Title: Cheap Flights to Sleepy Hollow , IL from CA $169 - 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 Sleepy Hollow , IL from CA $169 [View CA $169 flight on Fri, May 8, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YXX,to:ORD,departure:08/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:168.38&airProductToken=AQpmCjEI16YBEgM0NzIY-L0BIJgWKMy3jAMwnLiMAzhFQABYAWoFQkFTSUNyCExUUUQwWkJLCjEI16YBEgQxNjEwGJgWIK4cKPi5jAMw1LuMAzhFQAFYAWoFQkFTSUNyCExUUUQwWkJLEgoIARABGAEqAldTGAEiBAgBEAEoAigDKAQwAQ) - [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 [Hotels in Sleepy Hollow](https://expedia.ca/Sleepy-Hollow-Hotels.d3000435324.Travel-Guide-Hotels)[Things to do in Sleepy Hollow](https://expedia.ca/Things-To-Do-In-Sleepy-Hollow.d3000435324.Travel-Guide-Activities)[Sleepy Hollow Car Rentals](https://expedia.ca/Car-Rentals-In-Sleepy-Hollow.d3000435324.Car-Rental-Guide)[Sleepy Hollow Vacation Packages](https://expedia.ca/Sleepy-Hollow.d3000435324.Destination-Travel-Guides) ## Popular airlines to Sleepy Hollow - ![](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:Sleepy Hollow, Illinois, United States of America,departure:22/02/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](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:Sleepy Hollow, Illinois, United States of America,departure:22/02/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![](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:Sleepy Hollow, Illinois, United States of America,departure:22/02/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](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:Sleepy Hollow, Illinois, United States of America,departure:22/02/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](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:Sleepy Hollow, Illinois, United States of America,departure:22/02/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](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:Sleepy Hollow, Illinois, United States of America,departure:22/02/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Sleepy Hollow, Illinois, United States of America,departure:22/02/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:01/03/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](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\* - ![](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\* - ![](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 Sleepy Hollow? Prices were available within the past 7 days and start at CA $169 for one-way flights and CA $273 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, May 23 - Tue, May 26 YYC Calgary ORD Chicago CA $273 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:23/05/2026TANYT&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:272.51&airProductToken=AQozCjEIwYIBEgQxNjMzGJgWIK4cKP_fjQMw1uGNAzhCQABYAWoFQkFTSUNyCE9XQUNaTkJYCjMKMQjBggESBDE2MzIYrhwgmBYojoiOAzD2iY4DOEJAAFgBagVCQVNJQ3IIT1dBQ1pOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Apr 20 - Tue, Apr 21 YYC Calgary ORD Chicago CA $273 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:20/04/2026TANYT&leg2=from:ORD,to:YYC,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:272.52&airProductToken=AQpDCh8I1YIBEgM1NTAYmBYgg2ko0OyKAzDs7YoDOE5AAFgBCiAI1YIBEgQxNDExGINpIK4cKJDyigMwrPOKAzhOQAFYAQohCh8I1YIBEgM3NjQYrhwgmBYo1viKAzC8-ooDOE5AAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Mon, May 4 - Fri, May 8 YYC Calgary ORD Chicago CA $278 Roundtrip found 1 hour ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:04/05/2026TANYT&leg2=from:ORD,to:YYC,departure:08/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:277.16&airProductToken=AQoiCiAI16YBEgQxNjEwGJgWIK4cKPiMjAMw1I6MAzhBQABYAQoiCiAI16YBEgQxNjExGK4cIJgWKIa8jAMw8b2MAzhBQABYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sun, Apr 19 - Sun, Apr 26 YUL Montreal ORD Chicago CA $281 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:ORD,departure:19/04/2026TANYT&leg2=from:ORD,to:YUL,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:280.94&airProductToken=AQoyCjAIwYYBEgM1MjEYmF0grhwo--GKAzCZ44oDOEdAAFgBagVCQVNJQ3IIR05BMkE3QkEKMgowCMGGARIDNTIyGK4cIJhdKO6yiwMw9bOLAzhHQABYAWoFQkFTSUNyCEdOQTJBN0JBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwDQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Mar 23 - Mon, Mar 23 YUL Montreal ORD Chicago CA $290 Roundtrip found 19 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YUL,to:ORD,departure:23/03/2026TANYT&leg2=from:ORD,to:YUL,departure:23/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:289.55&airProductToken=AQpECiAIxJgBEgQ1NDI3GJhdIMx8KJSxiAMw0bKIAzhFQABYAQogCMSYARIEMzg5MxjMfCCuHCjjtIgDMMO1iAM4RUABWAEKRgohCMSYARIEMjM1OBiuHCDjtAEo0LaIAzCit4gDOEVAAFgBCiEIxJgBEgQ1MTM2GOO0ASCYXSj2t4gDMOG4iAM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ## Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD) ### July is typically the cheapest month to fly From CA $109 - CA $427 per traveller. Expedia.ca gives you the best tools to secure great deals on flights to Sleepy Hollow. 