Title: CA $155 Cheap Flights from Toronto (YTZ) 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) ## Popular airlines from Billy Bishop Toronto City Airport (YTZ) 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:ytz,to:mdw,departure:11/11/2025TANYT&leg2=from:mdw,to:ytz,departure:18/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ![Air Transat](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_TS.svg) Air Transat [](https://www.expedia.ca/Flights-Search?leg1=from:ytz,to:mdw,departure:11/11/2025TANYT&leg2=from:mdw,to:ytz,departure:18/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"TS"}}]) ![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 (YTZ) to Chicago (MDW) Prices were available within the past 7 days and start at CA $155 for one-way flights and CA $248 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) Thu, Mar 19 - Wed, Mar 25 YTZ Toronto MDW Chicago CA $248 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:19/03/2026TANYT&leg2=from:MDW,to:YTZ,departure:25/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:247.75&airProductToken=AQo1CjMI0IgBEgQyMzkzGPjMASDssAEo1oeIAzDEiIgDOE1AAFgBagVCQVNJQ3IITTJOMFpSWkwKNQozCNCIARIEMjM4OBjssAEg-MwBKIDKiAMw5sqIAzhNQABYAWoFQkFTSUNyCE0yTjBaUlpMEgoIARABGAEqAlBEGAEiBAgBEAEoAigDKAQwAQ) ![Air Transat](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TS.gif) Thu, Mar 19 - Wed, Mar 25 YTZ Toronto MDW Chicago CA $248 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:19/03/2026TANYT&leg2=from:MDW,to:YTZ,departure:25/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:247.88&airProductToken=AQozCjEI1KYBEgQ3MzE0GPjMASDssAEo1oeIAzDEiIgDOFFAAFgBagNCR1RyCFEyTjBaUlpMCjMKMQjUpgESBDcwNTgY7LABIPjMASiAyogDMObKiAM4UUAAWAFqA0JHVHIIUTJOMFpSWkwSCggBEAEYASoCVFMYASIECAEQASgCKAMoBDAN) ![Air Transat](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TS.gif) Thu, Jan 8 - Tue, Jan 13 YTZ Toronto MDW Chicago CA $254 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:08/01/2026TANYT&leg2=from:MDW,to:YTZ,departure:13/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:253.32&airProductToken=AQozCjEI1KYBEgQ3MDYwGPjMASDssAEol_KBAzCF84EDOFFAAFgBagNCR1RyCFEyTjBaUlpMCjMKMQjUpgESBDcwNTgY7LABIPjMASjcq4IDMMKsggM4UUAAWAFqA0JHVHIIUTJOMFpSWkwSCggBEAEYASoCVFMYASIECAEQASgCKAMoBDAN) ![Air Transat](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TS.gif) Thu, Mar 19 - Wed, Mar 25 YTZ Toronto MDW Chicago CA $265 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:19/03/2026TANYT&leg2=from:MDW,to:YTZ,departure:25/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:264.63&airProductToken=AQozCjEI1KYBEgQ3MzE0GPjMASDssAEo1oeIAzDEiIgDOFFAAFgBagNCR1RyCFEyTjBaUlpMEgoIARABGAEqAlRTGAEiBAgBEAEoAigDKAQwDQ) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Sun, Nov 16 - Fri, Feb 6 YTZ Toronto MDW Chicago CA $280 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:16/11/2025TANYT&leg2=from:MDW,to:YTZ,departure:06/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:279.25&airProductToken=AQo1CjMI0IgBEgQyMzg3GPjMASDssAEo9539AjDlnv0COE1AAFgBagVCQVNJQ3IITTROMFpSWkwKNQozCNCIARIEMjM4OBjssAEg-MwBKNy5hAMwwrqEAzhNQABYAWoFQkFTSUNyCE0yTjBaUlpMEgoIARABGAEqAlBEGAEiBAgBEAEoAigDKAQwAQ) ![Air Transat](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TS.gif) Tue, Apr 14 - Tue, Apr 21 YTZ Toronto MDW Chicago CA $297 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:14/04/2026TANYT&leg2=from:MDW,to:YTZ,departure:21/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:296.43&airProductToken=AQozCjEI1KYBEgQ3MzE0GPjMASDssAEolqyKAzCErYoDOFFAAFgBagNTVERyCFEyTjBaUlpTEgoIARABGAEqAlRTGAEiBAgBEAEoAigDKAQwDQ) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Tue, Apr 14 - Tue, Apr 21 YTZ Toronto MDW Chicago CA $297 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:14/04/2026TANYT&leg2=from:MDW,to:YTZ,departure:21/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:296.59&airProductToken=AQo4CjYI0IgBEgQyMzkzGPjMASDssAEolqyKAzCErYoDOE1AAFgBaghTVEFOREFSRHIITTJOMFpSWlMSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Sat, Feb 28 - Sun, Mar 22 YTZ Toronto MDW Chicago