Title: CA $153 Cheap Flights from Kitchener (YKF) 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 $153 Cheap Flights from Kitchener (YKF) to Chicago (ORD) [View CA $153 flight on Sat, Mar 14, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YKF,to:ORD,departure:14/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:152.71&airProductToken=AQpnCjIIwYYBEgQyNTA2GNgqIJjOASj7zIcDMLzNhwM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIDNTA3GJjOASCuHCinz4cDMJrQhwM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) - [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 Kitchener, ON (YKF-Region of Waterloo Intl.) to Chicago O'Hare International Airport (ORD) - ![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:ykf,to:ord,departure:16/10/2025TANYT&leg2=from:ord,to:ykf,departure:23/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![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:ykf,to:ord,departure:16/10/2025TANYT&leg2=from:ord,to:ykf,departure:23/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ## Plan, book, fly with confidence - ### Be in the know Get alerts if flight prices drop or rise\* - ### Book smarter Save up to 30% on select hotels after you book a flight\* - ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Kitchener (YKF) to Chicago (ORD) Prices were available within the past 7 days and start at CA $153 for one-way flights and CA $236 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, Mar 14 - Tue, Mar 17 YKF Kitchener ORD Chicago CA $236 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:14/03/2026TANYT&leg2=from:ORD,to:YKF,departure:17/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:235.41&airProductToken=AQpnCjIIwYYBEgQyNTEwGNgqIJjOASjtz4cDMLPQhwM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIDNTA5GJjOASCuHCim0YcDMJ7ShwM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQQpnCjEIwYYBEgM1MDgYrhwgmM4BKKfyhwMwivOHAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjIIwYYBEgQyNTEzGJjOASDYKiiX9IcDMNP0hwM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, Feb 7 - Sun, Feb 8 YKF Kitchener ORD Chicago CA $309 Roundtrip found 11 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:07/02/2026TANYT&leg2=from:ORD,to:YKF,departure:08/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:308.86&airProductToken=AQpuCjUIwYYBEgQyNTEyGNgqIJjOASj9x4QDMLnIhAM4R0AAWAFqCFNUQU5EQVJEcghHTkEyQTJURwo1CMGGARIENDk2MRiYzgEgrhwomMmEAzCVyoQDOEdAAVgBaghTVEFOREFSRHIIR05BMkEyVEcKbgo1CMGGARIENDk4NhiuHCCYzgEots6EAzCiz4QDOEdAAFgBaghTVEFOREFSRHIIR05BMkEyVEcKNQjBhgESBDI1MDkYmM4BINgqKOLQhAMwo9GEAzhHQAFYAWoIU1RBTkRBUkRyCEdOQTJBMlRHEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Fri, Nov 28 - Mon, Dec 1 YKF Kitchener ORD Chicago CA $370 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:28/11/2025TANYT&leg2=from:ORD,to:YKF,departure:01/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:369.28&airProductToken=AQpnCjIIwYYBEgQyNTEwGNgqIJjOASjap_4CMKqo_gI4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIDNTA5GJjOASCuHCiiqf4CMJqq_gI4R0ABWAFqBUJBU0lDcghHTkEyQTJCQQpoCjIIwYYBEgQ4OTAwGK4cIJjOASjIxv4CMKzH_gI4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoyCMGGARIEMjUwNxiYzgEg2Coowsj-AjCDyf4COEdAAVgBagVCQVNJQ3IIR05BMkEyQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, Nov 8 - Sun, Nov 9 YKF Kitchener ORD Chicago CA $370 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:YKF,departure:09/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:369.78&airProductToken=AQpoCjIIwYYBEgQyNTAyGNgqIJjOASiWwvwCMNfC_AI4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoyCMGGARIEODkwMRiYzgEgrhwou8P8AjCxxPwCOEdAAVgBagVCQVNJQ3IIR05BMkEyQkEKaAoyCMGGARIEODkwMBiuHCCYzgEoiM_8AjDsz_wCOEdAAFgBagVCQVNJQ3IIR05BMkEyQkEKMgjBhgESBDI1MDcYmM4BINgqKILR_AIww9H8AjhHQAFYAWoFQkFTSUNyCEdOQTJBMkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Thu, May 28 - Tue, Jun 2 YKF Kitchener ORD Chicago CA $375 