Title: CA $275 Cheap Flights from Vancouver (YVR) to Chicago (MDW) - 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 $275 Cheap Flights from Vancouver (YVR) to Chicago (MDW) [View CA $275 flight on Wed, Mar 11, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YVR,to:MDW,departure:11/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:274.73&airProductToken=AQqpAQo2CMSYARIEMzk0Mxi4jQEgkgEooKuHAzDvq4cDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNIM0JDCjYIxJgBEgQxNzA2GJIBIOO0ASj0rIcDMPKuhwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkQKNwjEmAESBDUyNzUY47QBIOywASiYr4cDMN-vhwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkQSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) - [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 Vancouver International Airport (YVR) to Chicago Midway Airport (MDW) - ![WestJet](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WS.svg) WestJet [](https://www.expedia.ca/Flights-Search?leg1=from:YVR,to:MDW,departure:10/12/2025TANYT&leg2=from:MDW,to:YVR,departure:17/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![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:YVR,to:MDW,departure:10/12/2025TANYT&leg2=from:MDW,to:YVR,departure:17/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Porter Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_PD.svg) Porter Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:YVR,to:MDW,departure:10/12/2025TANYT&leg2=from:MDW,to:YVR,departure:17/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ![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 Vancouver (YVR) to Chicago (MDW) Prices were available within the past 7 days and start at CA $275 for one-way flights and CA $441 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Dec 10 - Sat, Dec 13 YVR Vancouver MDW Chicago CA $441 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:MDW,departure:10/12/2025TANYT&leg2=from:MDW,to:YVR,departure:13/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:440.50&airProductToken=AQqmAQo2CMSYARIEMzk4Nxi4jQEgkgEovaz_AjCHrf8COEVAAFgBaglNQUlOQkFTSUNyCFZBVlNIM0JDCjQIxJgBEgM1NDIYkgEg4Fwoy6__AjDqsf8COEVAAVgBaglNQUlOQkFTSUNyCFZBVldBNUJDCjYIxJgBEgQxMDc2GOBcIOywASilsv8CMJuz_wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWV0E1QkMKpgEKNgjEmAESBDM3OTUY7LABIMx8KKbQ_wIwitH_AjhFQABYAWoJTUFJTkJBU0lDcghWQVZXQTVCQwo0CMSYARIDODgxGMx8IJIBKMPS_wIwttT_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZXQTVCQwo2CMSYARIEMzg1MxiSASC4jQEov9X_AjD_1f8COEVAAVgBaglNQUlOQkFTSUNyCFZBVlNIM0JDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Feb 13 - Wed, Feb 18 YVR Vancouver MDW Chicago CA $497 Roundtrip found 8 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:MDW,departure:13/02/2026TANYT&leg2=from:MDW,to:YVR,departure:18/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:496.83&airProductToken=AQqoAQo2CMSYARIEMzk0Mxi4jQEgkgEonIeFAzDqh4UDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJDCjUIxJgBEgMzMDIYkgEg47QBKJ6IhQMwooqFAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAo3CMSYARIENTQzMBjjtAEg7LABKPeKhQMwyYuFAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAqoAQo3CMSYARIENTQwNRjssAEg47QBKIbAhQMwy8CFAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAo1CMSYARIDNzI4GOO0ASCSASjvwIUDMJzDhQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkQKNgjEmAESBDM2OTgYkgEguI0BKOnFhQMwrMaFAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTSDNCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Feb 13 - Tue, Feb 17 YVR Vancouver MDW Chicago CA $506 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:MDW,departure:13/02/2026TANYT&leg2=from:MDW,to:YVR,departure:17/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:505.97&airProductToken=AQqoAQo2CMSYARIEMzk0Mxi4jQEgkgEonIeFAzDqh4UDOEVAAFgBaglNQUlOQkFTSUNyCFhBVlNBMEJRCjUIxJgBEgMzMDIYkgEg47QBKJ6IhQMwooqFAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAo3CMSYARIENTQzMBjjtAEg7LABKPeKhQMwyYuFAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAqoAQo3CMSYARIENTQ0NhjssAEg47QBKNC2hQMwlreFAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAo1CMSYARIDOTQ0GOO0ASCSASjnt4UDMJS6hQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkQKNgjEmAESBDM2OTgYkgEguI0BKMm6hQMwjLuFAzhFQAFYAWoJTUFJTkJBU0lDcghYQVZTQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Feb 13 - Tue, Feb 17 YVR Vancouver MDW Chicago CA $510 