Sleepy Hollow Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Sleepy Hollow Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$499
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
$684
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
$604
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,221
per person
Dec 17 - Dec 21
found 16 hours ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago - River North
Downtown Chicago
$764
per person
Dec 17 - Dec 21
found 16 hours ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Outstanding room. I highly recommend. Be sure to check out the 6th floor and all the amenities!
Reviewed on Sep 23, 2026
Park Hyatt Chicago
Downtown Chicago
$1,186
per person
Dec 17 - Dec 21
found 16 hours ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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Eaglewood Resort and Spa
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 ...
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
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 ...
Hyatt Place Itasca
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 ...
Comfort Inn & Suites Arlington Heights - Schaumburg
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 ...
Comfort Inn Chicago Schaumburg - O'Hare Airport
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. ...
Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir Rolling Meadows IL
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 ...
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
Book a stay at this business-friendly hotel in Mundelein. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Motel 6 Arlington Heights, IL - Chicago North Central
441 W Algonquin Rd Arlington Heights IL
Stay at this motel in Arlington Heights. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
Hyatt Place Chicago/ Schaumburg
1851 McConnor Parkway Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Plus Elgin - Chicago
2175 Marriott Dr West Dundee IL
Book a stay at this business-friendly hotel in West Dundee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Quality Inn Schaumburg - Chicago near the Mall
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 ...
Courtyard by Marriott Chicago Wood Dale
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 ...
Red Roof Inn PLUS+ Chicago - Hoffman Estates
2500 Hassell Road Hoffman Estates IL
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff ...
The Westin Chicago Northwest
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 ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Oct 20 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 4 days ago
Tue, Oct 20 - Thu, Oct 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237
Roundtrip
found 4 days ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237
Roundtrip
just found
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$252
Roundtrip
just found
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$281
Roundtrip
just found
Best points of interest in Sleepy Hollow
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