Title: CA $324 Cheap Flights from Ottawa (YOW) 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 $324 Cheap Flights from Ottawa (YOW) to Chicago (MDW) [View CA $324 flight on Wed, Dec 31, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YOW,to:MDW,departure:31/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:323.23&airProductToken=AQpqCjMI0IgBEgQyMjAyGNizASD4zAEohpeBAzDKl4EDOERAAFgBagVCQVNJQ3IIRDROMFpSWkwKMwjQiAESBDIzODcY-MwBIOywASiXmIEDMIWZgQM4REABWAFqBUJBU0lDcghENE4wWlJaTBIKCAEQARgBKgJQRBgBIgQIARABKAIoAygEMAE) - [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 Ottawa International Airport (YOW) to Chicago Midway Airport (MDW) - ![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:YOW,to:MDW,departure:29/12/2025TANYT&leg2=from:MDW,to:YOW,departure:05/01/2026TANYT&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:YOW,to:MDW,departure:29/12/2025TANYT&leg2=from:MDW,to:YOW,departure:05/01/2026TANYT&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 Ottawa (YOW) to Chicago (MDW) Prices were available within the past 7 days and start at CA $324 for one-way flights and CA $579 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, Dec 31 - Tue, Jan 6 YOW Ottawa MDW Chicago CA $579 Roundtrip found 18 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YOW,to:MDW,departure:31/12/2025TANYT&leg2=from:MDW,to:YOW,departure:06/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:578.67&airProductToken=AQpICiII0IgBEgQyMjAyGNizASD4zAEohpeBAzDKl4EDOERAAFgBCiII0IgBEgQyMzg3GPjMASDssAEol5iBAzCFmYEDOERAAVgBCkgKIgjQiAESBDIzODgY7LABIPjMASj83IEDMOLdgQM4REAAWAEKIgjQiAESBDIyNjUY-MwBINizASiK34EDMMXfgQM4REABWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, Dec 31 - Thu, Jan 1 YOW Ottawa MDW Chicago CA $590 Roundtrip found 18 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YOW,to:MDW,departure:31/12/2025TANYT&leg2=from:MDW,to:YOW,departure:01/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:589.16&airProductToken=AQpICiII0IgBEgQyMjAyGNizASD4zAEohpeBAzDKl4EDOERAAFgBCiII0IgBEgQyMzg3GPjMASDssAEol5iBAzCFmYEDOERAAVgBCkgKIgjQiAESBDIzOTQY7LABIPjMASiXp4EDMP2ngQM4REAAWAEKIgjQiAESBDIyNjkY-MwBINizASi3qIEDMPKogQM4REABWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Mon, Dec 29 - Thu, Jan 1 YOW Ottawa MDW Chicago CA $600 Roundtrip found 18 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YOW,to:MDW,departure:29/12/2025TANYT&leg2=from:MDW,to:YOW,departure:01/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:599.66&airProductToken=AQpICiII0IgBEgQyMjAyGNizASD4zAEoxoCBAzCKgYEDOERAAFgBCiII0IgBEgQyMzg3GPjMASDssAEo14GBAzDFgoEDOERAAVgBCkgKIgjQiAESBDIzOTQY7LABIPjMASiXp4EDMP2ngQM4REAAWAEKIgjQiAESBDIyNjkY-MwBINizASi3qIEDMPKogQM4REABWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, Dec 31 - Sun, Jan 4 YOW Ottawa MDW Chicago CA $611 Roundtrip found 18 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YOW,to:MDW,departure:31/12/2025TANYT&leg2=from:MDW,to:YOW,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:610.17&airProductToken=AQpICiII0IgBEgQyMjAyGNizASD4zAEohpeBAzDKl4EDOERAAFgBCiII0IgBEgQyMzg3GPjMASDssAEol5iBAzCFmYEDOERAAVgBCkgKIgjQiAESBDIzOTQY7LABIPjMASj3yIEDMN3JgQM4Q0AAWAEKIgjQiAESBDIyNjkY-MwBINizASiXyoEDMNLKgQM4Q0ABWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Mon, Dec 22 - Wed, Dec 31 YOW Ottawa MDW Chicago CA $612 