Title: CA $167 Cheap Flights from Calgary (YYC) 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 $167 Cheap Flights from Calgary (YYC) to Chicago (ORD) [View CA $167 flight on Thu, Apr 16, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYC,to:ORD,departure:16/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:166.48&airProductToken=AQozCjEIwYIBEgQ0MTYxGJgWIK4cKJfDigMw7sSKAzhCQABYAWoFQkFTSUNyCE9VQUNaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) - [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 Calgary International Airport (YYC) 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:YYC,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YYC,departure:27/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![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:YYC,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YYC,departure:27/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ![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:YYC,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YYC,departure:27/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![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:YYC,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YYC,departure:27/01/2026TANYT&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:YYC,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YYC,departure:27/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:YYC,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YYC,departure:27/01/2026TANYT&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:YYC,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YYC,departure:27/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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 Calgary (YYC) to Chicago (ORD) Prices were available within the past 7 days and start at CA $167 for one-way flights and CA $257 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Apr 13 - Tue, Apr 14 YYC Calgary ORD Chicago CA $257 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:13/04/2026TANYT&leg2=from:ORD,to:YYC,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:256.56&airProductToken=AQpDCh8I1YIBEgM1NTAYmBYgg2ko8J2KAzCMn4oDOE5AAFgBCiAI1YIBEgQyMjU4GINpIK4cKJCkigMwrqWKAzhOQAFYAQohCh8I1YIBEgM3NjQYrhwgmBYo9qmKAzDcq4oDOE5AAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, Jan 22 - Tue, Feb 3 YYC Calgary ORD Chicago CA $257 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:22/01/2026TANYT&leg2=from:ORD,to:YYC,departure:03/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:256.58&airProductToken=AQo4CjYI1YIBEgQxNjU1GJgWIK4cKJmSgwMw7JODAzhOQABYAWoKMV9iYXNpY2Vjb3IIR05BNEEyQk4KNwo1CNWCARIDNzY0GK4cIJgWKPWWhAMw25iEAzhOQABYAWoKMV9iYXNpY2Vjb3IIR05BNEEyQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, May 6 - Thu, May 7 YYC Calgary ORD Chicago CA $262 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:06/05/2026TANYT&leg2=from:ORD,to:YYC,departure:07/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:261.16&airProductToken=AQoiCiAI1YIBEgQxNjU1GJgWIK4cKNajjAMwnqWMAzhOQABYAQpCCh8IwYYBEgM1MjAYrhwgmF0o2ayMAzDgrYwDOEdAAFgBCh8IwYYBEgMzMjMYmF0gmBYouq6MAzDHsIwDOEdAAVgBEgoIARABGAEqAlVBGAEiBAgBEAEoCCgEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Jan 28 - Sun, Feb 15 YYC Calgary ORD Chicago CA $263 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:28/01/2026TANYT&leg2=from:ORD,to:YYC,departure:15/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:262.86&airProductToken=AQozCjEIwYIBEgQ0MTYxGJgWIK4cKJjWgwMw9NeDAzhCQABYAWoFQkFTSUNyCE9VQUNaU0JYCmcKMQjBggESAzk5NBiuHCCjsQEolJyFAzCvnYUDOEJAAFgBagVCQVNJQ3IIT1VBQ1pTQlgKMgjBggESBDE5NzMYo7EBIJgWKPadhQMw5Z-FAzhCQAFYAWoFQkFTSUNyCE9VQUNaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Feb 24 - Tue, Mar 3 YYC Calgary ORD Chicago CA $265 Roundtrip found 20 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:24/02/2026TANYT&leg2=from:ORD,to:YYC,departure:03/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:264.19&airProductToken=AQpCCh8I1YIBEgM1NTAYmBYgg2kou4KGAzDbg4YDOE5AAFgBCh8I1YIBEgM2NzUYg2kgrhwok4eGAzCuiIYDOE5AAVgBCiEKHwjVggESAzc2NBiuHCCYFijx0YYDMNfThgM4TkAAWAESCggBEAEYASoCVUEYASIECAEQASgEMAE) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Jan 20 - Tue, Jan 27 YYC Calgary ORD Chicago CA $268 