Title: CA $250 Cheap Alaska Airlines fights from Vancouver to Chicago - 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 $250 Cheap Alaska Airlines fights from Vancouver (YVR) to Chicago (CHI) [View CA $250 flight on Sun, Jan 25, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YVR,to:ORD,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:249.52&airProductToken=AQpgCi8IwaYBEgQzMDA4GLiNASCSASiosYMDMPOxgwM4WEAAWAFqAlNWcghHSDRUQVZCTgotCMGmARIDNDEwGJIBIK4cKNSzgwMwzrWDAzhYQAFYAWoCU1ZyCE9IMk9BVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) - [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 - ![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) ## Alaska Airlines flights from Vancouver to Chicago (YVR→CHI) Prices were available within the past 7 days and start at CA $250 for one-way flights and CA $435 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Jan 13 - Wed, Jan 14 YVR Vancouver ORD Chicago CA $435 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:13/01/2026TANYT&leg2=from:ORD,to:YVR,departure:14/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:434.53&airProductToken=AQpECiEIwaYBEgQyMDQyGLiNASCSASibq4IDMNqrggM4WEAAWAEKHwjBpgESAzUzOBiSASCuHCjur4IDMN6xggM4WEABWAEKRAofCMGmARIDNDA5GK4cIJIBKKa6ggMwyLyCAzhYQABYAQohCMGmARIEMzAwNRiSASC4jQEoyb2CAzCKvoIDOFhAAVgBEgoIARABGAEqAkFTGAEiBAgBEAEoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Feb 11 - Fri, Feb 13 YVR Vancouver ORD Chicago CA $437 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:11/02/2026TANYT&leg2=from:ORD,to:YVR,departure:13/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:436.52&airProductToken=AQpgCi8IwaYBEgQzMDA4GLiNASCSASjI8IQDMJPxhAM4WEAAWAFqAlNWcghHSDRUQVZCTgotCMGmARIDNDEwGJIBIK4cKPTyhAMw7vSEAzhYQAFYAWoCU1ZyCEdIMk9BVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Jan 27 - Wed, Feb 11 YVR Vancouver ORD Chicago CA $447 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:27/01/2026TANYT&leg2=from:ORD,to:YVR,departure:11/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:446.76&airProductToken=AQpgCi8IwaYBEgQzMDA4GLiNASCSASjox4MDMLPIgwM4WEAAWAFqAlNWcghHSDJUWFZCTgotCMGmARIDNDEwGJIBIK4cKJTKgwMwjsyDAzhYQAFYAWoCU1ZyCEdIMk9BVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Jan 21 - Mon, Jan 26 YVR Vancouver ORD Chicago CA $449 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:21/01/2026TANYT&leg2=from:ORD,to:YVR,departure:26/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:448.53&airProductToken=AQpgCi8IwaYBEgQyMDQyGLiNASCSASibhYMDMNqFgwM4WEAAWAFqAlNWcghHSDJUWFZCTgotCMGmARIDNDEwGJIBIK4cKNSGgwMwzoiDAzhYQAFYAWoCU1ZyCE9IMk9BVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sun, Jan 25 - Fri, Jan 30 YVR Vancouver ORD Chicago CA $451 Roundtrip found 16 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:25/01/2026TANYT&leg2=from:ORD,to:YVR,departure:30/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:450.82&airProductToken=AQpgCi8IwaYBEgQzMDA4GLiNASCSASiosYMDMPOxgwM4WEAAWAFqAlNWcghHSDRUQVZCTgotCMGmARIDNDEwGJIBIK4cKNSzgwMwzrWDAzhYQAFYAWoCU1ZyCE9IMk9BVkJOCpABCi4IwaYBEgQxNDQ3GK4cIJJoKJjtgwMwsu-DAzhYQABYAWoCU1ZyCEdIMk9BSkJOCi0IwaYBEgM1NzQYkmggkgEo1--DAzCX8YMDOFhAAVgBagJTVnIIR0gyT0FKQk4KLwjBpgESBDMwMDUYkgEguI0BKMnxgwMwivKDAzhYQAFYAWoCU1ZyCEdINFRBVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Jan 21 - Mon, Jan 26 YVR Vancouver ORD Chicago CA $454 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:ORD,departure:21/01/2026TANYT&leg2=from:ORD,to:YVR,departure:26/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:453.83&airProductToken=AQpgCi8IwaYBEgQzMDA4GLiNASCSASiohIMDMPOEgwM4WEAAWAFqAlNWcghHSDJUWFZCTgotCMGmARIDMjY1GJIBIK4cKL6FgwMwtoeDAzhYQAFYAWoCU1ZyCEdIMk9BVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ## Find the cheapest month to fly from Vancouver (YVR) to Chicago (CHI) ### September is typically the cheapest month to fly From CA $168 - CA $586 per traveller. ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:YVR,to:ORD,departure:11/01/2026TANYT&leg2=from:ORD,to:YVR,departure:17/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. Cheapest 23 min [Flights from CA $537 ](https://www.expedia.ca/Flights-Search?leg1=from:YVR,to:ORD,departure:11/01/2026TANYT&leg2=from:ORD,to:YVR,departure:17/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.ca/Flights-Search?leg1=from:YVR,to:MDW,departure:11/01/2026TANYT&leg2=from:MDW,to:YVR,departure:28/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. Closest 16 min [Flights from CA $844 ](https://www.expedia.ca/Flights-Search?leg1=from:YVR,to:MDW,departure:11/01/2026TANYT&leg2=from:MDW,to:YVR,departure:28/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Travel information | Origin airport | Vancouver Intl. | | ------------------- | --------------- | | Destination airport | O'Hare Intl. | | Distance | 2814 km | \*Available to Expedia members.