Search Deals onSleepy Hollow Vacation Packages
Sleepy Hollow Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg
Save 100% on your flight
per person
Apr 24 - Apr 29
found 5 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
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 staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and LEGOLAND® Discovery Center are located nearby.
Congress Plaza Hotel
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Soldier Field are located nearby.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this spa 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 Michigan Avenue are located nearby.
21c Museum Hotel Chicago
Downtown Chicago
Save 100% on your flight
per person
May 9 - May 14
found 12 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Soldier Field and Chicago Riverwalk are located nearby.
L7 Chicago by LOTTE
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this boutique 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 Chicago Riverwalk and Michigan Avenue are located nearby.
3-4 Night Vacations in Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Sleepy Hollow
River Hotel
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
L7 Chicago by LOTTE
225 N Wabash Ave, Chicago, IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and ...
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Save an average of 15% on thousands of hotels when you're signed in
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Book a stay at this eco-certified hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Swissotel - Chicago
323 E Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant 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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Apr 10 - Tue, Apr 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Thu, Jun 5 - Thu, Jun 19
LAX
Los Angeles Intl.
MDW
Midway Intl.
$210 Roundtrip, found 6 days ago
$210
Roundtrip
found 6 days ago
Fri, Jun 20 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$1,013 Roundtrip, found 3 days ago
$1,013
Roundtrip
found 3 days ago
Sat, Apr 19 - Sat, May 3
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,059 Roundtrip, found 4 days ago
$1,059
Roundtrip
found 4 days ago
Discover Other Travel Deals
- Wrigley Field Vacations
- McCormick Place Vacations
- Michigan Avenue Vacations
- Navy Pier Vacations
- Millennium Park Vacations
- Grant Park Vacations
- Soldier Field Vacations
- Lake Michigan Vacations
- Chicago Riverwalk Vacations
- United Center Vacations
- Northwestern University Vacations
- Art Institute of Chicago Vacations
Book your Sleepy Hollow Vacation
Prices are always lower in the app!
Book and go: Last-minute deals and trip details all in one place
Exclusive prices: Hot Rate® Hotels always cost less in the app
Fresh features: So slick you’ll never go back to desktop
