Title: £92 Cheap Flights from Portland to Chicago (PDX to MDW) - 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) # £92 Cheap Flights from Portland (PDX) to Chicago (MDW) [View £92 flight on Wed, 29 Oct 2025](https://expedia.co.uk/Flights-Search?trip=oneway&leg1=from:PDX,to:MDW,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:91.40&airProductToken=AQpwCjYIxJgBEgQyMzU5GO-4ASDMfCis0PsCMPDR-wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQlEKNgjEmAESBDM1NDMYzHwg7LABKL_S-wIwo9P7AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZTSDNCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) - [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 Midway Airport (MDW) - ![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:mdw,departure:05/10/2025TANYT&leg2=from:mdw,to:pdx,departure:12/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![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:mdw,departure:05/10/2025TANYT&leg2=from:mdw,to:pdx,departure:12/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:mdw,departure:05/10/2025TANYT&leg2=from:mdw,to:pdx,departure:12/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) ![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 25% 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.co.uk/login) ## Cheap Flights from Portland (PDX) to Chicago (MDW) Prices were available within the past 7 days and start at £92 for one-way flights and £268 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £268 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:267.70&airProductToken=AQpwCjYIxJgBEgQyMzU5GO-4ASDMfCis0PsCMPDR-wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQlEKNgjEmAESBDM1NDMYzHwg7LABKL_S-wIwo9P7AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZTSDNCUQpwCjYIxJgBEgQzNzk1GOywASDMfCjo4PsCMMzh-wI4RUAAWAFqCU1BSU5CQVNJQ3IIVUFWVEE1QkMKNgjEmAESBDIxNTEYzHwg77gBKJbj-wIw7uT7AjhFQAFYAWoJTUFJTkJBU0lDcghVQVZUQTVCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £269 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:268.80&airProductToken=AQpwCjYIxJgBEgQyMzU5GO-4ASDMfCis0PsCMPDR-wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQlEKNgjEmAESBDM1NDMYzHwg7LABKL_S-wIwo9P7AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZTSDNCUQpwCjYIxJgBEgQzNzc4GOywASDMfCjc3vsCMMLf-wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0I0QkMKNgjEmAESBDIxNTEYzHwg77gBKJbj-wIw7uT7AjhFQAFYAWoJTUFJTkJBU0lDcghYQVZTQTBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £308 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:307.50&airProductToken=AQpvCjUIxJgBEgM4ODgY77gBIOBcKLba-wIwytz7AjhFQABYAWoJTUFJTkJBU0lDcghUQVZUSDNCUQo2CMSYARIEMTA2MxjgXCDssAEohN77AjD13vsCOEVAAVgBaglNQUlOQkFTSUNyCFRBVlRIM0JRCnAKNgjEmAESBDM3OTUY7LABIMx8KOjg-wIwzOH7AjhFQABYAWoJTUFJTkJBU0lDcghVQVZUQTVCQwo2CMSYARIEMjE1MRjMfCDvuAEoluP7AjDu5PsCOEVAAVgBaglNQUlOQkFTSUNyCFVBVlRBNUJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £335 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:334.40&airProductToken=AQpwCjYIxJgBEgQyMzU5GO-4ASDMfCis0PsCMPDR-wI4VkAAWAFqCU1BSU5DTEFTQ3IIVkFWU0gzTUwKNgjEmAESBDM1NDMYzHwg7LABKL_S-wIwo9P7AjhWQAFYAWoJTUFJTkNMQVNDcghWQVZTSDNNTApwCjYIxJgBEgQzNzk1GOywASDMfCjo4PsCMMzh-wI4VUAAWAFqCU1BSU5DTEFTQ3IIVUFWVEE1TUUKNgjEmAESBDIxNTEYzHwg77gBKJbj-wIw7uT7AjhVQAFYAWoJTUFJTkNMQVNDcghVQVZUQTVNRRIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £347 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:346.20&airProductToken=AQpwCjYIxJgBEgQyMzY5GO-4ASDMfCiA0_sCMMbU-wI4RUAAWAFqCU1BSU5CQVNJQ3IIWEFWU0gzQkMKNgjEmAESBDQxNjkYzHwg7LABKNTW-wIws9f7AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQjRCQwpvCjYIxJgBEgQxMDYzGOywASDgXCis3_sCMJ7g-wI4RUAAWAFqCU1BSU5CQVNJQ3IIVUFWVEE1QkMKNQjEmAESAzUwMxjgXCDvuAEo7OH7AjCe5PsCOEVAAVgBaglNQUlOQkFTSUNyCFVBVlRBNUJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £348 