Title: Cheap Flights to Sleepy Hollow - Expedia.co.uk ![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) # £231 Cheap Flights to Sleepy Hollow [View £231 flight on Tue, 10 Nov 2026](https://expedia.co.uk/Flights-Search?trip=oneway&leg1=from:DUB,to:ORD,departure:10/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:230.50&airProductToken=AQpkCjAIxpIBEgM0MTcYgw0giikosuOcAzDS5JwDOE9AAFgBagVMSUdIVHIIT0oxUUlFTFQKMAjGkgESAzg1MxiKKSCuHCje5ZwDMPjonAM4T0ABWAFqBUxJR0hUcghPSjFRSUVMVBIKCAEQARgBKgJGSRgBIgQIARABKAIoAygEMAE) - [Return](?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.co.uk/Sleepy-Hollow-Hotels.d3000435324.Travel-Guide-Hotels)[Sleepy Hollow Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Sleepy-Hollow.d3000435324.Car-Hire-Guide)[Sleepy Hollow Holidays](https://expedia.co.uk/Sleepy-Hollow.d3000435324.Holidays-City-Breaks) ## 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.co.uk/Flights-Search?leg1=from:CMH,to:Sleepy Hollow, Illinois, United States of America,departure:16/03/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:23/03/2026TANYT&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_F9.svg) Frontier Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:CMH,to:Sleepy Hollow, Illinois, United States of America,departure:16/03/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:23/03/2026TANYT&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_AA.svg) American Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:CMH,to:Sleepy Hollow, Illinois, United States of America,departure:16/03/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:23/03/2026TANYT&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.co.uk/Flights-Search?leg1=from:CMH,to:Sleepy Hollow, Illinois, United States of America,departure:16/03/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:23/03/2026TANYT&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.co.uk/Flights-Search?leg1=from:CMH,to:Sleepy Hollow, Illinois, United States of America,departure:16/03/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:23/03/2026TANYT&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_NK.svg) Spirit Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:CMH,to:Sleepy Hollow, Illinois, United States of America,departure:16/03/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:23/03/2026TANYT&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_AS.svg) Alaska Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:CMH,to:Sleepy Hollow, Illinois, United States of America,departure:16/03/2026TANYT&leg2=from:Sleepy Hollow, Illinois, United States of America,to:CMH,departure:23/03/2026TANYT&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 25% 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.co.uk/login) ## Cheap round-trip flights to Sleepy Hollow Prices were available within the past 7 days and start at £231 for one-way flights and £349 for round trip, for the period specified. Be sure to select the 'Direct flights only' box above if you are looking for a non stop route. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![Finnair](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AY.gif) Tue, 25 Aug - Sat, 12 Sept DUB Dublin ORD Chicago £349 Return found 4 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:DUB,to:ORD,departure:25/08/2026TANYT&leg2=from:ORD,to:DUB,departure:12/09/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:348.26&airProductToken=AQo-CjwIwbIBEgQzODQ3GIMNIK4cKN7_lQMwvoOWAzhPQABYAWoERUNNUHIIT0tON1Q4QjR6CgjBggESBDM4NDcKcQo9CMGyARIEMzg5MBiuHCDriQEol9OXAzDj1pcDOE9AAFgBagRFQ01QcghPS043VDhCNHoKCMGCARIEMzg5MAowCMKCARIDODMyGOuJASCDDSj-15cDMNjYlwM4T0ABWAFqBEVDTVByCE9LTjdUOEI0EgoIAhABGAIqAkFZGAEiBAgBEAEoAigDKAQwAQ) ![Scandinavian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/SK.gif) Sat, 31 Oct - Wed, 4 Nov DUB Dublin ORD Chicago £354 Return found 6 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:DUB,to:ORD,departure:31/10/2026TANYT&leg2=from:ORD,to:DUB,departure:04/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:353.40&airProductToken=AQpmCjEI05YBEgM1MzgYgw0g4jsoovKbAzCf85sDOExAAFgBagZORVVHSFRyCExMRVU2R0hUCjEI05YBEgM5NDMY4jsgrhwo6vObAzCV-JsDOExAAVgBagZORVVHSFRyCExMRVU2R0hUCmcKMQjTlgESAzk0NBiuHCDiOyiwppwDMJWqnAM4TEAAWAFqBk5FVUdIVHIITExFVTZHSFQKMgjTlgESBDI1MzcY4jsggw0opa2cAzCsrpwDOExAAVgBagZORVVHSFRyCExMRVU2R0hUEgoIARABGAEqAlNLGAEiBAgBEAEoAigDKAQwDw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, 19 Nov - Mon, 23 Nov DUB Dublin ORD Chicago £384 Return found 3 