Title: £61 Cheap Flights from Portland to Chicago (PDX to CHI) - Expedia.co.uk ![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) # £61 Cheap Flights from Portland (PDX) to Chicago (CHI) [View £61 flight on Tue, 6 Jan 2026](https://expedia.co.uk/Flights-Search?trip=oneway&leg1=from:PDX,to:ORD,departure:06/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:60.70&airProductToken=AQowCi4IwaYBEgMzMjQY77gBIK4cKIvcgQMwhN6BAzhYQABYAWoCU1ZyCEdIMk9YVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) - [Return](?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 International Airport (PDX) to Chicago - ![Alaska Airlines](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:pdx,to:chi,departure:29/09/2025TANYT&leg2=from:chi,to:pdx,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![Delta](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:pdx,to:chi,departure:29/09/2025TANYT&leg2=from:chi,to:pdx,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Southwest Airlines](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:pdx,to:chi,departure:29/09/2025TANYT&leg2=from:chi,to:pdx,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![United](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:pdx,to:chi,departure:29/09/2025TANYT&leg2=from:chi,to:pdx,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![American Airlines](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:pdx,to:chi,departure:29/09/2025TANYT&leg2=from:chi,to:pdx,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Frontier Airlines](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:pdx,to:chi,departure:29/09/2025TANYT&leg2=from:chi,to:pdx,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:pdx,to:chi,departure:29/09/2025TANYT&leg2=from:chi,to:pdx,departure:06/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ## Plan, book, fly with confidence - ### Be in the know Get alerts if flight prices drop or rise\* - ### Book smarter Save up to 25% on select hotels after you book a flight\* - ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.co.uk/login) ## Cheap Flights from Portland (PDX) to Chicago (CHI) Prices were available within the past 7 days and start at £61 for one-way flights and £145 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) Thu, 23 Oct - Wed, 29 Oct PDX Portland ORD Chicago £145 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:ORD,departure:23/10/2025TANYT&leg2=from:ORD,to:PDX,departure:29/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:145.00&airProductToken=AQowCi4IwaYBEgMzNzYY77gBIK4cKKiX-wIwmZn7AjhYQABYAWoCU1ZyCE9IMk9BVkJOCjAKLgjBpgESAzMyNRiuHCDvuAEo2dX7AjDt1_sCOFhAAFgBagJTVnIIT0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Fri, 31 Oct - Sat, 8 Nov PDX Portland ORD Chicago £155 Return found 1 day ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:ORD,departure:31/10/2025TANYT&leg2=from:ORD,to:PDX,departure:08/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:154.60&airProductToken=AQowCi4IwaYBEgMzNzYY77gBIK4cKKjx-wIwmfP7AjhYQABYAWoCU1ZyCE9IN09BVkJOCjAKLgjBpgESAzMyNRiuHCDvuAEo1cb8AjDpyPwCOFhAAFgBagJTVnIIT0gyT1hWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Fri, 31 Oct - Sat, 8 Nov PDX Portland ORD Chicago £163 Return found 1 day ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:ORD,departure:31/10/2025TANYT&leg2=from:ORD,to:PDX,departure:08/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:162.80&airProductToken=AQowCi4IwaYBEgMzNzYY77gBIK4cKKjx-wIwmfP7AjhYQABYAWoCU1ZyCE9IN09BVkJOCmAKLQjBpgESAzU4NxiuHCCSASjow_wCMITG_AI4WEAAWAFqAlNWcghPSDJZWFVCTgovCMGmARIEMTQwOBiSASDvuAEot8b8AjD2xvwCOFhAAVgBagJTVnIIT0gyWVhVQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, 23 Oct - Wed, 29 Oct PDX Portland ORD Chicago £165 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:ORD,departure:23/10/2025TANYT&leg2=from:ORD,to:PDX,departure:29/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:165.00&airProductToken=AQowCi4IwaYBEgMzNzYY77gBIK4cKKiX-wIwmZn7AjhYQABYAWoCU1ZyCE9IMk9BVkJOCmEKLgjBpgESBDE0NDcYrhwgkmgoitb7AjCT2PsCOFhAAFgBagJTVnIIR0gyT1hKQk4KLwjBpgESBDEzOTIYkmgg77gBKL7Y-wIw4tn7AjhYQAFYAWoCU1ZyCEdIMk9YSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, 