Title: CA $249 Cheap Flights from Windsor (YQG) 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 $249 Cheap Flights from Windsor (YQG) to Chicago (MDW) [View CA $249 flight on Tue, Jan 6, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YQG,to:MDW,departure:06/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.33&airProductToken=AQppCjII0IgBEgQyNTcwGJg0IPjMASjz2oEDMK7bgQM4VkAAWAFqBUJBU0lDcghWNE4wWlJaTAozCNCIARIEMjM4Nxj4zAEg7LABKNzbgQMwytyBAzhWQAFYAWoFQkFTSUNyCFY0TjBaUlpMEgoIARABGAEqAlBEGAEiBAgBEAEoAigDKAQwAQ) - [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 Windsor, ON (YQG) to Chicago Midway Airport (MDW) - ![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:YQG,to:MDW,departure:02/01/2026TANYT&leg2=from:MDW,to:YQG,departure:09/01/2026TANYT&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 Windsor (YQG) to Chicago (MDW) Prices were available within the past 7 days and start at CA $249 for one-way flights and CA $517 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Fri, Apr 17 - Sun, Apr 19 YQG Windsor MDW Chicago CA $517 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQG,to:MDW,departure:17/04/2026TANYT&leg2=from:MDW,to:YQG,departure:19/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:516.94&airProductToken=AQppCjII0IgBEgQyNTcwGJg0IPjMASjXyooDMJLLigM4V0AAWAFqBUJBU0lDcghXMk4wWkRaTAozCNCIARIEMjM4Nxj4zAEg7LABKLvLigMwqcyKAzhXQAFYAWoFQkFTSUNyCFcyTjBaRFpMCmkKMwjQiAESBDIzODgY7LABIPjMASig44oDMIbkigM4V0AAWAFqBUJBU0lDcghXMk4wWkRaTAoyCNCIARIEMjU3Nxj4zAEgmDQopuaKAzDl5ooDOFdAAVgBagVCQVNJQ3IIVzJOMFpEWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, Apr 22 - Sun, Apr 26 YQG Windsor MDW Chicago CA $528 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQG,to:MDW,departure:22/04/2026TANYT&leg2=from:MDW,to:YQG,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:527.13&airProductToken=AQppCjII0IgBEgQyNTcwGJg0IPjMASj3gosDMLKDiwM4V0AAWAFqBUJBU0lDcghXMk4wWkRaTAozCNCIARIEMjM4Nxj4zAEg7LABKNuDiwMwyYSLAzhXQAFYAWoFQkFTSUNyCFcyTjBaRFpMCmkKMwjQiAESBDIzODgY7LABIPjMASiAsosDMOayiwM4V0AAWAFqBUJBU0lDcghXMk4wWkRaTAoyCNCIARIEMjU3Nxj4zAEgmDQohrWLAzDFtYsDOFdAAVgBagVCQVNJQ3IIVzJOMFpEWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Fri, Apr 17 - Sun, Apr 19 YQG Windsor MDW Chicago CA $550 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQG,to:MDW,departure:17/04/2026TANYT&leg2=from:MDW,to:YQG,departure:19/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:549.71&airProductToken=AQppCjII0IgBEgQyNTcwGJg0IPjMASjXyooDMJLLigM4V0AAWAFqBUJBU0lDcghXMk4wWkRaTAozCNCIARIEMjM5Mxj4zAEg7LABKPbNigMw5M6KAzhXQAFYAWoFQkFTSUNyCFcyTjBaRFpMCmkKMwjQiAESBDIzODgY7LABIPjMASig44oDMIbkigM4V0AAWAFqBUJBU0lDcghXMk4wWkRaTAoyCNCIARIEMjU3Nxj4zAEgmDQopuaKAzDl5ooDOFdAAVgBagVCQVNJQ3IIVzJOMFpEWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, Apr 22 - Sun, Apr 26 YQG Windsor MDW Chicago CA $560 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQG,to:MDW,departure:22/04/2026TANYT&leg2=from:MDW,to:YQG,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:559.90&airProductToken=AQppCjII0IgBEgQyNTcwGJg0IPjMASj3gosDMLKDiwM4V0AAWAFqBUJBU0lDcghXMk4wWkRaTAozCNCIARIEMjM5Mxj4zAEg7LABKJaGiwMwhIeLAzhXQAFYAWoFQkFTSUNyCFcyTjBaRFpMCmkKMwjQiAESBDIzODgY7LABIPjMASiAsosDMOayiwM4V0AAWAFqBUJBU0lDcghXMk4wWkRaTAoyCNCIARIEMjU3Nxj4zAEgmDQohrWLAzDFtYsDOFdAAVgBagVCQVNJQ3IIVzJOMFpEWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Thu, Jan 15 - Thu, Jan 22 YQG Windsor MDW Chicago CA $570 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQG,to:MDW,departure:15/01/2026TANYT&leg2=from:MDW,to:YQG,departure:22/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:569.44&airProductToken=AQppCjII0IgBEgQyNTcwGJg0IPjMASiTwIIDMM7AggM4WkAAWAFqBUJBU0lDcghaMk4wWlJaTAozCNCIARIEMjM4Nxj4zAEg7LABKPzAggMw6sGCAzhaQAFYAWoFQkFTSUNyCFoyTjBaUlpMCmkKMwjQiAESBDIzODgY7LABIPjMASiBkYMDMOeRgwM4WkAAWAFqBUJBU0lDcghaMk4wWlJaTAoyCNCIARIEMjU3Nxj4zAEgmDQogpSDAzDBlIMDOFpAAVgBagVCQVNJQ3IIWjJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Mon, Mar 