Cheap Flights to Sleepy Hollow , IL from CA $152

View CA $152 flight on Thu, Oct. 9, 2025Opens in a new window

Popular airlines to Sleepy Hollow

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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 $152 for one-way flights and CA $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Sat, Sep. 13 - Sun, Sep. 14
YTZ
Toronto
ORD
Chicago
CA $243 Roundtrip, found 7 hours ago
CA $243
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Sat, Sep. 13 from Toronto to Chicago, returning Sun, Sep. 14, priced at CA $243 found 7 hours ago
United
Fri, Nov. 28 - Sun, Nov. 30
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 4 hours ago
CA $244
Roundtrip
found 4 hours ago
Select United flight, departing Fri, Nov. 28 from Toronto to Chicago, returning Sun, Nov. 30, priced at CA $244 found 4 hours ago
American Airlines
Fri, Sep. 12 - Sun, Sep. 28
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 14 hours ago
CA $256
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Fri, Sep. 12 from Calgary to Chicago, returning Sun, Sep. 28, priced at CA $256 found 14 hours ago
WestJet
Fri, Nov. 14 - Mon, Nov. 17
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 9 hours ago
CA $256
Roundtrip
found 9 hours ago
Select WestJet flight, departing Fri, Nov. 14 from Calgary to Chicago, returning Mon, Nov. 17, priced at CA $256 found 9 hours ago
Alaska Airlines
Tue, Sep. 23 - Tue, Oct. 7
YEG
Edmonton
ORD
Chicago
CA $358 Roundtrip, found 4 days ago
CA $358
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Tue, Sep. 23 from Edmonton to Chicago, returning Tue, Oct. 7, priced at CA $358 found 4 days ago

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

June is typically the cheapest month to fly

From CA $105 - CA $339 per traveller.

Graph displaying average flight prices per month

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?
Sleepy Hollow is served by multiple airports, but most travellers use O'Hare Intl. Airport (ORD).
How far is ORD from central Sleepy Hollow?
The trip between O'Hare Intl. Airport (ORD) and downtown Sleepy Hollow is reasonably long. You'll need to travel 32 kilometres before you can check in to your city hotel.
What airport is best to fly into Sleepy Hollow?
There are two major airports that service Sleepy Hollow. O'Hare Airport is around 32 kilometres from the downtown area, while Midway Airport is around 56 kilometres away. After you find a great price and figure out where you're staying, you'll have more of an idea of which to head to.
How many airlines fly to Sleepy Hollow?
Sleepy Hollow is serviced by 51 air carriers from at least 237 airports across the globe.
Which airlines fly to Sleepy Hollow?
Sleepy Hollow receives the majority of its flights from United Airlines, American Airlines and Delta with United Airlines being the number one choice of airline. New York is the most popular city for travellers to jet off from.
How many nonstop flights are there to Sleepy Hollow?
With 7,564 direct flights each week, you'll be touching down in Sleepy Hollow before you have time to say, "Are we there yet?"
Where are the most popular flights to Sleepy Hollow departing from?
Travellers often set off from New York, Washington and Dallas airports when flying to Sleepy Hollow.
How long is the flight to Sleepy Hollow Airport?
If you're heading to Sleepy Hollow from New York, you're looking at a flight time of 2 hours and 44 minutes. Those leaving from Washington can expect to be on the plane for 2 hours and 15 minutes. From Dallas it's 2 hours and 18 minutes away.
How to book the cheapest flight to Sleepy Hollow?
We've all come across those fortunate travellers who somehow score incredibly cheap airfares every time they fly. Want to know how to do it for your Sleepy Hollow vacation? Don't wait until the very last minute to lock in your flight. Don't stop there, though. Do some research and check if there is more than one airport at your destination. Fares often differ depending on which airport you go for. Remember to compare fares across airlines too. Finally, be ready to lock in your seat quickly if you find a real bargain. It might not be available for too long! With a bit of knowledge and a little luck, the perfect airfare can be yours.
Do you have any tips for my flight to Sleepy Hollow?
We've pulled together all the info you need to make your journey as enjoyable as possible. Follow our top tips and you'll be breezing through airport security and seeing the best of Sleepy Hollow in no time at all. What to pack in your hand luggage:

  • Travelling on a plane can be a pleasure if you carry the right things. First things first, you'll need basic toiletry items, such as a toothbrush and hairbrush, a fresh change of clothes and a few magazines. Secondly, find room in your hand luggage for your phone and charger, any vital medications and perhaps a blow-up neck pillow too. Lastly, and most importantly, remember to take your passport, travel papers and your bank cards.

Do not pack the following items in your hand luggage:

  • While the list of prohibited items differs between airlines, the general rule of thumb is avoid carrying anything sharp, flammable or explosive. This includes things like screwdrivers, drills, fireworks and fuel. Sports equipment like hockey sticks, and objects that could injure passengers, such as swords and batons, aren't allowed in the cabin either.

What to wear on a flight:

  • The aisles of an airplane are no place for a fashion parade. Layer your clothing and opt for shoes that are flat and easy to take on and off.
  • Caused by sustained periods of immobility, deep vein thrombosis (DVT) is a blood clotting condition that can affect passengers on long-haul flights. Reduce the risks by drinking water, keeping your legs and feet moving and wearing compression socks to help improve your circulation.

How to get through airport security fast when flying to Sleepy Hollow?
A little pre-planning before you arrive at the airport can make your trip to Sleepy Hollow a piece of cake. Here are some handy tips and tricks for a stress-free journey through security:

  • Your ID and travel documents will need to be shown to airport security personnel. Keep them someplace accessible so you don't hold up the queue.
  • The X-ray machine comes next. Remove anything metal on you that is likely to set off the scanner's alarm. This includes things like headphones or earphones, as well as bulky coats or jackets. They'll need to be placed on the conveyor belt for screening.
  • For just a few minutes, you'll have to unplug from technology. Your phone, tablet and any other electronics also need to be sent through the scanner.
  • Travelling with a new cologne? No problem. As long as the volume is no larger than 3.4 ounces (100 millilitres) and it's stored in a zip-lock bag, you can keep it with you in your carry-on bag.
  • Choosing your footwear wisely can save you several precious minutes. Boots and bulky shoes are often required to be removed and X-rayed separately. Slip-on shoes usually aren't.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp or pointed objects, put them in your checked suitcase. They won't be allowed in the cabin.

Flights to Sleepy Hollow information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $243

Trending flights to Sleepy Hollow

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Sat, Sep. 13 - Sun, Sep. 14
YTZ
Toronto
ORD
Chicago
CA $243 Roundtrip, found 2 hours ago
CA $243
Roundtrip
found 2 hours ago
Select Air Canada flight, departing Sat, Sep. 13 from Toronto to Chicago, returning Sun, Sep. 14, priced at CA $243 found 2 hours ago
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