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Sleepy Hollow

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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
$188

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! (1,068 reviews)
Cooperative staff at front desk

Reviewed on Oct 27, 2025

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 ...
6.4/10 (1,018 reviews)
Great

Reviewed on Oct 28, 2025

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! (1,026 reviews)
100/10 recommend!
I stayed friday-sunday and I had to switch rooms on Saturday due to my tub filling up/backing up as I took a shower but they waived the entire resort fee so I'm still sticking to my word that everything was perfect, rooms were very clean and peaceful, it felt like home away from home and I'll definitely ...

Reviewed on Oct 27, 2025

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! (1,003 reviews)
Staff was great, room was good, would stay here again. Loved that we had parking available at all times and did not have to pay for it. Though secluded, area had many shopping options nearby. Would stay here again!

Reviewed on Oct 25, 2025

Courtyard by Marriott Chicago Wood Dale
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 ...
8/10 Very Good! (1,027 reviews)
Good for a short stay. No fridge and microwave in the room.

Reviewed on Oct 29, 2025

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! (1,003 reviews)
Staff was very accommodating and we were satisfied with our room. Very comfortable beds and the hot tub and pool area was a great way to unwind and relax after a day of walking through the city.

Reviewed on Oct 26, 2025

The Westin Chicago Northwest
Comfort Inn & Suites Arlington Heights - Buffalo Grove

Comfort Inn & Suites Arlington Heights - Buffalo Grove

2.5 out of 5
3700 N Wilke Rd, Arlington Heights, IL
Stay at this hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (378 reviews)
We checked in late at night, I had called earlier in the day to let them know and had no issues. The staff was always friendly and very nice. It was very easy to find parking and to get around the hotel. The best part, the pool was actually warm!

Reviewed on Oct 23, 2025

Comfort Inn & Suites Arlington Heights - Buffalo Grove
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! (730 reviews)
The room was very clean. Loved my stay.

Reviewed on Oct 25, 2025

Comfort Inn & Suites Arlington Heights - Schaumburg
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.