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:347.30&airProductToken=AQpwCjYIxJgBEgQyMzY5GO-4ASDMfCiA0_sCMMbU-wI4RUAAWAFqCU1BSU5CQVNJQ3IIWEFWU0gzQkMKNgjEmAESBDQxNjkYzHwg7LABKNTW-wIws9f7AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQjRCQwpwCjYIxJgBEgQzNzc4GOywASDMfCjc3vsCMMLf-wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0I0QkMKNgjEmAESBDIxNTEYzHwg77gBKJbj-wIw7uT7AjhFQAFYAWoJTUFJTkJBU0lDcghYQVZTQTBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £354 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:353.70&airProductToken=AQpwCjYIxJgBEgQyMzU5GO-4ASDMfCis0PsCMPDR-wI4VkAAWAFqCU1BSU5DTEFTQ3IIVkFWU0gzTUwKNgjEmAESBDM1NDMYzHwg7LABKL_S-wIwo9P7AjhWQAFYAWoJTUFJTkNMQVNDcghWQVZTSDNNTApwCjYIxJgBEgQzNzc4GOywASDMfCjc3vsCMMLf-wI4VkAAWAFqCU1BSU5DTEFTQ3IIVkFWU0I0TUUKNgjEmAESBDIxNTEYzHwg77gBKJbj-wIw7uT7AjhYQAFYAWoJTUFJTkNMQVNDcghYQVZTQTBNRRIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £374 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:373.10&airProductToken=AQpvCjUIxJgBEgM4ODgY77gBIOBcKLba-wIwytz7AjhUQABYAWoJTUFJTkNMQVNDcghUQVZUQTBNRQo2CMSYARIEMTA2MxjgXCDssAEohN77AjD13vsCOFRAAVgBaglNQUlOQ0xBU0NyCFRBVlRBME1FCnAKNgjEmAESBDM3OTUY7LABIMx8KOjg-wIwzOH7AjhVQABYAWoJTUFJTkNMQVNDcghVQVZUQTVNRQo2CMSYARIEMjE1MRjMfCDvuAEoluP7AjDu5PsCOFVAAVgBaglNQUlOQ0xBU0NyCFVBVlRBNU1FEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £431 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:430.10&airProductToken=AQpwCjYIxJgBEgQyMzY5GO-4ASDMfCiA0_sCMMbU-wI4WEAAWAFqCU1BSU5DTEFTQ3IIWEFWU0gzTUUKNgjEmAESBDQxNjkYzHwg7LABKNTW-wIws9f7AjhWQAFYAWoJTUFJTkNMQVNDcghWQVZTQjRNRQpvCjYIxJgBEgQxMDYzGOywASDgXCis3_sCMJ7g-wI4VUAAWAFqCU1BSU5DTEFTQ3IIVUFWVEE1TUUKNQjEmAESAzUwMxjgXCDvuAEo7OH7AjCe5PsCOFVAAVgBaglNQUlOQ0xBU0NyCFVBVlRBNU1FEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £440 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:439.70&airProductToken=AQpwCjYIxJgBEgQyMzU5GO-4ASDMfCis0PsCMPDR-wI4VEAAWAFqCU1BSU5FWFRSQXIIVEFWMkEwTUUKNgjEmAESBDM1NDMYzHwg7LABKL_S-wIwo9P7AjhUQAFYAWoJTUFJTkVYVFJBcghUQVYyQTBNRQpwCjYIxJgBEgQzNzk1GOywASDMfCjo4PsCMMzh-wI4VUAAWAFqCU1BSU5FWFRSQXIIVUFWMkE1TUUKNgjEmAESBDIxNTEYzHwg77gBKJbj-wIw7uT7AjhVQAFYAWoJTUFJTkVYVFJBcghVQVYyQTVNRRIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £449 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:448.30&airProductToken=AQpwCjYIxJgBEgQyMzU5GO-4ASDMfCis0PsCMPDR-wI4VkAAWAFqCU1BSU5DTEFTQ3IIVkFWU0gzTUwKNgjEmAESBDM1NDMYzHwg7LABKL_S-wIwo9P7AjhWQAFYAWoJTUFJTkNMQVNDcghWQVZTSDNNTApvCjYIxJgBEgQyNDAwGOywASDgXCiU3fsCMIje-wI4S0AAWAFqCU1BSU5DTEFTQ3IIS0FWVEI0TUMKNQjEmAESAzY3NRjgXCDvuAEo-977AjCw4fsCOEtAAVgBaglNQUlOQ0xBU0NyCEtBVlRCNE1DEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £451 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:450.50&airProductToken=AQpwCjYIxJgBEgQyMzY5GO-4ASDMfCiA0_sCMMbU-wI4WEAAWAFqCU1BSU5DTEFTQ3IIWEFWU0gzTUUKNgjEmAESBDQxNjkYzHwg7LABKNTW-wIws9f7AjhWQAFYAWoJTUFJTkNMQVNDcghWQVZTQjRNRQpwCjYIxJgBEgQzNzc4GOywASDMfCjc3vsCMMLf-wI4VkAAWAFqCU1BSU5DTEFTQ3IIVkFWU0I0TUUKNgjEmAESBDIxNTEYzHwg77gBKJbj-wIw7uT7AjhYQAFYAWoJTUFJTkNMQVNDcghYQVZTQTBNRRIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £481 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:480.60&airProductToken=AQpwCjYIxJgBEgQyMzU5GO-4ASDMfCis0PsCMPDR-wI4VEAAWAFqCU1BSU5FWFRSQXIIVEFWMkEwTUUKNgjEmAESBDM1NDMYzHwg7LABKL_S-wIwo9P7AjhUQAFYAWoJTUFJTkVYVFJBcghUQVYyQTBNRQpwCjYIxJgBEgQzNzc4GOywASDMfCjc3vsCMMLf-wI4WEAAWAFqCU1BSU5FWFRSQXIIWEFWMUE1TUUKNgjEmAESBDIxNTEYzHwg77gBKJbj-wIw7uT7AjhYQAFYAWoJTUFJTkVYVFJBcghYQVYxQTBNRRIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £524 