Cheap Flights to Sleepy Hollow

View AU$952 flight on Tue, 10 Feb 2026Opens in a new window

Popular airlines to Sleepy Hollow

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Cheap Tickets to Sleepy Hollow

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Wed, 25 Feb - Wed, 4 Mar
SYD
Sydney
ORD
Chicago
AU$1,192 Return, found 2 hours ago
AU$1,192
Return
found 2 hours ago
Select Air Canada flight, departing Wed, 25 Feb from Sydney to Chicago, returning Wed, 4 Mar, priced at AU$1,192 found 2 hours ago
American Airlines
Wed, 26 Aug - Wed, 2 Sept
SYD
Sydney
ORD
Chicago
AU$1,364 Return, found 4 days ago
AU$1,364
Return
found 4 days ago
Select American Airlines flight, departing Wed, 26 Aug from Sydney to Chicago, returning Wed, 2 Sept, priced at AU$1,364 found 4 days ago
Qantas Airways
Thu, 11 Dec - Tue, 23 Dec
BNE
Brisbane
ORD
Chicago
AU$1,405 Return, found 1 day ago
AU$1,405
Return
found 1 day ago
Select Qantas Airways flight, departing Thu, 11 Dec from Brisbane to Chicago, returning Tue, 23 Dec, priced at AU$1,405 found 1 day ago
Air New Zealand
Tue, 19 May - Tue, 26 May
MEL
Melbourne
ORD
Chicago
AU$1,499 Return, found 2 days ago
AU$1,499
Return
found 2 days ago
Select Air New Zealand flight, departing Tue, 19 May from Melbourne to Chicago, returning Tue, 26 May, priced at AU$1,499 found 2 days ago
Jetstar
Thu, 14 May - Mon, 25 May
CNS
Cairns
ORD
Chicago
AU$1,504 Return, found 4 days ago
AU$1,504
Return
found 4 days ago
Select Jetstar flight, departing Thu, 14 May from Cairns to Chicago, returning Mon, 25 May, priced at AU$1,504 found 4 days ago

Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD)

July is typically the cheapest month to fly

From AU$119 - AU$447 per traveller.

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Sleepy Hollow Flights

Have the time of your life in Sleepy Hollow

Flying to Sleepy Hollow is now easier than ever when you use Expedia to book your trip. We’ve got an extensive catalogue of Sleepy Hollow flight deals, giving you the greatest number of options to choose from. Whether you prefer to fly on weekdays or weekends, in the morning or at night, a quick search on Expedia.com.au will help you find cheap tickets to Sleepy Hollow in seconds. We even make it simple for you to stick with a certain airline if you’re trying to rack up frequent flyer points.

Tips for flying and packing light

If it’s been a while since you’ve travelled, you might be due for a refresher when it comes to flying. That’s where our helpful blog, Out There Starts Here, comes in. Wondering whether to pack for fine dining or more casual eats? Or whether you really need to bring a jacket? Written by seasoned travel experts, the articles on our blog provide you with the latest details about certain destinations, so you know just what to expect. Check out some of our recent articles for the smartest ways to see the sights.

Fly for less when you bundle airfare and accommodation

Our already low airfares are even more affordable when you bundle your flights with a stay at one of the hotels in Sleepy Hollow. By booking all of your travel plans with us, you’ll save time and money, and enjoy the convenience of having all of your arrangements in one place.

Get the power of planning in the palm of your hand

Booking your trip to Sleepy Hollow, Illinois has never been easier than when you use our mobile app to plan your dream getaway. The Expedia App is available on both Android and iOS, allowing you to reserve flights and hotels at any time of day, no matter what kind of phone you use. You’ll also get exclusive offers, receive flight updates, and can earn extra points. Wherever you are, the Expedia App helps you get where you want to be.

Join the Expedia Rewards Program

If you enjoy the finer things in life, sign up for our rewards program to receive exclusive benefits when you book with us. Expedia Rewards opens the door to member-only deals, +VIP Access hotel benefits, and earning Expedia Rewards points, that you can redeem your way. You’ll also get access to Unreal Deals that could save you the price of a plane ticket to Sleepy Hollow when bundled with your accommodation.

What are you waiting for?

Expedia.com.au helps you find cheap flights to Sleepy Hollow AU$1,192. So why wait another second to begin planning your trip? Start your search right now, and you could be boarding the next Sleepy Hollow-bound flight. Bon voyage!

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 holiday 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 holiday? 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 organised 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.

Flights to Sleepy Hollow information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
AU$1,191

Trending flights to Sleepy Hollow

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Wed, 25 Feb - Wed, 4 Mar
SYD
Sydney
ORD
Chicago
AU$1,192 Return, found 2 hours ago
AU$1,192
Return
found 2 hours ago
Select Air Canada flight, departing Wed, 25 Feb from Sydney to Chicago, returning Wed, 4 Mar, priced at AU$1,192 found 2 hours ago

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