Title: CA $270 Cheap Flights from Sioux Falls (FSD) 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 $270 Cheap Flights from Sioux Falls (FSD) to Chicago (ORD) [View CA $270 flight on Tue, Jan 20, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:FSD,to:ORD,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:269.80&airProductToken=AQqnAQo1CMSYARIEMTAwNhjFHCDMfCjU94IDMKT4ggM4RUAAWAFqCU1BSU5CQVNJQ3IIVkE3U0EwQlEKNgjEmAESBDE0MzMYzHwg47QBKLr5ggMwqPqCAzhFQAFYAWoJTUFJTkJBU0lDcghWQTdTQTBCUQo2CMSYARIEMTMwMhjjtAEgrhwoyvyCAzCh_YIDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNYMkJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) - [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 Sioux Falls Regional Airport (FSD) to Chicago O'Hare International Airport (ORD) - ![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:FSD,to:ORD,departure:04/01/2026TANYT&leg2=from:ORD,to:FSD,departure:11/01/2026TANYT&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:FSD,to:ORD,departure:04/01/2026TANYT&leg2=from:ORD,to:FSD,departure:11/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:FSD,to:ORD,departure:04/01/2026TANYT&leg2=from:ORD,to:FSD,departure:11/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Frontier Airlines](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:FSD,to:ORD,departure:04/01/2026TANYT&leg2=from:ORD,to:FSD,departure:11/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![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 Sioux Falls (FSD) to Chicago (ORD) Prices were available within the past 7 days and start at CA $270 for one-way flights and CA $344 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Jan 23 - Sat, Jan 24 FSD Sioux Falls ORD Chicago CA $344 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:FSD,to:ORD,departure:23/01/2026TANYT&leg2=from:ORD,to:FSD,departure:24/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:343.20&airProductToken=AQoiCiAIwYIBEgQzNjUzGMUcIK4cKM-fgwMwxaCDAzhPQABYAQoiCiAIwYIBEgQzNjUzGK4cIMUcKPamgwMw5KeDAzhPQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Jan 17 - Sun, Jan 18 FSD Sioux Falls ORD Chicago CA $344 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:FSD,to:ORD,departure:17/01/2026TANYT&leg2=from:ORD,to:FSD,departure:18/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:343.20&airProductToken=AQoiCiAI1YIBEgQxODU3GMUcIK4cKIrXggMwhNiCAzhLQABYAQohCh8I1YIBEgMzODEYrhwgxRwoluiCAzCG6YIDOEtAAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Jan 17 - Mon, Jan 19 FSD Sioux Falls ORD Chicago CA $364 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:FSD,to:ORD,departure:17/01/2026TANYT&leg2=from:ORD,to:FSD,departure:19/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:363.60&airProductToken=AQoiCiAI1YIBEgQxODU3GMUcIK4cKIrXggMwhNiCAzhLQABYAQohCh8I1YIBEgMzODEYrhwgxRwotvOCAzCm9IIDOExAAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 20 - Wed, Jan 21 FSD Sioux Falls ORD Chicago CA $569 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:FSD,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:FSD,departure:21/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:568.59&airProductToken=AQqnAQo1CMSYARIEMTAwNhjFHCDMfCjU94IDMKT4ggM4RUAAWAFqCU1BSU5CQVNJQ3IIVkE3U0EwQlEKNgjEmAESBDE0MzMYzHwg47QBKLr5ggMwqPqCAzhFQAFYAWoJTUFJTkJBU0lDcghWQTdTQTBCUQo2CMSYARIEMTMwMhjjtAEgrhwoyvyCAzCh_YIDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNYMkJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 20 - Thu, Jan 22 FSD Sioux Falls ORD Chicago CA $570 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:FSD,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:FSD,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:569.60&airProductToken=AQpoCiAIxJgBEgQxMDA2GMUcIMx8KNT3ggMwpPiCAzhFQABYAQohCMSYARIEMTQzMxjMfCDjtAEouvmCAzCo-oIDOEVAAVgBCiEIxJgBEgQxMzAyGOO0ASCuHCjK_IIDMKH9ggM4RUABWAEKQwofCMSYARIDOTUzGK4cIMx8KPqPgwMw3JCDAzhFQABYAQogCMSYARIENTIzNBjMfCDFHCiBkYMDMM6RgwM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Jan 20 - Wed, Jan 21 FSD Sioux Falls ORD Chicago CA $571 