Title: CA $186 Cheap Flights from Toronto (YYZ) 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 $186 Cheap Flights from Toronto (YYZ) to Chicago (MDW) [View CA $186 flight on Wed, Nov 12, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYZ,to:MDW,departure:12/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:185.94&airProductToken=AQpyCjcIxJgBEgQ0ODgxGJjOASDjtAEo9vP8AjDR9PwCOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCjcIxJgBEgQ0ODY5GOO0ASDssAEo9_T8AjDI9fwCOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) - [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 Toronto Pearson Intl. Airport (YYZ) 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:yyz,to:mdw,departure:24/10/2025TANYT&leg2=from:mdw,to:yyz,departure:31/10/2025TANYT&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:yyz,to:mdw,departure:24/10/2025TANYT&leg2=from:mdw,to:yyz,departure:31/10/2025TANYT&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 Toronto (YYZ) to Chicago (MDW) Prices were available within the past 7 days and start at CA $186 for one-way flights and CA $294 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, Feb 10 - Wed, Feb 25 YYZ Toronto MDW Chicago CA $294 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:10/02/2026TANYT&leg2=from:MDW,to:YYZ,departure:25/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:293.54&airProductToken=AQpICiIIxJgBEgQ0OTA3GJjOASDjtAEo7uWEAzDJ5oQDOEVAAFgBCiIIxJgBEgQzNTI3GOO0ASDssAEo6-aEAzC754QDOEVAAVgBCkgKIgjEmAESBDM4NTgY7LABIOO0ASjijoYDMKqPhgM4RUAAWAEKIgjEmAESBDUxNDYY47QBIJjOASi0kIYDMISRhgM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Jan 7 - Mon, Jan 12 YYZ Toronto MDW Chicago CA $315 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:07/01/2026TANYT&leg2=from:MDW,to:YYZ,departure:12/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:314.97&airProductToken=AQpyCjcIxJgBEgQ1MDMxGJjOASDjtAEotOWBAzCY5oEDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCjcIxJgBEgQzNTI3GOO0ASDssAEoq-iBAzD76IEDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCnAKNgjEmAESBDM3OTUY7LABIMx8KPChggMw1KKCAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCUQo2CMSYARIEMzg2NhjMfCCYzgEozqSCAzDUpYIDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Dec 2 - Mon, Dec 15 YYZ Toronto MDW Chicago CA $326 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:02/12/2025TANYT&leg2=from:MDW,to:YYZ,departure:15/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:325.33&airProductToken=AQpICiIIxJgBEgQ1MDczGJjOASDjtAEonNL-AjD70v4COEVAAFgBCiIIxJgBEgQ1Mjk4GOO0ASDssAEoq9P-AjD60_4COEVAAVgBCkYKIQjEmAESBDM3OTUY7LABIMx8KObm_wIwyuf_AjhFQABYAQohCMSYARIEMzg2NhjMfCCYzgEo3en_AjDr6v8COEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Dec 11 - Mon, Dec 15 YYZ Toronto MDW Chicago CA $336 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:11/12/2025TANYT&leg2=from:MDW,to:YYZ,departure:15/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:335.97&airProductToken=AQpyCjcIxJgBEgQ1MDMxGJjOASDjtAEo2bX_AjC5tv8COEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCjcIxJgBEgQ0ODU4GOO0ASDssAEo6rb_AjC-t_8COEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCnIKNwjEmAESBDQ4NjkY7LABIOO0ASiI6f8CMNfp_wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKNwjEmAESBDQ5NDMY47QBIJjOASiE6v8CMNvq_wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sun, Jan 18 - Thu, Jan 22 YYZ Toronto MDW Chicago CA $364 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:18/01/2026TANYT&leg2=from:MDW,to:YYZ,departure:22/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:363.13&airProductToken=AQpoCjII16YBEgQ2MzUzGJjOASDMfCiy4YIDMNTiggM4TEAAWAFqBUVDT05PcghMT1VEMFpFUwoyCNemARIEODA1NhjMfCDssAEomuSCAzD85IIDOExAAVgBagVFQ09OT3IITE9VRDBaRVMSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 5 - Sat, Nov 8 YYZ Toronto MDW Chicago CA $368 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:05/11/2025TANYT&leg2=from:MDW,to:YYZ,departure:08/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:367.47&airProductToken=AQpyCjcIxJgBEgQ1MDMxGJjOASDjtAEo46D8AjDAofwCOFZAAFgBaglNQUlOQ0xBU0NyCFZBVlNBME1MCjcIxJgBEgQ1Mjk4GOO0ASDssAEoy6P8AjCUpPwCOFZAAVgBaglNQUlOQ0xBU0NyCFZBVlNBME1MCnIKNwjEmAESBDM1MDEY7LABIOO0ASjXyPwCMJ_J_AI4VkAAWAFqCU1BSU5DTEFTQ3IIVkFWU0EwTUwKNwjEmAESBDQ5NDMY47QBIJjOASjcyfwCMKvK_AI4VkABWAFqCU1BSU5DTEFTQ3IIVkFWU0EwTUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Sat, Nov 8 - Sat, Nov 15 YYZ Toronto MDW Chicago CA $374 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:08/11/2025TANYT&leg2=from:MDW,to:YYZ,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:373.73&airProductToken=AQpoCjII16YBEgQ2MzUzGJjOASDMfCjIwvwCMNzD_AI4TEAAWAFqBUVDT05PcghMT1VEMFpFUwoyCNemARIEODA1NhjMfCDssAEovMX8AjCcxvwCOExAAVgBagVFQ09OT3IITE9VRDBaRVMSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Wed, Jan 7 - Sun, Jan 11 YYZ Toronto MDW Chicago