IsDOFhAAFgBagJTVnIIUUgyT1pKQk4KLgjBpgESAzQ2NhiSASDvuAEo_NSLAzDI1YsDOFhAAVgBagJTVnIIUUgyT1pKQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, 30 Apr - Sun, 3 May ORD Chicago PDX Portland £260 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:30/04/2026TANYT&leg2=from:PDX,to:ORD,departure:03/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:259.50&airProductToken=AQphCi4IwaYBEgQxNDcwGK4cIJJoKP7diwMwluCLAzhYQABYAWoCU1ZyCE9INU9BSkJOCi8IwaYBEgQxNDAyGJJoIO-4ASiw4YsDMNXiiwM4WEABWAFqAlNWcghPSDVPQUpCTgpgCi8IwaYBEgQxNDA4GO-4ASCSASjRgIwDMJCBjAM4WEAAWAFqAlNWcghPSDVPQUpCTgotCMGmARIDNDI5GJIBIK4cKLyBjAMwxIOMAzhYQAFYAWoCU1ZyCE9INU9BSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, 11 Jun - Tue, 16 Jun ORD Chicago PDX Portland £278 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:11/06/2026TANYT&leg2=from:PDX,to:ORD,departure:16/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:277.70&airProductToken=AQpvCjUIxJgBEgQxMzA2GK4cIMx8KOG6jwMwxruPAzhFQABYAWoJTUFJTkJBU0lDcghUQVZOQTBCQwo2CMSYARIEMjM5MRjMfCDvuAEowLyPAzCdvo8DOEVAAVgBaglNQUlOQkFTSUNyCFRBVk5BMEJDCm8KNgjEmAESBDIzNTkY77gBIMx8KOPrjwMwp-2PAzhFQABYAWoJTUFJTkJBU0lDcghYQVdOSDNCUQo1CMSYARIEMTU0NBjMfCCuHCjw7Y8DMM_ujwM4RUABWAFqCU1BSU5CQVNJQ3IIWEFXTkgzQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, 11 Jun - Tue, 16 Jun ORD Chicago PDX Portland £312 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PDX,departure:11/06/2026TANYT&leg2=from:PDX,to:ORD,departure:16/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:311.30&airProductToken=AQo2CjQI1YIBEgQyMzAwGK4cIO-4ASjVtY8DMOe3jwM4TEAAWAFqB0VDT05PTVlyCExBQTVQRkROCjYKNAjVggESBDI4MjIY77gBIK4cKMDzjwMwvfWPAzhLQABYAWoHRUNPTk9NWXIIS0FLNVBGRE4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAB) ## Travel information | Origin airport | O'Hare Intl. | | ------------------- | --------------- | | Destination airport | Portland Intl. | | Airlines serving | Alaska Airlines | | Return price | £196 | | Distance | 2774 km | ## Book with confidence # Compare flights from Chicago to Portland easily and book with confidence For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to Portland. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to Portland Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from CHI-All Airports to Portland Intl.. To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. Grab a great deal on your flight from CHI-All Airports (CHI) to Portland Intl. (PDX) The easiest way to view the best deals on flights from Chicago to Portland today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from CHI-All Airports to Portland Intl. start at just £197 and range up to £312\. To find an even better deal, try - being flexible on your dates – midweek flights can be cheaper - looking for other airports near Chicago and Portland - booking your flight during April, the cheapest month on this route - varying your flight times – early morning and late at night are sometimes cheaper Why you should book your Chicago to Portland flight with Expedia! We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from CHI-All Airports to Portland Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you. Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight. \*Available to Expedia members.