Title: CA $375 Cheap Flights from St. John's (YYT) 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 $375 Cheap Flights from St. John's (YYT) to Chicago (ORD) [View CA $375 flight on Wed, Jun 24, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYT,to:ORD,departure:24/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:374.65&airProductToken=AQpnCjIIwYYBEgQxNTE5GJieASCYXSiUxpADML7HkAM4R0AAWAFqBUJBU0lDcghHTkE1QTBCQQoxCMGGARIEODk2MRiYXSCuHCiEyJADMJ7JkAM4R0ABWAFqBUJBU0lDcghHTkE1QTBCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) - [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 St. John's Intl. Airport (YYT) to Chicago O'Hare International Airport (ORD) - ![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:yyt,to:ord,departure:31/10/2025TANYT&leg2=from:ord,to:yyt,departure:07/11/2025TANYT&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:yyt,to:ord,departure:31/10/2025TANYT&leg2=from:ord,to:yyt,departure:07/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:yyt,to:ord,departure:31/10/2025TANYT&leg2=from:ord,to:yyt,departure:07/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![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:yyt,to:ord,departure:31/10/2025TANYT&leg2=from:ord,to:yyt,departure:07/11/2025TANYT&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 St. John's (YYT) to Chicago (ORD) Prices were available within the past 7 days and start at CA $375 for one-way flights and CA $649 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) Tue, Dec 16 - Tue, Jan 6 YYT St. John's ORD Chicago CA $649 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYT,to:ORD,departure:16/12/2025TANYT&leg2=from:ORD,to:YYT,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:648.55&airProductToken=AQplCjEIwYYBEgM2NzMYmJ4BIJhdKOPs_wIwoe7_AjhHQABYAWoFQkFTSUNyCEdOQTVBMEJBCjAIwYYBEgM1MjEYmF0grhwowe__AjDu8P8COEdAAVgBagVCQVNJQ3IIR05BNUEwQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Dec 16 - Tue, Jan 6 YYT St. John's ORD Chicago CA $651 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYT,to:ORD,departure:16/12/2025TANYT&leg2=from:ORD,to:YYT,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:650.72&airProductToken=AQprCjQI1YIBEgQ4NzAwGJieASCYXSjj7P8CMKHu_wI4R0AAWAFqB0VDT05PTVlyCEdOQTVBMFRHCjMI1YIBEgQ4MzcxGJhdIK4cKMHv_wIw7vD_AjhHQAFYAWoHRUNPTk9NWXIIR05BNUEwVEcKogEKMwjVggESBDU0MDAYrhwgoQMotNuBAzCi3IEDOEdAAFgBagdFQ09OT01ZcghHQVgyQUtEUwo0CNWCARIEODExNBihAyCYzgEomd-BAzCQ4IEDOEdAAVgBagdFQ09OT01ZcghHTkE0QTJURwo1CNWCARIEODQwORiYzgEgmJ4BKJPhgQMwz-KBAzhHQAFYAWoHRUNPTk9NWXIIR05BNEEyVEcSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAB) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Dec 16 - Tue, Jan 6 YYT St. John's ORD Chicago CA $658 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYT,to:ORD,departure:16/12/2025TANYT&leg2=from:ORD,to:YYT,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:657.59&airProductToken=AQpnCjIIwYYBEgM2OTMYmJ4BIJjOASjc8P8CMMPy_wI4R0AAWAFqBUJBU0lDcghHTkE1QTBCQQoxCMGGARIDNTA5GJjOASCuHCji8_8CMNr0_wI4R0ABWAFqBUJBU0lDcghHTkE1QTBCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Dec 16 - Tue, Jan 6 YYT St. John's ORD Chicago CA $660 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYT,to:ORD,departure:16/12/2025TANYT&leg2=from:ORD,to:YYT,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:659.76&airProductToken=AQptCjUI1YIBEgQ4Njg2GJieASCYzgEo3PD_AjDD8v8COEdAAFgBagdFQ09OT01ZcghHTkE1QTBURwo0CNWCARIENTg1MhiYzgEgrhwopvP_AjC09P8COEdAAVgBagdFQ09OT01ZcghHTkE1QTBURwqiAQozCNWCARIENTQwMBiuHCChAyi024EDMKLcgQM4R0AAWAFqB0VDT05PTVlyCEdBWDJBS0RTCjQI1YIBEgQ4MTE0GKEDIJjOASiZ34EDMJDggQM4R0ABWAFqB0VDT05PTVlyCEdOQTRBMlRHCjUI1YIBEgQ4NDA5GJjOASCYngEok-GBAzDP4oEDOEdAAVgBagdFQ09OT01ZcghHTkE0QTJURxIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAE) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Jun 