Title: CA $127 Cheap Flights from Syracuse (SYR) 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 $127 Cheap Flights from Syracuse (SYR) to Chicago (ORD) [View CA $127 flight on Tue, May 26, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SYR,to:ORD,departure:26/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:126.70&airProductToken=AQpCCiAIwmwSBDE1MTUYko4BIKlRKNiAjgMwn4GOAzhMQABYAQoeCMJsEgM5MDUYqVEgrhwo0IGOAzD9go4DOExAAVgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ## Popular airlines from Hancock Intl. Airport (SYR) to Chicago O'Hare International Airport (ORD) - ![](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:SYR,to:ORD,departure:01/04/2026TANYT&leg2=from:ORD,to:SYR,departure:08/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](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:SYR,to:ORD,departure:01/04/2026TANYT&leg2=from:ORD,to:SYR,departure:08/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](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:SYR,to:ORD,departure:01/04/2026TANYT&leg2=from:ORD,to:SYR,departure:08/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:SYR,to:ORD,departure:01/04/2026TANYT&leg2=from:ORD,to:SYR,departure:08/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:SYR,to:ORD,departure:01/04/2026TANYT&leg2=from:ORD,to:SYR,departure:08/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](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\* - ![](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\* - ![](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 Syracuse (SYR) to Chicago (ORD) Prices were available within the past 7 days and start at CA $127 for one-way flights and CA $269 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, May 26 - Sat, May 30 SYR Syracuse ORD Chicago CA $269 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYR,to:ORD,departure:26/05/2026TANYT&leg2=from:ORD,to:SYR,departure:30/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:268.40&airProductToken=AQpeCi4IwmwSBDE1MTUYko4BIKlRKNiAjgMwn4GOAzhMQABYAWoCRE5yCFBDMkFVRUwxCiwIwmwSAzkwNRipUSCuHCjQgY4DMP2CjgM4TEABWAFqAkROcghQQzJBVUVMMQpfCi0IwmwSAzMxMhiuHCDBkwEo77GOAzCEs44DOExAAFgBagJETnIIVUMyQVVFTDEKLgjCbBIDODQ1GMGTASCSjgEo-rSOAzDHtY4DOExAAVgBagJETnIIVUMyQVVFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sun, May 24 - Sat, May 30 SYR Syracuse ORD Chicago CA $283 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYR,to:ORD,departure:24/05/2026TANYT&leg2=from:ORD,to:SYR,departure:30/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:282.30&airProductToken=AQpCCiAIwmwSBDE1MTUYko4BIKlRKJjqjQMw3-qNAzhMQABYAQoeCMJsEgM5MDUYqVEgrhwokOuNAzC97I0DOExAAVgBCkMKHwjCbBIDMzEyGK4cIMGTASjvsY4DMISzjgM4TEAAWAEKIAjCbBIDODQ1GMGTASCSjgEo-rSOAzDHtY4DOExAAVgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sun, May 31 - Sat, Jun 13 SYR Syracuse ORD Chicago CA $286 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYR,to:ORD,departure:31/05/2026TANYT&leg2=from:ORD,to:SYR,departure:13/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:285.60&airProductToken=AQpCCiAIwmwSBDE1MTUYko4BIKlRKPi4jgMwv7mOAzhMQABYAQoeCMJsEgM5MDUYqVEgrhwo8LmOAzCdu44DOExAAVgBCkMKHwjCbBIDMzEyGK4cIMGTASivz48DMMvQjwM4TEAAWAEKIAjCbBIDODQ1GMGTASCSjgEoutKPAzCG048DOExAAVgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, May 26 - Wed, May 27 SYR Syracuse ORD Chicago CA $291 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYR,to:ORD,departure:26/05/2026TANYT&leg2=from:ORD,to:SYR,departure:27/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:290.90&airProductToken=AQpCCiAIwmwSBDE1MTUYko4BIKlRKNiAjgMwn4GOAzhMQABYAQoeCMJsEgM5MDUYqVEgrhwo0IGOAzD9go4DOExAAVgBCkMKHwjCbBIDMzEyGK4cIMGTASjejY4DMPSOjgM4TEAAWAEKIAjCbBIDODQ1GMGTASCSjgEompOOAzDnk44DOExAAVgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Mon, Jun 8 - Sat, Jun 20 SYR Syracuse ORD Chicago CA $301 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYR,to:ORD,departure:08/06/2026TANYT&leg2=from:ORD,to:SYR,departure:20/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:300.60&airProductToken=AQpCCiAIwmwSBDE1MTUYko4BIKlRKPiSjwMwv5OPAzhMQABYAQoeCMJsEgM5MDUYqVEgrhwo8JOPAzCdlY8DOExAAVgBCkMKHwjCbBIDMzEyGK4cIMGTASiPnpADMKufkAM4TEAAWAEKIAjCbBIDODQ1GMGTASCSjgEomqGQAzDmoZADOExAAVgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Jun 23 - Sat, Jul 4 SYR Syracuse ORD Chicago CA $305 