Title: CA $506 Cheap Flights from Kelowna (YLW) 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 $506 Cheap Flights from Kelowna (YLW) to Chicago (MDW) [View CA $506 flight on Wed, Oct 22, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YLW,to:MDW,departure:22/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:505.37&airProductToken=AQqmAQoyCNemARIDNTE0GPiyASCYzgEopoz7AjCnjvsCOExAAFgBagVFQ09OT3IITENVRDBMRUsKNwjEmAESBDUwNzMYmM4BIOO0ASjZj_sCMKqQ-wI4TEABWAFqCU1BSU5DTEFTQ3IITEFWT0EwTVEKNwjEmAESBDUyOTgY47QBIOywASjvkPsCMLiR-wI4TEABWAFqCU1BSU5DTEFTQ3IITEFWT0EwTVESCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) - [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 Kelowna Intl. Airport (YLW) 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:ylw,to:mdw,departure:19/10/2025TANYT&leg2=from:mdw,to:ylw,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) ![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 Kelowna (YLW) to Chicago (MDW) Prices were available within the past 7 days and start at CA $506 for one-way flights and CA $848 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Wed, Oct 22 - Wed, Oct 29 YLW Kelowna MDW Chicago CA $848 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:MDW,departure:22/10/2025TANYT&leg2=from:MDW,to:YLW,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:847.45&airProductToken=AQqmAQoyCNemARIDNTE0GPiyASCYzgEopoz7AjCnjvsCOExAAFgBagVFQ09OT3IITENVRDBMRUsKNwjEmAESBDUwNzMYmM4BIOO0ASjZj_sCMKqQ-wI4TEABWAFqCU1BSU5DTEFTQ3IITEFWT0EwTVEKNwjEmAESBDUyOTgY47QBIOywASjvkPsCMLiR-wI4TEABWAFqCU1BSU5DTEFTQ3IITEFWT0EwTVEKowEKNgjEmAESBDM3NzgY7LABIMx8KLzT-wIwotT7AjhVQABYAWoJTUFJTkNMQVNDcghVQVRPQTBNUQo1CMSYARIEMjQ4NxjMfCCYFijb1PsCMIrW-wI4VUABWAFqCU1BSU5DTEFTQ3IIVUFUT0EwTVEKMgjXpgESBDM2MTMYmBYg-LIBKMTX-wIwmdj7AjhMQAFYAWoFRUNPTk9yCExBVUQwTEVLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sun, Oct 19 - Sat, Nov 1 YLW Kelowna MDW Chicago CA $875 Roundtrip found 18 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:MDW,departure:19/10/2025TANYT&leg2=from:MDW,to:YLW,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:874.70&airProductToken=AQqmAQoyCNemARIDNTE0GPiyASCYzgEoxur6AjDH7PoCOExAAFgBagVFQ09OT3IITENRRDBMRUsKNwjEmAESBDUyNTYYmM4BIOO0ASiP7_oCMNrv-gI4VUABWAFqCU1BSU5DTEFTQ3IIVUFVTkEwTVEKNwjEmAESBDM4NjkY47QBIOywASjs8foCML3y-gI4VUABWAFqCU1BSU5DTEFTQ3IIVUFVTkEwTVEKowEKNgjEmAESBDM3NzgY7LABIMx8KJz1-wIwgvb7AjhVQABYAWoJTUFJTkNMQVNDcghVQVRPQTBNUQo1CMSYARIEMjQ4NxjMfCCYFii79vsCMOr3-wI4VUABWAFqCU1BSU5DTEFTQ3IIVUFUT0EwTVEKMgjXpgESBDM2MTMYmBYg-LIBKKT5-wIw9vn7AjhMQAFYAWoFRUNPTk9yCExBVUQwTEVLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Nov 1 - Thu, Nov 6 YLW Kelowna MDW Chicago CA $894 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:MDW,departure:01/11/2025TANYT&leg2=from:MDW,to:YLW,departure:06/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:893.60&airProductToken=AQqYAQovCMGmARIEMzQzNhj4sgEgkgEonPn7AjDm-fsCOEdAAFgBagJNQXIIR0g1T0FKTU4KLQjBpgESAzM4NhiSASDMfCjJ-vsCMJD8-wI4R0ABWAFqAk1BcghHSDVPQUpNTgo2CMSYARIEMzU0MxjMfCDssAEo-__7AjDfgPwCOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1RCqMBCjYIxJgBEgQzNzc4GOywASDMfCj4rfwCMN6u_AI4VUAAWAFqCU1BSU5DTEFTQ3IIVUFUT0EwTVEKNQjEmAESBDI0ODcYzHwgmBYol6_8AjDGsPwCOFVAAVgBaglNQUlOQ0xBU0NyCFVBVE9BME1RCjII16YBEgQzNjEzGJgWIPiyASiAsvwCMNKy_AI4TEABWAFqBUVDT05PcghMQVVEMExFSxIKCAEQARgBKgJXUxgBIgQIARABKAIoAygEMAE) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sat, Nov 