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YOW,to:MDW,departure:22/12/2025TANYT&leg2=from:MDW,to:YOW,departure:31/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:611.51&airProductToken=AQpqCjMI0IgBEgQyMjAyGNizASD4zAEo5rGAAzCqsoADOENAAFgBagVCQVNJQ3IIQzROMFpSWkwKMwjQiAESBDIzODcY-MwBIOywASj3soADMOWzgAM4Q0ABWAFqBUJBU0lDcghDNE4wWlJaTApqCjMI0IgBEgQyMzg4GOywASD4zAEovJmBAzCimoEDOERAAFgBagVCQVNJQ3IIRDROMFpSWkwKMwjQiAESBDIyNjUY-MwBINizASjKm4EDMIWcgQM4REABWAFqBUJBU0lDcghENE4wWlJaTBIKCAEQARgBKgJQRBgBIgQIARABKAIoAygEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Mon, Dec 29 - Sun, Jan 4 YOW Ottawa MDW Chicago CA $621 Roundtrip found 18 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YOW,to:MDW,departure:29/12/2025TANYT&leg2=from:MDW,to:YOW,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:620.66&airProductToken=AQpICiII0IgBEgQyMjAyGNizASD4zAEoxoCBAzCKgYEDOERAAFgBCiII0IgBEgQyMzg3GPjMASDssAEo14GBAzDFgoEDOERAAVgBCkgKIgjQiAESBDIzOTQY7LABIPjMASj3yIEDMN3JgQM4Q0AAWAEKIgjQiAESBDIyNjkY-MwBINizASiXyoEDMNLKgQM4Q0ABWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Thu, Dec 25 - Tue, Jan 6 YOW Ottawa MDW Chicago CA $629 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YOW,to:MDW,departure:25/12/2025TANYT&leg2=from:MDW,to:YOW,departure:06/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:628.60&airProductToken=AQpICiII0IgBEgQyMjA4GNizASD4zAEohtaAAzDK1oADOERAAFgBCiII0IgBEgQyMzkzGPjMASDssAEokteAAzCA2IADOERAAVgBCkgKIgjQiAESBDIzODgY7LABIPjMASj83IEDMOLdgQM4REAAWAEKIgjQiAESBDIyNjcY-MwBINizASig4IEDMNvggQM4REABWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Fri, Dec 26 - Tue, Jan 6 YOW Ottawa MDW Chicago CA $640 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YOW,to:MDW,departure:26/12/2025TANYT&leg2=from:MDW,to:YOW,departure:06/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:639.09&airProductToken=AQpICiII0IgBEgQyMjA4GNizASD4zAEopuGAAzDq4YADOERAAFgBCiII0IgBEgQyMzkzGPjMASDssAEosuKAAzCg44ADOERAAVgBCkgKIgjQiAESBDIzODgY7LABIPjMASj83IEDMOLdgQM4REAAWAEKIgjQiAESBDIyNjcY-MwBINizASig4IEDMNvggQM4REABWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Thu, Jan 8 - Sun, Jan 11 YOW Ottawa MDW Chicago CA $642 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YOW,to:MDW,departure:08/01/2026TANYT&leg2=from:MDW,to:YOW,departure:11/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:641.74&airProductToken=AQpqCjMI0IgBEgQyMjAyGNizASD4zAEokPGBAzDU8YEDOENAAFgBagVCQVNJQ3IIQzJOMFpSWkwKMwjQiAESBDIzODcY-MwBIOywASic8oEDMIrzgQM4Q0ABWAFqBUJBU0lDcghDMk4wWlJaTApqCjMI0IgBEgQyMzk0GOywASD4zAEo15eCAzC9mIIDOENAAFgBagVCQVNJQ3IIQzJOMFpSWkwKMwjQiAESBDIyNjkY-MwBINizASj3mIIDMLKZggM4Q0ABWAFqBUJBU0lDcghDMk4wWlJaTBIKCAEQARgBKgJQRBgBIgQIARABKAIoAygEMAE) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Thu, Apr 23 - Mon, Apr 27 YOW Ottawa MDW Chicago CA $1,286 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YOW,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:YOW,departure:27/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1285.13&airProductToken=AQq2AQoyCNemARIDNTg5GNizASCYzgEopI2LAzD1jYsDOFNAAFgBagVFQ09OT3IIU083RDBaRVMKPwjXpgESBDYzNDAYmM4BIOO0ASiZj4sDMOuPiwM4U0ABWAFqBUVDT05PcghTTzdEMFpFU3oKCMSYARIENjM0MAo_CNemARIENzA1ORjjtAEg7LABKK-QiwMw-pCLAzhTQAFYAWoFRUNPTk9yCFNPN0QwWkVTegoIxJgBEgQ3MDU5CrQBCj4I16YBEgQ3Njk1GOywASDgXCidvosDMJa_iwM4U0AAWAFqBUVDT05PcghTTzdEMFpFU3oKCMSYARIENzY5NQo-CNemARIENzA3ORjgXCCYzgEo8cCLAzD4wYsDOFNAAVgBagVFQ09OT3IIU083RDBaRVN6CgjEmAESBDcwNzkKMgjXpgESAzU4OBiYzgEg2LMBKMPCiwMwhsOLAzhTQAFYAWoFRUNPTk9yCFNPN0QwWkVTEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ## Find the cheapest month to fly from Ottawa (YOW) to Chicago (MDW) ### July is typically the cheapest month to