Title: CA $126 Cheap Flights from Pensacola (PNS) 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 $126 Cheap Flights from Pensacola (PNS) to Chicago (ORD) [View CA $126 flight on Tue, Mar 31, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:PNS,to:ORD,departure:31/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:125.87&airProductToken=AQpaCi0IzpYBEgQxNjU3GK-TASDlWiiMj4kDMPKPiQM4R0AAWAFqAlJQcgZHQTIxTlIKKQjOlgESATEY5Vogrhwo15GJAzChk4kDOEdAAVgBagJSUHIGR0EyMU5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) - [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 Pensacola Intl. Airport (PNS) to Chicago O'Hare International Airport (ORD) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:PNS,to:ORD,departure:12/02/2026TANYT&leg2=from:ORD,to:PNS,departure:19/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![](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:PNS,to:ORD,departure:12/02/2026TANYT&leg2=from:ORD,to:PNS,departure:19/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:PNS,to:ORD,departure:12/02/2026TANYT&leg2=from:ORD,to:PNS,departure:19/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:PNS,to:ORD,departure:12/02/2026TANYT&leg2=from:ORD,to:PNS,departure:19/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:PNS,to:ORD,departure:12/02/2026TANYT&leg2=from:ORD,to:PNS,departure:19/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](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:PNS,to:ORD,departure:12/02/2026TANYT&leg2=from:ORD,to:PNS,departure:19/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Pensacola (PNS) to Chicago (ORD) Prices were available within the past 7 days and start at CA $126 for one-way flights and CA $281 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) Fri, May 15 - Wed, May 20 PNS Pensacola ORD Chicago CA $281 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PNS,to:ORD,departure:15/05/2026TANYT&leg2=from:ORD,to:PNS,departure:20/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:280.21&airProductToken=AQo0CjII1YIBEgQyMDA1GK-TASCuHCifiY0DMMKKjQM4S0AAWAFqBTJfZWNvcghLQUEyUEZEThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, May 15 - Wed, May 20 PNS Pensacola ORD Chicago CA $286 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PNS,to:ORD,departure:15/05/2026TANYT&leg2=from:ORD,to:PNS,departure:20/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:285.40&airProductToken=AQo0CjII1YIBEgQyMDA1GK-TASCuHCifiY0DMMKKjQM4S0AAWAFqBTJfZWNvcghLQUEyUEZETgo0CjII1YIBEgQyNjcyGK4cIK-TASjsv40DMIHBjQM4S0AAWAFqBTJfZWNvcghLQUEyUEZEThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, May 15 - Wed, May 20 PNS Pensacola ORD Chicago CA $298 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PNS,to:ORD,departure:15/05/2026TANYT&leg2=from:ORD,to:PNS,departure:20/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:297.63&airProductToken=AQpaCiwIzpYBEgQxNjU3GK-TASDlWiiHiY0DMO-JjQM4UkAAWAFqAlNEcgVSQTdOUgoqCM6WARIDNTgxGOVaIK4cKKWKjQMw8IuNAzhSQAFYAWoCU0RyBVJBN05SClwKLAjOlgESBDE2MDUYrhwgzHAoocKNAzDLw40DOEdAAFgBagJSUHIGR0EyMU5SCiwIzpYBEgM4NzgYzHAgr5MBKI3EjQMw7cSNAzhHQAFYAWoCUlByBkdBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, May 15 - Wed, May 20 PNS Pensacola ORD Chicago CA $303 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PNS,to:ORD,departure:15/05/2026TANYT&leg2=from:ORD,to:PNS,departure:20/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:302.82&airProductToken=AQpaCiwIzpYBEgQxNjU3GK-TASDlWiiHiY0DMO-JjQM4UkAAWAFqAlNEcgVSQTdOUgoqCM6WARIDNTgxGOVaIK4cKKWKjQMw8IuNAzhSQAFYAWoCU0RyBVJBN05SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, May 15 - Wed, May 20 PNS Pensacola ORD Chicago CA $307 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PNS,to:ORD,departure:15/05/2026TANYT&leg2=from:ORD,to:PNS,departure:20/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:306.53&airProductToken=AQpaCiwIzpYBEgQxNjU3GK-TASDlWiiHiY0DMO-JjQM4UkAAWAFqAlNEcgVSQTdOUgoqCM6WARIDNTgxGOVaIK4cKKWKjQMw8IuNAzhSQAFYAWoCU0RyBVJBN05SCl0KLAjOlgESBDE5ODYYrhwg5Voop72NAzDivo0DOFVAAFgBagJTRHIGVUExNE5SCi0IzpYBEgQxNjU2GOVaIK-TASj8v40DMPDAjQM4VUABWAFqAlNEcgZVQTE0TlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, May 16 - Tue, May 19 PNS Pensacola ORD Chicago CA $313 