Title: CA $158 Cheap Flights from Montreal (YUL) 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $158 Cheap Flights from Montreal (YUL) to Chicago (MDW) [View CA $158 flight on Wed, May 13, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YUL,to:MDW,departure:13/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:157.12&airProductToken=AQppCjII0IgBEgQyNDY2GJhdIPjMASjm8YwDMLjyjAM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAozCNCIARIEMjM5Mxj4zAEg7LABKPfyjAMw5POMAzhNQAFYAWoFQkFTSUNyCE0yTjBaUlpMEgoIARABGAEqAlBEGAEiBAgBEAEoAigDKAQwAQ) - [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 Trudeau International Airport (YUL) 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:yul,to:mdw,departure:19/10/2025TANYT&leg2=from:mdw,to:yul,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) - ![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:yul,to:mdw,departure:19/10/2025TANYT&leg2=from:mdw,to:yul,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:yul,to:mdw,departure:19/10/2025TANYT&leg2=from:mdw,to:yul,departure:26/10/2025TANYT&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 Montreal (YUL) to Chicago (MDW) Prices were available within the past 7 days and start at CA $158 for one-way flights and CA $240 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, May 20 - Mon, Jun 8 YUL Montreal MDW Chicago CA $240 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:20/05/2026TANYT&leg2=from:MDW,to:YUL,departure:08/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:239.53&airProductToken=AQppCjII0IgBEgQyNDYwGJhdIPjMASi1v40DMIfAjQM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAozCNCIARIEMjM5Mxj4zAEg7LABKNfBjQMwxMKNAzhNQAFYAWoFQkFTSUNyCE0yTjBaUlpMCmkKMwjQiAESBDIzODgY7LABIPjMASiQlY8DMPSVjwM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAoyCNCIARIEMjQ3Mxj4zAEgmF0ohZePAzDQl48DOE1AAVgBagVCQVNJQ3IITTJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, May 20 - Mon, Jun 8 YUL Montreal MDW Chicago CA $286 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:20/05/2026TANYT&leg2=from:MDW,to:YUL,departure:08/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:285.86&airProductToken=AQpxCjYIxJgBEgQ1MDU2GJhdIOO0ASiYvY0DMJG-jQM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKNwjEmAESBDM1MjcY47QBIOywASiPwI0DMNrAjQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, May 20 - Mon, Jun 8 YUL Montreal MDW Chicago CA $290 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:20/05/2026TANYT&leg2=from:MDW,to:YUL,departure:08/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:289.18&airProductToken=AQppCjII0IgBEgQyNDY2GJhdIPjMASjGwI0DMJjBjQM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAozCNCIARIEMjM5Mxj4zAEg7LABKNfBjQMwxMKNAzhNQAFYAWoFQkFTSUNyCE0yTjBaUlpMCmkKMwjQiAESBDIzODgY7LABIPjMASiQlY8DMPSVjwM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAoyCNCIARIEMjQ4Mxj4zAEgmF0olpiPAzDhmI8DOE1AAVgBagVCQVNJQ3IITTJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, May 13 - Wed, May 27 YUL Montreal MDW Chicago CA $290 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:13/05/2026TANYT&leg2=from:MDW,to:YUL,departure:27/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:289.60&airProductToken=AQppCjII0IgBEgQyNDU0GJhdIPjMASjn74wDMLnwjAM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAozCNCIARIEMjM5Mxj4zAEg7LABKPfyjAMw5POMAzhNQAFYAWoFQkFTSUNyCE0yTjBaUlpMCmkKMwjQiAESBDIzOTQY7LABIPjMASjckY4DMMKSjgM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAoyCNCIARIEMjQ4Nxj4zAEgmF0o_JKOAzDHk44DOE1AAVgBagVCQVNJQ3IITTJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, May 13 - Tue, May 26 YUL Montreal MDW Chicago CA $298 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:13/05/2026TANYT&leg2=from:MDW,to:YUL,departure:26/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:297.73&airProductToken=AQpxCjYIxJgBEgQ1MDU2GJhdIOO0ASi47owDMLHvjAM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKNwjEmAESBDM1MjcY47QBIOywASiv8YwDMPrxjAM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKbwo2CMSYARIEMjQxNxjssAEg4FwovYSOAzC2hY4DOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCjUIxJgBEgQyNDE2GOBcIJhdKOuHjgMwjomOAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, May 20 - Mon, Jun 8 YUL Montreal MDW Chicago