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.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $942, price is now $620 per person
$620
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,768, price is now $1,120 per person
$1,120
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) 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 – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,263, price is now $800 per person
$800
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,178, price is now $757 per person
$757
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,129, price is now $735 per person
$735
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $968, price is now $631 per person
$631
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) 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.
Don't see what you're looking for?
See all available trips from Columbus to Sleepy Hollow
View all tripsTop Hotel Deals
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
26.67 km from city center
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 ...
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
26.53 km from city center
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 ...
Motel 6 Elk Grove Village, IL
1000 W Devon Ave Elk Grove Village IL
25.41 km from city center
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 ...
Comfort Inn & Suites Arlington Heights - Buffalo Grove
3700 N Wilke Rd Arlington Heights IL
24.72 km from city center
Stay at this hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Country Inn & Suites by Radisson, Schaumburg, IL
1401 North Roselle Road Schaumburg IL
18.79 km from city center
Book a stay at this family-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
DoubleTree by Hilton Chicago - Arlington Heights
75 W Algonquin Rd Arlington Heights IL
26.48 km from city center
Book a stay at this business-friendly hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
22 West Algonquin Road Arlington Heights IL
26.62 km from city center
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 ...
Embassy Suites by Hilton Chicago Schaumburg Woodfield
1939 N Meacham Rd Schaumburg IL
21.35 km from city center
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 ...
Country Inn & Suites by Radisson, Elk Grove Village/Itasca
1160 W Devon Avenue Elk Grove Village IL
25.07 km from city center
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
29.37 km from city center
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
26.25 km from city center
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 ...
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road Schaumburg IL
22 km from city center
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd Wood Dale IL
28.66 km from city center
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 ...
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.
Wed, Mar 18 - Tue, Mar 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 4 days ago
$140
Roundtrip
found 4 days ago
Thu, May 7 - Tue, May 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 days ago
Mon, Jan 5 - Mon, Jan 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$695 Roundtrip, found 7 hours ago
$695
Roundtrip
found 7 hours ago
Mon, Jan 5 - Mon, Jan 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$777 Roundtrip, found 7 hours ago
$777
Roundtrip
found 7 hours ago
Mon, Jan 5 - Mon, Jan 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$788 Roundtrip, found 7 hours ago
$788
Roundtrip
found 7 hours ago