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:FSD,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:FSD,departure:21/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:570.71&airProductToken=AQozCjEIwYIBEgQ2MjExGMUcIK4cKJD4ggMwjfmCAzhCQABYAWoFQkFTSUNyCFFWQUhaTkJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Jan 20 - Wed, Jan 21 FSD Sioux Falls ORD Chicago CA $588 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:FSD,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:FSD,departure:21/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:587.20&airProductToken=AQozCjEIwYIBEgQ2MjExGMUcIK4cKJD4ggMwjfmCAzhCQABYAWoFQkFTSUNyCFFWQUhaTkJaCjMKMQjBggESBDYzNzYYrhwgxRwo34mDAzDXioMDOEJAAFgBagVCQVNJQ3IIUVZBSFpOQloSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Jan 20 - Wed, Jan 21 FSD Sioux Falls ORD Chicago CA $601 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:FSD,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:FSD,departure:21/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:600.60&airProductToken=AQozCjEIwYIBEgQ2Mzg4GMUcIK4cKJL7ggMwhPyCAzhCQABYAWoFQkFTSUNyCFFWQUhaTkJaCmgKMgjBggESBDIxNTYYrhwgo7EBKLKEgwMw4YWDAzhCQABYAWoFQkFTSUNyCFFWQUhaTkJaCjIIwYIBEgQzODIwGKOxASDFHCjCh4MDMMOIgwM4QkABWAFqBUJBU0lDcghRVkFIWk5CWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 20 - Wed, Jan 21 FSD Sioux Falls ORD Chicago CA $607 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:FSD,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:FSD,departure:21/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:606.88&airProductToken=AQpuCjUIxJgBEgQ1MjM0GMUcIMx8KLb7ggMwhPyCAzhFQABYAWoJTUFJTkJBU0lDcghVQVZOQTBCUQo1CMSYARIEMTQ3MRjMfCCuHCj__IIDMNv9ggM4RUABWAFqCU1BSU5CQVNJQ3IIVUFWTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 20 - Wed, Jan 21 FSD Sioux Falls ORD Chicago CA $610 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:FSD,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:FSD,departure:21/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:609.77&airProductToken=AQqnAQo1CMSYARIEMTAwNhjFHCDMfCjU94IDMKT4ggM4RUAAWAFqCU1BSU5CQVNJQ3IIVkE3U0EwQlEKNgjEmAESBDE0MzMYzHwg47QBKLr5ggMwqPqCAzhFQAFYAWoJTUFJTkJBU0lDcghWQTdTQTBCUQo2CMSYARIEMTMwMhjjtAEgrhwoyvyCAzCh_YIDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNYMkJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ## Find the cheapest month to fly from Sioux Falls (FSD) to Chicago (ORD) ### March is typically the cheapest month to fly From CA $202 - CA $598 per traveller. ## Frequently asked questions ### How much is a flight from FSD to ORD? ### Do I need to pay a cancellation fee if I cancel my flight from Joe Foss Field to ORD? ### How do I find cheap flights from Joe Foss Field to ORD that have flexible change policies? ### How many hours is the flight from Sioux Falls Regional Airport (FSD) to ORD? ### How far is the flight from Joe Foss Field to ORD? ### Which airlines fly direct from Sioux Falls Regional Airport (FSD) to O'Hare Intl. Airport (ORD)? ### Are Joe Foss Field to ORD flight tickets cheaper when they're purchased at the last minute? ## Travel information | Origin airport | Sioux Falls Regional | | ------------------- | -------------------- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $343 | | Distance | 737 km | | Average flight time | 1 hour 59 mins | ## Book with confidence # Sioux Falls to Chicago Flights **The easy way to book your flights from Sioux Falls to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Sioux Falls 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 Sioux Falls to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Sioux Falls Regional, FSD to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Sioux Falls to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Sioux Falls currently is just CA $344 rising to CA $610\. Here are more money-saving tips: - Fly in January 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 Sioux Falls** 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 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.