CA $314 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:20/05/2026TANYT&leg2=from:MDW,to:YUL,departure:08/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:313.03&airProductToken=AQpvCjUI0IgBEgQyNDYwGJhdIPjMASi1v40DMIfAjQM4TUAAWAFqCFNUQU5EQVJEcghNMk4wWlJaUwo2CNCIARIEMjM5Mxj4zAEg7LABKNfBjQMwxMKNAzhNQAFYAWoIU1RBTkRBUkRyCE0yTjBaUlpTCm8KNgjQiAESBDIzODgY7LABIPjMASiQlY8DMPSVjwM4TUAAWAFqCFNUQU5EQVJEcghNMk4wWlJaUwo1CNCIARIEMjQ3Mxj4zAEgmF0ohZePAzDQl48DOE1AAVgBaghTVEFOREFSRHIITTJOMFpSWlMSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Wed, May 20 - Mon, Jun 8 YUL Montreal MDW Chicago CA $322 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:20/05/2026TANYT&leg2=from:MDW,to:YUL,departure:08/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:321.95&airProductToken=AQppCjII0IgBEgQyNDU0GJhdIPjMASjHvo0DMJm_jQM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAozCNCIARIEMjM5Mxj4zAEg7LABKNfBjQMwxMKNAzhNQAFYAWoFQkFTSUNyCE0yTjBaUlpMCmkKMwjQiAESBDIzODgY7LABIPjMASiQlY8DMPSVjwM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAoyCNCIARIEMjQ4Mxj4zAEgmF0olpiPAzDhmI8DOE1AAVgBagVCQVNJQ3IITTJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, May 20 - Mon, Jun 8 YUL Montreal MDW Chicago CA $323 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:20/05/2026TANYT&leg2=from:MDW,to:YUL,departure:08/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:322.96&airProductToken=AQpxCjYIxJgBEgQ1MDU2GJhdIOO0ASiYvY0DMJG-jQM4VkAAWAFqCU1BSU5DTEFTQ3IIVkFWU0EwTUwKNwjEmAESBDM1MjcY47QBIOywASiPwI0DMNrAjQM4VkABWAFqCU1BSU5DTEFTQ3IIVkFWU0EwTUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, May 20 - Mon, Jun 8 YUL Montreal MDW Chicago CA $329 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:20/05/2026TANYT&leg2=from:MDW,to:YUL,departure:08/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:328.57&airProductToken=AQpxCjYIxJgBEgQ1MDU2GJhdIOO0ASiYvY0DMJG-jQM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKNwjEmAESBDM1MjcY47QBIOywASiPwI0DMNrAjQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, May 20 - Mon, Jun 8 YUL Montreal MDW Chicago CA $335 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:20/05/2026TANYT&leg2=from:MDW,to:YUL,departure:08/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:334.34&airProductToken=AQpxCjYIxJgBEgQ1MDU2GJhdIOO0ASiYvY0DMJG-jQM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKNwjEmAESBDM1MjcY47QBIOywASiPwI0DMNrAjQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Montreal (YUL) to Chicago (MDW) ### September is typically the cheapest month to fly From CA $226 - CA $595 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:YUL,to:ORD,departure:19/10/2025TANYT&leg2=from:ORD,to:YUL,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. Cheapest 23 min [Flights from CA $624](https://www.expedia.ca/Flights-Search?leg1=from:YUL,to:ORD,departure:19/10/2025TANYT&leg2=from:ORD,to:YUL,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Frequently asked questions ### How much is a flight from Montréal–Trudeau to Chicago Airport? > Start packing your bags, because round-trip journeys between YUL and MDW start from CA $240. That's based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can rise quickly, so book today to secure 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 YUL to Midway Intl. Airport (MDW)? > The majority of flights can be cancelled online, but each airline has its own set of terms and conditions. If you do decide to cancel your flight, go to our [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from YUL to Midway Airport that have flexible change policies? > Flights from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Airport offering flexible change policies are available from several carriers. Simply use our "No change fees" filter during your search. You'll only need to pay the difference in ticket price, with no added fees to worry about. ### How many hours is the flight from Pierre Elliott Trudeau Intl. Airport (YUL) to MDW? > It takes around 4 hours and 17 minutes to fly from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Airport. But with some movies and a good book, the hours will pass by quicker. ### How far is the flight from Pierre Elliott Trudeau Intl. Airport (YUL) to MDW? > A flight distance of just 1,200 kilometres separates Dorval and Chicago. Once you're in the air, you won't have time to do much more than read the magazine in your seat pocket. ### Which airlines fly direct from YUL to Chicago Airport? > Right now, no airlines offer flights directly from Montreal Airport to Chicago Airport. You'll need to book a flight with one or more stops. To score the best price and connections, lock in your fare well in advance. ### Are Montréal–Trudeau to Midway Airport flight tickets cheaper when they're purchased at the last minute? > Flight tickets from Montreal Airport to Midway Airport are available up to a year before departure on Expedia. And although you may nab great last-minute deal, it's not something you should count on. Also, booking your flights in advance means you'll have more options — and you can avoid landing the dreaded middle seat! We're constantly updating our fares to bring you the best bargains, so check back often for all the latest specials. ## Travel information | Origin airport | Pierre Elliott Trudeau Intl. | | --- | --- | | Destination airport | Midway Intl. | | Airlines serving | Delta, Porter Airlines, WestJet | | Roundtrip price | CA $240 | | Distance | 1188 km | ## Book with confidence ### Montreal to Chicago Flights **The easy way to book your flights from Montreal to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Montreal 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 Montreal to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Pierre Elliott Trudeau Intl., YUL to Midway Intl., MDW**  Sort your search results by price to find great deals on your flight from Montreal to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Montreal currently is just CA $240 rising to CA $335.   Here are more money-saving tips:  - Fly in May 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 Montreal**  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. ## Explore a world of travel with Expedia - 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. Marie (CIU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ciu/ord/sault-ste-marie-to-chicago) - [Flights from Charlotte (CLT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/clt/ord/charlotte-to-chicago) - [Flights from Columbus (CMH) to Chicago (ORD)](https://www.expedia.ca/lp/flights/cmh/ord/columbus-to-chicago) - [Flights from Cincinnati (CVG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/cvg/ord/cincinnati-to-chicago) - [Flights from Washington (DCA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dca/ord/washington-to-chicago) - [Flights from Delhi (DEL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/del/ord/delhi-to-chicago) - [Flights from Denver (DEN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/den/ord/denver-to-chicago) - [Flights from Dallas (DFW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dfw/ord/dallas-to-chicago) - [Flights from Duluth (DLH) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dlh/ord/duluth-to-chicago) - [Flights from Des Moines (DSM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dsm/ord/des-moines-to-chicago) - [Flights from Detroit (DTW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dtw/ord/detroit-to-chicago) - [Flights from Dubai (DXB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dxb/ord/dubai-to-chicago) - [Flights from Fargo (FAR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/far/ord/fargo-to-chicago) - [Flights from Fort Lauderdale (FLL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/fll/ord/fort-lauderdale-to-chicago) - [Flights from Flint (FNT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/fnt/ord/flint-to-chicago) - [Flights from Spokane (GEG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/geg/ord/spokane-to-chicago) - [Flights from Grand Forks (GFK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/gfk/ord/grand-forks-to-chicago) - [Flights from Green Bay (GRB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/grb/ord/green-bay-to-chicago) - [Flights from Grand Rapids (GRR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/grr/ord/grand-rapids-to-chicago) - [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.