24 - Tue, Jun 30 YYT St. John's ORD Chicago CA $673 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYT,to:ORD,departure:24/06/2026TANYT&leg2=from:ORD,to:YYT,departure:30/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:672.78&airProductToken=AQpnCjIIwYYBEgQxNTE5GJieASCYXSiUxpADML7HkAM4R0AAWAFqBUJBU0lDcghHTkE1QTBCQQoxCMGGARIEODk2MRiYXSCuHCiEyJADMJ7JkAM4R0ABWAFqBUJBU0lDcghHTkE1QTBCQQpnCjEIwYYBEgQ4OTYwGK4cIJhdKJSMkQMwn42RAzhHQABYAWoFQkFTSUNyCEdOQTVBMEJBCjIIwYYBEgQxNTIwGJhdIJieASjwjZEDMIiPkQM4R0ABWAFqBUJBU0lDcghHTkE1QTBCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sun, Dec 14 - Sun, Jan 4 YYT St. John's ORD Chicago CA $683 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYT,to:ORD,departure:14/12/2025TANYT&leg2=from:ORD,to:YYT,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:682.01&airProductToken=AQpnCjIIwYYBEgM2OTMYmJ4BIJjOASic2v8CMIPc_wI4R0AAWAFqBUJBU0lDcghHTkE1QTBCQQoxCMGGARIDNTA5GJjOASCuHCii3f8CMJre_wI4R0ABWAFqBUJBU0lDcghHTkE1QTBCQQpnCjEIwYYBEgQ4OTYyGK4cIJhdKM_IgQMwzMmBAzhHQABYAWoFQkFTSUNyCEdOQTVBMEJBCjIIwYYBEgQxNTIyGJhdIJieASjTyoEDMOrLgQM4R0ABWAFqBUJBU0lDcghHTkE1QTBCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Dec 16 - Tue, Jan 6 YYT St. John's ORD Chicago CA $686 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYT,to:ORD,departure:16/12/2025TANYT&leg2=from:ORD,to:YYT,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:685.65&airProductToken=AQprCjQIwYYBEgM2NzMYmJ4BIJhdKOPs_wIwoe7_AjhHQABYAWoIU1RBTkRBUkRyCEdOQTVBMFRHCjMIwYYBEgM1MjEYmF0grhwowe__AjDu8P8COEdAAVgBaghTVEFOREFSRHIIR05BNUEwVEcSCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sun, Dec 14 - Sun, Jan 4 YYT St. John's ORD Chicago CA $692 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYT,to:ORD,departure:14/12/2025TANYT&leg2=from:ORD,to:YYT,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:691.05&airProductToken=AQpnCjIIwYYBEgM2OTMYmJ4BIJjOASic2v8CMIPc_wI4R0AAWAFqBUJBU0lDcghHTkE1QTBCQQoxCMGGARIDNTA5GJjOASCuHCii3f8CMJre_wI4R0ABWAFqBUJBU0lDcghHTkE1QTBCQQpnCjEIwYYBEgM1MDgYrhwgmM4BKOPIgQMwxsmBAzhHQABYAWoFQkFTSUNyCEdOQTVBMEJBCjIIwYYBEgM2OTgYmM4BIJieASjTyoEDMI_MgQM4R0ABWAFqBUJBU0lDcghHTkE1QTBCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Mon, Nov 10 - Fri, Nov 21 YYT St. John's ORD Chicago CA $853 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYT,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:YYT,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:852.01&airProductToken=AQppCiEI0IgBEgMyOTgYmJ4BINizASiu2PwCMOfZ_AI4UEAAWAEKIQjQiAESAzE1OBjYswEgmM4BKOTa_AIwrdv8AjhQQAFYAQohCNCIARIENjA2NRiYzgEgrhwoptz8AjCe3fwCOFBAAVgBCmoKIQjQiAESBDYwMzEYrhwgmM4BKILb_QIw9dv9AjhMQABYAQohCNCIARIDMjA1GJjOASD4yQEoqOH9AjCs4v0COExAAVgBCiII0IgBEgQyMjgzGPjJASCYngEo6-L9AjDZ4_0COExAAVgBEgoIARABGAEqAlBEGAEiBAgBEAEoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Jul 10 - Fri, Jul 17 YYT St. John's ORD Chicago CA $1,486 Roundtrip found 16 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYT,to:ORD,departure:10/07/2026TANYT&leg2=from:ORD,to:YYT,departure:17/07/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1485.99&airProductToken=AQpmCjEI16YBEgM3NjEYmJ4BIJgWKOT6kQMw3v2RAzhMQABYAWoFRUNPTk9yCExDVkQwSEVTCjEI16YBEgQxNjEwGJgWIK4cKOf-kQMwt4CSAzhMQAFYAWoFRUNPTk9yCExUVkQwWkVTCpsBCjEI16YBEgQ4NDYwGK4cIMx8KJTKkgMw7sqSAzhNQABYAWoFRUZMRVhyCE1PMEQwWkZTCjII16YBEgQ1NDAyGMx8IJjOASily5IDMKXMkgM4TUABWAFqBUVGTEVYcghNTzBEMFpGUwoyCNemARIDNzgwGJjOASCYngEovM-SAzD10JIDOE1AAVgBagVFRkxFWHIITU8wRDBaRlMSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from