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:523.60&airProductToken=AQpwCjYIxJgBEgQyMzY5GO-4ASDMfCiA0_sCMMbU-wI4WEAAWAFqCU1BSU5FWFRSQXIIWEFWMUgzTUUKNgjEmAESBDQxNjkYzHwg7LABKNTW-wIws9f7AjhYQAFYAWoJTUFJTkVYVFJBcghYQVYxQTVNRQpvCjYIxJgBEgQxMDYzGOywASDgXCis3_sCMJ7g-wI4VUAAWAFqCU1BSU5FWFRSQXIIVUFWMkE1TUUKNQjEmAESAzUwMxjgXCDvuAEo7OH7AjCe5PsCOFVAAVgBaglNQUlORVhUUkFyCFVBVjJBNU1FEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 29 Oct - Thu, 30 Oct PDX Portland MDW Chicago £565 Return found 1 hour ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:29/10/2025TANYT&leg2=from:MDW,to:PDX,departure:30/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:564.40&airProductToken=AQpwCjYIxJgBEgQyMzY5GO-4ASDMfCiA0_sCMMbU-wI4WEAAWAFqCU1BSU5FWFRSQXIIWEFWMUgzTUUKNgjEmAESBDQxNjkYzHwg7LABKNTW-wIws9f7AjhYQAFYAWoJTUFJTkVYVFJBcghYQVYxQTVNRQpwCjYIxJgBEgQzNzc4GOywASDMfCjc3vsCMMLf-wI4WEAAWAFqCU1BSU5FWFRSQXIIWEFWMUE1TUUKNgjEmAESBDIxNTEYzHwg77gBKJbj-wIw7uT7AjhYQAFYAWoJTUFJTkVYVFJBcghYQVYxQTBNRRIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ## Find the cheapest month to fly from Portland (PDX) to Chicago (MDW) ### October is typically the cheapest month to fly From £87 - £331 per traveller. Flight from Portland to Chicago route information | Origin airport | Portland Intl. | | --- | --- | | Destination airport | Midway Intl. | | Return price | £268 | | Distance | 2794 km | | Average flight time | 5 hours 57 mins | ## 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 2 flights per day, 19 airlines cover the route. And Southwest Airlines fly direct, getting you to Midway Intl. in just 7hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Portland Intl. to Midway 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 Portland Intl. (PDX) to Midway Intl. (MDW) 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 Midway Intl. start at just £268 and range up to £565.   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 Midway 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.   ## Frequently asked questions ### How much is a flight from Portland Intl. Airport (PDX) to Chicago Airport? > Based on airfares listed within the last 7 days on Expedia for flights departing within the next year, round-trip flights from PDX Airport to Midway Airport start from £268. Book now to secure the best price for your adventure. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from PDX to Midway Intl. Airport (MDW)? > Most flights can be conveniently cancelled online, but whether you are charged a fee all comes down to your airline. If you do have to cancel your holiday, follow the easy instructions in the [Customer Service Portal](https://www.expedia.co.uk/service/?langid=1033). ### How do I find cheap flights from Portland Airport to Midway Airport that have flexible change policies? > Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for PDX Airport to MDW flights, you'll see a "no change fees" filter for you to select. ### How far is the flight from Portland Airport to Midway Airport? > The flying distance between Portland Intl. Airport (PDX) and Midway Intl. Airport (MDW) is 2,800 kilometres. Work your way through your travel song playlist or make a start on the latest bestseller and the trip will whiz by. ### Which airlines fly direct from Portland Intl. Airport (PDX) to MDW? > Operating 30 flights each month, Southwest Airlines (WN) is a popular choice when flying directly from Portland Airport to Midway Intl. Airport (MDW). ### Are Portland Airport to Chicago Airport flight tickets cheaper when they're purchased at the last minute? > Last-minute planners can occasionally find a bargain, with some of the cheapest fares from PDX to Midway Intl. Airport (MDW) arising a few weeks before the departure date. If you'd rather book ahead, Expedia compares and updates the best flight deals regularly — as early as a year in advance in some cases. 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