Title: CA $192 Cheap Flights from Calgary (YYC) to Chicago (MDW) - 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 $192 Cheap Flights from Calgary (YYC) to Chicago (MDW) [View CA $192 flight on Sun, Nov 23, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYC,to:MDW,departure:23/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:191.38&airProductToken=AQpvCjUIxJgBEgQyNDkyGJgWIMx8KK_s_QIw0u39AjhFQABYAWoJTUFJTkJBU0lDcghWQVZOQTBCUQo2CMSYARIEMzc5NRjMfCDssAEolu79AjD77v0COEVAAVgBaglNQUlOQkFTSUNyCFZBVk5BMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) - [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 Midway Airport (MDW) - ![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:mdw,departure:15/11/2025TANYT&leg2=from:mdw,to:yyc,departure:22/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:mdw,departure:15/11/2025TANYT&leg2=from:mdw,to:yyc,departure:22/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![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 (MDW) Prices were available within the past 7 days and start at CA $192 for one-way flights and CA $310 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Nov 23 - Sat, Nov 29 YYC Calgary MDW Chicago CA $310 Roundtrip found 20 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:MDW,departure:23/11/2025TANYT&leg2=from:MDW,to:YYC,departure:29/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:309.60&airProductToken=AQpFCiAIxJgBEgQyNDkyGJgWIMx8KK_s_QIw0u39AjhFQABYAQohCMSYARIEMzc5NRjMfCDssAEolu79AjD77v0COEVAAVgBCkUKIQjEmAESBDM3OTUY7LABIMx8KOOy_gIwzLP-AjhFQABYAQogCMSYARIEMjQ4NRjMfCCYFiiStf4CMMm2_gI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Jan 18 - Fri, Jan 23 YYC Calgary MDW Chicago CA $332 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:MDW,departure:18/01/2026TANYT&leg2=from:MDW,to:YYC,departure:23/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:331.75&airProductToken=AQpvCjUIxJgBEgQyNDkyGJgWIMx8KKriggMw3uOCAzhFQABYAWoJTUFJTkJBU0lDcghWQVdTQTBCUQo2CMSYARIEMzc5MhjMfCDssAEokuSCAzD95IIDOEVAAVgBaglNQUlOQkFTSUNyCFZBV1NBMEJRCqgBCjcIxJgBEgQ1NDA1GOywASDjtAEoxpuDAzCNnIMDOEVAAFgBaglNQUlOQkFTSUNyCFhBVVNBMEJRCjYIxJgBEgQyNjk3GOO0ASDMfCjJnIMDMMKdgwM4RUABWAFqCU1BSU5CQVNJQ3IIWEFVU0EwQlEKNQjEmAESBDI0ODUYzHwgmBYo95-DAzCsoYMDOEVAAVgBaglNQUlOQkFTSUNyCFhBVVNBMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Jan 9 - Sat, Jan 10 YYC Calgary MDW Chicago CA $338 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:MDW,departure:09/01/2026TANYT&leg2=from:MDW,to:YYC,departure:10/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:337.16&airProductToken=AQpFCiAIxJgBEgQyNDkyGJgWIMx8KIr9gQMwvv6BAzhFQABYAQohCMSYARIEMzc5MhjMfCDssAEo8v6BAzDd_4EDOEVAAVgBCkUKIQjEmAESBDM3NzgY7LABIMx8KKmKggMwlIuCAzhFQABYAQogCMSYARIEMjQ4NRjMfCCYFijXjYIDMIyPggM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Nov 18 - Tue, Dec 2 YYC Calgary MDW Chicago CA $342 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:MDW,departure:18/11/2025TANYT&leg2=from:MDW,to:YYC,departure:02/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:341.42&airProductToken=AQpvCjUIxJgBEgQyNDkyGJgWIMx8KI-0_QIwt7X9AjhFQABYAWoJTUFJTkJBU0lDcghYQTBOQTBCUQo2CMSYARIEMzc5NRjMfCDssAEo9rX9AjDbtv0COEVAAVgBaglNQUlOQkFTSUNyCFhBME5BMEJRCm8KNgjEmAESBDM3OTUY7LABIMx8KMbU_gIwqtX-AjhFQABYAWoJTUFJTkJBU0lDcghWQVZOQTBCUQo1CMSYARIEMjQ4NRjMfCCYFijy1v4CMK3Y_gI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 15 - Thu, Nov 20 YYC Calgary MDW Chicago CA $343 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:MDW,departure:15/11/2025TANYT&leg2=from:MDW,to:YYC,departure:20/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:342.47&airProductToken=AQpvCjUIxJgBEgQyNDkyGJgWIMx8KK-S_QIw0pP9AjhFQABYAWoJTUFJTkJBU0lDcghWQVVTQTBCQwo2CMSYARIEMzc5NRjMfCDssAEolpT9AjD7lP0COEVAAVgBaglNQUlOQkFTSUNyCFZBVVNBMEJDCqYBCjYIxJgBEgQyNDAwGOywASDgXCjwyf0CMOjK_QI4RUAAWAFqCU1BSU5CQVNJQ3IIWEFWT0EwQlEKNQjEmAESBDI4MjUY4FwgzHwoic39AjCqzv0COEVAAVgBaglNQUlOQkFTSUNyCFhBVk9BMEJRCjUIxJgBEgQyNDg1GMx8IJgWKPLP_QIwqdH9AjhFQAFYAWoJTUFJTkJBU0lDcghYQVZPQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 15 - Tue, Nov 18 YYC Calgary MDW Chicago CA $347 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:MDW,departure:15/11/2025TANYT&leg2=from:MDW,to:YYC,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:346.67&airProductToken=AQpvCjUIxJgBEgQyNDkyGJgWIMx8KK-S_QIw0pP9AjhFQABYAWoJTUFJTkJBU0lDcghWQVVTQTBCQwo2CMSYARIEMzc5NRjMfCDssAEolpT9AjD7lP0COEVAAVgBaglNQUlOQkFTSUNyCFZBVVNBMEJDCm8KNgjEmAESBDM3OTUY7LABIMx8KIO3_QIw7Lf9AjhFQABYAWoJTUFJTkJBU0lDcghYQTBOQTBCUQo1CMSYARIEMjQ4NRjMfCCYFiiyuf0CMOm6_QI4RUABWAFqCU1BSU5CQVNJQ3IIWEEwTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Dec 25 - Tue, Dec 30 YYC Calgary MDW Chicago CA $353 