Title: CA $177 Cheap Flights from Toronto (YTO) to Chicago (ORD) - 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 $177 Cheap Flights from Toronto (YTO) to Chicago (ORD) [View CA $177 flight on Wed, Feb 18, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YHM,to:ORD,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:176.96&airProductToken=AQpnCjIIwYYBEgQyNDk2GPhhIJjOASiawoUDMOrChQM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIDNTA5GJjOASCuHCjsw4UDMOnEhQM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) - [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 Toronto to Chicago, IL (ORD-O'Hare Intl.) - ![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:YTO,to:ORD,departure:22/01/2026TANYT&leg2=from:ORD,to:YTO,departure:29/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:YTO,to:ORD,departure:22/01/2026TANYT&leg2=from:ORD,to:YTO,departure:29/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:YTO,to:ORD,departure:22/01/2026TANYT&leg2=from:ORD,to:YTO,departure:29/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:YTO,to:ORD,departure:22/01/2026TANYT&leg2=from:ORD,to:YTO,departure:29/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![Air Canada](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada [](https://www.expedia.ca/Flights-Search?leg1=from:YTO,to:ORD,departure:22/01/2026TANYT&leg2=from:ORD,to:YTO,departure:29/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:YTO,to:ORD,departure:22/01/2026TANYT&leg2=from:ORD,to:YTO,departure:29/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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 Toronto (YTO) to Chicago (ORD) Prices were available within the past 7 days and start at CA $177 for one-way flights and CA $281 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Thu, Feb 5 - Sat, Feb 7 YHM Hamilton ORD Chicago CA $281 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YHM,to:ORD,departure:05/02/2026TANYT&leg2=from:ORD,to:YHM,departure:07/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:280.66&airProductToken=AQpnCjIIwYYBEgQyNDk0GPhhIJjOASioroQDMO6uhAM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIDNTA3GJjOASCuHCjDr4QDMLawhAM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQQpoCjIIwYYBEgQ4OTAwGK4cIJjOASjIw4QDMKzEhAM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoyCMGGARIEMjQ5NRiYzgEg-GEox8WEAzCIxoQDOEdAAVgBagVCQVNJQ3IIR05BMkEyQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, Feb 14 - Sun, Feb 15 YKF Kitchener ORD Chicago CA $281 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:14/02/2026TANYT&leg2=from:ORD,to:YKF,departure:15/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:280.70&airProductToken=AQpnCjIIwYYBEgQyNTA2GNgqIJjOASivk4UDMPWThQM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIDNTA3GJjOASCuHCjjlIUDMNaVhQM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQQpnCjEIwYYBEgM1MDYYrhwgmM4BKLCghQMwk6GFAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjIIwYYBEgQyNTE5GJjOASDYKiilooUDMOaihQM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Feb 9 - Mon, Feb 16 YYZ Toronto ORD Chicago CA $281 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:09/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:16/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:280.98&airProductToken=AQo0CjIIwYIBEgQzNjEwGJjOASCuHCjk3oQDMNzfhAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAplCjAIwYIBEgQyMzQ1GK4cIEMo-KeFAzDnqIUDOEJAAFgBagVCQVNJQ3IIT1ZBQ1pTQlgKMQjBggESBDU2NjUYQyCYzgEorKmFAzCTqoUDOEJAAVgBagVCQVNJQ3IIT1ZBQ1pTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, Feb 26 - Sat, Feb 28 YYZ Toronto ORD Chicago CA $281 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:26/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:280.98&airProductToken=AQo3CjUI1YIBEgQyMDY2GJjOASCuHCiZmYYDMJaahgM4TkAAWAFqCEVDT0JBU0lDcghHTkEyQTJCTgo3CjUI1YIBEgQzNDQwGK4cIJjOASizr4YDMKKwhgM4TkAAWAFqCEVDT0JBU0lDcghHTkEyQTJCThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Feb 9 - Mon, Feb 16 YYZ Toronto ORD Chicago CA $289 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:09/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:16/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:288.68&airProductToken=AQpnCjIIwYIBEgQ1ODg3GJjOASDvWSiu2YQDMKLahAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAoxCMGCARIEMjEwOBjvWSCuHCj92oQDMJvchAM4QkABWAFqBUJBU0lDcghPVkFDWlNCWAppCjIIwYIBEgQxNzg0GK4cIOKaASi2qIUDMLSphQM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAozCMGCARIENTAzMBjimgEgmM4BKP-qhQMw_auFAzhCQAFYAWoFQkFTSUNyCE9WQUNaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Feb 16 - Mon, Feb 23 YYZ Toronto ORD Chicago CA $298 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:16/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:23/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:297.08&airProductToken=AQpxCjcIxJgBEgQ1MDMxGJjOASDjtAEovqeFAzCXqIUDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCjYIxJgBEgQ0NDgxGOO0ASCuHCjSqoUDMKirhQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKcQo2CMSYARIEMTMwMhiuHCDjtAEoifyFAzDe_IUDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCjcIxJgBEgQzODk5GOO0ASCYzgEoqP2FAzD8_YUDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Feb 