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:MDW,departure:13/02/2026TANYT&leg2=from:MDW,to:YVR,departure:17/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:509.17&airProductToken=AQqoAQo2CMSYARIEMzk0Mxi4jQEgkgEonIeFAzDqh4UDOEVAAFgBaglNQUlOQkFTSUNyCFhBVlNBMEJRCjUIxJgBEgMzMDIYkgEg47QBKJ6IhQMwooqFAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAo3CMSYARIENTQzMBjjtAEg7LABKPeKhQMwyYuFAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAqoAQo3CMSYARIENTQ0NhjssAEg47QBKNC2hQMwlreFAzhFQABYAWoJTUFJTkJBU0lDcghWQTdTWDBCUQo1CMSYARIDNTY1GOO0ASCSASihuYUDMM27hQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQkMKNgjEmAESBDM4NTMYkgEguI0BKP-7hQMwv7yFAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTSDNCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Dec 10 - Sat, Dec 13 YVR Vancouver MDW Chicago CA $519 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:MDW,departure:10/12/2025TANYT&leg2=from:MDW,to:YVR,departure:13/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:518.21&airProductToken=AQqmAQo2CMSYARIEMzg4Nxi4jQEgkgEomLL_AjDisv8COEVAAFgBaglNQUlOQkFTSUNyCFZBVldBMEJRCjQIxJgBEgM5NDkYkgEgzHwom7T_AjDntf8COEVAAVgBaglNQUlOQkFTSUNyCFhBVlRBMEJECjYIxJgBEgQzNTQzGMx8IOywASjktv8CMNe3_wI4RUABWAFqCU1BSU5CQVNJQ3IIWEFWVEEwQkQKpgEKNgjEmAESBDM3OTUY7LABIMx8KKbQ_wIwitH_AjhFQABYAWoJTUFJTkJBU0lDcghWQVZXQTVCQwo0CMSYARIDODgxGMx8IJIBKMPS_wIwttT_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZXQTVCQwo2CMSYARIEMzg1MxiSASC4jQEov9X_AjD_1f8COEVAAVgBaglNQUlOQkFTSUNyCFZBVlNIM0JDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Dec 10 - Sat, Dec 13 YVR Vancouver MDW Chicago CA $528 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:MDW,departure:10/12/2025TANYT&leg2=from:MDW,to:YVR,departure:13/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:527.40&airProductToken=AQqmAQo2CMSYARIEMzk4Nxi4jQEgkgEovaz_AjCHrf8COEVAAFgBaglNQUlOQkFTSUNyCFZBVlNIM0JDCjQIxJgBEgM1MzYYkgEgzHwota3_AjD9rv8COEVAAVgBaglNQUlOQkFTSUNyCFZBVldBNUJDCjYIxJgBEgQ0MTY5GMx8IOywASjmr_8CMNKw_wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWV0E1QkMKqAEKNwjEmAESBDQ4NTgY7LABIOO0ASihzv8CMOjO_wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU1g1QkMKNQjEmAESAzc2NRjjtAEg8hIo39H_AjDT0_8COEVAAVgBaglNQUlOQkFTSUNyCFZBVlNIM0JRCjYIxJgBEgQzNTg0GPISILiNASiQ1P8CMLTV_wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0gzQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Jan 14 - Wed, Jan 21 YVR Vancouver MDW Chicago CA $542 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:MDW,departure:14/01/2026TANYT&leg2=from:MDW,to:YVR,departure:21/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:541.66&airProductToken=AQqmAQo2CMSYARIEMzYzMBi4jQEgkgEonbaCAzDptoIDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNIM0JDCjQIxJgBEgM1NDIYkgEg4Fwoq7iCAzDHuoIDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJECjYIxJgBEgQxMDc2GOBcIOywASinu4IDMJe8ggM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkQKqAEKNwjEmAESBDU0NDYY7LABIOO0ASjxhoMDMLGHgwM4RUAAWAFqCU1BSU5CQVNJQ3IIVkE3TkEwQlEKNQjEmAESAzU2NRjjtAEgkgEorYmDAzDdi4MDOEVAAVgBaglNQUlOQkFTSUNyCFZBN05BMEJRCjYIxJgBEgQzODUzGJIBILiNASifjIMDMN-MgwM4RUABWAFqCU1BSU5CQVNJQ3IIVkE3TkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Mar 13 - Tue, Mar 17 YVR Vancouver MDW Chicago CA $552 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:MDW,departure:13/03/2026TANYT&leg2=from:MDW,to:YVR,departure:17/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:551.05&airProductToken=AQqoAQo2CMSYARIEMzc2NBi4jQEgkgEolMaHAzDbxocDOEVAAFgBaglNQUlOQkFTSUNyCFhBVlNBMEJRCjUIxJgBEgM4MTAYkgEg47QBKNTJhwMwz8uHAzhFQAFYAWoJTUFJTkJBU0lDcghYQVZUQTBCRAo3CMSYARIENTIxOBjjtAEg7LABKMnMhwMwms2HAzhFQAFYAWoJTUFJTkJBU0lDcghYQVZUQTBCRAqoAQo3CMSYARIENTIxOBjssAEg47QBKKjvhwMw7O-HAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAo1CMSYARIDNzI4GOO0ASCSASiU8IcDMMDyhwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkQKNgjEmAESBDM2ODIYkgEguI0BKIr0hwMwy_SHAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTSDNCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Jan 7 - Thu, Jan 15 YVR Vancouver MDW Chicago CA $553 Roundtrip found 10 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:MDW,departure:07/01/2026TANYT&leg2=from:MDW,to:YVR,departure:15/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:552.49&airProductToken=AQqmAQo2CMSYARIEMzk0Mxi4jQEgkgEo_OaBAzDH54EDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNIM0JRCjQIxJgBEgM1NDIYkgEg4Fwoy-mBAzDn64EDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJECjYIxJgBEgQxMDc2GOBcIOywASjH7IEDMLftgQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkQKqAEKNwjEmAESBDU0MDUY7LABIOO0ASjEwYIDMIvCggM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkQKNQjEmAESAzcyOBjjtAEgkgEosMKCAzDdxIIDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJECjYIxJgBEgQzNjk4GJIBILiNASihx4IDMObHggM4RUABWAFqCU1BSU5CQVNJQ3IIVUFWU0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Feb 13 - Tue, Feb 17 YVR Vancouver MDW Chicago CA $561 