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:MDW,departure:25/12/2025TANYT&leg2=from:MDW,to:YYC,departure:30/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:352.11&airProductToken=AQpFCiAIxJgBEgQyNDkyGJgWIMx8KKrUgAMw0tWAAzhFQABYAQohCMSYARIENDE2ORjMfCDssAEoitiAAzD32IADOEVAAVgBCkUKIQjEmAESBDM3NzgY7LABIMx8KMyOgQMwtI-BAzhFQABYAQogCMSYARIEMjQ4NRjMfCCYFij7kYEDMLaTgQM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Dec 29 - Tue, Jan 13 YYC Calgary MDW Chicago CA $358 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:MDW,departure:29/12/2025TANYT&leg2=from:MDW,to:YYC,departure:13/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:357.90&airProductToken=AQpFCiAIxJgBEgQyNDkyGJgWIMx8KKqBgQMw0oKBAzhFQABYAQohCMSYARIENDE2ORjMfCDssAEoioWBAzD3hYEDOEVAAVgBCkUKIQjEmAESBDM2ODEY7LABIMx8KIWtggMw8a2CAzhFQABYAQogCMSYARIEMjQ4NRjMfCCYFii3r4IDMOywggM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 5 - Sat, Nov 8 YYC Calgary MDW Chicago CA $373 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:MDW,departure:05/11/2025TANYT&leg2=from:MDW,to:YYC,departure:08/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:372.86&airProductToken=AQpFCiAIxJgBEgQyNDkyGJgWIMx8KPmh_AIwm6P8AjhFQABYAQohCMSYARIEMzc5NRjMfCDssAEo3KP8AjC8pPwCOEVAAVgBCkUKIQjEmAESBDM3NzgY7LABIMx8KLjE_AIwnsX8AjhFQABYAQogCMSYARIEMjQ4NxjMfCCYFijXxfwCMIbH_AI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 20 - Thu, Jan 29 YYC Calgary MDW Chicago CA $384 Roundtrip found 23 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:MDW,departure:20/01/2026TANYT&leg2=from:MDW,to:YYC,departure:29/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:383.20&airProductToken=AQpvCjUIxJgBEgQyNDkyGJgWIMx8KOr4ggMwnvqCAzhWQABYAWoJTUFJTkNMQVNDcghWQVdTQTBNTAo2CMSYARIEMzc5MhjMfCDssAEo0vqCAzC9-4IDOFZAAVgBaglNQUlOQ0xBU0NyCFZBV1NBME1MCqgBCjcIxJgBEgQ1NDA1GOywASDjtAEoht-DAzDN34MDOFZAAFgBaglNQUlOQ0xBU0NyCFZBV1NBME1MCjYIxJgBEgQyNjk3GOO0ASDMfCiJ4IMDMILhgwM4VkABWAFqCU1BSU5DTEFTQ3IIVkFXU0EwTUwKNQjEmAESBDI0ODUYzHwgmBYot-ODAzDs5IMDOFZAAVgBaglNQUlOQ0xBU0NyCFZBV1NBME1MEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ## Find the cheapest month to fly from Calgary (YYC) to Chicago (MDW) ### January is typically the cheapest month to fly From CA $298 - CA $887 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:ORD,departure:15/11/2025TANYT&leg2=from:ORD,to:YYC,departure:25/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. 23 min [Flights from CA $974](https://www.expedia.ca/Flights-Search?leg1=from:YYC,to:ORD,departure:15/11/2025TANYT&leg2=from:ORD,to:YYC,departure:25/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Frequently asked questions ### How much is a flight from YYC Calgary International Airport to Midway Intl. Airport (MDW)? > Based on fares available within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between YYC Calgary International Airport and Chicago Airport start from CA $310. Book now to secure the best price for your journey. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from YYC to Midway Intl. Airport (MDW)? > We understand that things come up unexpectedly, so we've made it as simple as possible for you to cancel your flight online. Just visit the [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from YYC Calgary International Airport to MDW that have flexible change policies? > Many carriers will allow you to move your flight without a change fee. All you pay is the fare difference. When searching for Calgary Intl. Airport (YYC) to MDW flights, you'll see a "No change fees" box for you to select. ### How many hours is the flight from YYC to MDW? > Consider bringing your own entertainment (like some downloaded podcasts), as it takes an average of 5 hours and 24 minutes to touch down in MDW from Calgary Intl. Airport (YYC). A good pair of noise-cancelling headphones will also be useful. ### How far is the flight from YYC Calgary International Airport to Midway Intl. Airport (MDW)? > Around 2,300 kilometres separates Calgary and Chicago, so pack something to keep you busy for a couple of hours. That thrilling novel you haven't had time to start will do the trick. ### Which airlines fly direct from Calgary Intl. Airport (YYC) to MDW? > If you want to travel straight from YYC to Midway Intl. Airport (MDW), you'll need to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly on this route. ### Are YYC Calgary International Airport to Chicago Airport flight tickets cheaper when they're purchased at the last minute? > Booking last minute from YYC to Chicago Airport can be hit-or-miss. You may be able to score a bargain, but then again, you could miss out entirely! If you'd rather play it safe and start planning your trip early on, Expedia compares flight deals up to 12 months in advance. Just keep in mind that not all airlines release their prices so far in advance. Our suggestion? Check back often as prices are updated frequently. ## Travel information | Origin airport | Calgary Intl. | | --- | --- | | Destination airport | Midway Intl. | | Airlines serving | Delta, WestJet | | Roundtrip price | CA $310 | | Distance | 2234 km | ## Book with confidence ### 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 Midway 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 Midway Intl., MDW**  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 $310 rising to CA $544.   