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:28/05/2026TANYT&leg2=from:ORD,to:YKF,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:374.94&airProductToken=AQpoCjIIwYYBEgQyNTAyGNgqIJjOASiEl44DMMWXjgM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoyCMGGARIEODkwMRiYzgEgrhwon5iOAzCRmY4DOEdAAVgBagVCQVNJQ3IIR05BMkEyQkEKaAoyCMGGARIEODkwNhiuHCCYzgEo3NKOAzDE044DOEtAAFgBagVCQVNJQ3IIS05BMkEwQkEKMgjBhgESBDI1MTEYmM4BINgqKMfUjgMwjdWOAzhLQAFYAWoFQkFTSUNyCEtOQTJBMEJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, Mar 28 - Wed, Apr 1 YKF Kitchener ORD Chicago CA $380 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:28/03/2026TANYT&leg2=from:ORD,to:YKF,departure:01/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:379.21&airProductToken=AQpnCjIIwYYBEgQyNTEwGNgqIJjOASit7YgDMPPtiAM4S0AAWAFqBUJBU0lDcghLTkEyQTBCQQoxCMGGARIDNTA5GJjOASCuHCjm7ogDMN7viAM4S0ABWAFqBUJBU0lDcghLTkEyQTBCQQpnCjEIwYYBEgM1MDgYrhwgmM4BKJubiQMwgZyJAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjIIwYYBEgQyNTEzGJjOASDYKij3nIkDMLOdiQM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, Mar 14 - Tue, Mar 17 YKF Kitchener ORD Chicago CA $384 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:14/03/2026TANYT&leg2=from:ORD,to:YKF,departure:17/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:383.97&airProductToken=AQpoCjIIwYYBEgQyNTAyGNgqIJjOASiky4cDMOXLhwM4TEAAWAFqBUJBU0lDcghMTkEyQTBCQQoyCMGGARIEODkwMRiYzgEgrhwov8yHAzC1zYcDOExAAVgBagVCQVNJQ3IITE5BMkEwQkEKaAoyCMGGARIEODkwNBiuHCCYzgEoxO-HAzCo8IcDOEdAAFgBagVCQVNJQ3IIR05BMkEyQkEKMgjBhgESBDI1MTEYmM4BINgqKKfyhwMw7fKHAzhHQAFYAWoFQkFTSUNyCEdOQTJBMkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, Oct 25 - Sat, Nov 1 YKF Kitchener ORD Chicago CA $397 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:25/10/2025TANYT&leg2=from:ORD,to:YKF,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:396.04&airProductToken=AQpnCjIIwYYBEgQyNTEwGNgqIJjOASjtqPsCMLOp-wI4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIDNTExGJjOASCuHCimqvsCMJir-wI4R0ABWAFqBUJBU0lDcghHTkEyQTJCQQpoCjIIwYYBEgQ4OTAwGK4cIJjOASjM9PsCMLD1-wI4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoyCMGGARIEMjUwNxiYzgEg2Cooxvb7AjCH9_sCOEdAAVgBagVCQVNJQ3IIR05BMkEyQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Thu, Nov 6 - Sun, Nov 9 YKF Kitchener ORD Chicago CA $402 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:06/11/2025TANYT&leg2=from:ORD,to:YKF,departure:09/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:401.31&airProductToken=AQpoCjIIwYYBEgQyNTAyGNgqIJjOASjWq_wCMJes_AI4S0AAWAFqBUJBU0lDcghLTkEyQTBCQQoyCMGGARIEODkwMRiYzgEgrhwo-6z8AjDxrfwCOEtAAVgBagVCQVNJQ3IIS05BMkEwQkEKaAoyCMGGARIEODkwMBiuHCCYzgEoiM_8AjDsz_wCOEdAAFgBagVCQVNJQ3IIR05BMkEyQkEKMgjBhgESBDI1MDcYmM4BINgqKILR_AIww9H8AjhHQAFYAWoFQkFTSUNyCEdOQTJBMkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Thu, Oct 23 - Sun, Oct 26 YKF Kitchener ORD Chicago CA $745 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:23/10/2025TANYT&leg2=from:ORD,to:YKF,departure:26/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:744.67&airProductToken=AQplCjAI16YBEgM1NjcY2CogmBYo-I37AjD3j_sCOExAAFgBagVFQ09OT3IITENRRDBMRVcKMQjXpgESBDE1ODgYmBYgrhwo55H7AjC3k_sCOExAAVgBagVFQ09OT3IITFRRRDBaRVcKZQoxCNemARIEMTYxMRiuHCCYFiiItPsCMPO1-wI4TEAAWAFqBUVDT05PcghMVFFEMFpFVwowCNemARIDNTgyGJgWINgqKPm4-wIw2Lr7AjhMQAFYAWoFRUNPTk9yCExDVUQwTEVXEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ## 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:YKF,to:ORD,departure:16/10/2025TANYT&leg2=from:ORD,to:YKF,departure:19/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. Cheapest 23 min [Flights from CA $495](https://www.expedia.ca/Flights-Search?leg1=from:YKF,to:ORD,departure:16/10/2025TANYT&leg2=from:ORD,to:YKF,departure:19/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flight from Kitchener to Chicago (YKF - ORD) route information | Origin airport | Region of Waterloo Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | Air Canada, WestJet | | Roundtrip price | CA $235 | | Distance | 631 km | ## Kitchener to Chicago Flights **The easy way to book your flights from Kitchener to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Kitchener 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 Kitchener to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Region of Waterloo Intl., YKF to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Kitchener to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Kitchener currently is just CA $236 rising to CA $745.   