CA $306 Roundtrip found 10 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:28/02/2026TANYT&leg2=from:MDW,to:YTZ,departure:22/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:305.50&airProductToken=AQo1CjMI0IgBEgQyMzg3GPjMASDssAEo4LCGAzDOsYYDOFZAAFgBagVCQVNJQ3IIVjROMFpSWkwKNQozCNCIARIEMjM4OBjssAEg-MwBKKCoiAMwhqmIAzhNQABYAWoFQkFTSUNyCE0yTjBaUlpMEgoIARABGAEqAlBEGAEiBAgBEAEoAigDKAQwAQ) ![Air Transat](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TS.gif) Tue, Apr 14 - Tue, Apr 21 YTZ Toronto MDW Chicago CA $308 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:14/04/2026TANYT&leg2=from:MDW,to:YTZ,departure:21/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:307.05&airProductToken=AQozCjEI1KYBEgQ3MzE0GPjMASDssAEolqyKAzCErYoDOFFAAFgBagNCR1RyCFEyTjBaUlpMEgoIARABGAEqAlRTGAEiBAgBEAEoAigDKAQwDQ) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Thu, Mar 19 - Wed, Mar 25 YTZ Toronto MDW Chicago CA $310 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:19/03/2026TANYT&leg2=from:MDW,to:YTZ,departure:25/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:309.70&airProductToken=AQo1CjMI0IgBEgQyMzg3GPjMASDssAEom4WIAzCJhogDOFZAAFgBagVCQVNJQ3IIVjJOMFpSWkwKNQozCNCIARIEMjM4OBjssAEg-MwBKIDKiAMw5sqIAzhNQABYAWoFQkFTSUNyCE0yTjBaUlpMEgoIARABGAEqAlBEGAEiBAgBEAEoAigDKAQwAQ) ## Find the cheapest month to fly from Toronto (YTZ) to Chicago (MDW) ### September is typically the cheapest month to fly From CA $203 - CA $573 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:YTZ,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:YTZ,departure:16/11/2025TANYT&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 $374](https://www.expedia.ca/Flights-Search?leg1=from:YTZ,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:YTZ,departure:16/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## 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 Billy Bishop Toronto City, YTZ 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 $248 rising to CA $310.   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 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 Billy Bishop Airport to Midway Intl. Airport (MDW)? > Start packing your bags, because round-trip journeys between Billy Bishop Airport and Midway Airport start from CA $248. That's based on airfares available within the last 7 days on Expedia for flights departing within the next year. Prices can go up quickly, so book now to lock in the best deal. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Billy Bishop Toronto City Airport (YTZ) to Chicago Airport? > We understand that things crop up unexpectedly, so we've made it as easy as possible for you to cancel your flight online. Just head to the [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from Billy Bishop Airport to MDW that have flexible change policies? > Select our "No change fees" filter to find flexible travel options for your flight from Billy Bishop Toronto City Airport (YTZ) to MDW. This allows you to snag a fantastic price in advance and still have the freedom to reschedule without any additional fees. Just keep in mind that fare differences may still apply. ### How far is the flight from YTZ to Midway Airport? > With a flight distance of 710 kilometres, it's just a hop from Billy Bishop Airport to MDW. It might be a quick one, but it's still worth bringing something to keep you entertained on board. ### Which airlines fly direct from Billy Bishop Airport to MDW? > Porter Airlines (PD) will get you from YTZ to Chicago Airport safely and comfortably. Take your pick of 26 direct flights each month along this route. ### Are YTZ to MDW flight tickets cheaper when they're purchased at the last minute? > Flight prices are constantly going up and down, so it's no sure thing. While last-minute flight deals between Billy Bishop Airport and Chicago Airport are of course possible, it also makes sense to monitor prices well before you fly. In fact, some airlines publicize their prices up to 12 months before the departure date. 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