28 Oct - Tue, 4 Nov PDX Portland ORD Chicago £170 Return found 2 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:ORD,departure:28/10/2025TANYT&leg2=from:ORD,to:PDX,departure:04/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:169.70&airProductToken=AQowCi4IwaYBEgMzMjQY77gBIK4cKIjI-wIwgcr7AjhYQABYAWoCU1ZyCE9IMk9YVkJOCjAKLgjBpgESAzMyNRiuHCDvuAEo1Zn8AjDpm_wCOFhAAFgBagJTVnIIT0gyT1hWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Fri, 12 Dec - Sun, 14 Dec PDX Portland ORD Chicago £174 Return found 3 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:ORD,departure:12/12/2025TANYT&leg2=from:ORD,to:PDX,departure:14/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:173.60&airProductToken=AQowCi4IwaYBEgMzMjQY77gBIK4cKOjC_wIw3cT_AjhYQABYAWoCU1ZyCE9INE9BVkJOCmEKLgjBpgESBDE0NjQYrhwgkgEo8Nf_AjCJ2v8COFhAAFgBagJTVnIIT0gyWUFVQk4KLwjBpgESBDIwMjgYkgEg77gBKNLa_wIwitv_AjhYQAFYAWoCU1ZyCE9IMllBVUJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, 28 Oct - Tue, 4 Nov PDX Portland ORD Chicago £177 Return found 2 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:ORD,departure:28/10/2025TANYT&leg2=from:ORD,to:PDX,departure:04/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:176.80&airProductToken=AQowCi4IwaYBEgMzMjQY77gBIK4cKIjI-wIwgcr7AjhYQABYAWoCU1ZyCE9IMk9YVkJOCmEKLgjBpgESBDE0NDcYrhwgkmgohpr8AjCPnPwCOFhAAFgBagJTVnIIR0gyT1hKQk4KLwjBpgESBDEzOTIYkmgg77gBKLqc_AIw3p38AjhYQAFYAWoCU1ZyCEdIMk9YSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, 11 Nov - Mon, 17 Nov PDX Portland ORD Chicago £180 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PDX,departure:17/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:179.40&airProductToken=AQowCi4IwaYBEgMzMjQY77gBIK4cKITm_AIw_ef8AjhYQABYAWoCU1ZyCE9IMk9YVkJOCjAKLgjBpgESAzQxMxiuHCDvuAEozKj9AjDjqv0COFhAAFgBagJTVnIIT0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Fri, 31 Oct - Sat, 8 Nov PDX Portland ORD Chicago £180 Return found 1 day ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:ORD,departure:31/10/2025TANYT&leg2=from:ORD,to:PDX,departure:08/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:180.00&airProductToken=AQpgCi8IwaYBEgQxNDA3GO-4ASCSASj27PsCMLrt-wI4WEAAWAFqAlNWcghPSDdPQUpCTgotCMGmARIDNDEwGJIBIK4cKOft-wIw4O_7AjhYQAFYAWoCU1ZyCE9IN09BSkJOCjAKLgjBpgESAzQxMxiuHCDvuAEorMP8AjDDxfwCOFhAAFgBagJTVnIIT0gyT1hWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, 11 Nov - Mon, 17 Nov PDX Portland ORD Chicago £187 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:PDX,departure:17/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:186.50&airProductToken=AQpgCi4IwaYBEgM1NzcY77gBIJJoKI7m_AIwquf8AjhYQABYAWoCU1ZyCEdIMk9YSkJOCi4IwaYBEgQxNDc4GJJoIK4cKJXp_AIwk-v8AjhYQAFYAWoCU1ZyCEdIMk9YSkJOCjAKLgjBpgESAzMyNRiuHCDvuAEo9av9AjCJrv0COFhAAFgBagJTVnIIT0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Portland (PDX) to Chicago (CHI) ### August is typically the cheapest month to fly From £77 - £170 per traveller. Flight from Portland to Chicago route information | Origin airport | Portland Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Return price | £145 | | Distance | 2774 km | ## Compare flights from Portland to Chicago easily and book with confidence For travelling on business or for pleasure, Expedia makes it easy to book your flights from Portland to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to CHI-All Airports in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Portland Intl. to CHI-All Airports.   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 Portland Intl. (PDX) to CHI-All Airports (CHI) The easiest way to view the best deals on flights from Portland to Chicago 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 Portland Intl. to CHI-All Airports start at just £145 and range up to £187.   