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYR,to:ORD,departure:23/06/2026TANYT&leg2=from:ORD,to:SYR,departure:04/07/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:304.90&airProductToken=AQpDCiAIwmwSAzM3NBiSjgEgwZMBKJS8kAMw1ryQAzhMQABYAQofCMJsEgM4MTEYwZMBIK4cKIDBkAMwucKQAzhMQAFYAQpDCh8IwmwSAzMxMhiuHCDBkwEoz7uRAzDrvJEDOExAAFgBCiAIwmwSAzg0NRjBkwEgko4BKNq-kQMwpr-RAzhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sun, May 24 - Wed, May 27 SYR Syracuse ORD Chicago CA $306 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYR,to:ORD,departure:24/05/2026TANYT&leg2=from:ORD,to:SYR,departure:27/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:306.00&airProductToken=AQpCCiAIwmwSBDE1MTUYko4BIKlRKJjqjQMw3-qNAzhMQABYAQoeCMJsEgM5MDUYqVEgrhwokOuNAzC97I0DOExAAVgBCkMKHwjCbBIDMzEyGK4cIMGTASjejY4DMPSOjgM4TEAAWAEKIAjCbBIDODQ1GMGTASCSjgEompOOAzDnk44DOExAAVgBEgoIARABGAEqAkI2GAEiBAgBEAEoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, May 6 - Sun, May 10 SYR Syracuse ORD Chicago CA $338 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYR,to:ORD,departure:06/05/2026TANYT&leg2=from:ORD,to:SYR,departure:10/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:337.40&airProductToken=AQo0CjIIwYIBEgQ0NTMzGJKOASCuHCj-pYwDMJinjAM4QkAAWAFqBUJBU0lDcghPVkZIWk5CWAo0CjIIwYIBEgQzODc0GK4cIJKOASiMzowDMITPjAM4QkAAWAFqBUJBU0lDcghPVkZIWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Sep 19 - Mon, Sep 21 SYR Syracuse ORD Chicago CA $397 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYR,to:ORD,departure:19/09/2026TANYT&leg2=from:ORD,to:SYR,departure:21/09/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:396.20&airProductToken=AQpvCjYIxJgBEgQ1MzU1GJKOASDLASiUmpgDMN-amAM4RUAAWAFqCU1BSU5CQVNJQ3IIVkZWTkEwQlEKNQjEmAESBDI5ODUYywEgrhwojJuYAzCunJgDOEVAAVgBaglNQUlOQkFTSUNyCFZGVk5BMEJRCm8KNQjEmAESBDE1MzMYrhwgzHwoorWYAzCDtpgDOEVAAFgBaglNQUlOQkFTSUNyCFZGVk5BMEJRCjYIxJgBEgQyNTQ2GMx8IJKOASirt5gDMLS4mAM4RUABWAFqCU1BSU5CQVNJQ3IIVkZWTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Jun 3 - Mon, Jun 8 SYR Syracuse ORD Chicago CA $465 Roundtrip found 13 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYR,to:ORD,departure:03/06/2026TANYT&leg2=from:ORD,to:SYR,departure:08/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:464.90&airProductToken=AQo0CjII1YIBEgQxMDY3GJKOASCuHCiY4I4DMKDhjgM4TEAAWAFqBTJfZWNvcghMRkEyQURETgo0CjII1YIBEgQyNDgxGK4cIJKOASiXmY8DMI-ajwM4TEAAWAFqBTJfZWNvcghMRkEyQUREThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) ## 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:SYR,to:MDW,departure:01/04/2026TANYT&leg2=from:MDW,to:SYR,departure:18/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. CheapestClosest 16 min [Flights from CA $419 ](https://www.expedia.ca/Flights-Search?leg1=from:SYR,to:MDW,departure:01/04/2026TANYT&leg2=from:MDW,to:SYR,departure:18/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Find the cheapest month to fly from Syracuse (SYR) to Chicago (ORD) ### February is typically the cheapest month to fly From CA $208 - CA $476 per traveller. ## Frequently asked questions ### How much is a flight from Syracuse Hancock Intl. Airport to O'Hare Airport? ### Do I need to pay a cancellation fee if I cancel my flight from Hancock Intl. Airport (SYR) to O'Hare Intl. Airport (ORD)? ### How do I find cheap flights from SYR to ORD that have flexible change policies? ### How many hours is the flight from SYR to O'Hare Airport? ### How far is the flight from Syracuse Hancock Intl. Airport to ORD? ### Which airlines fly direct from Syracuse Hancock Intl. Airport to O'Hare Airport? ### Are Syracuse Hancock Intl. Airport to ORD flight tickets cheaper when they're purchased at the last minute? ## Travel information | Origin airport | Hancock Intl. | | ------------------- | ------------------------------------------------- | | Destination airport | O'Hare Intl. | | Airlines serving | American Airlines, Delta, JetBlue Airways, United | | Roundtrip price | CA $268 | | Distance | 967 km | | Average flight time | 1 hour 27 mins | ## Book with confidence # North Syracuse to Chicago Flights **The easy way to book your flights from Syracuse to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Syracuse 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 Syracuse to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Hancock Intl., SYR to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Syracuse to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Syracuse currently is just CA $269 rising to CA $465\. Here are more money-saving tips: - Fly in May 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 Syracuse** 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 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.