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PNS,to:ORD,departure:16/05/2026TANYT&leg2=from:ORD,to:PNS,departure:19/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:312.40&airProductToken=AQpFCiEIxJgBEgQzMDY3GK-TASDgXCjMkY0DMJKSjQM4RUAAWAEKIAjEmAESBDI4OTQY4FwgrhwoxJKNAzDFk40DOEVAAVgBCkUKIAjEmAESBDEyNjQYrhwg4FwotLKNAzCss40DOEVAAFgBCiEIxJgBEgQzMTk4GOBcIK-TASiKtI0DMNG0jQM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, May 16 - Sat, May 23 PNS Pensacola ORD Chicago CA $349 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PNS,to:ORD,departure:16/05/2026TANYT&leg2=from:ORD,to:PNS,departure:23/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:348.90&airProductToken=AQpFCiEIxJgBEgQzMDY3GK-TASDgXCjMkY0DMJKSjQM4RUAAWAEKIAjEmAESBDI4OTQY4FwgrhwoxJKNAzDFk40DOEVAAVgBCkUKIAjEmAESBDExNzgYrhwg4FwohuGNAzCA4o0DOEVAAFgBCiEIxJgBEgQxMDEzGOBcIK-TASjl4o0DMKvjjQM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, May 15 - Wed, May 20 PNS Pensacola ORD Chicago CA $371 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PNS,to:ORD,departure:15/05/2026TANYT&leg2=from:ORD,to:PNS,departure:20/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:370.01&airProductToken=AQpoCjMIwYIBEgQyNTU2GK-TASDimgEovYuNAzCsjI0DOEJAAFgBagVCQVNJQ3IIUzdBWlpOQlgKMQjBggESAzY4ORjimgEgrhwo4YyNAzDpjY0DOEJAAVgBagVCQVNJQ3IIUzdBWlpOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, May 15 - Wed, May 20 PNS Pensacola ORD Chicago CA $376 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PNS,to:ORD,departure:15/05/2026TANYT&leg2=from:ORD,to:PNS,departure:20/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:375.20&airProductToken=AQpoCjMIwYIBEgQyNTU2GK-TASDimgEovYuNAzCsjI0DOEJAAFgBagVCQVNJQ3IIUzdBWlpOQlgKMQjBggESAzY4ORjimgEgrhwo4YyNAzDpjY0DOEJAAVgBagVCQVNJQ3IIUzdBWlpOQlgKNAoyCMGCARIENDE1MBiuHCCvkwEo0r-NAzDpwI0DOEJAAFgBagVCQVNJQ3IIT1ZBWlpOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, May 15 - Wed, May 20 PNS Pensacola ORD Chicago CA $377 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PNS,to:ORD,departure:15/05/2026TANYT&leg2=from:ORD,to:PNS,departure:20/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:376.91&airProductToken=AQo4CjYI1YIBEgQyMDA1GK-TASCuHCifiY0DMMKKjQM4S0AAWAFqCTdfZWNvdW5yc3IIS0FBMlBGRE0SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ## Find the cheapest month to fly from Pensacola (PNS) to Chicago (ORD) ### March is typically the cheapest month to fly From CA $169 - CA $503 per traveller. __Flight from Pensacola to Chicago (PNS - ORD) route information__ | Origin airport | Pensacola Intl. | | ------------------- | --------------- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $280 | | Distance | 1272 km | | Average flight time | 4 hours 35 mins | ## Pensacola to Chicago Flights **The easy way to book your flights from Pensacola to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Pensacola 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 Pensacola to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Pensacola Intl., PNS to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Pensacola to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Pensacola currently is just CA $281 rising to CA $377\. 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 Pensacola** 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 PNS to O'Hare Airport? ### Do I need to pay a cancellation fee if I cancel my flight from Pensacola Airport to ORD? ### How do I find cheap flights from Pensacola Airport to ORD that have flexible change policies? ### How many hours is the flight from PNS to O'Hare Airport? ### How far is the flight from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)? ### Which airlines fly direct from Pensacola Airport to O'Hare Intl. Airport (ORD)? ### Are Pensacola Airport 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) - [Flights from Portland to Rosemont ](https://www.expedia.ca/lp/flights/178299/7581/portland-to-rosemont) - 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[Flights from Wilmington (ILM) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ilm/chi/wilmington-to-chicago) - [Flights from Indianapolis (IND) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ind/chi/indianapolis-to-chicago) - [Flights from Nakhon Phanom (KOP) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/kop/mdw/nakhon-phanom-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/las/mdw/las-vegas-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Montego Bay (MBJ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mbj/mdw/montego-bay-to-chicago) - [Flights from Orlando (MCO) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mco/mdw/orlando-to-chicago) - [Flights