Sleepy Hollow Hotels near Chicago

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Nov 11 - Nov 12
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Nov 12 - Nov 13
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Nov 14 - Nov 16
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Nov 21 - Nov 23

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Top Trending Hotels Near Sleepy Hollow, Chicago

Reception
River Hotel

River Hotel

4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (4794)
"Beautiful hotel. Had a nice stay"
United States
Esther
The price is P5,813
P6,824 total
includes taxes & fees
Nov 24 - Nov 25
River Hotel
Outdoor pool, cabanas (surcharge), pool umbrellas
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, (2138)
"Very nice hotel "
United States
Patrick
The price is P5,613
P6,589 total
includes taxes & fees
Nov 23 - Nov 24
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
River North, 13 km from Sleepy Hollow
8.8 out of 10, Excellent, (3097)
"Awesome location and excellent service, the staff was great!"
United States
Salvador
The price is P6,375
P7,484 total
includes taxes & fees
Dec 10 - Dec 11
Eurostars Magnificent Mile
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, (2226)
"Room was spotless…staff was great!"
United States
Tamika
The price is P6,260
P9,356 total
includes taxes & fees
Nov 25 - Nov 26
Sable at Navy Pier Chicago, Curio Collection by Hilton
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, (2891)
"Had a wonderful stay! The hotel was very comfortable, clean, and relaxing. The staff were friendly and helpful, and the room was cozy and well-maintained. Would definitely stay here again!"
United States
Angel
The price is P5,844
P6,860 total
includes taxes & fees
Dec 7 - Dec 8
Aloft Chicago Mag 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, (2292)
"Didn’t have breakfast there… checking in I was not greeted, I stood in line while the agent was on his personal cell phone and eventually he looked up. He had no customer service what so ever, and I was put in a room with two beds and he showed no compassion. I had to call to speak to a supervisor about him. I was moved the next day to a room with a king, but with a broken exhaust fan and broken refrigerator. My experience at this property was not great "
United States
Jamel
The price is P6,693
P9,587 total
includes taxes & fees
Nov 24 - Nov 25
Hilton Chicago
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, (1674)
"Great hotel and amenities "
United States
Adrienne
The price is P5,306
P6,229 total
includes taxes & fees
Nov 23 - Nov 24
Crowne Plaza Chicago West Loop by IHG
Terrace/patio
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4021)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is P6,715
P7,882 total
includes taxes & fees
Nov 12 - Nov 13
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, (3273)
"Comfortable stay , great location."
United States
Carlos A.
The price is P5,971
P7,009 total
includes taxes & fees
Dec 7 - Dec 8
Hilton Chicago/Magnificent Mile Suites
Exterior
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, (4156)
"Great location! "
Canada
Meghan
The price is P5,525
P6,486 total
includes taxes & fees
Dec 7 - Dec 8
Hilton Garden Inn Chicago Downtown/Magnificent Mile
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, (9553)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
Congress Plaza Hotel
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, (2563)
"Rooms are clean, staff are nice and friendly "
United States
Karen
The price is P4,722
P6,582 total
includes taxes & fees
Nov 12 - Nov 13
Freehand Chicago
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, (2753)
"Great staff and a very nice locating "
United States
Madison
The price is P6,108
P8,834 total
includes taxes & fees
Dec 8 - Dec 9
Hotel Riu Plaza Chicago
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
River North, 12.6 km from Sleepy Hollow
8.2 out of 10, Very Good, (317)
"very clean and modern, staff was very friendly"
United States
Edrick
The price is P4,425
P5,194 total
includes taxes & fees
Dec 7 - Dec 8
FOUND Hotel Chicago River North
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, sun 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, (1005)
"Really great location and warm and friendly staff"
United Kingdom
David
The price is P5,903
P7,638 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn & Suites Chicago - Downtown by IHG
Egyptian cotton sheets, premium bedding, pillowtop 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, (3699)
"Great stay"
Canada
Jeremy
The price is P5,020
P5,893 total
includes taxes & fees
Dec 8 - Dec 9
The Whitehall Hotel, BW Premier Collection
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2063)
"Beautiful hotel, great location, helpful staff, and an exceptional price!"
United States
McAndrew
Silversmith Hotel Chicago Downtown
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, (2054)
"Great place to stay."
United States
Aaron
The price is P6,465
P9,063 total
includes taxes & fees
Nov 24 - Nov 25
Palmer House a Hilton Hotel
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, (1702)
"Staff members was vey nice "
United States
Damonica
The price is P4,905
P5,758 total
includes taxes & fees
Nov 24 - Nov 25
Hilton Garden Inn Chicago Downtown South Loop
Bar (on property)
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
River North, 12 km from Sleepy Hollow
8.8 out of 10, Excellent, (3341)
"Great stay!"
United States
Shanell
The price is P6,131
P7,198 total
includes taxes & fees
Nov 24 - Nov 25
voco Chicago Downtown - Riverwalk by IHG
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 and neighborhoods for the activities you enjoy most.
Downtown Chicago which includes 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 showing 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.

Lincoln Park featuring modern architecture and a city

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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

10/10 Excellent
"Clean room "
Tiera 2-night trip
Posted 2 days ago
Hotel Felix River North/Magnificent Mile

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Frequently asked questions

What's it like in Sleepy Hollow?
Sleepy Hollow is a neighborhood that travelers 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 room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to get the best deals available in Sleepy Hollow.
What can I see and do in this Chicago neighborhood?
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.