7 - Wed, Feb 11 YYZ Toronto ORD Chicago CA $301 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:07/02/2026TANYT&leg2=from:ORD,to:YYZ,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:300.54&airProductToken=AQo0CjIIwYIBEgQzNjEwGJjOASCuHCikyIQDMJzJhAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Feb 9 - Mon, Feb 16 YYZ Toronto ORD Chicago CA $306 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:09/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:16/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:305.59&airProductToken=AQo0CjIIwYIBEgQzNjEwGJjOASCuHCjk3oQDMNzfhAM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Feb 26 - Tue, Mar 10 YYZ Toronto ORD Chicago CA $308 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:26/02/2026TANYT&leg2=from:ORD,to:YYZ,departure:10/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:307.96&airProductToken=AQo0CjIIwYIBEgQzNTI0GJjOASCuHCj0l4YDMPuYhgM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWApnCjEIwYIBEgQxNTg3GK4cIO9ZKIOghwMw-6CHAzhCQABYAWoFQkFTSUNyCE9VQUNaU0JYCjIIwYIBEgQ1ODg0GO9ZIJjOASiFoocDMPKihwM4QkABWAFqBUJBU0lDcghPVUFDWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Sat, Oct 10 - Sun, Oct 11 YYZ Toronto ORD Chicago CA $485 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:10/10/2026TANYT&leg2=from:ORD,to:YYZ,departure:11/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:484.68&airProductToken=AQpDCkEI0IgBEgQ2MDczGJjOASCuHCjri5oDMOOMmgM4TEAAWAFqCFNUQU5EQVJEcghMMk4xWk9aU3oKCMGCARIENjA3MwpDCkEI0IgBEgQ2MDExGK4cIJjOASiolJoDMI2VmgM4TEAAWAFqCFNUQU5EQVJEcghMMk4xWk9aU3oKCMGCARIENjAxMRIKCAEQARgBKgJQRBgBIgQIARABKAIoAygEMAE) ## Find the cheapest month to fly from Toronto (YTO) to Chicago (ORD) ### January is typically the cheapest month to fly From CA $213 - CA $511 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:YYZ,to:MDW,departure:22/01/2026TANYT&leg2=from:MDW,to:YYZ,departure:01/02/2026TANYT&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 $321 ](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:MDW,departure:22/01/2026TANYT&leg2=from:MDW,to:YYZ,departure:01/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Travel information | Origin airport | John C. Munro Hamilton Intl. | | ------------------- | ---------------------------- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $281 | | Distance | 662 km | ## Book with confidence # Ontario to Chicago Flights **The easy way to book your flights from Toronto to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Toronto 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 O'Hare 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 Toronto to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from YTO-All Airports, YTO to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Toronto to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Toronto currently is just CA $281 rising to CA $485\. Here are more money-saving tips: - Fly in February 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 Toronto** 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. 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[Flights from Baltimore (BWI) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/bwi/mdw/baltimore-to-chicago) - [Flights from Blaine (BWS) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/bws/chi/blaine-to-chicago) - [Flights from Belize City (BZE) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/bze/mdw/belize-city-to-chicago) - [Flights from Charleston (CHS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/chs/mdw/charleston-to-chicago) - [Flights from Cleveland (CLE) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/cle/mdw/cleveland-to-chicago) - [Flights from Danville (DAN) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/dan/chi/danville-to-chicago) - [Flights from Delhi (DEL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/del/mdw/delhi-to-chicago) - [Flights from Des Moines (DSM) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/dsm/mdw/des-moines-to-chicago) - [Flights from Detroit (DTW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago) - [Flights from Detroit (DTW) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/dtw/pwk/detroit-to-chicago) - [Flights from Exeter (EXT) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ext/chi/exeter-to-chicago) - [Flights from Fishers Island (FID) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/fid/mdw/fishers-island-to-chicago) - [Flights from Flint (FNT) to Waukegan (UGN) ](https://www.expedia.ca/lp/flights/fnt/ugn/flint-to-waukegan) - [Flights from Green Bay (GRB) to Waukegan (UGN) ](https://www.expedia.ca/lp/flights/grb/ugn/green-bay-to-waukegan) - [Flights from Grand Rapids (GRR) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/grr/pwk/grand-rapids-to-chicago) - [Flights from Gary (GYY) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/gyy/chi/gary-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/iag/chi/niagara-falls-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/iag/mdw/niagara-falls-to-chicago) - [Flights