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Cheap Flights to Sleepy Hollow

Fall in love at first flight with your vacation to Sleepy Hollow by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Sleepy Hollow on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Sleepy Hollow, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Sleepy Hollow

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Sleepy Hollow with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Sleepy Hollow?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Sleepy Hollow are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Sleepy Hollow?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Sleepy Hollow.

What airport is best to fly into Sleepy Hollow?

When you’re planning your trip to Sleepy Hollow, convenience is the name of the game. Luckily, Sleepy Hollow Dupage Airport is nearby so you can deplane and get going on checking off everything on your Sleepy Hollow must-do list.

How much are flights to Sleepy Hollow?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Sleepy Hollow on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Sleepy Hollow?

The trick to saving a stack of cash on your flight to Sleepy Hollow? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as  right now, why wait?

Sleepy Hollow Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$172

Last Minute Hotel Deals in Sleepy Hollow

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

4 out of 5
1200 N Mittel Blvd, Wood Dale, IL
Stay at this 4-star business-friendly hotel in Wood Dale. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8/10 Very Good! (1,018 reviews)
"the staff was nice and helpful during check in. i can not say the same about the waitress in the restaurant, where i had to bring my own water from the counter. the was NO any kind of soap in the room (that i stayed). overall room was clean and i had a chance to sleep."

Reviewed on Sep 21, 2025

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DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
1725 E Algonquin Road, Schaumburg, IL
Stay at this 3-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and a free area shuttle. Our guests praise the helpful staff and the ...
6.6/10 (1,032 reviews)
"Friendly staff. Always someone cleaning up inside and out. Room was clean and it was really quiet. I enjoyed walking around the pond in the back. I saw ducks, geese, turtles, bull frogs, really pretty blue dragon flies and even a snake. After a long drive it was nice to just connect with nature and ..."

Reviewed on Sep 23, 2025

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Wyndham Garden Schaumburg Chicago Northwest
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd, Itasca, IL
Stay at this 4-star spa resort in Itasca. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,035 reviews)
"Very friend"

Reviewed on Sep 23, 2025

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Eaglewood Resort and Spa
Courtyard by Marriott Chicago Wood Dale

Courtyard by Marriott Chicago Wood Dale

3 out of 5
900 N Wood Dale Rd, Wood Dale, IL
Book a stay at this business-friendly hotel in Wood Dale. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,014 reviews)
"The room was clean, free parking is always a plus"

Reviewed on Sep 25, 2025

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Courtyard by Marriott Chicago Wood Dale
Comfort Inn Chicago Schaumburg - O'Hare Airport

Comfort Inn Chicago Schaumburg - O'Hare Airport

2.5 out of 5
1300 E Higgins Rd, Schaumburg, IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
7/10 Good! (935 reviews)
"the stay was great"

Reviewed on Sep 17, 2025

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Comfort Inn Chicago Schaumburg - O'Hare Airport
Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
2112 S Arlington Heights Rd, Arlington Heights, IL
Stay at this 3-star business-friendly hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
8.2/10 Very Good! (646 reviews)
Barking dog
"Front desk was welcoming, room was clean minus a few shaving hairs in the bathroom sink. Bed was clean and comfortable, but unfortunately, there was a dog on my floor that wouldn’t quit barking when I went down to let management know. She said dogs were not allowed but service dogs are and that they ..."

Reviewed on Sep 24, 2025

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Comfort Inn & Suites Arlington Heights - Schaumburg
Motel 6 Elk Grove Village, IL

Motel 6 Elk Grove Village, IL

2 out of 5
1000 W Devon Ave, Elk Grove Village, IL
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,013 reviews)
"Nice place."

Reviewed on Sep 20, 2025

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Motel 6 Elk Grove Village, IL
The Westin Chicago Northwest

The Westin Chicago Northwest

4 out of 5
400 Park Blvd, Itasca, IL
Stay at this 4-star business-friendly hotel in Itasca. Enjoy breakfast (surcharge), a free area shuttle, and a 24-hour fitness center. Our guests praise the ...
8.6/10 Excellent! (1,018 reviews)
"Very nice"

Reviewed on Sep 22, 2025

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The Westin Chicago Northwest
See all 483 properties in Sleepy Hollow
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.