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Cheap Flights to Sleepy Hollow , IL from CA $191

View CA $191 flight on Fri, Sep 11, 2026Opens in a new window

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How much is the cheapest flight to Sleepy Hollow?

Prices were available within the past 7 days and start at CA $191 for one-way flights and CA $320 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
United
American Airlines
Delta
WestJet

Alternative airports near Sleepy Hollow

Prices were available within the past 7 days. Prices and availability are subject to change.

Frequently asked questions

What is the name of Sleepy Hollow's airport?
Many travellers like to fly into O'Hare Intl. Airport (ORD) when visiting the bustling city of Sleepy Hollow.
How far is O'Hare Intl. Airport (ORD) from central Sleepy Hollow?
O'Hare Intl. Airport (ORD) is 32 kilometres from downtown Sleepy Hollow, so be prepared for a bit of a journey into the city centre.
What airport is best to fly into Sleepy Hollow?
Before booking flights to Sleepy Hollow, it's a smart idea to think about which airport is most convenient. O'Hare Airport is 32 kilometres from the downtown area. If you land at Chicago Airport, you'll be 56 kilometres away from the heart of the city.
How many airlines fly to Sleepy Hollow?
Sleepy Hollow is serviced by 51 airlines from 237 airports around the world.
Which airlines fly to Sleepy Hollow?
United Airlines, American Airlines and Delta fly the most frequently to Sleepy Hollow. The majority of flights begin in New York, with United Airlines having the most services on this route.
How many nonstop flights are there to Sleepy Hollow?
Arranging an exciting Sleepy Hollow vacation is simple when there are 7,564 direct flights each week to choose from.
Where are the most popular flights to Sleepy Hollow departing from?
Flights to Sleepy Hollow departing from New York, Washington and Dallas airports are in high demand.
How long is the flight to Sleepy Hollow Airport?
Where you depart from determines how long you'll be strapped into your seat. From New York to Sleepy Hollow, the average flight time is 2 hours and 44 minutes. From Washington it takes about 2 hours and 15 minutes, and from Dallas it's 2 hours and 18 minutes.
How to book the cheapest flight to Sleepy Hollow?
We've all come across those fortunate jet-setters who somehow score incredibly cheap plane tickets wherever they go. Want to know how to do it for your Sleepy Hollow vacation? Don't leave it until the last moment to lock in your flight. Don't stop there, however. Do some research and check if there are multiple airports at your destination. Ticket prices often differ depending on which airport you jet into. Be sure to compare fares across airlines too. And finally, don't forget that the early bird catches the worm. Know what a typical airfare costs and be ready to snap up a ticket as soon as you see a great bargain. The sweetest deals don't last long.
Do you have any tips for my flight to Sleepy Hollow?
Depending on where you're coming from, your trip to Sleepy Hollow could be as easy as pie or it could drag on forever. We've pulled together some handy tips that will help you start your next big adventure on a positive note. What to pack in your hand luggage:
  • 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?
The secret is to be organized before you arrive at security. That way, you'll be hopping onto that plane to Sleepy Hollow in a flash. Follow these helpful tips and get your trip off to a flying start:
  • 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.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!

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $320

Trending flights to Sleepy Hollow

Prices were available within the past 7 days and start at CA $191 for one-way flights and CA $320 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
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