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Sleepy Hollow

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Sleepy Hollow Flights as Low as $88

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

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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 June, 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 15 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 $88, 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 $88 right now, why wait?

Sleepy Hollow Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$88

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 (1,000 reviews)
Room 216 was in need of some maintenance. AC unit wasn’t working properly, some kid used a blue pen to draw on the arms of the chair, and the water pressure wasn’t very good for the toilet or the shower. Otherwise staff was friendly and facility was decent

Reviewed on Apr 26, 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! (1,048 reviews)
This resort was just ok imo. Pretty old and dated. Not the worst place I’ve been but needs work. Carpet old , old scratched up furnishings in the rooms. ATP no hotel should have a tub only glassed in showers. Didn’t use the amenities like the bowling alley as it was closed when we arrived. This place ...

Reviewed on Apr 26, 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! (1,001 reviews)
Nothing unique about the property. Room was clean beds adequate. What i didnt like was that I had to pay extra for breakfast. I was told when I checked in that buffet breakfast was available I wasn't told I had to pay for it

Reviewed on May 1, 2026

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk 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
Book a stay at this 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! (1,133 reviews)
I was able to stay very comfortably. Thank you

Reviewed on Apr 30, 2026

Comfort Inn & Suites Arlington Heights - Schaumburg
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! (1,008 reviews)
Really run down, stuffy rooms

Reviewed on Apr 28, 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! (1,071 reviews)
Very good

Reviewed on May 1, 2026

Hyatt Place Itasca
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)
We had to move 3 times because the ACs were not working peoperly. The van only runs on the hour and only if you call we had to wait an hour on pick up because the driver decided to get gas first. The Van is old and filthy and the pick up driver didn't help with the luggage, they only begin to run ...

Reviewed on Apr 26, 2026

Courtyard by Marriott Chicago Wood Dale
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! (1,003 reviews)
air conditioning was weak

Reviewed on Apr 30, 2026

The Westin Chicago Northwest
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.