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Sleepy Hollow

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Sleepy Hollow Flights as Low as $80

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

Spirit Airlines
Wed, Jul 16 - Wed, Jul 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$80 Roundtrip, found 2 hours ago
$80
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Jul 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $80 found 2 hours ago
Spirit Airlines
Mon, Sep 22 - Fri, Sep 26
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$112 Roundtrip, found 10 hours ago
$112
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Mon, Sep 22 from George Bush Intercontinental to O'Hare Intl., returning Fri, Sep 26, priced at $112 found 10 hours ago
Spirit Airlines
Fri, Sep 5 - Mon, Sep 8
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 15 hours ago
$120
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Fri, Sep 5 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $120 found 15 hours ago
Frontier Airlines
Mon, Sep 22 - Fri, Sep 26
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$131 Roundtrip, found 10 hours ago
$131
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Mon, Sep 22 from George Bush Intercontinental to O'Hare Intl., returning Fri, Sep 26, priced at $131 found 10 hours ago
United
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 8 hours ago
$132
Roundtrip
found 8 hours ago
Select United flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $132 found 8 hours ago
American Airlines
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 8 hours ago
$132
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $132 found 8 hours ago
American Airlines
Sat, Aug 16 - Tue, Aug 19
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$141 Roundtrip, found 17 hours ago
$141
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Aug 16 from Charlotte-Douglas Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $141 found 17 hours ago
Delta
Tue, Aug 19 - Tue, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$142 Roundtrip, found 9 hours ago
$142
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $142 found 9 hours ago
Spirit Airlines
Wed, Jul 9 - Sun, Jul 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$155 Roundtrip, just found
$155
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Jul 9 from Los Angeles Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $155 just found
Frontier Airlines
Mon, Aug 11 - Fri, Aug 15
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 3 days ago
$172
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Aug 11 from Sky Harbor Intl. to O'Hare Intl., returning Fri, Aug 15, priced at $172 found 3 days ago
Contour Airlines
Mon, Aug 25 - Thu, Aug 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 16 hours ago
$189
Roundtrip
found 16 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 16 hours ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$201 Roundtrip, just found
$201
Roundtrip
just found
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $201 just found
Hawaiian Airlines
Tue, Sep 23 - Tue, Sep 30
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Tue, Sep 23 from Sky Harbor Intl. to O'Hare Intl., returning Tue, Sep 30, priced at $218 found 1 day ago
Alaska Airlines
Tue, Oct 7 - Sat, Oct 11
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Oct 7 from Sky Harbor Intl. to O'Hare Intl., returning Sat, Oct 11, priced at $227 found 1 day ago
JetBlue Airways
Tue, Jul 8 - Tue, Jul 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$293 Roundtrip, found 8 hours ago
$293
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Tue, Jul 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $293 found 8 hours ago
Sun Country Airlines
Sun, Jul 13 - Mon, Jul 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$317 Roundtrip, found 8 hours ago
$317
Roundtrip
found 8 hours ago
Select Sun Country Airlines flight, departing Sun, Jul 13 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jul 21, priced at $317 found 8 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 July, 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 $80, 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 $80 right now, why wait?

Sleepy Hollow Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$80

Last Minute Hotel Deals in Sleepy Hollow

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! (1,110 reviews)
"Everything is great"

Reviewed on Jun 13, 2025

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Hyatt Regency Schaumburg Chicago
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 ...
5.4/10 (75 reviews)
"The name of the hotel was Grand Royal Hotel O'Hare by Expedia but it was Holiday inn there and also in gps. So we were confused. Water was dripping in the bath and we couldn't stop it. It needs to be repaired. Bed was nice. If you need to be close to the airport, this hotel is great."

Reviewed on Jun 15, 2025

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Grand Royal Hotel O'Hare - Chicago
Comfort Inn & Suites Arlington Heights - Schaumburg
Comfort Inn & Suites Arlington Heights - Schaumburg
3 out of 5
2112 S Arlington Heights Rd, Arlington Heights, IL
Stay at this 3-star business-friendly hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
8.4/10 Very Good! (418 reviews)
"I found this to be a good hotel--clean, good breakfast, safe area, easily accessible, and overall in good condition. The one exception is that the bathtub was in a bit of disrepair (the finish was degrading), but the rest of the room and the building overall were very good. I would recommend it."

Reviewed on Jun 15, 2025

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Comfort Inn & Suites Arlington Heights - Schaumburg
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! (1,001 reviews)
"I really loved my stay at this strategically located hotel which is surrounded by a beautiful evergreen landscape. I was attending a college graduation ceremony nearby and also wanted to explore the city of Chicago. This hotel’s location facilitated all that and more. The rooms and facilities are ..."

Reviewed on Jun 14, 2025

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DoubleTree by Hilton Chicago - Arlington Heights
Wyndham Garden Schaumburg Chicago Northwest
Wyndham Garden Schaumburg Chicago Northwest
3 out of 5
1725 E Algonquin Road, Schaumburg, IL
Stay at this 3-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and a free area shuttle. Our guests praise the helpful staff and the ...
6.8/10 (1,005 reviews)
"Great staff"

Reviewed on Jun 14, 2025

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Wyndham Garden Schaumburg Chicago Northwest
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! (833 reviews)
"Good place to stay"

Reviewed on Jun 15, 2025

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Comfort Inn Chicago Schaumburg - O'Hare Airport
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! (1,017 reviews)
"The staff on all shifts were exceptionally friendly and helpful, gave helpful recommendations and helped with changing the channels on the TV without making us feel stupid. The breakfast had many options and lots of room for seating. Quiet and safe feeling."

Reviewed on Jun 16, 2025

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Hyatt Place Chicago/Hoffman Estates
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 ...
8.4/10 Very Good! (1,015 reviews)
"I didn’t stay too much in the hotel but every time I did it was clean and refreshed! They had a lot of parties this weekend I loved it, it was lovely and didn’t disturb at all. The celebrations were gorgeous and the staff were still attentive to the guest there who didn’t attend the parties."

Reviewed on Jun 15, 2025

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The Westin Chicago Northwest
See all 473 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.