Title: CA $279 Cheap Flights from Regina (YQR) 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 $279 Cheap Flights from Regina (YQR) to Chicago (MDW) [View CA $279 flight on Fri, Jan 9, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YQR,to:MDW,departure:09/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:278.57&airProductToken=AQpGCiEIxJgBEgQ2ODc4GJiMASDMfCiJ_4EDMJiAggM4VkAAWAEKIQjEmAESBDQxNjkYzHwg7LABKLqBggMwoIKCAzhWQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) - [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 Regina Intl. Airport (YQR) 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:YQR,to:MDW,departure:23/12/2025TANYT&leg2=from:MDW,to:YQR,departure:30/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Regina (YQR) to Chicago (MDW) Prices were available within the past 7 days and start at CA $279 for one-way flights and CA $490 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) Tue, Mar 17 - Mon, Mar 30 YQR Regina MDW Chicago CA $490 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQR,to:MDW,departure:17/03/2026TANYT&leg2=from:MDW,to:YQR,departure:30/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:489.66&airProductToken=AQpGCiEIxJgBEgQ2ODc4GJiMASDMfCjp8IcDMPPxhwM4VkAAWAEKIQjEmAESBDM3OTkYzHwg7LABKPDyhwMwzPOHAzhWQAFYAQpGCiEIxJgBEgQzNzkyGOywASDMfCjXg4kDMLqEiQM4VkAAWAEKIQjEmAESBDY4NzYYzHwgmIwBKPmEiQMwlYaJAzhWQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Feb 24 - Sun, Mar 15 YQR Regina MDW Chicago CA $549 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQR,to:MDW,departure:24/02/2026TANYT&leg2=from:MDW,to:YQR,departure:15/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:548.36&airProductToken=AQpGCiEIxJgBEgQ2ODc4GJiMASDMfCjJhIYDMNOFhgM4VkAAWAEKIQjEmAESBDM3OTkYzHwg7LABKIGHhgMw5YeGAzhWQAFYAQpsCiIIxJgBEgQ1MjE4GOywASDjtAEo6NiHAzCs2YcDOFZAAFgBCiIIxJgBEgQ1NDA2GOO0ASCYzgEosNuHAzD724cDOFZAAVgBCiIIxJgBEgQ3MTU5GJjOASCYjAEoxd6HAzCX4IcDOFZAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Dec 21 - Thu, Dec 25 YQR Regina MDW Chicago CA $620 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQR,to:MDW,departure:21/12/2025TANYT&leg2=from:MDW,to:YQR,departure:25/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:619.59&airProductToken=AQpGCiEIxJgBEgQ2ODc4GJiMASDMfCikqYADML2qgAM4VkAAWAEKIQjEmAESBDQxNjkYzHwg7LABKIqrgAMw96uAAzhWQAFYAQpGCiEIxJgBEgQzNzc4GOywASDMfCis1oADMJTXgAM4VkAAWAEKIQjEmAESBDY4NzYYzHwgmIwBKJnYgAMwtNmAAzhWQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Mar 1 - Thu, Mar 19 YQR Regina MDW Chicago CA $640 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQR,to:MDW,departure:01/03/2026TANYT&leg2=from:MDW,to:YQR,departure:19/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:639.19&airProductToken=AQpGCiEIxJgBEgQ2ODc4GJiMASDMfCjpvIYDMPO9hgM4VkAAWAEKIQjEmAESBDM3OTkYzHwg7LABKKG_hgMwhcCGAzhWQAFYAQpGCiEIxJgBEgQzNzc4GOywASDMfCjmhYgDMMeGiAM4WEAAWAEKIQjEmAESBDY4NzYYzHwgmIwBKJmJiAMwtYqIAzhWQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Apr 1 - Thu, Apr 23 YQR Regina MDW Chicago CA $658 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQR,to:MDW,departure:01/04/2026TANYT&leg2=from:MDW,to:YQR,departure:23/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:657.07&airProductToken=AQpGCiEIxJgBEgQ2ODc4GJiMASDMfCjJmYkDMNOaiQM4VkAAWAEKIQjEmAESBDM3OTkYzHwg7LABKNCbiQMwrJyJAzhWQAFYAQpGCiEIxJgBEgQzNzc4GOywASDMfCi8j4sDMJuQiwM4VEAAWAEKIQjEmAESBDY4NzYYzHwgmIwBKPmSiwMwlZSLAzhWQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Mar 29 - Mon, Apr 13 YQR Regina MDW Chicago CA $705 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQR,to:MDW,departure:29/03/2026TANYT&leg2=from:MDW,to:YQR,departure:13/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:704.90&airProductToken=AQpGCiEIxJgBEgQ2ODc4GJiMASDMfCjp94gDMPP4iAM4VkAAWAEKIQjEmAESBDM3OTkYzHwg7LABKPD5iAMwzPqIAzhWQAFYAQpGCiEIxJgBEgQzNzk1GOywASDMfCiUoYoDMPKhigM4WEAAWAEKIQjEmAESBDY4NzYYzHwgmIwBKLmiigMw1aOKAzhYQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Apr 3 - Tue, Apr 14 YQR