from Wilmington (ILM) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ilm/chi/wilmington-to-chicago) - [Flights from Indianapolis (IND) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ind/chi/indianapolis-to-chicago) - [Flights from Nakhon Phanom (KOP) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/kop/mdw/nakhon-phanom-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/las/mdw/las-vegas-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Montego Bay (MBJ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mbj/mdw/montego-bay-to-chicago) - [Flights from Orlando (MCO) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mco/mdw/orlando-to-chicago) - [Flights from Michigan City (MGC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mgc/mdw/michigan-city-to-chicago) - [Flights from Muscle Shoals (MSL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/msl/mdw/muscle-shoals-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/msp/chi/minneapolis-to-chicago) - [Flights from New York (NYC) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/nyc/chi/new-york-to-chicago) - [Flights from Omaha (OMA) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/oma/mdw/omaha-to-chicago) - [Flights from Chicago (ORD) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ord/chi/chicago-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago) - [Flights from Pueblo (PUB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/pub/mdw/pueblo-to-chicago) - [Flights from Punta Cana (PUJ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/puj/chi/punta-cana-to-chicago) - [Flights from Roanoke (ROA) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/roa/mdw/roanoke-to-chicago) - [Flights from Selinsgrove (SEG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/seg/mdw/selinsgrove-to-chicago) - [Flights from Sacramento (SMF) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/smf/mdw/sacramento-to-chicago) - [Flights from St. Louis (STL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/stl/mdw/st-louis-to-chicago) - [Flights from Newburgh (SWF) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/swf/mdw/newburgh-to-chicago) - [Flights from Sydney (SYD) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/syd/mdw/sydney-to-chicago) - [Flights from Syracuse (SYR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/syr/mdw/syracuse-to-chicago) - [Flights from Fort Leonard Wood (TBN) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/tbn/mdw/fort-leonard-wood-to-chicago) - [Flights from Ua Pou (UAP) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/uap/chi/ua-pou-to-chicago) - [Flights from Fort Frances (YAG) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yag/chi/fort-frances-to-chicago) - [Flights from Brandon (YBR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ybr/mdw/brandon-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ycd/chi/nanaimo-to-chicago) - [Flights from St. Catharines (YCM) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ycm/chi/st-catharines-to-chicago) - [Flights from Edmonton (YEA) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yea/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yeg/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago) - [Flights from Flin Flon (YFO) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yfo/chi/flin-flon-to-chicago) - [Flights from Hamilton (YHM) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago) - [Flights from Kamloops (YKA) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yka/chi/kamloops-to-chicago) - [Flights from Kelowna (YLW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago) - [Flights from Montreal (YMQ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ymq/chi/montreal-to-chicago) - [Flights from Ottawa (YOW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago) - [Flights from Regina (YQR) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yqr/chi/regina-to-chicago) - [Flights from Regina (YQR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqr/mdw/regina-to-chicago) - [Flights from Gander (YQX) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yqx/chi/gander-to-chicago) - [Flights from Sudbury (YSB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago) - [Flights from Timmins (YTS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago) - [Flights from Toronto (YTZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/ywg/pwk/winnipeg-to-chicago) - [Flights from Whitehorse (YXY) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yxy/chi/whitehorse-to-chicago) - [Flights from Calgary (YYC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago) - [Flights from Victoria (YYJ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yyj/chi/victoria-to-chicago) - [Flights from St. John's (YYT) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yyt/chi/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/yyz/pwk/toronto-to-chicago) \*Available to Expedia members.