Search Hotels in Sleepy Hollow, Chicago

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Check prices for these dates

Tonight
7 Jan - 8 Jan
Tomorrow
8 Jan - 9 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

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Our top choices for Sleepy Hollow hotels

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2697)
"Great fun place to stay close to most things in downtown "
United States
Kayla
The price is Rp906.120
Rp1.359.164 total
includes taxes & fees
3 Feb - 4 Feb
Freehand Chicago
Lobby
River Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (4888)
"Would stay there again"
United States
Zach
The price is Rp1.367.453
Rp1.605.252 total
includes taxes & fees
20 Jan - 21 Jan
River Hotel
Lobby
Aloft Chicago Mag Mile

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, (3014)
"Great place to stay"
United States
Elisha
The price is Rp1.273.608
Rp1.495.089 total
includes taxes & fees
21 Jan - 22 Jan
Aloft Chicago Mag Mile
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3125)
"Second time to stay here, everything is great!"
United States
Wei
The price is Rp1.517.308
Rp2.253.407 total
includes taxes & fees
1 Feb - 2 Feb
Hotel Riu Plaza Chicago
Lobby
Congress Plaza Hotel

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, (9782)
"Wonderful stay!"
United States
Zach
Congress Plaza Hotel
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
8.2 out of 10, Very good, (2814)
"Great hotel staff and location. "
United States
Jacqueline
The price is Rp1.592.680
Rp2.361.494 total
includes taxes & fees
14 Jan - 15 Jan
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

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, (2221)
"Fantastic stay! Looking forward to staying here again!!"
United States
Amber
The price is Rp1.429.122
Rp1.677.646 total
includes taxes & fees
14 Jan - 15 Jan
DoubleTree by Hilton Chicago - Magnificent Mile
Property amenity
The Wade

The Wade

The Wade
4.5 star property
Streeterville, 13.8 km from Sleepy Hollow
8.4 out of 10, Very good, (1580)
"Easy check in and out, excellent room service and dining menu."
United States
Kevin Bradford
The price is Rp1.692.558
Rp1.986.894 total
includes taxes & fees
12 Jan - 13 Jan
The Wade
View from room
Hilton Chicago/Magnificent Mile Suites

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, (3673)
"Great stay!!!"
United States
Lorenzo Martrel
The price is Rp1.497.830
Rp1.758.304 total
includes taxes & fees
13 Jan - 14 Jan
Hilton Chicago/Magnificent Mile Suites
Exterior
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1514)
"Very nice and quiet, excellent location"
United States
Anthony
The price is Rp949.412
Rp1.607.008 total
includes taxes & fees
2 Feb - 3 Feb
Claridge House Chicago, Tapestry Collection by Hilton
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4171)
"Stay was great and in a great location!! "
United States
Ashley
The price is Rp1.726.074
Rp2.026.239 total
includes taxes & fees
29 Jan - 30 Jan
citizenM Chicago Downtown
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (2047)
"Great stay"
United States
Kramer
The price is Rp1.367.453
Rp1.605.252 total
includes taxes & fees
20 Jan - 21 Jan
Club Quarters Hotel Wacker at Michigan, Chicago
Nightclub
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (3369)
"Nice Hotel, convenient location fot shopping and walking around"
United States
Kerima
The price is Rp1.393.595
Rp1.635.942 total
includes taxes & fees
11 Jan - 12 Jan
Club Quarters Hotel, Central Loop, Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2329)
"Great stay!"
United States
Angela
The price is Rp1.695.072
Rp2.560.455 total
includes taxes & fees
13 Jan - 14 Jan
Sable at Navy Pier Chicago, Curio Collection by Hilton
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3454)
"The Hotel was amazing great location "
United States
Donnisha
The price is Rp2.413.152
Rp3.324.647 total
includes taxes & fees
20 Jan - 21 Jan
Hyatt Regency Chicago
Indoor pool
Hilton Garden Inn Chicago Downtown/Magnificent Mile

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
8.6 out of 10, Excellent, (4332)
"Amazing staff and perfect location "
United States
Brandi
The price is Rp1.305.448
Rp1.532.466 total
includes taxes & fees
14 Jan - 15 Jan
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3170)
"Clean, nicely priced, nice staff, and perfectly located to food and nightlife "
United States
Calvin
The price is Rp1.449.792
Rp1.701.911 total
includes taxes & fees
8 Feb - 9 Feb
Eurostars Magnificent Mile
Exterior
Arlo Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1927)
"Clean and comfy room, friendly staff, great location. "
United States
Agata
The price is Rp1.691.798
Rp2.486.884 total
includes taxes & fees
4 Feb - 5 Feb
Arlo Chicago
Bar (on property)
The Whitehall Hotel, BW Premier Collection

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, (3856)
"great location"
Mexico
Isabel
The price is Rp1.282.802
Rp1.505.880 total
includes taxes & fees
12 Jan - 13 Jan
The Whitehall Hotel, BW Premier Collection
Exterior
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3017)
"Every thing is perfect, the location, safe for solo travel. "
United States
Ken
The price is Rp968.612
Rp1.629.045 total
includes taxes & fees
1 Feb - 2 Feb
Warwick Allerton - Chicago
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.
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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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

The Loop - Downtown featuring a river or creek

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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 which includes rides

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Top Sleepy Hollow Hotel Reviews

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent
"Everything was awsome"
Alisha 5-night trip
Posted 1 day ago
Club Quarters Hotel Wacker at Michigan, Chicago

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.