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:20/01/2026TANYT&leg2=from:ORD,to:YYC,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:267.86&airProductToken=AQpmCjEIwYYBEgMxMzAYmBYgmM4BKLP4ggMwofqCAzhHQABYAWoFQkFTSUNyCEdOQTRBMkJBCjEIwYYBEgM1MDcYmM4BIK4cKMP7ggMwtvyCAzhHQAFYAWoFQkFTSUNyCEdOQTRBMkJBCjUKMwjVggESAzUzNxiuHCCYFijcxoMDMNjKgwM4TkAAWAFqCEVDT0JBU0lDcghHTkE0QTJCThIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, May 5 - Thu, May 7 YYC Calgary ORD Chicago CA $269 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:05/05/2026TANYT&leg2=from:ORD,to:YYC,departure:07/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:268.85&airProductToken=AQpECiAI1YIBEgQxOTUzGJgWIINpKJCZjAMwrpqMAzhOQABYAQogCNWCARIEMTQxMRiDaSCuHCjumowDMIWcjAM4TkABWAEKQgofCMGGARIDNTIwGK4cIJhdKNmsjAMw4K2MAzhHQABYAQofCMGGARIDMzIzGJhdIJgWKLqujAMwx7CMAzhHQAFYARIKCAEQARgBKgJVQRgBIgQIARABKAgoBDAB) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Apr 29 - Thu, May 7 YYC Calgary ORD Chicago CA $273 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:29/04/2026TANYT&leg2=from:ORD,to:YYC,departure:07/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:272.46&airProductToken=AQpECiAIwYYBEgMxMzIYmBYgmM4BKKzSiwMwltSLAzhHQABYAQogCMGGARIDNTA3GJjOASCuHCjn1IsDMNrViwM4R0ABWAEKQgofCMGGARIDNTIwGK4cIJhdKNmsjAMw4K2MAzhHQABYAQofCMGGARIDMzIzGJhdIJgWKLqujAMwx7CMAzhHQAFYARIKCAEQARgBKgJBQxgBIgQIARABKAgoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sat, May 30 - Tue, Jun 2 YYC Calgary ORD Chicago CA $288 Roundtrip found 15 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:30/05/2026TANYT&leg2=from:ORD,to:YYC,departure:02/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:287.99&airProductToken=AQoiCiAI16YBEgQxNjEwGJgWIK4cKMexjgMwl7OOAzhBQABYAQoiCiAI16YBEgQxNjExGK4cIJgWKKbVjgMwi9eOAzhBQABYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, May 6 - Wed, May 13 YYC Calgary ORD Chicago CA $315 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:06/05/2026TANYT&leg2=from:ORD,to:YYC,departure:13/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:314.64&airProductToken=AQpECiAIxJgBEgQ0MDcyGJgWIPISKMOhjAMwzqKMAzhFQABYAQogCMSYARIEMjM3NxjyEiCuHCirpIwDMOiljAM4RUABWAEKRAogCMSYARIEMjI0NxiuHCDyEijP8owDMKj0jAM4RUAAWAEKIAjEmAESBDQxMTMY8hIgmBYor_aMAzCy94wDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ## Find the cheapest month to fly from Calgary (YYC) to Chicago (ORD) ### May is typically the cheapest month to fly From CA $208 - CA $398 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:YYC,to:MDW,departure:20/01/2026TANYT&leg2=from:MDW,to:YYC,departure:27/01/2026TANYT&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 $425 ](https://www.expedia.ca/Flights-Search?leg1=from:YYC,to:MDW,departure:20/01/2026TANYT&leg2=from:MDW,to:YYC,departure:27/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) __Flight from Calgary to Chicago (YYC - ORD) route information__ | Origin airport | Calgary Intl. | | ------------------- | --------------------------------------------------------------------------------------- | | Destination airport | O'Hare Intl. | | Airlines serving | Air Canada, Alaska Airlines, American Airlines, Delta, Porter Airlines, United, WestJet | | Roundtrip price | CA $257 | | Distance | 2211 km | | Average flight time | 4 hours 35 mins | ## Calgary to Chicago Flights **The easy way to book your flights from Calgary to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Calgary 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 Calgary to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Calgary Intl., YYC to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Calgary to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Calgary currently is just CA $257 rising to CA $315\. 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 Calgary** 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 Calgary Intl. Airport (YYC) to ORD? ### Do I need to pay a cancellation fee if I cancel my flight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)? ### How do I find cheap flights from YYC to O'Hare Airport that have flexible change policies? ### How many hours is the flight from Calgary Intl. Airport (YYC) to O'Hare Intl. Airport (ORD)? ### How far is the flight from YYC Calgary International Airport to O'Hare Intl. Airport (ORD)? ### Which airlines fly direct from YYC to ORD? ### Are YYC to ORD flight tickets cheaper when they're purchased at the last minute? ## Explore a world of travel with Expedia - 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) - 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[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.