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Sleepy Hollow

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Sleepy Hollow Flights as Low as $56

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

Frontier Airlines
Wed, Aug 12 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$56 Roundtrip, found 21 hours ago
$56
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $56 found 21 hours ago
Frontier Airlines
Tue, Jun 9 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$66 Roundtrip, found 4 hours ago
$66
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 16, priced at $66 found 4 hours ago
Frontier Airlines
Tue, Jun 2 - Tue, Jun 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 20 hours ago
$68
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Tue, Jun 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 2, priced at $68 found 20 hours ago
Frontier Airlines
Wed, May 27 - Tue, Jun 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 6 hours ago
$68
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, May 27 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 2, priced at $68 found 6 hours ago
Frontier Airlines
Wed, May 27 - Fri, May 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 4 hours ago
$132
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, May 27 from Los Angeles Intl. to O'Hare Intl., returning Fri, May 29, priced at $132 found 4 hours ago
Spirit Airlines
Fri, Jul 3 - Sat, Jul 4
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 5 days ago
$147
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Fri, Jul 3 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jul 4, priced at $147 found 5 days ago
Spirit Airlines
Thu, Jul 2 - Fri, Jul 3
LGA
LaGuardia
ORD
O'Hare Intl.
$154 Roundtrip, found 4 days ago
$154
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Jul 2 from LaGuardia to O'Hare Intl., returning Fri, Jul 3, priced at $154 found 4 days ago
United
Wed, Aug 12 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$169 Roundtrip, found 21 hours ago
$169
Roundtrip
found 21 hours ago
Select United flight, departing Wed, Aug 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $169 found 21 hours ago
American Airlines
Tue, Jul 28 - Tue, Aug 4
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$169 Roundtrip, found 4 hours ago
$169
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Jul 28 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 4, priced at $169 found 4 hours ago
JetBlue Airways
Tue, Jun 16 - Tue, Jun 23
BOS
Logan Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 6 days ago
$171
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Jun 16 from Logan Intl. to O'Hare Intl., returning Tue, Jun 23, priced at $171 found 6 days ago
Delta
Wed, Jul 22 - Tue, Jul 28
LGA
LaGuardia
ORD
O'Hare Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 22 from LaGuardia to O'Hare Intl., returning Tue, Jul 28, priced at $177 found 1 day ago
JetBlue Airways
Mon, Jul 20 - Wed, Aug 5
BOS
Logan Intl.
ORD
O'Hare Intl.
$205 Roundtrip, found 10 hours ago
$205
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Mon, Jul 20 from Logan Intl. to O'Hare Intl., returning Wed, Aug 5, priced at $205 found 10 hours ago
Delta
Tue, Jun 30 - Tue, Jul 7
DAL
Love Field
ORD
O'Hare Intl.
$308 Roundtrip, found 16 hours ago
$308
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Jun 30 from Love Field to O'Hare Intl., returning Tue, Jul 7, priced at $308 found 16 hours ago
Alaska Airlines
Fri, May 29 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Fri, May 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $314 found 1 day ago
Sun Country Airlines
Sat, Jul 4 - Thu, Aug 6
BOS
Logan Intl.
ORD
O'Hare Intl.
$505 Roundtrip, found 1 day ago
$505
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sat, Jul 4 from Logan Intl. to O'Hare Intl., returning Thu, Aug 6, priced at $505 found 1 day ago
Contour Airlines
Mon, May 18 - Thu, May 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$668 Roundtrip, found 20 hours ago
$668
Roundtrip
found 20 hours ago
Select Contour Airlines flight, departing Mon, May 18 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, May 21, priced at $668 found 20 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 $56, 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 $56 right now, why wait?

Sleepy Hollow Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$56

Last Minute Hotel Deals in Sleepy Hollow

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 ...
5.4/10 (1,003 reviews)
Good location,

Reviewed on May 9, 2026

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Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
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! (1,073 reviews)
Beautiful property! I enjoyed the peaceful setting. Close to everything. Staff at the hotel was excellent all around!

Reviewed on May 11, 2026

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Eaglewood Resort and Spa
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! (1,023 reviews)
Breakfast staff and front counter staffs were very kind.

Reviewed on May 10, 2026

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DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
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! (1,092 reviews)
Clean room good Staff

Reviewed on May 12, 2026

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Hyatt Place Itasca
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)
I didn't utilize the hot tub or pool because I was only there for the night. But, my stay was overall good just for the one night that I was there

Reviewed on May 11, 2026

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Quality Inn Schaumburg - Chicago near the Mall
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! (1,150 reviews)
Had bed bugs. Notified hotel staff and no action. Breakfast was decent and average. The whole bathroom needs updated. Will not stay here again.

Reviewed on May 12, 2026

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Comfort Inn & Suites Arlington Heights - Schaumburg
The Westin Chicago Northwest

The Westin Chicago Northwest

4 out of 5
400 Park Blvd Itasca IL
Book a stay at this business-friendly hotel in Itasca. Enjoy breakfast (surcharge), a free area shuttle, and a 24-hour fitness center. Our guests praise the ...
8.8/10 Excellent! (1,009 reviews)
Pool area very relaxing, with hot tub. Hotel is busy with weddings and events on the weekends.

Reviewed on May 11, 2026

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The Westin Chicago Northwest
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. ...
8.8/10 Excellent! (1,010 reviews)
Staff was friendly. Room was cleaned and beds were comfortable.

Reviewed on May 11, 2026

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Holiday Inn Express Chicago NW - Arlington Heights by IHG
See all 530 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.