To find an even better deal, try   - being flexible on your dates – midweek flights can be cheaper - looking for other airports near Portland and Chicago - booking your flight during October, the cheapest month on this route - varying your flight times – early morning and late at night are sometimes cheaper  Why you should book your Portland to Chicago flight with Expedia! We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Portland Intl. to CHI-All Airports 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.   ## Explore a world of travel with Expedia - Trending Routes - Trending Flights - Top Flights Destinations - Related Airlines - Nearby Airports - Cheap Flights from Other Airports - Expedia's Latest Trends ### Top Routes from Portland - [Portland to Chicago (PDX - ORD)](https://expedia.co.uk/lp/flights/pdx/ord/portland-to-chicago) - [Portland to Newark Liberty Intl. Airport (PDX - EWR)](https://expedia.co.uk/lp/flights/pdx/ewr/portland-to-newark-liberty-intl-airport) - [Portland to Paris (PDX - CDG)](https://expedia.co.uk/lp/flights/pdx/cdg/portland-to-paris) - [Portland to Boston (PDX - BOS)](https://expedia.co.uk/lp/flights/pdx/bos/portland-to-boston) - [Portland to Amsterdam (PDX - AMS)](https://expedia.co.uk/lp/flights/pdx/ams/portland-to-amsterdam) - [Portland to Denver (PDX - DEN)](https://expedia.co.uk/lp/flights/pdx/den/portland-to-denver) - [Portland to New York (PDX - JFK)](https://expedia.co.uk/lp/flights/pdx/jfk/portland-to-new-york) - [Portland to Seville (PDX - SVQ)](https://expedia.co.uk/lp/flights/pdx/svq/portland-to-seville) - [Portland to Tokyo (PDX - NRT)](https://expedia.co.uk/lp/flights/pdx/nrt/portland-to-tokyo) - [Portland to London (PDX - LHR)](https://expedia.co.uk/lp/flights/pdx/lhr/portland-to-london) - [Portland to Lisbon (PDX - LIS)](https://expedia.co.uk/lp/flights/pdx/lis/portland-to-lisbon) - [Portland to Atlanta (PDX - ATL)](https://expedia.co.uk/lp/flights/pdx/atl/portland-to-atlanta) ### Top Routes to Chicago - [Dublin to Chicago (DUB - CHI)](https://expedia.co.uk/lp/flights/dub/chi/dublin-to-chicago) - [Bristol to Chicago (BRS - CHI)](https://expedia.co.uk/lp/flights/brs/chi/bristol-to-chicago) - [Birmingham to Chicago (BHX - CHI)](https://expedia.co.uk/lp/flights/bhx/chi/birmingham-to-chicago) - [Toronto to Chicago (YTO - CHI)](https://expedia.co.uk/lp/flights/yto/chi/toronto-to-chicago) - [Newcastle to Chicago (NCL - CHI)](https://expedia.co.uk/lp/flights/ncl/chi/newcastle-to-chicago) - [New York to Chicago (NYC - CHI)](https://expedia.co.uk/lp/flights/nyc/chi/new-york-to-chicago) - [London to Chicago (LON - CHI)](https://expedia.co.uk/lp/flights/lon/chi/london-to-chicago) - [Manchester to Chicago (MAN - CHI)](https://expedia.co.uk/lp/flights/man/chi/manchester-to-chicago) - [Edinburgh to Chicago (EDI - CHI)](https://expedia.co.uk/lp/flights/edi/chi/edinburgh-to-chicago) - [Glasgow to Chicago (GLA - CHI)](https://expedia.co.uk/lp/flights/gla/chi/glasgow-to-chicago) ### Top Routes from Portland - [British Airways Portland to London](https://expedia.co.uk/lp/flight-routes/british-airways-from-portland-intl-to-heathrow/ba/pdx/lhr) ### Top Flight Destinations - [Flights to Las Vegas](https://expedia.co.uk/Cheap-Flights-To-Las-Vegas.d178276.Travel-Guide-Flights) - [Flights to New York](https://expedia.co.uk/Cheap-Flights-To-New-York.d178293.Travel-Guide-Flights) - [Flights to Orlando](https://expedia.co.uk/Cheap-Flights-To-Orlando.d178294.Travel-Guide-Flights) - [Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights to San Diego](https://expedia.co.uk/Cheap-Flights-To-San-Diego.d3073.Travel-Guide-Flights) - [Flights to San Francisco](https://expedia.co.uk/Cheap-Flights-To-San-Francisco.d178305.Travel-Guide-Flights) - [Flights to Los Angeles](https://expedia.co.uk/Cheap-Flights-To-Los-Angeles.d178280.Travel-Guide-Flights) - [Flights to Boston](https://expedia.co.uk/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights) - 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