St. John's (YYT) to Chicago (ORD) ### September is typically the cheapest month to fly From CA $545 - CA $1,512 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:YYT,to:MDW,departure:31/10/2025TANYT&leg2=from:MDW,to:YYT,departure:07/11/2025TANYT&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 $1,593](https://www.expedia.ca/Flights-Search?leg1=from:YYT,to:MDW,departure:31/10/2025TANYT&leg2=from:MDW,to:YYT,departure:07/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flight from St. John's to Chicago (YYT - ORD) route information | Origin airport | St. John's Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | Air Canada, Porter Airlines, United, WestJet | | Roundtrip price | CA $649 | | Distance | 2802 km | ## St. John's to Chicago Flights **The easy way to book your flights from St. John's to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from St. John's 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 St. John's to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from St. John's Intl., YYT to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from St. John's to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from St. John's currently is just CA $649 rising to CA $1,486.   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 St. John's**  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 YYT to O'Hare Intl. Airport (ORD)? > Pack your bags, because round-trip journeys between St. John's Intl. Airport (YYT) and O'Hare Airport start from CA $649. That's based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can go up quickly, so book now to secure 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 YYT to O'Hare Intl. Airport (ORD)? > Most flights can be cancelled online, but every airline has its own set of terms and conditions. If you do have to cancel your flight, visit our [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from St. John's Intl. Airport to O'Hare Intl. Airport (ORD) that have flexible change policies? > Plenty of airlines offer the option to reschedule your flight without a change fee. All you pay is the cost difference between flights. When searching for YYT to O'Hare Airport flights, you'll see a "No change fees" box for you to pick. ### How many hours is the flight from St. John's Intl. Airport (YYT) to ORD? > Consider bringing your own entertainment (like some downloaded podcasts), as it takes an average of 5 hours and 47 minutes to arrive at O'Hare Intl. Airport (ORD) from St. John's Intl. Airport. A set of noise-cancelling headphones will also be useful. ### How far is the flight from St. John's Intl. Airport to O'Hare Airport? > It's around 2,800 kilometres between St. John's and Chicago, so expect to be strapped into your seat for a while. Keep yourself occupied with things like a magazine or a thrilling novel. ### Which airlines fly direct from YYT to O'Hare Airport? > You won't find any airlines operating directly between YYT and ORD, so be ready to make at least one stop on your journey. A layover, whether short or long, can be a welcome way to break up a trip! ### Are St. John's Intl. Airport to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? > Flight tickets from St. John's Intl. Airport (YYT) to