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:DUB,to:ORD,departure:19/11/2026TANYT&leg2=from:ORD,to:DUB,departure:23/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:383.71&airProductToken=AQqAAQo-CMGCARIENjc2NRiDDSDriQEotsmdAzCLyp0DOFNAAFgBagVCQVNJQ3IIT0xON1Q4QjR6CgjCggESBDY3NjUKPgjBggESBDcwMDYY64kBIK4cKNHKnQMw7c6dAzhPQAFYAWoFQkFTSUNyCE9MTjdUOEI0egoIwoIBEgQ3MDA2CnIKMAjBggESAjg2GK4cIOuJASjy-50DMMP_nQM4QkAAWAFqBUJBU0lDcghPTE43VDhCNAo-CMGCARIENjc2NBjriQEggw0o2YCeAzCzgZ4DOFNAAVgBagVCQVNJQ3IIT0xON1Q4QjR6CgjCggESBDY3NjQSCggCEAEYAioCQUEYASIECAEQASgCKAMoBDAL) ![Icelandair](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/fi.gif) Tue, 3 Nov - Sun, 8 Nov DUB Dublin ORD Chicago £391 Return found 2 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:DUB,to:ORD,departure:03/11/2026TANYT&leg2=from:ORD,to:DUB,departure:08/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:390.10&airProductToken=AQpkCjAIxpIBEgM0MTcYgw0giiko0pScAzDylZwDOFhAAFgBagVMSUdIVHIIWEoyTUlFTFQKMAjGkgESAzg1MxiKKSCuHCj-lpwDMJianAM4WEABWAFqBUxJR0hUcghYSjJNSUVMVApkCjAIxpIBEgM4NTIYrhwgiiko_tKcAzD11ZwDOFhAAFgBagVMSUdIVHIIWEoyTUlFTFQKMAjGkgESAzQxNhiKKSCDDSis1pwDMMfXnAM4WEABWAFqBUxJR0hUcghYSjJNSUVMVBIKCAEQARgBKgJGSRgBIgQIARABKAIoAygEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, 9 May - Sat, 16 May DUB Dublin ORD Chicago £392 Return found 3 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:DUB,to:ORD,departure:09/05/2026TANYT&leg2=from:ORD,to:DUB,departure:16/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:391.90&airProductToken=AQpeCi0IwmwSAzM1NBiDDSDBkwEopMGMAzDHxIwDOExAAFgBagJETnIIUE8yMk1WTDEKLQjCbBIDODExGMGTASCuHCjnx4wDMJzJjAM4TEABWAFqAkROcghQTzIyTVZMMQpdCi0IwmwSBDEzMDYYrhwgqVEo65GNAzD1ko0DOExAAFgBagJETnIIT08yMk1WTDEKLAjCbBIDODQxGKlRIIMNKJyXjQMwwJqNAzhMQAFYAWoCRE5yCE9PMjJNVkwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ## Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD) ### July is typically the cheapest month to fly From £58 - £230 per traveller. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=FTG_SPRING_PROMO_) ## 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. ## Book with confidence # Expedia flights to Sleepy Hollow Searching for cheap flights to Sleepy Hollow? No travel company presents more choices than Expedia if you're looking to compare flights to Sleepy Hollow. With more airlines, cheaper flights, fewer stops, and more departure and arrival times travellers should ensure they search on Expedia before any holiday to Illinois. Expedia provides the cheapest flights to many destinations in Illinois and you may find even greater savings if you combine your flight with a hotel stay in Sleepy Hollow. Expedia is the largest online travel agency which means that Expedia have access to cheap flights. So make sure you check Expedia regularly for these bargain flights because the cheapest airline tickets sell out fast. Expedia is not only free for everyone to use but it quick and easy to use. Find the lowest flight prices guaranteed and book directly through Expedia. Browse through hundreds of cheap flight offers to find the one that suits your budget by simply inputting your travel dates. Expedia will then find the cheapest flights to Sleepy Hollow for that period and let you choose your preferred time and airline. If you need additional assistance, Expedia Customer Service representatives are available from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends. Our capable staff will be able to help you with any questions regarding your Sleepy Hollow flight, or other booking questions that may arise. When you book flights with Expedia you can rest assured that you have booked the best flight at the lowest price. ## Travel information | Destination airport | O'Hare Intl. | | ----------------------------- | ------------ | | Destination airport IATA code | ORD | | Destination city name | Chicago | | Return price | £348 | ## Trending flights to Sleepy Hollow Prices were available within the past 7 days and start at £231 for one-way flights and £349 for round trip, for the period specified. Be sure to select the 'Direct flights only' box above if you are looking for a non stop route. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![TAP Portugal](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TP.gif) Tue, 10 Mar - Sun, 22 Mar LGW London ORD Chicago £400 Return just found [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:LGW,to:ORD,departure:10/03/2026TANYT&leg2=from:ORD,to:LGW,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:399.63&airProductToken=AQp4CkEI1KABEgQxMzM3GMuxASCLkgEow6GHAzDtoocDOE9AAFgBagdESVNDSU5UcghPRjBEU0lIN3oKCM6SARIEMTMzNwozCNSgARIDMjQzGIuSASCuHCitqocDMOyuhwM4T0AAWAFqB0RJU0NJTlRyCE9GMERTSUg3CmwKMwjUoAESAzI0NBiuHCCLkgEoka2IAzDssIgDOE9AAFgBagdESVNDSU5UcghPRjBEU0lINwo1CNSgARIEMTMzNhiLkgEgy7EBKIyyiAMwsbOIAzhPQABYAWoHRElTQ0lOVHIIT0YwRFNJSDcSCggBEAEYASoCVFAYASIECAEQASgCKAMoBDAN) \*Available to Expedia members.