22 - Mon, Nov 24 YLW Kelowna MDW Chicago CA $896 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:MDW,departure:22/11/2025TANYT&leg2=from:MDW,to:YLW,departure:24/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:896.00&airProductToken=AQqiAQoyCNemARIEMzgyMBj4sgEgkgEo4eL9AjCv4_0COExAAFgBagVFQ09OT3IITFRVRjVaRUcKNAjEmAESAzU1NBiSASDgXCj84_0CMJ3m_QI4S0ABWAFqCU1BSU5DTEFTQ3IIS0FWVEE1TUwKNgjEmAESBDEwNzYY4Fwg7LABKN_n_QIw1Oj9AjhLQAFYAWoJTUFJTkNMQVNDcghLQVZUQTVNTAqiAQo2CMSYARIEMzc5NRjssAEgzHwow_r9AjCs-_0COFVAAFgBaglNQUlOQ0xBU0NyCFVBVE9BME1RCjUIxJgBEgQyNDg1GMx8IJgWKPL8_QIwqf79AjhVQAFYAWoJTUFJTkNMQVNDcghVQVRPQTBNUQoxCNemARIDMTg5GJgWIPiyASjQ__0CMJuA_gI4TEABWAFqBUVDT05PcghMQVVEMExFSxIKCAEQARgBKgJXUxgBIgQIARABKAIoAygEMAE) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sun, Nov 16 - Tue, Nov 18 YLW Kelowna MDW Chicago CA $898 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:MDW,departure:16/11/2025TANYT&leg2=from:MDW,to:YLW,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:897.73&airProductToken=AQqiAQoyCNemARIEMzgyMBj4sgEgkgEooZ_9AjDvn_0COExAAFgBagVFQ09OT3IITFRVRDBaRUcKNAjEmAESAzU0MhiSASDgXCjKof0CMOqj_QI4S0ABWAFqCU1BSU5DTEFTQ3IIS0FWVEEwTUUKNgjEmAESBDEwNzYY4Fwg7LABKJ-k_QIwlKX9AjhLQAFYAWoJTUFJTkNMQVNDcghLQVZUQTBNRQqiAQo2CMSYARIEMzc5NRjssAEgzHwog7f9AjDst_0COFVAAFgBaglNQUlOQ0xBU0NyCFVBVE9BME1RCjUIxJgBEgQyNDg1GMx8IJgWKLK5_QIw6br9AjhVQAFYAWoJTUFJTkNMQVNDcghVQVRPQTBNUQoxCNemARIDMTg5GJgWIPiyASiQvP0CMNu8_QI4TEABWAFqBUVDT05PcghMQVVEMExFVxIKCAEQARgBKgJXUxgBIgQIARABKAIoAygEMAE) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Wed, Oct 22 - Wed, Oct 29 YLW Kelowna MDW Chicago CA $902 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:MDW,departure:22/10/2025TANYT&leg2=from:MDW,to:YLW,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:901.08&airProductToken=AQqmAQoyCNemARIDNTE0GPiyASCYzgEopoz7AjCnjvsCOExAAFgBagVFQ09OT3IITENVRDBMRUsKNwjEmAESBDUwNzMYmM4BIOO0ASjZj_sCMKqQ-wI4TEABWAFqCU1BSU5DTEFTQ3IITEFWT0EwTVEKNwjEmAESBDUyOTgY47QBIOywASjvkPsCMLiR-wI4TEABWAFqCU1BSU5DTEFTQ3IITEFWT0EwTVEKogEKNgjEmAESBDM3NzgY7LABIMx8KLzT-wIwotT7AjhVQABYAWoJTUFJTkNMQVNDcghVQVRPQTBNUQo1CMSYARIEMjQ4NxjMfCCYFijb1PsCMIrW-wI4VUABWAFqCU1BSU5DTEFTQ3IIVUFUT0EwTVEKMQjXpgESAzE4NRiYFiD4sgEot9j7AjCC2fsCOExAAVgBagVFQ09OT3IITEFVRDBMRUsSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sun, Nov 23 - Mon, Nov 24 YLW Kelowna MDW Chicago CA $907 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:MDW,departure:23/11/2025TANYT&leg2=from:MDW,to:YLW,departure:24/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:906.50&airProductToken=AQqiAQoyCNemARIEMzgyMBj4sgEgkgEoge79AjDP7v0COExAAFgBagVFQ09OT3IITFRVRDBaRUcKNAjEmAESAzU0MhiSASDgXCiq8P0CMMry_QI4S0ABWAFqCU1BSU5DTEFTQ3IIS0FWVEEwTUUKNgjEmAESBDEwNzYY4Fwg7LABKP_y_QIw9PP9AjhLQAFYAWoJTUFJTkNMQVNDcghLQVZUQTBNRQqiAQo2CMSYARIEMzc5NRjssAEgzHwow_r9AjCs-_0COFVAAFgBaglNQUlOQ0xBU0NyCFVBVE9BME1RCjUIxJgBEgQyNDg1GMx8IJgWKPL8_QIwqf79AjhVQAFYAWoJTUFJTkNMQVNDcghVQVRPQTBNUQoxCNemARIDMTg5GJgWIPiyASjQ__0CMJuA_gI4TEABWAFqBUVDT05PcghMQVVEMExFSxIKCAEQARgBKgJXUxgBIgQIARABKAIoAygEMAE) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Oct 