from Michigan City (MGC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/mgc/mdw/michigan-city-to-chicago) - [Flights from Muscle Shoals (MSL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/msl/mdw/muscle-shoals-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/msp/chi/minneapolis-to-chicago) - [Flights from New York (NYC) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/nyc/chi/new-york-to-chicago) - [Flights from Omaha (OMA) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/oma/mdw/omaha-to-chicago) - [Flights from Chicago (ORD) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ord/chi/chicago-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago) - [Flights from Pueblo (PUB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/pub/mdw/pueblo-to-chicago) - [Flights from Punta Cana (PUJ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/puj/chi/punta-cana-to-chicago) - [Flights from Roanoke (ROA) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/roa/mdw/roanoke-to-chicago) - [Flights from Selinsgrove (SEG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/seg/mdw/selinsgrove-to-chicago) - [Flights from Sacramento (SMF) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/smf/mdw/sacramento-to-chicago) - [Flights from St. Louis (STL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/stl/mdw/st-louis-to-chicago) - [Flights from Newburgh (SWF) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/swf/mdw/newburgh-to-chicago) - [Flights from Sydney (SYD) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/syd/mdw/sydney-to-chicago) - [Flights from Syracuse (SYR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/syr/mdw/syracuse-to-chicago) - [Flights from Fort Leonard Wood (TBN) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/tbn/mdw/fort-leonard-wood-to-chicago) - [Flights from Ua Pou (UAP) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/uap/chi/ua-pou-to-chicago) - [Flights from Fort Frances (YAG) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yag/chi/fort-frances-to-chicago) - [Flights from Brandon (YBR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ybr/mdw/brandon-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ycd/chi/nanaimo-to-chicago) - [Flights from St. Catharines (YCM) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ycm/chi/st-catharines-to-chicago) - [Flights from Edmonton (YEA) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yea/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yeg/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago) - [Flights from Flin Flon (YFO) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yfo/chi/flin-flon-to-chicago) - [Flights from Hamilton (YHM) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago) - [Flights from Kamloops (YKA) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yka/chi/kamloops-to-chicago) - [Flights from Kelowna (YLW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago) - [Flights from Montreal (YMQ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/ymq/chi/montreal-to-chicago) - [Flights from Ottawa (YOW) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago) - [Flights from Regina (YQR) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yqr/chi/regina-to-chicago) - [Flights from Regina (YQR) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yqr/mdw/regina-to-chicago) - [Flights from Gander (YQX) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yqx/chi/gander-to-chicago) - [Flights from Sudbury (YSB) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago) - [Flights from Timmins (YTS) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago) - [Flights from Toronto (YTZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/ywg/pwk/winnipeg-to-chicago) - [Flights from Whitehorse (YXY) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yxy/chi/whitehorse-to-chicago) - [Flights from Calgary (YYC) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago) - [Flights from Victoria (YYJ) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yyj/chi/victoria-to-chicago) - [Flights from St. John's (YYT) to Chicago (CHI) ](https://www.expedia.ca/lp/flights/yyt/chi/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (MDW) ](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (PWK) ](https://www.expedia.ca/lp/flights/yyz/pwk/toronto-to-chicago) \*Available to Expedia members.