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.
21c Museum Hotel Chicago
Downtown Chicago
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star 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.
Sentral Michigan Avenue
Downtown Chicago
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star business-friendly aparthotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
Kasa Magnificent Mile Chicago
Downtown Chicago
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Downtown Chicago
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue 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
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd, Schaumburg, IL
22.49 km from city center
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 ...
Hyatt Place Chicago/Hoffman Estates
2750 Greenspoint Pkwy, Hoffman Estates, IL
13.16 km from city center
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 ...
Eaglewood Resort and Spa
1401 Nordic Rd, Itasca, IL
26.53 km from city center
Stay at this 4-star spa resort in Itasca. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our ...
The Westin Chicago Northwest
400 Park Blvd, Itasca, IL
26.15 km from city center
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 ...
Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir, Rolling Meadows, IL
22.04 km from city center
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 ...
Country Inn & Suites by Radisson, Schaumburg, IL
1401 North Roselle Road, Schaumburg, IL
18.79 km from city center
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 ...
DoubleTree by Hilton Chicago Schaumburg
800 National Pkwy, Schaumburg, IL
21.31 km from city center
Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful ...
Hyatt Place Itasca
1150 North Arlington Heights Road, Itasca, IL
27.27 km from city center
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
26.67 km from city center
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 ...
Country Inn & Suites by Radisson, Elk Grove Village/Itasca
1160 W Devon Avenue, Elk Grove Village, IL
25.07 km from city center
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 ...
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 ...
DoubleTree by Hilton Chicago - Arlington Heights
75 W Algonquin Rd, Arlington Heights, IL
26.48 km from city center
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 ...
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 ...
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.
Sat, May 24 - Sat, May 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Sun, May 25 - Tue, May 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Wed, Jul 16 - Sun, Jul 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Wed, Jul 16 - Sun, Jul 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Best points of interest in Sleepy Hollow
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations