Title: CA $440 Cheap Flights from Edmonton (YEG) 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 $440 Cheap Flights from Edmonton (YEG) to Chicago (MDW) [View CA $440 flight on Sun, Jan 25, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YEG,to:MDW,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:439.02&airProductToken=AQqlAQoxCNemARIDNDMyGJgxIJjOASiJroMDMPKvgwM4TEAAWAFqBUVDT05PcghMQ1VEMExFVwo3CMSYARIENTA3MxiYzgEg47QBKN2wgwMww7GDAzhVQAFYAWoJTUFJTkNMQVNDcghVQVVUQTBNTAo3CMSYARIENTQ0NhjjtAEg7LABKPWygwMwxrODAzhVQAFYAWoJTUFJTkNMQVNDcghVQVVUQTBNTBIKCAEQARgBKgJXUxgBIgQIARABKAIoAygEMAE) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Flight 1 Leaving from Going to Departing Flight 2 Leaving from Going to Departing ## Popular airlines from Edmonton Intl. Airport (YEG) to Chicago Midway Airport (MDW) - ![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:YEG,to:MDW,departure:29/12/2025TANYT&leg2=from:MDW,to:YEG,departure:05/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:YEG,to:MDW,departure:29/12/2025TANYT&leg2=from:MDW,to:YEG,departure:05/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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 Edmonton (YEG) to Chicago (MDW) Prices were available within the past 7 days and start at CA $440 for one-way flights and CA $399 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, Apr 5 - Thu, Apr 9 YEG Edmonton MDW Chicago CA $399 Roundtrip found 13 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YEG,to:MDW,departure:05/04/2026TANYT&leg2=from:MDW,to:YEG,departure:09/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:398.80&airProductToken=AQpFCiAIxJgBEgQ3MjAwGJgxIOBcKLXBiQMwucOJAzhWQABYAQohCMSYARIEMTA2MxjgXCDssAEoqsSJAzCfxYkDOFZAAVgBCkUKIQjEmAESBDM3NzgY7LABIMx8KIbyiQMw5_KJAzhWQABYAQogCMSYARIENjg3NxjMfCCYMSiP9IkDMMP1iQM4VkABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Feb 12 - Mon, Feb 23 YEG Edmonton MDW Chicago CA $478 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YEG,to:MDW,departure:12/02/2026TANYT&leg2=from:MDW,to:YEG,departure:23/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:477.92&airProductToken=AQpFCiAIxJgBEgQ3MjAwGJgxIOBcKPH4hAMw9fqEAzhWQABYAQohCMSYARIEMTA2MxjgXCDssAEo6PuEAzDc_IQDOFZAAVgBCkUKIQjEmAESBDM3NzgY7LABIMx8KLb4hQMwnPmFAzhWQABYAQogCMSYARIENjg3NxjMfCCYMSir-oUDMN_7hQM4VkABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Feb 3 - Mon, Feb 23 YEG Edmonton MDW Chicago CA $479 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YEG,to:MDW,departure:03/02/2026TANYT&leg2=from:MDW,to:YEG,departure:23/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:478.89&airProductToken=AQpFCiAIxJgBEgQ3MjAwGJgxIOBcKNGThAMw1ZWEAzhWQABYAQohCMSYARIEMTA2MxjgXCDssAEoxJaEAzC5l4QDOFZAAVgBCkUKIQjEmAESBDM3NzgY7LABIMx8KLb4hQMwnPmFAzhWQABYAQogCMSYARIENjg3NxjMfCCYMSir-oUDMN_7hQM4VkABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 6 - Wed, Jan 7 YEG Edmonton MDW Chicago CA $511 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YEG,to:MDW,departure:06/01/2026TANYT&leg2=from:MDW,to:YEG,departure:07/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:510.50&airProductToken=AQpFCiAIxJgBEgQ2ODg4GJgxIMx8KM_cgQMw-d2BAzhWQABYAQohCMSYARIENDE2ORjMfCDssAEo2t-BAzDA4IEDOFZAAVgBCkUKIQjEmAESBDM3NzgY7LABIMx8KNbngQMwvuiBAzhWQABYAQogCMSYARIENjg3NxjMfCCYMSjL6YEDMIPrgQM4VkABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 6 - Thu, Jan 8 YEG Edmonton MDW Chicago CA $534 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YEG,to:MDW,departure:06/01/2026TANYT&leg2=from:MDW,to:YEG,departure:08/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:533.61&airProductToken=AQpFCiAIxJgBEgQ2ODg4GJgxIMx8KM_cgQMw-d2BAzhWQABYAQohCMSYARIENDE2ORjMfCDssAEo2t-BAzDA4IEDOFZAAVgBCkUKIQjEmAESBDM3NzgY7LABIMx8KPbygQMw3vOBAzhWQABYAQogCMSYARIENjg3NxjMfCCYMSjr9IEDMKP2gQM4VkABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Feb 10 - Thu, Feb 12 YEG Edmonton MDW Chicago CA $557 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YEG,to:MDW,departure:10/02/2026TANYT&leg2=from:MDW,to:YEG,departure:12/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:556.60&airProductToken=AQpFCiAIxJgBEgQ3MjAwGJgxIOBcKLHihAMwteSEAzhWQABYAQohCMSYARIEMTA2MxjgXCDssAEopOWEAzCZ5oQDOFZAAVgBCkUKIQjEmAESBDM3NzgY7LABIMx8KNb8hAMwvP2EAzhWQABYAQogCMSYARIENjg3NxjMfCCYMSjL_oQDMP__hAM4VkABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Mar 27 - Sun, Mar 