Title: CA $204 Cheap Flights from Anchorage (ANC) 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 $204 Cheap Flights from Anchorage (ANC) to Chicago (ORD) [View CA $204 flight on Tue, Mar 10, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:ANC,to:ORD,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:203.60&airProductToken=AQptCjQIxJgBEgM5MjUYoBMgkgEonp6HAzD0n4cDOEVAAFgBaglNQUlOQkFTSUNyCFZBVldBNUJDCjUIxJgBEgQxNTY0GJIBIK4cKLeghwMwsKKHAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZXQTVCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) - [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 Ted Stevens Anchorage International Airport (ANC) to Chicago O'Hare International Airport (ORD) - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:ANC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:ANC,departure:22/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![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:ANC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:ANC,departure:22/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:ANC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:ANC,departure:22/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:ANC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:ANC,departure:22/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:ANC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:ANC,departure:22/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Hawaiian Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_HA.svg) Hawaiian Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:ANC,to:ORD,departure:15/01/2026TANYT&leg2=from:ORD,to:ANC,departure:22/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"HA"}}]) - ![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 Anchorage (ANC) to Chicago (ORD) Prices were available within the past 7 days and start at CA $204 for one-way flights and CA $478 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) Sat, May 23 - Wed, May 27 ANC Anchorage ORD Chicago CA $478 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ANC,to:ORD,departure:23/05/2026TANYT&leg2=from:ORD,to:ANC,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:477.40&airProductToken=AQozCjEIwYIBEgQxMzU0GKATIK4cKKDojQMwqeuNAzhCQABYAWoFQkFTSUNyCE9WQUhaTkJYCmgKMgjBggESBDEzODQYrhwg77kBKKmQjgMwjpKOAzhCQABYAWoFQkFTSUNyCE9WQUhaTkJYCjIIwYIBEgQxOTgxGO-5ASCgEyi4k44DMJ2WjgM4QkABWAFqBUJBU0lDcghPVkFIWk5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, May 23 - Wed, May 27 ANC Anchorage ORD Chicago CA $478 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ANC,to:ORD,departure:23/05/2026TANYT&leg2=from:ORD,to:ANC,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:477.40&airProductToken=AQovCi0IwaYBEgM0MzcYoBMgrhwo--iNAzD0640DOFhAAFgBagJTVnIIT0gyT0FWQk4KXgotCMGmARIDNzE1GK4cIJIBKLSMjgMwxo6OAzhYQABYAWoCU1ZyCE9IMk9BSkJOCi0IwaYBEgM1MzUYkgEgoBMotJGOAzCSk44DOFhAAVgBagJTVnIIT0gyT0FKQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, May 23 - Wed, May 27 ANC Anchorage ORD Chicago CA $482 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ANC,to:ORD,departure:23/05/2026TANYT&leg2=from:ORD,to:ANC,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:481.22&airProductToken=AQovCi0IwaYBEgM0MzcYoBMgrhwo--iNAzD0640DOFhAAFgBagJTVnIIT0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, May 23 - Wed, May 27 ANC Anchorage ORD Chicago CA $491 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ANC,to:ORD,departure:23/05/2026TANYT&leg2=from:ORD,to:ANC,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:490.90&airProductToken=AQpeCi0IwaYBEgMyMjAYoBMgkgEoseCNAzCH4o0DOFhAAFgBagJTVnIIT0gyT0FKQk4KLQjBpgESAzQwORiSASCuHCjB440DMMPljQM4WEABWAFqAlNWcghPSDJPQUpCTgpeCi0IwaYBEgM3MTUYrhwgkgEotIyOAzDGjo4DOFhAAFgBagJTVnIIT0gyT0FKQk4KLQjBpgESAzUzNRiSASCgEyi0kY4DMJKTjgM4WEABWAFqAlNWcghPSDJPQUpCThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, May 23 - Wed, May 27 ANC Anchorage ORD Chicago CA $495 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ANC,to:ORD,departure:23/05/2026TANYT&leg2=from:ORD,to:ANC,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:494.72&airProductToken=AQpfCi4IwaYBEgQxNDg2GKATIJIBKKDkjQMw9-WNAzhYQABYAWoCU1ZyCE9IMk9BSkJOCi0IwaYBEgMzMjgYkgEgrhwogemNAzD86o0DOFhAAVgBagJTVnIIT0gyT0FKQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, May 