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Sleepy Hollow

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Sleepy Hollow Flights as Low as $68

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

Frontier Airlines
Wed, Jul 9 - Tue, Jul 15
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jul 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $68 found 1 day ago
Frontier Airlines
Thu, May 8 - Sun, May 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, May 11, priced at $78 found 1 day ago
Spirit Airlines
Tue, Apr 22 - Tue, Apr 29
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Apr 22 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Apr 29, priced at $94 found 1 day ago
JetBlue Airways
Mon, Jul 14 - Tue, Jul 15
BOS
Logan Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Jul 14 from Logan Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $97 found 3 days ago
American Airlines
Wed, Jun 4 - Sat, Jun 7
BOS
Logan Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jun 4 from Logan Intl. to O'Hare Intl., returning Sat, Jun 7, priced at $97 found 3 days ago
United
Sun, May 11 - Sun, Jun 22
BOS
Logan Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select United flight, departing Sun, May 11 from Logan Intl. to O'Hare Intl., returning Sun, Jun 22, priced at $97 found 2 days ago
Delta
Wed, May 7 - Sat, May 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 4 days ago
$97
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, May 7 from Logan Intl. to O'Hare Intl., returning Sat, May 10, priced at $97 found 4 days ago
Frontier Airlines
Fri, Apr 11 - Sat, Apr 19
MCO
Orlando Intl.
ORD
O'Hare Intl.
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 11 from Orlando Intl. to O'Hare Intl., returning Sat, Apr 19, priced at $101 found 1 day ago
Spirit Airlines
Wed, May 14 - Sat, May 17
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$108 Roundtrip, found 5 hours ago
$108
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Wed, May 14 from George Bush Intercontinental to O'Hare Intl., returning Sat, May 17, priced at $108 found 5 hours ago
Spirit Airlines
Wed, Apr 23 - Sat, Apr 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 6 days ago
$124
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Apr 23 from Los Angeles Intl. to O'Hare Intl., returning Sat, Apr 26, priced at $124 found 6 days ago
Frontier Airlines
Sat, Apr 26 - Thu, May 1
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Apr 26 from Sky Harbor Intl. to O'Hare Intl., returning Thu, May 1, priced at $160 found 2 days ago
Contour Airlines
Fri, May 9 - Sun, May 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 20 hours ago
$189
Roundtrip
found 20 hours ago
Select Contour Airlines flight, departing Fri, May 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, May 11, priced at $189 found 20 hours ago
Delta
Mon, May 12 - Tue, May 13
DAL
Love Field
ORD
O'Hare Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, May 12 from Love Field to O'Hare Intl., returning Tue, May 13, priced at $197 found 4 days ago
Alaska Airlines
Tue, Apr 29 - Wed, May 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Apr 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 7, priced at $218 found 1 day ago
Hawaiian Airlines
Tue, Apr 22 - Sat, Apr 26
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$238 Roundtrip, found 2 days ago
$238
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Tue, Apr 22 from Sky Harbor Intl. to O'Hare Intl., returning Sat, Apr 26, priced at $238 found 2 days ago
Sun Country Airlines
Thu, Sep 18 - Mon, Sep 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$313 Roundtrip, found 6 days ago
$313
Roundtrip
found 6 days ago
Select Sun Country Airlines flight, departing Thu, Sep 18 from Los Angeles Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $313 found 6 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 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 $68, 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 $68 right now, why wait?

Sleepy Hollow Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$68

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
The price is $133 per night from Apr 6 to Apr 7
$133
includes taxes & fees
Apr 6 - Apr 7
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 ...
8.4/10 Very Good! (1,001 reviews)
"I have stayed overnight at, Schaumburg Hyatt Regency three separate times within four months. I have dined in the restaurant for breakfast, utilized the workout facility, as well as ordered in room dining. Each individual experience has been enjoyable. The room was spacious, and clean with decent ..."

Reviewed on Mar 31, 2025

Hyatt Regency Schaumburg Chicago
Hyatt Place Chicago/Hoffman Estates
Hyatt Place Chicago/Hoffman Estates
3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
The price is $94 per night from Apr 13 to Apr 14
$94
includes taxes & fees
Apr 13 - Apr 14
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! (1,000 reviews)
"Loved it!"

Reviewed on Mar 29, 2025

Hyatt Place Chicago/Hoffman Estates
Country Inn & Suites by Radisson, Schaumburg, IL
Country Inn & Suites by Radisson, Schaumburg, IL
3 out of 5
1401 North Roselle Road, Schaumburg, IL
The price is $119 per night from Apr 27 to Apr 28
$119
includes taxes & fees
Apr 27 - Apr 28
Stay at this 3-star family-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,012 reviews)
"We had a wonderful stay. We were doing a staycation and a trip to Medieval Times which is just up the street! We enjoyed the pool and appreciated the breakfast. The staff was very friendly and helpful. My only complaint is the bed, it was rather hard. I like a firm mattress with a cushy pillow top. ..."

Reviewed on Mar 30, 2025

Country Inn & Suites by Radisson, Schaumburg, IL
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
The price is $102 per night from Apr 16 to Apr 17
$102
includes taxes & fees
Apr 16 - Apr 17
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. ...
6.8/10 (762 reviews)
"Pool is very small and not heated."

Reviewed on Mar 25, 2025

Comfort Inn Chicago Schaumburg - O'Hare Airport
Hyatt Place Itasca
Hyatt Place Itasca
3 out of 5
1150 North Arlington Heights Road, Itasca, IL
The price is $88 per night from Apr 13 to Apr 14
$88
includes taxes & fees
Apr 13 - Apr 14
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 ...
8.6/10 Excellent! (1,001 reviews)
"Very nice"

Reviewed on Apr 1, 2025

Hyatt Place Itasca
Motel 6 Rolling Meadows, IL - Chicago Northwest
Motel 6 Rolling Meadows, IL - Chicago Northwest
2 out of 5
1800 Winnetka Cir, Rolling Meadows, IL
The price is $63 per night from Apr 7 to Apr 8
$63
includes taxes & fees
Apr 7 - Apr 8
Stay at this motel in Rolling Meadows. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.6/10 (1,130 reviews)
"Everything was great. The room was clean comfortable and the staff was excellent."

Reviewed on Mar 30, 2025

Motel 6 Rolling Meadows, IL - Chicago Northwest
Country Inn & Suites by Radisson, Elk Grove Village/Itasca
Country Inn & Suites by Radisson, Elk Grove Village/Itasca
3 out of 5
1160 W Devon Avenue, Elk Grove Village, IL
The price is $97 per night from Apr 10 to Apr 11
$97
includes taxes & fees
Apr 10 - Apr 11
Stay at this 3-star business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,000 reviews)
"Nice location. Would stay again"

Reviewed on Mar 30, 2025

Country Inn & Suites by Radisson, Elk Grove Village/Itasca
Courtyard by Marriott Chicago Wood Dale
Courtyard by Marriott Chicago Wood Dale
3 out of 5
900 N Wood Dale Rd, Wood Dale, IL
The price is $119 per night from Apr 6 to Apr 7
$119
includes taxes & fees
Apr 6 - Apr 7
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! (1,000 reviews)
"Great"

Reviewed on Mar 31, 2025

Courtyard by Marriott Chicago Wood Dale
See all 492 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.