Title: Cheap Flights to Winnetka , IL from CA $158 - Expedia.ca ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.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) # Cheap Flights to Winnetka , IL from CA $158 [View CA $158 flight on Mon, Feb 2, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYC,to:ORD,departure:02/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:157.18&airProductToken=AQozCjEI16YBEgQxNjEwGJgWIK4cKKCMhAMw942EAzhFQABYAWoFQkFTSUNyCExUUUQwWkJNEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) - [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 [Winnetka Travel Guide](https://expedia.ca/Winnetka.dx175751)[Hotels in Winnetka](https://expedia.ca/Winnetka-Hotels.d175751.Travel-Guide-Hotels)[Winnetka Car Rentals](https://expedia.ca/Car-Rentals-In-Winnetka.d175751.Car-Rental-Guide)[Winnetka Vacation Packages](https://expedia.ca/Winnetka.d175751.Destination-Travel-Guides) ## Popular airlines to Winnetka - ![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:CMH,to:Winnetka, Illinois, United States of America,departure:10/01/2026TANYT&leg2=from:Winnetka, Illinois, United States of America,to:CMH,departure:17/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winnetka, Illinois, United States of America,departure:10/01/2026TANYT&leg2=from:Winnetka, Illinois, United States of America,to:CMH,departure:17/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winnetka, Illinois, United States of America,departure:10/01/2026TANYT&leg2=from:Winnetka, Illinois, United States of America,to:CMH,departure:17/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winnetka, Illinois, United States of America,departure:10/01/2026TANYT&leg2=from:Winnetka, Illinois, United States of America,to:CMH,departure:17/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winnetka, Illinois, United States of America,departure:10/01/2026TANYT&leg2=from:Winnetka, Illinois, United States of America,to:CMH,departure:17/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winnetka, Illinois, United States of America,departure:10/01/2026TANYT&leg2=from:Winnetka, Illinois, United States of America,to:CMH,departure:17/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Winnetka, Illinois, United States of America,departure:10/01/2026TANYT&leg2=from:Winnetka, Illinois, United States of America,to:CMH,departure:17/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![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 Winnetka? Prices were available within the past 7 days and start at CA $158 for one-way flights and CA $250 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Feb 6 - Mon, Feb 23 YYC Calgary ORD Chicago CA $250 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:06/02/2026TANYT&leg2=from:ORD,to:YYC,departure:23/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:249.52&airProductToken=AQoiCiAI16YBEgQxNjEwGJgWIK4cKKC5hAMw97qEAzhFQABYAQoiCiAI16YBEgQxNjExGK4cIJgWKMT6hQMwr_yFAzhFQABYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, May 21 - Tue, May 26 YYC Calgary ORD Chicago CA $250 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:21/05/2026TANYT&leg2=from:ORD,to:YYC,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:249.80&airProductToken=AQoiCiAI1YIBEgQxOTY4GJgWIK4cKMbKjQMwjsyNAzhOQABYAQpDCiAI1YIBEgQxMjE3GK4cIINpKN-BjgMw_4KOAzhOQABYAQofCNWCARIDNzIwGINpIJgWKOGHjgMw-oiOAzhOQAFYARIKCAEQARgBKgJVQRgBIgQIARABKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Jan 22 - Tue, Jan 27 YYC Calgary ORD Chicago CA $256 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:22/01/2026TANYT&leg2=from:ORD,to:YYC,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:255.89&airProductToken=AQozCjEIwYIBEgQ0MTYxGJgWIK4cKNiSgwMwtJSDAzhCQABYAWoFQkFTSUNyCE9VQUNaU0JYCmcKMgjBggESBDEzNjIYrhwgo7EBKKPLgwMwyMyDAzhCQABYAWoFQkFTSUNyCE9VQUNaU0JYCjEIwYIBEgM1MTEYo7EBIJgWKPzMgwMw6s6DAzhCQAFYAWoFQkFTSUNyCE9VQUNaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Sun, Feb 1 - Tue, Feb 3 YUL Montreal MDW Chicago CA $259 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:MDW,departure:01/02/2026TANYT&leg2=from:MDW,to:YUL,departure:03/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:258.76&airProductToken=AQpHCiEI0IgBEgQyNDY2GJhdIPjMASiZgYQDMO6BhAM4TUAAWAEKIgjQiAESBDIzOTMY-MwBIOywASjSgoQDMMCDhAM4TUABWAEKRwoiCNCIARIEMjM4OBjssAEg-MwBKPyXhAMw4piEAzhNQABYAQohCNCIARIEMjQ3ORj4zAEgmF0ov5mEAzCKmoQDOE1AAVgBEgoIARABGAEqAlBEGAEiBAgBEAEoBDAB) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Fri, Feb 13 - Mon, Feb 16 YUL Montreal ORD Chicago CA $259 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:ORD,departure:13/02/2026TANYT&leg2=from:ORD,to:YUL,departure:16/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:258.76&airProductToken=AQozCjEIwYYBEgQ4OTY3GJhdIK4cKL2LhQMw4oyFAzhHQABYAWoFQkFTSUNyCEdOQTJBN0JBCjMKMQjBhgESBDg5NTgYrhwgmF0ou6iFAzC4qYUDOEdAAFgBagVCQVNJQ3IIR05BMkE3QkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ## Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD) ### June is typically the cheapest month to fly From CA $108 - CA $444 per traveller. Expedia.ca gives you the best tools to secure great deals on flights to Winnetka. 