23 - Wed, May 27 ANC Anchorage ORD Chicago CA $526 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ANC,to:ORD,departure:23/05/2026TANYT&leg2=from:ORD,to:ANC,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:525.75&airProductToken=AQozCjEIwYIBEgQxMzU0GKATIK4cKKDojQMwqeuNAzhCQABYAWoFQkFTSUNyCE9WQUhaTkJYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, May 23 - Wed, May 27 ANC Anchorage ORD Chicago CA $533 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ANC,to:ORD,departure:23/05/2026TANYT&leg2=from:ORD,to:ANC,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:532.70&airProductToken=AQozCjEIwYIBEgQxMzU0GKATIK4cKKDojQMwqeuNAzhCQABYAWoFQkFTSUNyCE9WQUhaTkJYCmcKMgjBggESBDExMjAYrhwgo7EBKPGPjgMwlJGOAzhCQABYAWoFQkFTSUNyCFFWQUtaTkJYCjEIwYIBEgMzOTUYo7EBIKATKKySjgMwzZWOAzhCQAFYAWoFQkFTSUNyCFFWQUtaTkJYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, May 23 - Wed, May 27 ANC Anchorage ORD Chicago CA $535 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ANC,to:ORD,departure:23/05/2026TANYT&leg2=from:ORD,to:ANC,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:535.00&airProductToken=AQpwCjYIxJgBEgQyMDU5GKATIOO0ASio6I0DMK3rjQM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWTkEwQlEKNgjEmAESBDE3MTYY47QBIK4cKI_tjQMw4-2NAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZOQTBCUQptCjUIxJgBEgQxNTY0GK4cIJIBKMSPjgMw1pGOAzhFQABYAWoJTUFJTkJBU0lDcghYQVZPQTBCUQo0CMSYARIDOTM2GJIBIKATKOWTjgMwvpWOAzhFQAFYAWoJTUFJTkJBU0lDcghYQVZPQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, May 23 - Wed, May 27 ANC Anchorage ORD Chicago CA $537 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ANC,to:ORD,departure:23/05/2026TANYT&leg2=from:ORD,to:ANC,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:536.05&airProductToken=AQovCi0IwaYBEgM0MzcYoBMgrhwo--iNAzD0640DOFhAAFgBagJTVnIIT0gyT0FWQk4SCggBEAEYASoCQVMYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, May 23 - Wed, May 27 ANC Anchorage ORD Chicago CA $540 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ANC,to:ORD,departure:23/05/2026TANYT&leg2=from:ORD,to:ANC,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:539.25&airProductToken=AQptCjQIxJgBEgM5MjUYoBMgkgEo2t6NAzCz4I0DOEVAAFgBaglNQUlOQkFTSUNyCFhBVk9BMEJRCjUIxJgBEgQyMDU1GJIBIK4cKPzgjQMw9uKNAzhFQAFYAWoJTUFJTkJBU0lDcghYQVZPQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ## Find the cheapest month to fly from Anchorage (ANC) to Chicago (ORD) ### September is typically the cheapest month to fly From CA $437 - CA $646 per traveller. __Flight from Anchorage to Chicago (ANC - ORD) route information__ | Origin airport | Ted Stevens Anchorage Intl. | | ------------------- | --------------------------- | | Destination airport | O'Hare Intl. | | Airlines serving | Alaska Airlines | | Roundtrip price | CA $477 | | Distance | 4540 km | | Average flight time | 6 hours 24 mins | ## Anchorage to Chicago Flights **The easy way to book your flights from Anchorage to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Anchorage 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 Anchorage to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Ted Stevens Anchorage Intl., ANC to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Anchorage to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Anchorage currently is just CA $478 rising to CA $569\. 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 Anchorage** 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 Ted Stevens Anchorage International Airport to O'Hare Intl. Airport (ORD)? ### Do I need to pay a cancellation fee if I cancel my flight from Ted Stevens Anchorage Intl. Airport (ANC) to O'Hare Intl. Airport (ORD)? ### How do I find cheap flights from Ted Stevens Anchorage International Airport to ORD that have flexible change policies? ### How many hours is the flight from Ted Stevens Anchorage International Airport to O'Hare Airport? ### How far is the flight from Ted Stevens Anchorage International Airport to O'Hare Intl. Airport (ORD)? ### Which airlines fly direct from Ted Stevens Anchorage Intl. 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[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.