29 YEG Edmonton MDW Chicago CA $594 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YEG,to:MDW,departure:27/03/2026TANYT&leg2=from:MDW,to:YEG,departure:29/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:593.84&airProductToken=AQpFCiAIxJgBEgQ2OTA1GJgxIMx8KJPgiAMwvuGIAzhWQABYAQohCMSYARIEMzc5ORjMfCDssAEosOOIAzCM5IgDOFZAAVgBCkUKIQjEmAESBDM3OTkY7LABIMx8KPT6iAMw2PuIAzhUQABYAQogCMSYARIENjg3NxjMfCCYMSjPg4kDMIOFiQM4VkABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Mar 15 - Sat, Mar 21 YEG Edmonton MDW Chicago CA $622 Roundtrip found 20 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YEG,to:MDW,departure:15/03/2026TANYT&leg2=from:MDW,to:YEG,departure:21/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:621.92&airProductToken=AQpFCiAIxJgBEgQ3MjAwGJgxIOBcKJXVhwMwmdeHAzhWQABYAQohCMSYARIEMTA2MxjgXCDssAEoitiHAzD_2IcDOFZAAVgBCkUKIQjEmAESBDIwNjAY7LABIOBcKMqfiAMwv6CIAzhYQABYAQogCMSYARIENjg3MBjgXCCYMSjxpogDMKWpiAM4VkABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jan 5 - Wed, Jan 7 YEG Edmonton MDW Chicago CA $630 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YEG,to:MDW,departure:05/01/2026TANYT&leg2=from:MDW,to:YEG,departure:07/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:629.01&airProductToken=AQpFCiAIxJgBEgQ2OTE2GJgxIMx8KK_RgQMw2dKBAzhWQABYAQohCMSYARIEMzc5NRjMfCDssAEokduBAzCM3IEDOFZAAVgBCkUKIQjEmAESBDM3NzgY7LABIMx8KNbngQMwvuiBAzhWQABYAQogCMSYARIENjg3NxjMfCCYMSjL6YEDMIPrgQM4VkABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sun, Jan 25 - Sat, Jan 31 YEG Edmonton MDW Chicago CA $793 Roundtrip found 18 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YEG,to:MDW,departure:25/01/2026TANYT&leg2=from:MDW,to:YEG,departure:31/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:792.18&airProductToken=AQqlAQoxCNemARIDNDMyGJgxIJjOASiJroMDMPKvgwM4TEAAWAFqBUVDT05PcghMQ1VEMExFVwo3CMSYARIENTA3MxiYzgEg47QBKN2wgwMww7GDAzhVQAFYAWoJTUFJTkNMQVNDcghVQVVUQTBNTAo3CMSYARIENTQ0NhjjtAEg7LABKPWygwMwxrODAzhVQAFYAWoJTUFJTkNMQVNDcghVQVVUQTBNTAqhAQo2CMSYARIEMzc3OBjssAEgzHwoyfaDAzC094MDOExAAFgBaglNQUlOQ0xBU0NyCExBM05BME1RCjUIxJgBEgQyNDg1GMx8IJgWKPf5gwMwqvuDAzhMQAFYAWoJTUFJTkNMQVNDcghMQTNOQTBNUQowCNemARIDMTc2GJgWIJgxKND8gwMwkP2DAzhMQAFYAWoFRUNPTk9yCExBVUQwTEVXEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) ## 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:YEG,to:ORD,departure:29/12/2025TANYT&leg2=from:ORD,to:YEG,departure:01/01/2026TANYT&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 $1,058 ](https://www.expedia.ca/Flights-Search?leg1=from:YEG,to:ORD,departure:29/12/2025TANYT&leg2=from:ORD,to:YEG,departure:01/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) __Flight from Edmonton to Chicago (YEG - MDW) route information__ | Origin airport | Edmonton Intl. | | ------------------- | -------------- | | Destination airport | Midway Intl. | | Airlines serving | Delta, WestJet | | Roundtrip price | CA $399 | | Distance | 2290 km | ## Edmonton to Chicago Flights **The easy way to book your flights from Edmonton to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Edmonton 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 Edmonton to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Edmonton Intl., YEG to Midway Intl., MDW** Sort your search results by price to find great deals on your flight from Edmonton to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Edmonton currently is just CA $399 rising to CA $793\. Here are more money-saving tips: - Fly in April when flight prices are normally at their lowest - Book about a month to 6 weeks before you travel for the best prices to Chicago - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! **Reasons to choose Expedia for your flight to Chicago from Edmonton** 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 Edmonton Intl. Airport (YEG) to Midway Airport? ### Do I need to pay a cancellation fee if I cancel my flight from Edmonton Airport to MDW? ### How do I find cheap flights from Edmonton Airport to Midway Airport that have flexible change policies? ### How many hours is the flight from YEG to Midway Intl. Airport (MDW)? ### How far is the flight from Edmonton Airport to MDW? ### Which airlines fly direct from Edmonton Intl. Airport (YEG) to Midway Airport? ### Are Edmonton 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 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.