fly From CA $338 - CA $1,189 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:YOW,to:ORD,departure:29/12/2025TANYT&leg2=from:ORD,to:YOW,departure:15/01/2026TANYT&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 $869 ](https://www.expedia.ca/Flights-Search?leg1=from:YOW,to:ORD,departure:29/12/2025TANYT&leg2=from:ORD,to:YOW,departure:15/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) __Flight from Ottawa to Chicago (YOW - MDW) route information__ | Origin airport | Macdonald-Cartier Intl. | | ------------------- | ------------------------ | | Destination airport | Midway Intl. | | Airlines serving | Porter Airlines, WestJet | | Roundtrip price | CA $579 | | Distance | 1041 km | ## Ottawa to Chicago Flights **The easy way to book your flights from Ottawa to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Ottawa 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 Ottawa to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Macdonald-Cartier Intl., YOW to Midway Intl., MDW** Sort your search results by price to find great deals on your flight from Ottawa to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Ottawa currently is just CA $579 rising to CA $1,286\. Here are more money-saving tips: - Fly in December 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 Ottawa** 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 YOW to Chicago Airport? ### Do I need to pay a cancellation fee if I cancel my flight from Ottawa Intl. Airport to MDW? ### How do I find cheap flights from Ottawa Intl. Airport to Midway Intl. Airport (MDW) that have flexible change policies? ### How many hours is the flight from YOW to Chicago Airport? ### How far is the flight from YOW to MDW? ### Which airlines fly direct from Macdonald-Cartier Intl. Airport (YOW) to Midway Airport? ### Are Ottawa International Airport to Chicago Airport flight tickets cheaper when they're purchased at the last minute? ## Explore a world of travel with Expedia - Flights ### Flights - [Flights from Lincoln to Rush Street ](https://www.expedia.ca/lp/flights/602964/6175183/lincoln-to-rush-street) - [Flights from Waterloo (ALO) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/alo/ord/waterloo-to-chicago) - [Flights from Ahmedabad (AMD) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/amd/ord/ahmedabad-to-chicago) - [Flights from Atlanta (ATL) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/atl/ord/atlanta-to-chicago) - [Flights from Austin (AUS) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/aus/ord/austin-to-chicago) - [Flights from Bangor (BGR) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/bgr/ord/bangor-to-chicago) - [Flights from Bellingham (BLI) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/bli/ord/bellingham-to-chicago) - [Flights from Nashville (BNA) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/bna/ord/nashville-to-chicago) - [Flights from Mumbai (BOM) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/bom/ord/mumbai-to-chicago) - [Flights from Burlington (BTV) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/btv/ord/burlington-to-chicago) - [Flights from Buffalo (BUF) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/buf/ord/buffalo-to-chicago) - [Flights from Baltimore (BWI) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/bwi/ord/baltimore-to-chicago) - [Flights from Sault Ste. 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[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.