Here are more money-saving tips:  - Fly in March 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 Kitchener**  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 Kitchener/Waterloo Airport to ORD? > If you're travelling from Kitchener/Waterloo Airport to O'Hare Intl. Airport (ORD), round-trip flights start from CA $236. This price is based on airfares available within the last 7 days on Expedia for flights departing within the next year, so don't let a good deal pass you by. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from YKF to O'Hare Intl. Airport (ORD)? > Most flights can be cancelled online, but every airline has its own set of terms and conditions. If you do have to cancel your flight, check out our [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from Kitchener/Waterloo Airport to ORD that have flexible change policies? > Flights from Region of Waterloo Intl. Airport (YKF) to O'Hare Intl. Airport (ORD) with flexible change policies are available with many airlines. Simply use our "No change fees" filter during your search. You'll only need to cover the difference in ticket price, without any added fees to worry about. ### How far is the flight from Kitchener/Waterloo Airport to O'Hare Intl. Airport (ORD)? > You won't need a lengthy novel for this flight — it's only 640 kilometres from Kitchener to Chicago. Sit down, order some food and you'll be there in no time. ### Which airlines fly direct from Kitchener/Waterloo Airport to ORD? > You won't find any airlines flying directly between Region of Waterloo Intl. Airport (YKF) and O'Hare Intl. Airport (ORD), so be prepared to make at least one stop on your journey. A layover can be a nice way to break up a trip! ### Are YKF to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? > Booking last minute from YKF to O'Hare Intl. Airport (ORD) can be hit-or-miss. You may be able to score a bargain, but you could also completely miss out! If you'd rather start your travel planning ahead of time, Expedia compares flight deals up to 12 months in advance. Just bear in mind that not all airlines list their prices so far in advance. Our suggestion? Check back often as updates are made frequently. ## Explore a world of travel with Expedia - Flights ### 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) - [Flights from San Francisco to Evanston](https://www.expedia.ca/lp/flights/178305/8049/san-francisco-to-evanston) - [Flights from Seattle to Rosemont](https://www.expedia.ca/lp/flights/178307/7581/seattle-to-rosemont) - [Flights from Washington to Evanston](https://www.expedia.ca/lp/flights/178318/8049/washington-to-evanston) - [Flights from Lincoln to Rush Street](https://www.expedia.ca/lp/flights/602964/6175183/lincoln-to-rush-street) - [Flights from Winnipeg to Rosemont](https://www.expedia.ca/lp/flights/6141041/7581/winnipeg-to-rosemont) - [Flights from Ashland (AHM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ahm/chi/ashland-to-chicago) - [Flights from Ann Arbor (ARB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/arb/mdw/ann-arbor-to-chicago) - [Flights from Aspen (ASE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ase/mdw/aspen-to-chicago) - [Flights from Atlanta (ATL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/atl/mdw/atlanta-to-chicago) - [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.