31 - Wed, Nov 5 YLW Kelowna MDW Chicago CA $907 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:MDW,departure:31/10/2025TANYT&leg2=from:MDW,to:YLW,departure:05/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:906.62&airProductToken=AQqiAQoyCNemARIEMzgyMBj4sgEgkgEo5er7AjC16_sCOExAAFgBagVFQ09OT3IITFRVRDBaRUcKNAjEmAESAzU1NBiSASDgXCiA7PsCMKDu-wI4S0ABWAFqCU1BSU5DTEFTQ3IIS0FWVEEwTUUKNgjEmAESBDEwNzYY4Fwg7LABKJDv-wIwgvD7AjhLQAFYAWoJTUFJTkNMQVNDcghLQVZUQTBNRQqjAQo2CMSYARIEMzc3OBjssAEgzHwo2KL8AjC-o_wCOFVAAFgBaglNQUlOQ0xBU0NyCFVBVE9BME1RCjUIxJgBEgQyNDg3GMx8IJgWKPej_AIwpqX8AjhVQAFYAWoJTUFJTkNMQVNDcghVQVRPQTBNUQoyCNemARIEMzYxMxiYFiD4sgEo4Kb8AjCyp_wCOExAAVgBagVFQ09OT3IITEFVRDBMRUsSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sun, Oct 19 - Sat, Nov 1 YLW Kelowna MDW Chicago CA $912 Roundtrip found 18 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:MDW,departure:19/10/2025TANYT&leg2=from:MDW,to:YLW,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:911.45&airProductToken=AQqmAQoyCNemARIDNTE0GPiyASCYzgEoxur6AjDH7PoCOExAAFgBagVFQ09OT3IITENRRDBMRUsKNwjEmAESBDUyNTYYmM4BIOO0ASiP7_oCMNrv-gI4VUABWAFqCU1BSU5DTEFTQ3IIVUFVTkEwTVEKNwjEmAESBDM4NjkY47QBIOywASjs8foCML3y-gI4VUABWAFqCU1BSU5DTEFTQ3IIVUFVTkEwTVEKogEKNgjEmAESBDM3NzgY7LABIMx8KJz1-wIwgvb7AjhVQABYAWoJTUFJTkNMQVNDcghVQVRPQTBNUQo1CMSYARIEMjQ4NxjMfCCYFii79vsCMOr3-wI4VUABWAFqCU1BSU5DTEFTQ3IIVUFUT0EwTVEKMQjXpgESAzE4NRiYFiD4sgEol_r7AjDi-vsCOExAAVgBagVFQ09OT3IITEFVRDBMRUsSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Oct 31 - Wed, Nov 5 YLW Kelowna MDW Chicago CA $961 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YLW,to:MDW,departure:31/10/2025TANYT&leg2=from:MDW,to:YLW,departure:05/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:960.25&airProductToken=AQqiAQoyCNemARIEMzgyMBj4sgEgkgEo5er7AjC16_sCOExAAFgBagVFQ09OT3IITFRVRDBaRUcKNAjEmAESAzU1NBiSASDgXCiA7PsCMKDu-wI4S0ABWAFqCU1BSU5DTEFTQ3IIS0FWVEEwTUUKNgjEmAESBDEwNzYY4Fwg7LABKJDv-wIwgvD7AjhLQAFYAWoJTUFJTkNMQVNDcghLQVZUQTBNRQqiAQo2CMSYARIEMzc3OBjssAEgzHwo2KL8AjC-o_wCOFVAAFgBaglNQUlOQ0xBU0NyCFVBVE9BME1RCjUIxJgBEgQyNDg3GMx8IJgWKPej_AIwpqX8AjhVQAFYAWoJTUFJTkNMQVNDcghVQVRPQTBNUQoxCNemARIDMTg1GJgWIPiyASjTp_wCMJ6o_AI4TEABWAFqBUVDT05PcghMQVVEMExFSxIKCAEQARgBKgJXUxgBIgQIARABKAIoAygEMAE) ## 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:YLW,to:ORD,departure:19/10/2025TANYT&leg2=from:ORD,to:YLW,departure:01/11/2025TANYT&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 $735](https://www.expedia.ca/Flights-Search?leg1=from:YLW,to:ORD,departure:19/10/2025TANYT&leg2=from:ORD,to:YLW,departure:01/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Frequently asked questions ### How much is a flight from Kelowna Intl. Airport (YLW) to Midway Airport? > Start packing your bags, because round-trip journeys from Kelowna Intl. Airport to MDW start from CA $848. