Sleepy Hollow Hotels, Chicago

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Check prices for these dates

Tonight
2 Dec - 3 Dec
Tomorrow
3 Dec - 4 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

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4928 Cheap Hotels in Sleepy Hollow - Specials, Reviews, & Last Minute Deals

Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2179)
"Great stay "
United States
Melinda
The price is AU$175
includes taxes & fees
10 Dec - 11 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (4865)
"Front desk is amazing, rooms are clean and great location"
United States
Glen
The price is AU$164
includes taxes & fees
7 Dec - 8 Dec
River Hotel
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3149)
"Amazing and will be staying again!"
United States
Angie
The price is AU$176
includes taxes & fees
7 Dec - 8 Dec
Eurostars Magnificent Mile
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.4 out of 10, Very good, (2333)
"We had a great stay and will be back again."
United States
Amber
The price is AU$234
includes taxes & fees
25 Dec - 26 Dec
Hilton Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
Streeterville, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2267)
"Perfect environment and location"
China
YIWEI
The price is AU$222
includes taxes & fees
23 Dec - 24 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
10.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1736)
"The location was great!!"
United States
Yvette
The price is AU$228
includes taxes & fees
23 Dec - 24 Dec
Crowne Plaza Chicago West Loop by IHG
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (2959)
"Great location, the staff was friendly and the room was very clean. "
United States
Breanna
The price is AU$154
includes taxes & fees
7 Dec - 8 Dec
Aloft Chicago Mag Mile
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4112)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is AU$192
includes taxes & fees
25 Dec - 26 Dec
citizenM Chicago Downtown
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Streeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3421)
"Great stay!"
United States
Rose
The price is AU$149
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
River North, 12.9 km from Sleepy Hollow
8.4 out of 10, Very good, (4229)
"Great location. "
United States
Rodger
The price is AU$148
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2092)
"Lovely hotel in a great spot!"
United States
Natasha
Silversmith Hotel Chicago Downtown
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
West Loop, 10.8 km from Sleepy Hollow
8.4 out of 10, Very good, (1021)
"Amazing staff clean and secure hotel "
United States
Aniyah
The price is AU$175
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn & Suites Chicago - Downtown by IHG
Rooftop terrace
Best Western River North Hotel

Best Western River North Hotel

2.5 star property
River North, 12.6 km from Sleepy Hollow
7.8 out of 10, Good, (1014)
"Staff was very friendly "
United States
david
The price is AU$156
includes taxes & fees
7 Dec - 8 Dec
Best Western River North Hotel
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
The Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (9696)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is AU$174
includes taxes & fees
5 Dec - 6 Dec
Congress Plaza Hotel
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
River North, 12.6 km from Sleepy Hollow
8.4 out of 10, Very good, (349)
"love this place definitely coming back !"
United States
Dayanara
The price is AU$114
includes taxes & fees
11 Dec - 12 Dec
FOUND Hotel Chicago River North
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 13.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2898)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is AU$206
includes taxes & fees
8 Dec - 9 Dec
Hotel Riu Plaza Chicago
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
River North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2622)
"Rooms are clean, staff are nice and friendly "
United States
Karen
The price is AU$147
includes taxes & fees
2 Jan - 3 Jan 2026
Freehand Chicago
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 star property
Streeterville, 13.5 km from Sleepy Hollow
8.2 out of 10, Very good, (3758)
"Great location "
United States
Carlos
The price is AU$142
includes taxes & fees
10 Dec - 11 Dec
The Whitehall Hotel, BW Premier Collection
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1743)
"Staff was courteous, room was clean, convenient location for us. Price was good as well."
United States
Jamie
The price is AU$142
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Chicago Downtown South Loop
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 12.1 km from Sleepy Hollow
8.4 out of 10, Very good, (2123)
"Great place to stay."
United States
Aaron
The price is AU$225
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
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.
View all properties

Our guide on where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.
Downtown Chicago featuring a city

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Magnificent Mile - River North

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

The Loop - Downtown which includes a river or creek

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Chicago showing a city and modern architecture

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Sleepy Hollow Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"The staff and the location were wonderful."
Elizabeth 2-night trip
Posted 1 day ago
Congress Plaza Hotel

Frequently asked questions

What's it like in Sleepy Hollow?
Sleepy Hollow is a neighbourhood that travellers like for its restaurants.
If I need to cancel my hotel reservation in Sleepy Hollow, will I receive a refund?
Yes! The majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of your booking. Put your dates in and click on "Search", then filter by "fully refundable" to view the top deals on offer in Sleepy Hollow.
What can I see and do in this Chicago neighbourhood?
Hawthorne Works Museum, Balzekas Museum of Lithuanian Culture and Wintrust Sports Complex are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing around the area, United Center and Bridgeport Art Center are a couple of other sights to visit.

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