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Sleepy Hollow

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Sleepy Hollow Flights as Low as $115

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
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United
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American Airlines
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Frontier Airlines
United
Alaska Airlines
Delta

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 July, 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 16 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 $115, 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 $115 right now, why wait?

Sleepy Hollow Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$115

Last Minute Hotel Deals in Sleepy Hollow

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

2 out of 5
22 West Algonquin Road Arlington Heights IL
Stay at this hotel in Arlington Heights. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Woodfield Mall and Allstate Arena are located ...
5.4/10 (1,002 reviews)
"For the price this place costs, the lack of amenities and an overall low quality was more than expected, but I would like to think that a room without cockroaches and mold should be the *bare minimum* of what to expect. I've stayed at some bad cheap hotels before, but this is the first time I strongly ..."

Reviewed on May 20, 2026

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd Itasca IL
Book a stay at this 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 ...
8.8/10 Excellent! (1,086 reviews)
"The staff was very helpful and nice. When I arrived at Eaglewood Resort and spa, I needed some cough drops, which the store there didn't have, so one of the managers had some personal ones and gave me some. I also had a medical emergency, the staff was very helpful before, during, and after the emergency. ..."

Reviewed on May 23, 2026

Eaglewood Resort and Spa
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
Book a stay at this 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! (1,003 reviews)
"If the property is going to be under construction . There should be a note upon booking ."

Reviewed on May 22, 2026

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
The Westin Chicago Northwest

The Westin Chicago Northwest

4 out of 5
400 Park Blvd Itasca IL
Book a stay at this business-friendly hotel in Itasca. Enjoy breakfast (surcharge), a free area shuttle, and a 24-hour fitness center. Our guests praise the ...
8.8/10 Excellent! (1,005 reviews)
"Ok"

Reviewed on May 22, 2026

The Westin Chicago Northwest
Quality Inn Schaumburg - Chicago near the Mall

Quality Inn Schaumburg - Chicago near the Mall

2.5 out of 5
600 North Martingale 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 helpful staff and the clean ...
8.6/10 Excellent! (1,000 reviews)
"I usually have a great time staying here"

Reviewed on May 21, 2026

Quality Inn Schaumburg - Chicago near the Mall
Hyatt Place Itasca

Hyatt Place Itasca

3 out of 5
1150 North Arlington Heights Road Itasca IL
Book a stay at this business-friendly hotel in Itasca. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,106 reviews)
"Great stay in the burbs close to the airport"

Reviewed on May 20, 2026

Hyatt Place Itasca
Holiday Inn Express Chicago NW - Arlington Heights by IHG

Holiday Inn Express Chicago NW - Arlington Heights by IHG

2.5 out of 5
2111 S Arlington Heights Rd Arlington Heights IL
Stay at this hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,002 reviews)
"Staff did not change to new towels after 1st stay."

Reviewed on May 22, 2026

Holiday Inn Express Chicago NW - Arlington Heights by IHG
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. ...
7.2/10 Good! (1,000 reviews)
"Muy buen lugar"

Reviewed on May 21, 2026

Comfort Inn Chicago Schaumburg - O'Hare Airport
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.