CA $378 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:07/01/2026TANYT&leg2=from:MDW,to:YYZ,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:377.27&airProductToken=AQpoCjII16YBEgQ2MzUzGJjOASDMfCjS5YEDMPTmgQM4TEAAWAFqBUVDT05PcghMT1VEMFpFUwoyCNemARIEODA1NhjMfCDssAEouuiBAzCc6YEDOExAAVgBagVFQ09OT3IITE9VRDBaRVMSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Nov 20 - Thu, Nov 27 YYZ Toronto MDW Chicago CA $380 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:20/11/2025TANYT&leg2=from:MDW,to:YYZ,departure:27/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:379.06&airProductToken=AQpyCjcIxJgBEgQ1MjU2GJjOASDjtAEopMz9AjD2zP0COEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCjcIxJgBEgQ0ODY5GOO0ASDssAEo9879AjDIz_0COEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 12 - Fri, Nov 21 YYZ Toronto MDW Chicago CA $385 Roundtrip found 23 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:MDW,departure:12/11/2025TANYT&leg2=from:MDW,to:YYZ,departure:21/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:384.13&airProductToken=AQpICiIIxJgBEgQ0ODgxGJjOASDjtAEo9vP8AjDR9PwCOEVAAFgBCiIIxJgBEgQ0ODY5GOO0ASDssAEo9_T8AjDI9fwCOEVAAVgBCkgKIgjEmAESBDQ4NjkY7LABIOO0ASiW2_0CMOPb_QI4RUAAWAEKIgjEmAESBDQ5NDMY47QBIJjOASiD3P0CMNXc_QI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ## Find the cheapest month to fly from Toronto (YYZ) to Chicago (MDW) ### September is typically the cheapest month to fly From CA $293 - CA $598 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:YYZ,to:ORD,departure:24/10/2025TANYT&leg2=from:ORD,to:YYZ,departure:26/10/2025TANYT&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 $546](https://www.expedia.ca/Flights-Search?leg1=from:YYZ,to:ORD,departure:24/10/2025TANYT&leg2=from:ORD,to:YYZ,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flight from Toronto to Chicago (YYZ - MDW) route information | Origin airport | Pearson Intl. | | --- | --- | | Destination airport | Midway Intl. | | Airlines serving | Delta, WestJet | | Roundtrip price | CA $286 | | Distance | 692 km | ## Toronto to Chicago Flights **The easy way to book your flights from Toronto to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Toronto 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 Toronto to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Pearson Intl., YYZ to Midway Intl., MDW**  Sort your search results by price to find great deals on your flight from Toronto to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Toronto currently is just CA $294 rising to CA $385.   Here are more money-saving tips:  - Fly in February 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 Toronto**  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 Pearson Intl. Airport (YYZ) to MDW? > If you're planning on travelling between YYZ and MDW, round-trip flights start from CA $294. 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 today 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 Pearson Intl. Airport (YYZ) to Midway Airport? > Most flights can be cancelled online, but every air carrier has its own set of terms and conditions. If you do decide to cancel your flight, visit our [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from Pearson Intl. Airport (YYZ) to Midway Intl. Airport (MDW) that have flexible change policies? > Select our "No change fees" filter to find flexible travel options for your flight from YYZ to MDW. This allows you to snag a great price in advance and still have the freedom to reschedule without any extra fees. Keep in mind that you'll need to cover the fare difference. ### How many hours is the flight from Toronton Pearson to Midway Airport? > The flight time from Toronto Pearson Airport to Midway Airport is roughly 3 hours and 53 minutes. Put on your earphones, listen to a gripping podcast and the hours in the air will whiz by. ### How far is the flight from YYZ to Midway Intl. Airport (MDW)? > The distance from Toronto Pearson Airport (YYZ) to Midway Airport (MDW) is only 700 kilometres. You'll be disembarking the plane and collecting your baggage from the carousel in no time. ### Which airlines fly direct from YYZ to Midway Intl. Airport (MDW)? > You won't find any airlines flying directly between Toronto Pearson Airport and MDW, so be prepared to make at least one stop on your journey. A layover, whether short or long, can be a welcome way to break up a trip! ### Are Toronton Pearson to Chicago Airport flight tickets cheaper when they're purchased at the last minute? > It is possible to nab an awesome last-minute deal from Toronto Pearson Airport to MDW, but it's also possible to miss out entirely! As many airlines publish prices up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to pounce when you spot a bargain. 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