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Sleepy Hollow

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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
Tue, Aug 26 - Sat, Aug 30
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$72 Roundtrip, found 1 day ago
$72
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 26 from George Bush Intercontinental to O'Hare Intl., returning Sat, Aug 30, priced at $72 found 1 day ago
Spirit Airlines
Sat, Aug 23 - Wed, Aug 27
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 21 hours ago
$72
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Sat, Aug 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 27, priced at $72 found 21 hours ago
Spirit Airlines
Wed, Sep 17 - Tue, Sep 30
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$80 Roundtrip, found 11 hours ago
$80
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Wed, Sep 17 from George Bush Intercontinental to O'Hare Intl., returning Tue, Sep 30, priced at $80 found 11 hours ago
Spirit Airlines
Sun, Sep 7 - Thu, Sep 11
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$90 Roundtrip, found 4 hours ago
$90
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sun, Sep 7 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Sep 11, priced at $90 found 4 hours ago
Frontier Airlines
Sat, Aug 9 - Fri, Aug 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 6 days ago
$102
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Aug 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Fri, Aug 15, priced at $102 found 6 days ago
Frontier Airlines
Thu, Aug 21 - Sat, Aug 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$106 Roundtrip, found 6 days ago
$106
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Aug 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $106 found 6 days ago
American Airlines
Thu, Sep 4 - Thu, Sep 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 4 from Logan Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $119 found 1 day ago
United
Thu, Sep 4 - Thu, Sep 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select United flight, departing Thu, Sep 4 from Logan Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $119 found 1 day ago
Spirit Airlines
Tue, Sep 9 - Sun, Sep 14
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$128 Roundtrip, found 8 hours ago
$128
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Tue, Sep 9 from Los Angeles Intl. to O'Hare Intl., returning Sun, Sep 14, priced at $128 found 8 hours ago
Delta
Sat, Oct 18 - Sat, Oct 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 17 hours ago
$132
Roundtrip
found 17 hours ago
Select Delta flight, departing Sat, Oct 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Oct 18, priced at $132 found 17 hours ago
JetBlue Airways
Thu, Sep 4 - Thu, Sep 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Sep 4 from Logan Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $134 found 1 day ago
Contour Airlines
Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 5 days ago
$193
Roundtrip
found 5 days ago
Select Contour Airlines flight, departing Mon, Sep 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $193 found 5 days ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$194 Roundtrip, found 4 hours ago
$194
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $194 found 4 hours ago
Alaska Airlines
Sat, Nov 15 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 5 days ago
$216
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 19, priced at $216 found 5 days 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 6 days ago
$325
Roundtrip
found 6 days 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 6 days ago
Sun Country Airlines
Wed, Oct 15 - Sun, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$333 Roundtrip, found 18 hours ago
$333
Roundtrip
found 18 hours ago
Select Sun Country Airlines flight, departing Wed, Oct 15 from Los Angeles Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $333 found 18 hours 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 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 $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
$71

Last Minute Hotel Deals in Sleepy Hollow

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! (1,000 reviews)
"Our stay was great aside from the shower head spraying water so hard it was spraying out onto the floor. We were unable to adjust the shower head."

Reviewed on Jul 28, 2025

Get rates
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
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)
"Great place to stay. Would visit again"

Reviewed on Jul 31, 2025

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Courtyard by Marriott Chicago Wood Dale
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! (1,010 reviews)
"Very Good Service"

Reviewed on Jul 22, 2025

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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! (1,180 reviews)
"Staff were nice, beautiful lobby, room was great, and the breakfast was outstanding; would definitely stay again! Also, conveniently close to the mall, plenty of dining options, and the highway. Highly recommend"

Reviewed on Jul 28, 2025

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Hyatt Regency Schaumburg Chicago
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! (879 reviews)
"Bed was super comfy and room was very clean. Breakfast was typical for a hotel"

Reviewed on Jul 28, 2025

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Comfort Inn Chicago Schaumburg - O'Hare Airport
Motel 6 Elk Grove Village, IL

Motel 6 Elk Grove Village, IL

2 out of 5
1000 W Devon Ave, Elk Grove Village, IL
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,005 reviews)
"Monica was reall"

Reviewed on Jul 31, 2025

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Motel 6 Elk Grove Village, IL
Holiday Inn Express Chicago NW - Arlington Heights by IHG

Holiday Inn Express Chicago NW - Arlington Heights by IHG

2.5 out of 5
2111 S Arlington Heights Rd, Arlington Heights, IL
Stay at this hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (983 reviews)
"The hotel is very clean and staff very friendly. The beds were very firm, which was a little uncomfortable for us. The outside noise from traffic was"

Reviewed on Jul 31, 2025

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Holiday Inn Express Chicago NW - Arlington Heights by IHG
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 (133 reviews)
"Pics need to be updated need a lot of updates HOTEL close to airport but close to commercial buildings"

Reviewed on Jul 22, 2025

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Grand Royal Hotel O'Hare - Chicago
See all 491 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.