ORD are available up to a year before departure on Expedia. And although you may nab a fantastic last-minute deal, it's not something you should bank on. Also, booking your flights well in advance means you'll have more choices — and you can avoid landing the dreaded middle seat! We frequently update our fares to bring you the best bargains, so check back often for all the latest specials. ## Explore a world of travel with Expedia - Flights ### Flights - [Flights from Calgary to Rosemont](https://www.expedia.ca/lp/flights/178245/7581/calgary-to-rosemont) - [Flights from Denver to Northwest Chicago](https://www.expedia.ca/lp/flights/178254/6350697/denver-to-northwest-chicago) - [Flights from Los Angeles to Evanston](https://www.expedia.ca/lp/flights/178280/8049/los-angeles-to-evanston) - [Flights from Mexico City to Northwest Chicago](https://www.expedia.ca/lp/flights/178285/6350697/mexico-city-to-northwest-chicago) - [Flights from New York to Evanston](https://www.expedia.ca/lp/flights/178293/8049/new-york-to-evanston) - [Flights from Ottawa to Evanston](https://www.expedia.ca/lp/flights/178296/8049/ottawa-to-evanston) - [Flights from Philadelphia to Rosemont](https://www.expedia.ca/lp/flights/178297/7581/philadelphia-to-rosemont) - [Flights from Portland to Rosemont](https://www.expedia.ca/lp/flights/178299/7581/portland-to-rosemont) - [Flights from San Francisco to Evanston](https://www.expedia.ca/lp/flights/178305/8049/san-francisco-to-evanston) - [Flights from Seattle to Rosemont](https://www.expedia.ca/lp/flights/178307/7581/seattle-to-rosemont) - [Flights from Washington to Evanston](https://www.expedia.ca/lp/flights/178318/8049/washington-to-evanston) - [Flights from Lincoln to Rush Street](https://www.expedia.ca/lp/flights/602964/6175183/lincoln-to-rush-street) - [Flights from Winnipeg to Rosemont](https://www.expedia.ca/lp/flights/6141041/7581/winnipeg-to-rosemont) - [Flights from Ashland (AHM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ahm/chi/ashland-to-chicago) - [Flights from Ann Arbor (ARB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/arb/mdw/ann-arbor-to-chicago) - [Flights from Aspen (ASE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ase/mdw/aspen-to-chicago) - [Flights from Atlanta (ATL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/atl/mdw/atlanta-to-chicago) - [Flights from Aurora (AUZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/auz/mdw/aurora-to-chicago) - [Flights from Hartford (BDL) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bdl/chi/hartford-to-chicago) - [Flights from León (BJX) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bjx/mdw/leon-to-chicago) - [Flights from Bellingham (BLI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bli/mdw/bellingham-to-chicago) - [Flights from Belleville (BLV) to Chicago (CHI)](https://www.expedia.ca/lp/flights/blv/chi/belleville-to-chicago) - [Flights from Boston (BOS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bos/mdw/boston-to-chicago) - [Flights from Burlington (BTV) to Chicago (CHI)](https://www.expedia.ca/lp/flights/btv/chi/burlington-to-chicago) - [Flights from Burlington (BTV) to Chicago (MDW)](https://www.expedia.ca/lp/flights/btv/mdw/burlington-to-chicago) - [Flights from Buffalo (BUF) to Chicago (CHI)](https://www.expedia.ca/lp/flights/buf/chi/buffalo-to-chicago) - [Flights from Buffalo (BUF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/buf/mdw/buffalo-to-chicago) - [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.