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 $108
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 October, 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 13 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 $108, 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 $108 right now, why wait?
Destination airport | O'Hare Intl. |
|---|---|
Destination airport IATA code | ORD |
Roundtrip price | $108 |
Last Minute Hotel Deals in Sleepy Hollow
DoubleTree by Hilton Chicago - Arlington Heights
Eaglewood Resort and Spa
"The room in the North tower had an excellent view of the Golf course . A lot of unexpected additional fees including parking and resort fee that should be better presented and declared when booking through orbits. The room we stayed in was not as clean as expected . There was a splatter of a beverage ..."
Reviewed on Jul 30, 2026
DoubleTree by Hilton Libertyville - Mundelein
Hyatt Place Itasca
"We only stayed for overnight before flying. Complementary breakfast is not bad. Fast check in and out process."
Reviewed on Jul 30, 2026
The Westin Chicago Northwest
"Quiet and comfortable. My room was very spacious."
Reviewed on Jul 29, 2026
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
"Great friendly staff that honors membership. Hotel was clean and quiet."
Reviewed on Jul 27, 2026
Motel 6 Rolling Meadows, IL - Chicago Northwest
Hyatt Regency Schaumburg Chicago
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