Cheap 2025 Sleepy Hollow Hotels
Choose from 4641 Sleepy Hollow Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
12.91 km from Sleepy Hollow
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. ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Free Cancellation
13.04 km from Sleepy Hollow
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
13.81 km from Sleepy Hollow
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
12.66 km from Sleepy Hollow
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
11.9 km from Sleepy Hollow
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 ...
The Wade
644 N Lake Shore Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
13.77 km from Sleepy Hollow
Stay at this 4.5-star luxury hotel in Chicago. Enjoy room service, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...
Freehand Chicago
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
12.93 km from Sleepy Hollow
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
Swissotel - Chicago
323 E Wacker Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
13.02 km from Sleepy Hollow
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 ...
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
22.79 km from Sleepy Hollow
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
12.86 km from Sleepy Hollow
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
11.78 km from Sleepy Hollow
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
13.54 km from Sleepy Hollow
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
13.94 km from Sleepy Hollow
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Free Cancellation
10.86 km from Sleepy Hollow
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 ...
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
13.87 km from Sleepy Hollow
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
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.
Sleepy Hollow, Chicago Hotel Guide
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More Sleepy Hollow Hotel Deals for Seniors and Members
- Embassy Suites by Hilton Chicago Downtown River North
- InterContinental Chicago Magnificent Mile by IHG
- Hilton Chicago/Magnificent Mile Suites
- citizenM Chicago Downtown
- Congress Plaza Hotel
- The Wade
- Freehand Chicago
- Swissotel - Chicago
- Hilton Chicago O'Hare Airport
- Hotel Felix River North/Magnificent Mile