16 - Fri, Mar 20 YQG Windsor MDW Chicago CA $601 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQG,to:MDW,departure:16/03/2026TANYT&leg2=from:MDW,to:YQG,departure:20/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:600.79&airProductToken=AQpHCiEI0IgBEgQyNTcwGJg0IPjMASjX4ocDMJLjhwM4VkAAWAEKIgjQiAESBDIzODcY-MwBIOywASi744cDMKnkhwM4VkABWAEKRwoiCNCIARIEMjM4OBjssAEg-MwBKOCRiAMwxpKIAzhWQABYAQohCNCIARIEMjU3Nxj4zAEgmDQo5pSIAzCllYgDOFZAAVgBEgoIARABGAEqAlBEGAEiBAgBEAEoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Mon, Mar 16 - Thu, Mar 19 YQG Windsor MDW Chicago CA $619 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQG,to:MDW,departure:16/03/2026TANYT&leg2=from:MDW,to:YQG,departure:19/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:618.64&airProductToken=AQpHCiEI0IgBEgQyNTcwGJg0IPjMASjX4ocDMJLjhwM4VkAAWAEKIgjQiAESBDIzODcY-MwBIOywASi744cDMKnkhwM4VkABWAEKRwoiCNCIARIEMjM4OBjssAEg-MwBKMCGiAMwpoeIAzhXQABYAQohCNCIARIEMjU3Nxj4zAEgmDQoxomIAzCFiogDOFdAAVgBEgoIARABGAEqAlBEGAEiBAgBEAEoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Mon, Mar 16 - Sun, Mar 22 YQG Windsor MDW Chicago CA $641 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQG,to:MDW,departure:16/03/2026TANYT&leg2=from:MDW,to:YQG,departure:22/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:640.69&airProductToken=AQpHCiEI0IgBEgQyNTcwGJg0IPjMASjX4ocDMJLjhwM4VkAAWAEKIgjQiAESBDIzODcY-MwBIOywASi744cDMKnkhwM4VkABWAEKRwoiCNCIARIEMjM4OBjssAEg-MwBKKCoiAMwhqmIAzhaQABYAQohCNCIARIEMjU3Nxj4zAEgmDQopquIAzDlq4gDOFpAAVgBEgoIARABGAEqAlBEGAEiBAgBEAEoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Tue, Mar 17 - Fri, Mar 20 YQG Windsor MDW Chicago CA $664 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQG,to:MDW,departure:17/03/2026TANYT&leg2=from:MDW,to:YQG,departure:20/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:663.78&airProductToken=AQpHCiEI0IgBEgQyNTcwGJg0IPjMASj37YcDMLLuhwM4REAAWAEKIgjQiAESBDIzODcY-MwBIOywASjb7ocDMMnvhwM4REABWAEKRwoiCNCIARIEMjM4OBjssAEg-MwBKOCRiAMwxpKIAzhWQABYAQohCNCIARIEMjU3Nxj4zAEgmDQo5pSIAzCllYgDOFZAAVgBEgoIARABGAEqAlBEGAEiBAgBEAEoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Thu, Mar 19 - Sun, Mar 22 YQG Windsor MDW Chicago CA $674 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQG,to:MDW,departure:19/03/2026TANYT&leg2=from:MDW,to:YQG,departure:22/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:673.50&airProductToken=AQppCjII0IgBEgQyNTcwGJg0IPjMASi3hIgDMPKEiAM4VkAAWAFqBUJBU0lDcghWNk4wWlJaTAozCNCIARIEMjM5Mxj4zAEg7LABKNaHiAMwxIiIAzhWQAFYAWoFQkFTSUNyCFY2TjBaUlpMCmkKMwjQiAESBDIzODgY7LABIPjMASigqIgDMIapiAM4WkAAWAFqBUJBU0lDcghaMk4wWlJaTAoyCNCIARIEMjU3Nxj4zAEgmDQopquIAzDlq4gDOFpAAVgBagVCQVNJQ3IIWjJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ## 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:YQG,to:ORD,departure:02/01/2026TANYT&leg2=from:ORD,to:YQG,departure:09/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. 23 min [Flights from CA $950 ](https://www.expedia.ca/Flights-Search?leg1=from:YQG,to:ORD,departure:02/01/2026TANYT&leg2=from:ORD,to:YQG,departure:09/01/2026TANYT&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 YQG to MDW? ### Do I need to pay a cancellation fee if I cancel my flight from YQG to Midway Intl. Airport (MDW)? ### How do I find cheap flights from Windsor Intl. Airport to Chicago Airport that have flexible change policies? ### How many hours is the flight from YQG to MDW? ### How far is the flight from YQG to MDW? ### Which airlines fly direct from Windsor Airport (YQG) to MDW? ### Are YQG to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute? ## Travel information | Origin airport | Windsor | | ------------------- | ------------ | | Destination airport | Midway Intl. | | Roundtrip price | CA $517 | | Distance | 395 km | ## Book with confidence # Windsor to Chicago Flights **The easy way to book your flights from Windsor to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Windsor 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 Windsor to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Windsor, YQG to Midway Intl., MDW** Sort your search results by price to find great deals on your flight from Windsor to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Windsor currently is just CA $517 rising to CA $674\. Here are more money-saving tips: - Fly in April 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 Windsor** 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 New York (LGA) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/lga/ord/new-york-to-chicago) - [Flights from London (LHR) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/lhr/ord/london-to-chicago) - [Flights from Kansas City (MCI) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/mci/ord/kansas-city-to-chicago) - [Flights from Orlando (MCO) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/mco/ord/orlando-to-chicago) - [Flights from Memphis (MEM) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/mem/ord/memphis-to-chicago) - [Flights from Mexico City (MEX) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/mex/ord/mexico-city-to-chicago) - [Flights from Miami (MIA) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/mia/ord/miami-to-chicago) - [Flights from Milwaukee (MKE) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/mke/ord/milwaukee-to-chicago) - [Flights from Minot (MOT) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/mot/ord/minot-to-chicago) - [Flights from Madison (MSN) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/msn/ord/madison-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/msp/ord/minneapolis-to-chicago) - [Flights from Ogdensburg (OGS) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/ogs/ord/ogdensburg-to-chicago) - [Flights from Omaha (OMA) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/oma/ord/omaha-to-chicago) - [Flights from Ontario (ONT) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/ont/ord/ontario-to-chicago) - [Flights from Plattsburgh (PBG) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/pbg/ord/plattsburgh-to-chicago) - [Flights from Portland (PDX) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/pdx/ord/portland-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/phl/ord/philadelphia-to-chicago) - [Flights from Pittsburgh (PIT) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/pit/ord/pittsburgh-to-chicago) - [Flights from Raleigh (RDU) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/rdu/ord/raleigh-to-chicago) - [Flights from Rockford (RFD) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/rfd/ord/rockford-to-chicago) - [Flights from San Diego (SAN) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/san/ord/san-diego-to-chicago) - [Flights from Louisville (SDF) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/sdf/ord/louisville-to-chicago) - [Flights from Seattle (SEA) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/sea/ord/seattle-to-chicago) - [Flights from San Francisco (SFO) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/sfo/ord/san-francisco-to-chicago) - [Flights from Salt Lake City (SLC) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/slc/ord/salt-lake-city-to-chicago) - [Flights from Syracuse (SYR) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/syr/ord/syracuse-to-chicago) - [Flights from Sault Ste. 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.