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 $58

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

Frontier Airlines
Tue, May 12 - Wed, May 13
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$58 Roundtrip, found 12 hours ago
$58
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from George Bush Intercontinental to O'Hare Intl., returning Wed, May 13, priced at $58 found 12 hours ago
Frontier Airlines
Tue, May 5 - Wed, May 6
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$68 Roundtrip, found 18 hours ago
$68
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from George Bush Intercontinental to O'Hare Intl., returning Wed, May 6, priced at $68 found 18 hours ago
Frontier Airlines
Tue, May 5 - Sat, May 9
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$74 Roundtrip, found 18 hours ago
$74
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from George Bush Intercontinental to O'Hare Intl., returning Sat, May 9, priced at $74 found 18 hours ago
Spirit Airlines
Wed, Apr 29 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$75 Roundtrip, found 1 hour ago
$75
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 2, priced at $75 found 1 hour ago
Frontier Airlines
Wed, Apr 29 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 1 hour ago
$76
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 2, priced at $76 found 1 hour ago
Frontier Airlines
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 12, priced at $78 just found
Frontier Airlines
Thu, May 28 - Sat, Jun 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 8 hours ago
$110
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, May 28 from Los Angeles Intl. to O'Hare Intl., returning Sat, Jun 6, priced at $110 found 8 hours ago
Frontier Airlines
Thu, Apr 30 - Sat, May 2
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 3 days ago
$124
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Harry Reid Intl. to O'Hare Intl., returning Sat, May 2, priced at $124 found 3 days ago
Frontier Airlines
Sat, May 2 - Thu, May 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 2 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, May 7, priced at $137 found 2 days ago
Frontier Airlines
Wed, May 6 - Sat, May 9
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 6 from Ronald Reagan Washington National to O'Hare Intl., returning Sat, May 9, priced at $142 found 1 day ago
Delta
Tue, May 26 - Tue, Jun 9
STL
Lambert-St. Louis Intl.
ORD
O'Hare Intl.
$161 Roundtrip, found 12 hours ago
$161
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, May 26 from Lambert-St. Louis Intl. to O'Hare Intl., returning Tue, Jun 9, priced at $161 found 12 hours ago
Bargain Flight
Tue, Jun 23 - Tue, Jun 30
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Jun 23 from Ronald Reagan Washington National to O'Hare Intl., returning Tue, Jun 30, priced at $171 found 1 day ago
American Airlines
Tue, May 12 - Wed, May 13
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$174 Roundtrip, found 12 hours ago
$174
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, May 12 from George Bush Intercontinental to O'Hare Intl., returning Wed, May 13, priced at $174 found 12 hours ago
Alaska Airlines
Tue, May 5 - Tue, May 19
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, May 5 from Harry Reid Intl. to O'Hare Intl., returning Tue, May 19, priced at $257 found 2 days ago
JetBlue Airways
Wed, May 6 - Sat, May 9
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$298 Roundtrip, found 1 day ago
$298
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, May 6 from Ronald Reagan Washington National to O'Hare Intl., returning Sat, May 9, priced at $298 found 1 day ago
Sun Country Airlines
Sun, May 17 - Thu, May 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$552 Roundtrip, found 2 days ago
$552
Roundtrip
found 2 days ago
Select Sun Country Airlines flight, departing Sun, May 17 from Los Angeles Intl. to O'Hare Intl., returning Thu, May 21, priced at $552 found 2 days 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 May, 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 $58, 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 $58 right now, why wait?

Sleepy Hollow Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$57

Last Minute Hotel Deals in Sleepy Hollow

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! (1,110 reviews)
Convenient location, quiet and easy free parking made this a great place to stay while visiting family in Arlington Heights.

Reviewed on Apr 12, 2026

Get rates
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! (1,017 reviews)
Air / heat made a tremendous humming noise.

Reviewed on Apr 14, 2026

Get rates
Quality Inn Schaumburg - Chicago near the Mall
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! (1,034 reviews)
I expected the resort to look better than what we saw on arrival. Staff professional. We were disappointed in the room upon entering. The carpet was old, patio was not well kept, the view was not a good view of the golf course (south elevator room 903) and when I went to take a shower I saw dried ...

Reviewed on Apr 14, 2026

Get rates
Eaglewood Resort and Spa
Hyatt Place Chicago/Hoffman Estates

Hyatt Place Chicago/Hoffman Estates

3 out of 5
2750 Greenspoint Pkwy Hoffman Estates IL
Book a stay at this 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! (1,089 reviews)
The beds were small, but the rooms were spacious and clean. The staff members were exceptionally nice. There was a variety of breakfast items to choose from and everything tasted great. We will definitely stay there again.

Reviewed on Apr 12, 2026

Get rates
Hyatt Place Chicago/Hoffman Estates
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! (1,045 reviews)
The staff here are very good! They listen and they act! Had some trouble on my first night being beside the elevator and an exhaust that is open. Brought this to their attention and was given a new room! Food was the usual breakfast and was good! Parking is free as compared with other hotels where ...

Reviewed on Apr 14, 2026

Get rates
Hyatt Place Itasca
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 ...
5.6/10 (1,004 reviews)
There was a problem with the door and they had to switch rooms and gave us a much smaller one and i reserved a 2bed, they gave us a 1bed room. Not to mention the room was too hot (heat wouldn'twork, couldn'tturn it off), it wad also dirty and smelled bad. I know it was a "cheap" hotel but could do ...

Reviewed on Apr 13, 2026

Get rates
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
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! (1,013 reviews)
Breakfast was great, nice hotel overall

Reviewed on Apr 14, 2026

Get rates
Comfort Inn Chicago Schaumburg - O'Hare Airport
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! (1,013 reviews)
Staff said breakfast not included. Bedding had stains. Carpet needed to be vacuumed better. Hairs in the tub. Vent in restroom ceiling was dirty. Definitely needed a better cleaning. We've stayed at Hiltons before so this was below the standards of other Hilton hotels.

Reviewed on Apr 13, 2026

Get rates
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
See all 512 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.