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:MDW,departure:13/02/2026TANYT&leg2=from:MDW,to:YVR,departure:17/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:560.51&airProductToken=AQqoAQo2CMSYARIEMzk0Mxi4jQEgkgEonIeFAzDqh4UDOEVAAFgBaglNQUlOQkFTSUNyCFhBVlNBMEJDCjUIxJgBEgMzMDIYkgEg47QBKJ6IhQMwooqFAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAo3CMSYARIENTQzMBjjtAEg7LABKPeKhQMwyYuFAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCRAqoAQo3CMSYARIENTQwNRjssAEg47QBKOa0hQMwq7WFAzhFQABYAWoJTUFJTkJBU0lDcghYQVZUQTBCRAo1CMSYARIDNzI4GOO0ASCSASjPtYUDMPy3hQM4RUABWAFqCU1BSU5CQVNJQ3IIWEFWVEEwQkQKNgjEmAESBDM2ODIYkgEguI0BKMa5hQMwh7qFAzhFQAFYAWoJTUFJTkJBU0lDcghYQVZTQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=FTG_BF_PROMO_) ## 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:10/12/2025TANYT&leg2=from:ORD,to:YVR,departure:14/12/2025TANYT&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 $581](https://www.expedia.ca/Flights-Search?leg1=from:YVR,to:ORD,departure:10/12/2025TANYT&leg2=from:ORD,to:YVR,departure:14/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flight from Vancouver to Chicago (YVR - MDW) route information | Origin airport | Vancouver Intl. | | --- | --- | | Destination airport | Midway Intl. | | Airlines serving | Delta, WestJet | | Roundtrip price | CA $440 | | Distance | 2836 km | ## Vancouver to Chicago Flights **The easy way to book your flights from Vancouver to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Vancouver 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 Midway 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 Vancouver to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Vancouver Intl., YVR to Midway Intl., MDW**  Sort your search results by price to find great deals on your flight from Vancouver to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Vancouver currently is just CA $441 rising to CA $1,193.   Here are more money-saving tips:  - Fly in December 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 Vancouver**  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. ## Frequently asked questions ### How much is a flight from YVR to Midway Airport? > If you're travelling from YVR to Chicago Airport, round-trip flights start from CA $441. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year, so don't hang about. Book today and save yourself both money and time. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Vancouver Intl. Airport (YVR) to Chicago Airport? > Every air carrier has its own set of terms and conditions. If you do decide to cancel, follow the easy instructions on our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from Vancouver Intl. Airport (YVR) to Chicago Airport that have flexible change policies? > Flights from Vancouver Intl. Airport (YVR) to Midway Intl. Airport (MDW) with flexible change policies are available from several carriers. Simply use our "No change fees" filter when searching. You'll only need to pay the difference in ticket price, without any added fees to worry about. ### How many hours is the flight from YVR to Chicago Airport? > You may like to bring your own entertainment (like some downloaded TV shows), as it takes an average of 6 hours and 2 minutes to touch down in Midway Intl. Airport (MDW) from Vancouver Intl. Airport. A pair of noise-cancelling earphones will be useful too. ### How far is the flight from YVR to Midway Airport? > It's around 2,900 kilometres between Vancouver Intl. Airport and Midway Intl. Airport (MDW), so expect to be in your seat for a while. Keep yourself occupied by packing things like your e-reader or a good old-fashioned book. ### Which airlines fly direct from Vancouver Intl. Airport (YVR) to Chicago Airport? > You won't find any airlines operating directly between Vancouver Intl. Airport and MDW, so be prepared to make at least one stop on your journey. A layover can be a good way to break up a trip! ### Are Vancouver Intl. Airport (YVR) to Chicago Airport flight tickets cheaper when they're purchased at the last minute? > Booking last minute from Vancouver Intl. Airport (YVR) to Chicago Airport can be hit-or-miss. It is possible to find a bargain, but then again, you could miss out entirely! If you'd rather play it safe and start your travel planning early, Expedia compares flight deals up to 12 months in advance. Just remember that not all airlines release their prices that far in advance. Our advice? Check back often as prices are updated regularly. ## Explore a world of travel with Expedia - Flights ### Flights - [Flights from Lincoln to Rush Street](https://www.expedia.ca/lp/flights/602964/6175183/lincoln-to-rush-street) - [Flights from Waterloo (ALO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/alo/ord/waterloo-to-chicago) - [Flights