Here are more money-saving tips:  - Fly in November 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. 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Marie (CIU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ciu/ord/sault-ste-marie-to-chicago) - [Flights from Charlotte (CLT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/clt/ord/charlotte-to-chicago) - [Flights from Columbus (CMH) to Chicago (ORD)](https://www.expedia.ca/lp/flights/cmh/ord/columbus-to-chicago) - [Flights from Cincinnati (CVG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/cvg/ord/cincinnati-to-chicago) - [Flights from Washington (DCA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dca/ord/washington-to-chicago) - [Flights from Delhi (DEL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/del/ord/delhi-to-chicago) - [Flights from Denver (DEN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/den/ord/denver-to-chicago) - [Flights from Dallas (DFW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dfw/ord/dallas-to-chicago) - [Flights from Duluth (DLH) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dlh/ord/duluth-to-chicago) - [Flights from Des Moines (DSM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dsm/ord/des-moines-to-chicago) - [Flights from Detroit (DTW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dtw/ord/detroit-to-chicago) - [Flights from Dubai (DXB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dxb/ord/dubai-to-chicago) - [Flights from Fargo (FAR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/far/ord/fargo-to-chicago) - [Flights from Fort Lauderdale (FLL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/fll/ord/fort-lauderdale-to-chicago) - [Flights from Flint (FNT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/fnt/ord/flint-to-chicago) - [Flights from Spokane (GEG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/geg/ord/spokane-to-chicago) - [Flights from Grand Forks (GFK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/gfk/ord/grand-forks-to-chicago) - [Flights from Green Bay (GRB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/grb/ord/green-bay-to-chicago) - [Flights from Grand Rapids (GRR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/grr/ord/grand-rapids-to-chicago) - [Flights from Great Falls (GTF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/gtf/ord/great-falls-to-chicago) - [Flights from Houston (HOU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/hou/ord/houston-to-chicago) - [Flights from Hyderabad (HYD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/hyd/ord/hyderabad-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/iag/ord/niagara-falls-to-chicago) - [Flights from Indianapolis (IND) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ind/ord/indianapolis-to-chicago) - [Flights from New York (JFK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/jfk/ord/new-york-to-chicago) - [Flights from Karachi (KHI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/khi/ord/karachi-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/las/ord/las-vegas-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/lax/ord/los-angeles-to-chicago) - [Flights from New York (LGA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/lga/ord/new-york-to-chicago) - [Flights from London (LHR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/lhr/ord/london-to-chicago) - [Flights from Kansas City (MCI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mci/ord/kansas-city-to-chicago) - [Flights from Orlando (MCO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mco/ord/orlando-to-chicago) - [Flights from Memphis (MEM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mem/ord/memphis-to-chicago) - [Flights from Mexico City (MEX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mex/ord/mexico-city-to-chicago) - [Flights from Miami (MIA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mia/ord/miami-to-chicago) - [Flights from Milwaukee (MKE) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mke/ord/milwaukee-to-chicago) - [Flights from Minot (MOT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mot/ord/minot-to-chicago) - [Flights from Madison (MSN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/msn/ord/madison-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (ORD)](https://www.expedia.ca/lp/flights/msp/ord/minneapolis-to-chicago) - [Flights from Ogdensburg (OGS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ogs/ord/ogdensburg-to-chicago) - [Flights from Omaha (OMA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/oma/ord/omaha-to-chicago) - [Flights from Ontario (ONT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ont/ord/ontario-to-chicago) - [Flights from Plattsburgh (PBG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pbg/ord/plattsburgh-to-chicago) - [Flights from Portland (PDX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pdx/ord/portland-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/phl/ord/philadelphia-to-chicago) - [Flights from Pittsburgh (PIT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pit/ord/pittsburgh-to-chicago) - [Flights from Raleigh (RDU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/rdu/ord/raleigh-to-chicago) - [Flights from Rockford (RFD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/rfd/ord/rockford-to-chicago) - [Flights from San Diego (SAN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/san/ord/san-diego-to-chicago) - [Flights from Louisville (SDF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/sdf/ord/louisville-to-chicago) - [Flights from Seattle (SEA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/sea/ord/seattle-to-chicago) - [Flights from San Francisco (SFO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/sfo/ord/san-francisco-to-chicago) - [Flights from Salt Lake City (SLC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/slc/ord/salt-lake-city-to-chicago) - [Flights from Syracuse (SYR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/syr/ord/syracuse-to-chicago) - [Flights from Sault Ste. Marie (YAM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yam/ord/sault-ste-marie-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ycd/ord/nanaimo-to-chicago) - [Flights from St. Catharines (YCM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ycm/ord/st-catharines-to-chicago) - [Flights from Edmonton (YEG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yeg/ord/edmonton-to-chicago) - [Flights from Fredericton (YFC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yfc/ord/fredericton-to-chicago) - [Flights from Kingston (YGK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ygk/ord/kingston-to-chicago) - [Flights from Hamilton (YHM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yhm/ord/hamilton-to-chicago) - [Flights from Halifax (YHZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yhz/ord/halifax-to-chicago) - [Flights from Kamloops (YKA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yka/ord/kamloops-to-chicago) - [Flights from Kitchener (YKF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ykf/ord/kitchener-to-chicago) - [Flights from Kelowna (YLW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ylw/ord/kelowna-to-chicago) - [Flights from Ottawa (YOW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yow/ord/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ypq/ord/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqb/ord/quebec-to-chicago) - [Flights from Windsor (YQG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqg/ord/windsor-to-chicago) - [Flights from Moncton (YQM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqm/ord/moncton-to-chicago) - [Flights from Regina (YQR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqr/ord/regina-to-chicago) - [Flights from Thunder Bay (YQT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqt/ord/thunder-bay-to-chicago) - [Flights from Sudbury (YSB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ysb/ord/sudbury-to-chicago) - [Flights from Saint John (YSJ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ysj/ord/saint-john-to-chicago) - [Flights from Toronto (YTZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ytz/ord/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yul/ord/montreal-to-chicago) - [Flights from Vancouver (YVR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yvr/ord/vancouver-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ywg/ord/winnipeg-to-chicago) - [Flights from Saskatoon (YXE) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxe/ord/saskatoon-to-chicago) - [Flights from London (YXU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxu/ord/london-to-chicago) - [Flights from Abbotsford (YXX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxx/ord/abbotsford-to-chicago) - [Flights from North Bay (YYB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyb/ord/north-bay-to-chicago) - [Flights from Calgary (YYC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyc/ord/calgary-to-chicago) - [Flights from Charlottetown (YYG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyg/ord/charlottetown-to-chicago) - [Flights from Victoria (YYJ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyj/ord/victoria-to-chicago) - [Flights from St. John's (YYT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyt/ord/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Flights from Sarnia (YZR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yzr/ord/sarnia-to-chicago) \*Available to Expedia members.