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Check prices for these dates

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28 Apr - 29 Apr
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29 Apr - 30 Apr
This weekend
1 May - 3 May
Next weekend
8 May - 10 May

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Our top choices for Sleepy Hollow hotels

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, (2,478 reviews)
"Excellent staff, beautiful views."
United States
Daniel
The price is 5.105.661 ₫
6.967.989 ₫ total
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,417 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is 3.896.425 ₫
5.291.358 ₫ total
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel
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, (2,239 reviews)
"Super nice staff, nice room, great location. We really enjoyed our stay. "
United States
Jim
The price is 3.141.641 ₫
4.539.506 ₫ total
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown
Front of property

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, (3,993 reviews)
"Nice hotel, lovely rooftop bar, good breakfast. Would definitely stay here again."
United States
Rory
The price is 3.499.564 ₫
4.903.277 ₫ total
includes taxes & fees
25 May - 26 May
Hotel Riu Plaza Chicago
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,144 reviews)
"Very convenient location, kind staff, and comfy rooms. "
United States
Molly Christina
The price is 3.784.459 ₫
4.499.606 ₫ total
includes taxes & fees
26 May - 27 May
River Hotel
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,102 reviews)
"Great location! Loved staying here"
United States
Nicole
The price is 6.378.124 ₫
8.369.797 ₫ total
includes taxes & fees
25 May - 26 May
Arlo Chicago
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, (1,967 reviews)
"Easy check in and clean rooms, comfortable beds and easy access to everything downtown."
United States
Megan
The price is 3.448.560 ₫
4.100.235 ₫ total
includes taxes & fees
26 May - 27 May
Hilton Garden Inn Chicago Downtown South Loop
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,054 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is 3.503.938 ₫
4.937.723 ₫ total
includes taxes & fees
26 May - 27 May
Staypineapple, An Iconic Hotel, The Loop
Exterior detail

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, (575 reviews)
"Great location great staff great hotel!"
United States
Refak
The price is 2.466.079 ₫
2.894.931 ₫ total
includes taxes & fees
30 Apr - 1 May
FOUND Hotel Chicago River North
Lobby

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, (10,162 reviews)
"Bed was super comfy and location was great. "
United States
Kelly
The price is 3.515.744 ₫
4.179.952 ₫ total
includes taxes & fees
8 May - 9 May
Congress Plaza Hotel
Restaurant

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,686 reviews)
"Great location, right across the street from the park."
United States
Jamison
The price is 3.059.150 ₫
3.637.237 ₫ total
includes taxes & fees
26 May - 27 May
Best Western Grant Park Hotel
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,760 reviews)
"Always a great stay! Love this hotel. Great area with great restaurants and fun things to do close by. "
United States
Matt
The price is 4.188.855 ₫
5.754.012 ₫ total
includes taxes & fees
25 May - 26 May
Hilton Chicago
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 13.9 km from Sleepy Hollow
8.2 out of 10, Very good, (1,388 reviews)
"This hotel is superb value and I will definitely return"
United Kingdom
Andrew
The price is 4.648.928 ₫
5.527.434 ₫ total
includes taxes & fees
6 May - 7 May
The Chicago Hotel Collection Ambassador Gold Coast
Lobby

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Theatre District, 11.6 km from Sleepy Hollow
8.4 out of 10, Very good, (1,012 reviews)
"A fantastic hotel for solo travelers - perfect area, close to museums and restaurants, great bar"
United States
Michelle Renee
The price is 3.556.845 ₫
4.228.984 ₫ total
includes taxes & fees
25 May - 26 May
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Lobby sitting area

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, (2,230 reviews)
"Perfect location great room for the price "
United States
Lisa
The price is 3.082.599 ₫
3.618.878 ₫ total
includes taxes & fees
30 Apr - 1 May
Club Quarters Hotel Wacker at Michigan, 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, (2,923 reviews)
"Clean place good location "
United States
Milca
The price is 2.631.866 ₫
3.598.728 ₫ total
includes taxes & fees
25 May - 26 May
Freehand Chicago
Nightclub

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,095 reviews)
"Nice hotel perfect location "
United States
YOEL
The price is 3.398.505 ₫
4.040.722 ₫ total
includes taxes & fees
25 May - 26 May
Central Loop Hotel
Lobby sitting area

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
8.4 out of 10, Very good, (1,894 reviews)
"Nice, clean, and quiet hotel. Staff was super nice and the bed was comfortable. Will make reservations again!"
United States
Natalie
The price is 2.808.269 ₫
3.395.112 ₫ total
includes taxes & fees
25 May - 26 May
Hotel Saint Clair- Magnificent Mile
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,137 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is 4.536.609 ₫
6.321.762 ₫ total
includes taxes & fees
8 May - 9 May
Fairmont Chicago at Millennium Park
Exterior

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,227 reviews)
"Very close to location, walkable, good staff."
United States
Eric
The price is 3.983.364 ₫
4.676.070 ₫ total
includes taxes & fees
25 May - 26 May
Bluegreen Vacations Hotel Blake, an Ascend Collection 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.
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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.

Downtown Chicago

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

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.

USA, Illinois, Chicago, Lincoln Park lagoon

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Top Sleepy Hollow Hotel Reviews

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

10/10 Excellent
"We enjoyed our stay. Location was perfect. Room could use a bit of sprucing but was fine otherwise. Lobby was a nice place to have coffee in the morning and play pool in the evening"
Carol K 3-night trip
Posted 3 hours ago
Aloft Chicago Mag Mile

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, Jedlica Performing Arts Center and Balzekas Museum of Lithuanian Culture are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Wintrust Sports Complex and Firehouse Community Arts Center of Chicago are also worth a stop.