Cheap Flights to Sleepy Hollow: Sleepy Hollow Flight Deals

View €58 flight on Tue, 10 Feb 2026Opens in a new window

Popular airlines to Sleepy Hollow

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Cheap round-trip flights to Sleepy Hollow

Prices were available within the past 7 days and start at €58 for one-way flights and €109 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, 21 Apr - Mon, 4 May
JFK
New York
ORD
Chicago
€109 Return, found 5 days ago
€109
Return
found 5 days ago
Select American Airlines flight, departing Tue, 21 Apr from New York to Chicago, returning Mon, 4 May, priced at €109 found 5 days ago
JetBlue Airways
Fri, 6 Mar - Mon, 9 Mar
JFK
New York
ORD
Chicago
€118 Return, found 20 hours ago
€118
Return
found 20 hours ago
Select JetBlue Airways flight, departing Fri, 6 Mar from New York to Chicago, returning Mon, 9 Mar, priced at €118 found 20 hours ago
Delta
Fri, 6 Mar - Mon, 9 Mar
JFK
New York
ORD
Chicago
€118 Return, found 20 hours ago
€118
Return
found 20 hours ago
Select Delta flight, departing Fri, 6 Mar from New York to Chicago, returning Mon, 9 Mar, priced at €118 found 20 hours ago
United
Thu, 29 Jan - Mon, 2 Feb
EWR
New York
ORD
Chicago
€171 Return, found 3 days ago
€171
Return
found 3 days ago
Select United flight, departing Thu, 29 Jan from New York to Chicago, returning Mon, 2 Feb, priced at €171 found 3 days ago
Scandinavian Airlines
Sat, 14 Feb - Mon, 16 Feb
DUB
Dublin
ORD
Chicago
€381 Return, found 3 hours ago
€381
Return
found 3 hours ago
Select Scandinavian Airlines flight, departing Sat, 14 Feb from Dublin to Chicago, returning Mon, 16 Feb, priced at €381 found 3 hours ago

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

June is typically the cheapest month to fly

From €66 - €273 per traveller.

Alternative airports near Sleepy Hollow

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 32 minutes. Flights from €326
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre32 min
Flights from €326

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.

Book with confidence

Expedia.ie is an online travel company that specialises in securing the best prices for flights to Sleepy Hollow. With Expedia you get highly specialised services, combining the best of technology, in-depth knowledge and the best connections in order to offer great deals to Sleepy Hollow. Expedia shares your passion for travel and has built the best online travel service that promotes and encourages travel. Whether you are looking for cheap flights to Sleepy Hollow, or are just on the lookout for the best flights to Sleepy Hollow, you are sure to find the best deals with Expedia.ie.

"One of the many benefits of booking your flights through Expedia is that we are one of the world’s largest online travel agency, which means we use our collective experience and work tirelessly to bring you the best prices. With Expedia you get a user-friendly internet experience and a dedicated customer support service that ensures that everything goes smoothly. The goal of Expedia is to offer premium services at the lowest price, all at one single place. If you wish to save even more try combing a hotel in Sleepy Hollow to your flight and create a personalised low cost city break or holiday to your favourite destination. Book early and you could save even more!

If you have an Expedia.ie itinerary number and have a question or concern about your travel plans you can call us on (01) 524 5005 from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends and an Expedia agent will help you.

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
€110

Trending flights to Sleepy Hollow

Prices were available within the past 7 days and start at €58 for one-way flights and €109 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Scandinavian Airlines
Sat, 14 Feb - Mon, 16 Feb
DUB
Dublin
ORD
Chicago
€381 Return, found 3 hours ago
€381
Return
found 3 hours ago
Select Scandinavian Airlines flight, departing Sat, 14 Feb from Dublin to Chicago, returning Mon, 16 Feb, priced at €381 found 3 hours ago
*Available to Expedia members.