from Ahmedabad (AMD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/amd/ord/ahmedabad-to-chicago) - [Flights from Atlanta (ATL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/atl/ord/atlanta-to-chicago) - [Flights from Austin (AUS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/aus/ord/austin-to-chicago) - [Flights from Bangor (BGR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bgr/ord/bangor-to-chicago) - [Flights from Bellingham (BLI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bli/ord/bellingham-to-chicago) - [Flights from Nashville (BNA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bna/ord/nashville-to-chicago) - [Flights from Mumbai (BOM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bom/ord/mumbai-to-chicago) - [Flights from Burlington (BTV) to Chicago (ORD)](https://www.expedia.ca/lp/flights/btv/ord/burlington-to-chicago) - [Flights from Buffalo (BUF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/buf/ord/buffalo-to-chicago) - [Flights from Baltimore (BWI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bwi/ord/baltimore-to-chicago) - [Flights from Sault Ste. 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Marie (YAM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yam/ord/sault-ste-marie-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ycd/ord/nanaimo-to-chicago) - [Flights from St. Catharines (YCM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ycm/ord/st-catharines-to-chicago) - [Flights from Edmonton (YEG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yeg/ord/edmonton-to-chicago) - [Flights from Fredericton (YFC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yfc/ord/fredericton-to-chicago) - [Flights from Kingston (YGK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ygk/ord/kingston-to-chicago) - [Flights from Hamilton (YHM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yhm/ord/hamilton-to-chicago) - [Flights from Halifax (YHZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yhz/ord/halifax-to-chicago) - [Flights from Kamloops (YKA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yka/ord/kamloops-to-chicago) - [Flights from Kitchener (YKF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ykf/ord/kitchener-to-chicago) - [Flights from Kelowna (YLW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ylw/ord/kelowna-to-chicago) - [Flights from Ottawa (YOW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yow/ord/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ypq/ord/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqb/ord/quebec-to-chicago) - [Flights from Windsor (YQG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqg/ord/windsor-to-chicago) - [Flights from Moncton (YQM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqm/ord/moncton-to-chicago) - [Flights from Regina (YQR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqr/ord/regina-to-chicago) - [Flights from Thunder Bay (YQT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqt/ord/thunder-bay-to-chicago) - [Flights from Sudbury (YSB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ysb/ord/sudbury-to-chicago) - [Flights from Saint John (YSJ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ysj/ord/saint-john-to-chicago) - [Flights from Toronto (YTZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ytz/ord/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yul/ord/montreal-to-chicago) - [Flights from Vancouver (YVR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yvr/ord/vancouver-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ywg/ord/winnipeg-to-chicago) - [Flights from Saskatoon (YXE) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxe/ord/saskatoon-to-chicago) - [Flights from London (YXU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxu/ord/london-to-chicago) - [Flights from Abbotsford (YXX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxx/ord/abbotsford-to-chicago) - [Flights from North Bay (YYB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyb/ord/north-bay-to-chicago) - [Flights from Calgary (YYC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyc/ord/calgary-to-chicago) - [Flights from Charlottetown (YYG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyg/ord/charlottetown-to-chicago) - [Flights from Victoria (YYJ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyj/ord/victoria-to-chicago) - [Flights from St. John's (YYT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyt/ord/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Flights from Sarnia (YZR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yzr/ord/sarnia-to-chicago) \*Available to Expedia members.