Regina MDW Chicago CA $721 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQR,to:MDW,departure:03/04/2026TANYT&leg2=from:MDW,to:YQR,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:720.65&airProductToken=AQpGCiEIxJgBEgQ2ODc4GJiMASDMfCiJsIkDMJOxiQM4WEAAWAEKIQjEmAESBDM3OTkYzHwg7LABKJCyiQMw7LKJAzhYQAFYAQpGCiEIxJgBEgQzNzk1GOywASDMfCi0rIoDMJKtigM4VkAAWAEKIQjEmAESBDY4NzYYzHwgmIwBKNmtigMw9a6KAzhWQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Dec 21 - Fri, Dec 26 YQR Regina MDW Chicago CA $771 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQR,to:MDW,departure:21/12/2025TANYT&leg2=from:MDW,to:YQR,departure:26/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:770.01&airProductToken=AQpGCiEIxJgBEgQ2ODc4GJiMASDMfCikqYADML2qgAM4VkAAWAEKIQjEmAESBDQxNjkYzHwg7LABKIqrgAMw96uAAzhWQAFYAQpGCiEIxJgBEgQzNzc4GOywASDMfCjM4YADMLTigAM4WEAAWAEKIQjEmAESBDY4NzYYzHwgmIwBKLnjgAMw1OSAAzhYQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Feb 9 - Fri, Feb 20 YQR Regina MDW Chicago CA $777 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQR,to:MDW,departure:09/02/2026TANYT&leg2=from:MDW,to:YQR,departure:20/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:776.04&airProductToken=AQpGCiEIxJgBEgQ2ODc4GJiMASDMfCjp24QDMPPchAM4VkAAWAEKIQjEmAESBDM3OTUYzHwg7LABKPHkhAMw7OWEAzhWQAFYAQpGCiEIxJgBEgQzNzc4GOywASDMfCjW1oUDMLzXhQM4VEAAWAEKIQjEmAESBDY4NzYYzHwgmIwBKLnZhQMw1dqFAzhUQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Wed, Jan 28 - Fri, Jan 30 YQR Regina MDW Chicago CA $961 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YQR,to:MDW,departure:28/01/2026TANYT&leg2=from:MDW,to:YQR,departure:30/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:961.00&airProductToken=AQqjAQoyCNemARIEMzUyNRiYjAEgmBYowdmDAzCz2oMDOExAAFgBagVFQ09OT3IITEFWRDBMRUsKNQjEmAESBDI0OTIYmBYgzHwoit6DAzC-34MDOFVAAVgBaglNQUlOQ0xBU0NyCFVBVE5BME1MCjYIxJgBEgQzNzkyGMx8IOywASjy34MDMN3ggwM4VUABWAFqCU1BSU5DTEFTQ3IIVUFUTkEwTUwKogEKNgjEmAESBDM2ODEY7LABIMx8KKXsgwMwke2DAzhIQABYAWoJTUFJTkNMQVNDcghIQVRPQTBNUQo1CMSYARIEMjQ4NRjMfCCYFijX7oMDMIrwgwM4SEABWAFqCU1BSU5DTEFTQ3IISEFUT0EwTVEKMQjXpgESAzM5NBiYFiCYjAEopvGDAzD88YMDOExAAVgBagVFQ09OT3IITEFWRDBMRUsSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ## 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:YQR,to:ORD,departure:23/12/2025TANYT&leg2=from:ORD,to:YQR,departure:30/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. 23 min [Flights from CA $932 ](https://www.expedia.ca/Flights-Search?leg1=from:YQR,to:ORD,departure:23/12/2025TANYT&leg2=from:ORD,to:YQR,departure:30/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) __Flight from Regina to Chicago (YQR - MDW) route information__ | Origin airport | Regina Intl. | | ------------------- | ------------ | | Destination airport | Midway Intl. | | Airlines serving | WestJet | | Roundtrip price | CA $490 | | Distance | 1604 km | ## Regina to Chicago Flights **The easy way to book your flights from Regina to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Regina 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 Regina to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Regina Intl., YQR to Midway Intl., MDW** Sort your search results by price to find great deals on your flight from Regina to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Regina currently is just CA $490 rising to CA $961\. 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 Regina** 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 YQR to MDW? ### Do I need to pay a cancellation fee if I cancel my flight from Regina Intl. Airport (YQR) to Midway Airport? ### How do I find cheap flights from Regina Airport to Chicago Airport that have flexible change policies? ### How far is the flight from Regina Intl. Airport (YQR) to Chicago Airport? ### Which airlines fly direct from Regina Intl. Airport (YQR) to Chicago Airport? ### Are Regina Airport to MDW 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 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.