Title: Cheap Flights to Southwest Side , IL from CA $154 - Expedia.ca ![Chicago, IL showing interior views, heritage elements and an airport](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by by Midway Intl Airport ![](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights to Southwest Side , IL from CA $154 [View CA $154 flight on Tue, Mar 3, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYC,to:MDW,departure:03/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:153.63&airProductToken=AQpvCjUIxJgBEgQyNDkyGJgWIMx8KKrRhgMw3tKGAzhFQABYAWoJTUFJTkJBU0lDcghWQVdOQTBCUQo2CMSYARIEMzY4MRjMfCDssAEoktOGAzD704YDOEVAAVgBaglNQUlOQkFTSUNyCFZBV05BMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) - [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 [Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.ca/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide)[Southwest Side Vacation Packages](https://expedia.ca/Southwest-Side.d553248635976475403.Destination-Travel-Guides) ## Popular airlines - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways - ![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) ## How much is the cheapest flight to Southwest Side? Prices were available within the past 7 days and start at CA $154 for one-way flights and CA $224 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, Feb 18 - Fri, Feb 27 YUL Montreal MDW Chicago CA $224 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:18/02/2026TANYT&leg2=from:MDW,to:YUL,departure:27/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:223.88&airProductToken=AQppCjII0IgBEgQyNDUyGJhdIPjMASihvoUDMPa-hQM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAozCNCIARIEMjM4Nxj4zAEg7LABKLy_hQMwqsCFAzhNQAFYAWoFQkFTSUNyCE0yTjBaUlpMCmkKMwjQiAESBDIzODgY7LABIPjMASiBpoYDMOemhgM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAoyCNCIARIEMjQ3ORj4zAEgmF0ov6eGAzCKqIYDOE1AAVgBagVCQVNJQ3IITTJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, May 2 - Tue, May 12 YYC Calgary ORD Chicago CA $251 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:02/05/2026TANYT&leg2=from:ORD,to:YYC,departure:12/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:250.28&airProductToken=AQoiCiAI1YIBEgQxNjU1GJgWIK4cKNb2iwMwnviLAzhOQABYAQpDCiAI1YIBEgQxMTEzGK4cIINpKOnmjAMwh-iMAzhOQABYAQofCNWCARIDNzIwGINpIJgWKKHqjAMwuuuMAzhOQAFYARIKCAEQARgBKgJVQRgBIgQIARABKAQwAQ) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Feb 27 - Mon, Mar 16 YYC Calgary ORD Chicago CA $251 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:27/02/2026TANYT&leg2=from:ORD,to:YYC,departure:16/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:250.28&airProductToken=AQoiCiAI16YBEgQxNjEwGJgWIK4cKMClhgMwl6eGAzhBQABYAQoiCiAI16YBEgQxNjExGK4cIJgWKKjmhwMwk-iHAzhBQABYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Feb 18 - Fri, Feb 27 YUL Montreal MDW Chicago CA $251 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:18/02/2026TANYT&leg2=from:MDW,to:YUL,departure:27/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:250.48&airProductToken=AQpxCjYIxJgBEgQ1MDU2GJhdIOO0ASj0vYUDMIG_hQM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKNwjEmAESBDU0NDYY47QBIOywASj1wIUDMMbBhQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQlEKbwo2CMSYARIEMTI4NRjssAEg4Fwo0KOGAzDIpIYDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBMEJRCjUIxJgBEgQxNjY5GOBcIJhdKIunhgMwoaiGAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Jan 27 - Tue, Mar 3 YYC Calgary ORD Chicago CA $261 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:27/01/2026TANYT&leg2=from:ORD,to:YYC,departure:03/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:260.83&airProductToken=AQozCjEIwYIBEgQ0MTYxGJgWIK4cKPjKgwMw1MyDAzhCQABYAWoFQkFTSUNyCE9XQUNaTkJYCjMKMQjBggESBDM3NzcYrhwgmBYou9KGAzCx1IYDOEJAAFgBagVCQVNJQ3IIT1dBQ1pOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) Expedia.ca gives you the best tools to secure great deals on flights to Southwest Side. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Southwest Side. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Southwest Side. Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Southwest Side flights with full confidence knowing that you've found the best deal online. Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Southwest Side. Looking to save even more? Get additional savings by bundling your Southwest Side flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Southwest Side trip! ## Frequently asked questions ### How do I find cheap flights to Southwest Side that have flexible change policies? ### Which airlines fly to Southwest Side? > - United Airlines - 12,777 flights to or near Southwest Side each month, including 12,777 flights to O'Hare Intl. Airport (ORD) per month. > - American Airlines - 9,109 flights to or near Southwest Side each month, including 9,109 flights to O'Hare Intl. Airport (ORD) per month. > - Delta - 1,023 flights to or near Southwest Side each month, including 1,023 flights to O'Hare Intl. Airport (ORD) per month. ### How can I find cheap tickets to Southwest Side? ### How much is a flight to Southwest Side? ### What are the most popular airports to fly into in Southwest Side? ### When is the cheapest time to fly to Southwest Side? ### How much is a plane ticket to Southwest Side? ### What is the best time to go to Southwest Side? ### What months are the cheapest to book a flight to Southwest Side? __Flights to Southwest Side information__ | Destination airport | Midway Intl. | | ----------------------------- | ------------ | | Destination airport IATA code | MDW | | Destination city name | Chicago | | Roundtrip price | CA $224 | ## Trending flights to Southwest Side Prices were available within the past 7 days and start at CA $154 for one-way flights and CA $224 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, Feb 18 - Fri, Feb 27 YUL Montreal MDW Chicago CA $224 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:18/02/2026TANYT&leg2=from:MDW,to:YUL,departure:27/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:223.88&airProductToken=AQppCjII0IgBEgQyNDUyGJhdIPjMASihvoUDMPa-hQM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAozCNCIARIEMjM4Nxj4zAEg7LABKLy_hQMwqsCFAzhNQAFYAWoFQkFTSUNyCE0yTjBaUlpMCmkKMwjQiAESBDIzODgY7LABIPjMASiBpoYDMOemhgM4TUAAWAFqBUJBU0lDcghNMk4wWlJaTAoyCNCIARIEMjQ3ORj4zAEgmF0ov6eGAzCKqIYDOE1AAVgBagVCQVNJQ3IITTJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [1 Star Hotels in South Englewood ](https://www.expedia.ca/1Star-South-Englewood-Chicago-Hotels.s10-n6132433-0.Travel-Guide-Filter-Hotels) - 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