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can increase quickly, so book now to lock in the best deal. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Kelowna Intl. Airport to MDW? > This can differ between airlines, as each has its own set of terms and conditions. Head to the [Customer Service Portal](https://www.expedia.ca/helpcenter), where there are instructions on how to cancel your flight online. ### How do I find cheap flights from YLW to Midway Airport that have flexible change policies? > Select our "No change fees" filter to find flexible ticketing options for your flight from Kelowna Intl. Airport (YLW) to MDW. This allows you to secure a great price in advance and still have the freedom to make changes without any additional fees. You'll just need to pay the fare difference, if applicable. ### How far is the flight from Kelowna Intl. Airport (YLW) to Chicago Airport? > It's around 2,600 kilometres between YLW and Midway Airport, so expect to be up in the air for a while. Keep yourself entertained by packing things like playing cards (if you're travelling with friends) or a gripping book. ### Which airlines fly direct from YLW to Chicago Airport? > Currently, no airlines offer direct flights from Kelowna Intl. Airport (YLW) to Chicago Airport. You'll have to book a flight with one or more stops. To score the best price and connections, lock in your airfare well ahead of time. ### Are Kelowna Intl. Airport (YLW) to Chicago Airport flight tickets cheaper when they're purchased at the last minute? > It is possible to score an awesome last-minute deal from Kelowna Intl. Airport (YLW) to MDW, but it's also possible to miss out altogether! As many airlines publish prices up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to book when you spot a good bargain. Expedia compares air carrier prices and updates flight deals regularly, so you can be certain you're always seeing the latest offers. ## Travel information | Origin airport | Kelowna Intl. | | --- | --- | | Destination airport | Midway Intl. | | Airlines serving | WestJet | | Roundtrip price | CA $847 | | Distance | 2573 km | ## Book with confidence ### Kelowna to Chicago Flights **The easy way to book your flights from Kelowna to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Kelowna 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 Kelowna to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Kelowna Intl., YLW to Midway Intl., MDW**  Sort your search results by price to find great deals on your flight from Kelowna to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Kelowna currently is just CA $848 rising to CA $961.   Here are more money-saving tips:  - Fly in October 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 Kelowna**  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. ## Explore a world of travel with Expedia - 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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