Search Cheap Flights toSleepy Hollow
Search 400 airlines and 321,000 hotels worldwide.
Stop Planning & Start Exploring
FREE 24 hour cancellation on most flights
Sleepy Hollow Flights as Low as $107
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
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 September, 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 $107, 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 $107 right now, why wait?
Destination airport | O'Hare Intl. |
|---|---|
Destination airport IATA code | ORD |
Roundtrip price | $107 |
Last Minute Hotel Deals in Sleepy Hollow
Sheraton Suites Chicago Elk Grove
"there is nothing near hotel, so I expected the hotel has a good food options and convenient store inside, but very little options only."
Reviewed on Jul 8, 2026
Hyatt Place Itasca
"Hard to believe some of the travelers who left negative responses were at the same hotel as us. Spacious, clean room with couches to watch TV, high quality Samsung TV, comfortable bed, good shower (albeit small toilet/shower room), breakfast a cut above other hotels of this class, friendly, helpful ..."
Reviewed on Jul 7, 2026
The Westin Chicago Northwest
"Clean and big rooms very friendly staff"
Reviewed on Jul 8, 2026
Eaglewood Resort and Spa
"I love this hotel. Very welcoming! And the room was so comfortable and a experience"
Reviewed on Jul 8, 2026
Quality Inn Schaumburg - Chicago near the Mall
"Very clean hotel room was very clean. The hotel was close to a lot shopping and restaurants. I would definitely stay again"
Reviewed on Jul 8, 2026
Comfort Inn Chicago Schaumburg - O'Hare Airport
"Checking in was easy. The room smelled like B.O. Luckily, I had room spray. The carpets felt dirty and damp. We wore our socks and sandals around the room. When checking in, they said that the pool was open from 9 am to 9 pm. At 7 pm, we were unable to get in there, and no workers were to be found. ..."
Reviewed on Jul 7, 2026
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
"Place was perfect"
Reviewed on Jul 8, 2026
DoubleTree by Hilton Chicago - Arlington Heights
"Nice staff and clean."
Reviewed on Jul 9, 2026
Nearby Cities
Popular Flight Routes
- Atlanta to New York
- Detroit to Las Vegas
- Dallas to Atlanta
- Dallas to Yosemite National Park
- Toronto to Edmonton
- Chicago to Tulum
- Houston to Lake Tahoe
- Chicago to Las Vegas
- Dallas to Miami
- Dallas to Lake Tahoe
- New York to Miami
- New York to Las Vegas
- Miami to Atlanta
- Minneapolis St Paul to Fort Walton Beach Destin
- Dallas to Branson
- Cleveland to Vero Beach
- Managua to Miami
- Atlanta to Boston
- Austin to Tulum
- Calgary to Vancouver