Search Cheap Flights to
Sleepy 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 $72

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

Spirit Airlines
Sat, Aug 2 - Tue, Aug 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 10 hours ago
$72
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Sat, Aug 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 5, priced at $72 found 10 hours ago
Spirit Airlines
Sat, Aug 16 - Sat, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $82 found 1 day ago
Spirit Airlines
Sat, Sep 27 - Tue, Sep 30
LGA
LaGuardia
ORD
O'Hare Intl.
$90 Roundtrip, found 23 hours ago
$90
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Sat, Sep 27 from LaGuardia to O'Hare Intl., returning Tue, Sep 30, priced at $90 found 23 hours ago
Spirit Airlines
Sun, Aug 31 - Thu, Sep 4
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$90 Roundtrip, found 3 days ago
$90
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sun, Aug 31 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Sep 4, priced at $90 found 3 days ago
Frontier Airlines
Wed, Jul 30 - Sat, Aug 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jul 30 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 2, priced at $102 found 1 day ago
Frontier Airlines
Mon, Aug 25 - Tue, Aug 26
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$115 Roundtrip, found 6 days ago
$115
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Aug 25 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $115 found 6 days ago
United
Thu, Aug 21 - Thu, Aug 28
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$119 Roundtrip, found 6 days ago
$119
Roundtrip
found 6 days ago
Select United flight, departing Thu, Aug 21 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Aug 28, priced at $119 found 6 days ago
American Airlines
Thu, Aug 21 - Thu, Aug 28
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$119 Roundtrip, found 6 days ago
$119
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Aug 21 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Aug 28, priced at $119 found 6 days ago
United
Thu, Aug 28 - Sat, Aug 30
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$125 Roundtrip, found 6 days ago
$125
Roundtrip
found 6 days ago
Select United flight, departing Thu, Aug 28 from Ronald Reagan Washington National to O'Hare Intl., returning Sat, Aug 30, priced at $125 found 6 days ago
Frontier Airlines
Fri, Aug 29 - Sat, Aug 30
DEN
Denver Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Aug 29 from Denver Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $127 found 4 days ago
Delta
Sat, Aug 16 - Sat, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 4 hours ago
$132
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $132 found 4 hours ago
Bargain Flight
Thu, Sep 4 - Thu, Sep 4
MEM
Memphis Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 3 days ago
$153
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Thu, Sep 4 from Memphis Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $153 found 3 days ago
Contour Airlines
Mon, Aug 25 - Thu, Aug 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 9 hours ago
$189
Roundtrip
found 9 hours ago
Select Contour Airlines flight, departing Mon, Aug 25 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $189 found 9 hours ago
Delta
Tue, Aug 19 - Tue, Aug 19
DAL
Love Field
ORD
O'Hare Intl.
$199 Roundtrip, found 5 days ago
$199
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Aug 19 from Love Field to O'Hare Intl., returning Tue, Aug 19, priced at $199 found 5 days ago
JetBlue Airways
Tue, Sep 23 - Fri, Sep 26
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$203 Roundtrip, found 12 hours ago
$203
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Tue, Sep 23 from Ronald Reagan Washington National to O'Hare Intl., returning Fri, Sep 26, priced at $203 found 12 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Dec 23 - Tue, Dec 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$325 Roundtrip, found 1 day ago
$325
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Dec 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 30, priced at $325 found 1 day ago

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 August, 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 $72, 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 $72 right now, why wait?

Sleepy Hollow Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$72

Last Minute Hotel Deals in Sleepy Hollow

Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
1000 Busse Rd, Elk Grove Village, IL
Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
5.8/10 (114 reviews)
"Perfect location"

Reviewed on Jul 15, 2025

Get rates
Grand Royal Hotel O'Hare - Chicago
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 ...
8.2/10 Very Good! (1,014 reviews)
"Good"

Reviewed on Jul 11, 2025

Get rates
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
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. ...
7/10 Good! (862 reviews)
"Cleaning Staff is so kind and polite."

Reviewed on Jul 1, 2025

Get rates
Comfort Inn Chicago Schaumburg - O'Hare Airport
DoubleTree by Hilton Chicago - Arlington Heights

DoubleTree by Hilton Chicago - Arlington Heights

4 out of 5
75 W Algonquin Rd, Arlington Heights, IL
Stay at this 4-star business-friendly hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
8/10 Very Good! (1,020 reviews)
Good customer service
"Overall good customer service but management discriminates against customers using expedia and hotels.com"

Reviewed on Jul 14, 2025

Get rates
DoubleTree by Hilton Chicago - Arlington Heights
Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
1800 East Golf Rd, Schaumburg, IL
Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,157 reviews)
Will Stay Again
"Very kind and welcoming staff. Room was simple but impeccable. Easy check in and parking."

Reviewed on Jul 10, 2025

Get rates
Hyatt Regency Schaumburg Chicago
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 ...
8.6/10 Excellent! (1,006 reviews)
"Everyone was very nice and everything was so clean!"

Reviewed on Jul 13, 2025

Get rates
Courtyard by Marriott Chicago Wood Dale
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! (1,013 reviews)
"Good"

Reviewed on Jul 14, 2025

Get rates
The Westin Chicago Northwest
Hyatt Place Chicago/Hoffman Estates

Hyatt Place Chicago/Hoffman Estates

3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Stay at this 3-star business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,026 reviews)
"Breakfast was simple but good"

Reviewed on Jul 16, 2025

Get rates
Hyatt Place Chicago/Hoffman Estates
See all 486 properties in Sleepy Hollow
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.