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 Winnetka. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Winnetka. 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 Winnetka 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 Winnetka. Looking to save even more? Get additional savings by bundling your Winnetka 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 Winnetka trip! ## Frequently asked questions ### What is the name of Winnetka's airport? ### How far is O'Hare Intl. Airport (ORD) from central Winnetka? ### What airport is best to fly into Winnetka? ### How many airlines fly to Winnetka? ### Which airlines fly to Winnetka? ### How many nonstop flights are there to Winnetka? ### Where are the most popular flights to Winnetka departing from? ### How long is the flight to Winnetka Airport? ### How to book the cheapest flight to Winnetka? ### Do you have any tips for my flight to Winnetka? > - First and foremost, put in your passport, travel docs, bank cards and medications. Next, you'll want some entertainment to while away the time. A juicy novel and a phone crammed with your favourite movies are some wonderful options. If you hope to catch more than just forty winks, a quality neck pillow and a pair of noise-cancelling headphones will also be useful. Finally, find room for a toothbrush and some deodorant so you'll arrive at your destination looking fresh and raring to go. > > > Do not pack the following items in your hand luggage: > > > - While the list of banned items can differ between air carriers, the general rule to follow is avoid carrying anything sharp, flammable or explosive. This includes box cutters, razor blades, spray paint and flares. Sporting equipment like hockey sticks, and objects that could harm other people, such as pepper spray and firearms, won't be allowed on board either. > > > What to wear on a flight: > > > - You'll want to choose comfort over style. Prepare for temperature changes by donning layers, and pick flat, slightly roomy shoes like slip-ons. > - It's likely you've heard about deep vein thrombosis (DVT), a blood clot condition caused by long periods of inactivity. To lower your risk on board, stay hydrated, consider wearing compression socks and do gentle foot and leg exercises in your seat. ### How to get through airport security fast when flying to Winnetka? > - First things first. Your boarding pass and passport will need to be shown to airport security personnel. Keep them handy so you don't have to dig around for them. > - The X-ray machine comes next. Empty your pockets and remove anything metal that is likely to set off the scanner's alarm. This includes items like headphones or earphones, as well as heavy coats or jackets. They'll all need to go on the X-ray conveyor belt. > - All electronic gadgets, including your tablet and phone, are also required to be scanned separately. > - Any gels or liquids, such as lip balm or cologne, that you want to take on board need to be in containers no greater than 3.4 ounces (100 millilitres). Also, everything must fit inside a quart-size (one litre), zip-lock bag. > - There's a good chance you'll be asked to take your shoes off for scanning, so wearing lightweight sneakers is always a smart idea. > - Airlines won't allow any pocket knives or other sharp items in the cabin. If you need to bring these kinds of items, put them in your checked luggage. __Flights to Winnetka information__ | Destination airport | O'Hare Intl. | | ----------------------------- | ------------ | | Destination airport IATA code | ORD | | Destination city name | Chicago | | Roundtrip price | CA $250 | ## Trending flights to Winnetka Prices were available within the past 7 days and start at CA $158 for one-way flights and CA $250 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Feb 6 - Mon, Feb 23 YYC Calgary ORD Chicago CA $250 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:06/02/2026TANYT&leg2=from:ORD,to:YYC,departure:23/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:249.52&airProductToken=AQoiCiAI16YBEgQxNjEwGJgWIK4cKKC5hAMw97qEAzhFQABYAQoiCiAI16YBEgQxNjExGK4cIJgWKMT6hQMwr_yFAzhFQABYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [5 Star Hotels in Glenview ](https://www.expedia.ca/5Star-Glenview-Hotels.s50-0-d8006.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Gross Point ](https://www.expedia.ca/5Star-Gross-Point-Chicago-Hotels.s50-n6132100-0.Travel-Guide-Filter-Hotels) - [Hotels near Baha'i House of Worship ](https://www.expedia.ca/Bahai-House-Of-Worship-Hotels.0-l6152644-0.Travel-Guide-Filter-Hotels) - 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