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 Sleepy Hollow. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Sleepy Hollow. 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 Sleepy Hollow 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 Sleepy Hollow. Looking to save even more? Get additional savings by bundling your Sleepy Hollow 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 Sleepy Hollow trip! ## Frequently asked questions ### What is the name of Sleepy Hollow's airport? ### How far is O'Hare Intl. Airport (ORD) from central Sleepy Hollow? ### What airport is best to fly into Sleepy Hollow? ### How many airlines fly to Sleepy Hollow? ### Which airlines fly to Sleepy Hollow? ### How many nonstop flights are there to Sleepy Hollow? ### Where are the most popular flights to Sleepy Hollow departing from? ### How long is the flight to Sleepy Hollow Airport? ### How to book the cheapest flight to Sleepy Hollow? ### Do you have any tips for my flight to Sleepy Hollow? > - The trick to having a worry-free flight experience is to pack in advance. Start with the essentials: passport, travel documents, bank cards and vital medications. Next, bring on board items that'll help keep you busy, like your laptop or a thrilling novel. It's also wise to bring your chargers, a comfy neck pillow and a pair of earphones. Finally, don't forget to chuck in toiletry items like a toothbrush, lip balm and a fresh set of clothes. > > > Do not pack the following items in your hand luggage: > > > - While the list of restricted items can differ between airlines, the general rule of thumb is nothing flammable, sharp or explosive. This includes things like tools, metal cutlery, fuels and bleaching agents. Sporting equipment like baseball bats, and items that could harm passengers, such as firearms and swords, won't be allowed on board either. > > > What to wear on a flight: > > > - Go for comfort over style. Prepare for temperature changes in the cabin by wearing layers, and opt for flat, enclosed footwear like slip-ons. > - Most travellers have heard about deep vein thrombosis (DVT), a blood clotting condition caused by long periods of inactivity. To lower your risk on board, drink lots of water, consider wearing compression tights or socks and keep your legs and feet moving. ### How to get through airport security fast when flying to Sleepy Hollow? > - Security personnel first need to verify that you have a valid passport and travel documents before you can proceed any further. Keep them within easy reach. > - Time to strip down. Well sort of. Your jacket, belt, keys and other items in your pocket, like your headphones, will need to go through the X-ray machine. Make your life easier by removing them as your turn draws near. > - All electronic gadgets, including your laptop and phone, are also required to be separately scanned. > - Don't forget to remove gels and liquids from your carry-on bag. They often need to be sent through the X-ray separately. Each product should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit in a single quart-size (one litre), clear zip-lock bag. > - Lightweight sneakers are a good footwear choice as you're less likely to be asked to remove them when passing through security. Boots and other heavy shoes are usually subjected to additional screening. > - Airlines will not allow any pocket knives or other sharp items in your carry-on luggage. If you need to bring these kinds of items, check them in. __Flights to Sleepy Hollow information__ | Destination airport | O'Hare Intl. | | ----------------------------- | ------------ | | Destination airport IATA code | ORD | | Destination city name | Chicago | | Roundtrip price | CA $273 | ## Trending flights to Sleepy Hollow Prices were available within the past 7 days and start at CA $169 for one-way flights and CA $273 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, May 23 - Tue, May 26 YYC Calgary ORD Chicago CA $273 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:23/05/2026TANYT&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:272.51&airProductToken=AQozCjEIwYIBEgQxNjMzGJgWIK4cKP_fjQMw1uGNAzhCQABYAWoFQkFTSUNyCE9XQUNaTkJYCjMKMQjBggESBDE2MzIYrhwgmBYojoiOAzD2iY4DOEJAAFgBagVCQVNJQ3IIT1dBQ1pOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) \*Available to Expedia members.