Hotels in Sleepy Hollow, Chicago
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Our top choices for Sleepy Hollow hotels
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonStreeterville, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,478 reviews)
"Excellent staff, beautiful views."
Daniel
The price is RM749
RM1,025 total
includes taxes & fees
26 May - 27 May
Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,420 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
Cynthia
The price is RM584
RM812 total
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,241 reviews)
"Super nice staff, nice room, great location. We really enjoyed our stay. "
Jim
The price is RM471
RM681 total
includes taxes & fees
25 May - 26 May
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,002 reviews)
"Great location, rooms good "
Lynette
The price is RM525
RM735 total
includes taxes & fees
27 May - 28 May
River Hotel
River HotelThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,137 reviews)
"Very convenient location, kind staff, and comfy rooms. "
Molly Christina
The price is RM534
RM635 total
includes taxes & fees
26 May - 27 May
Arlo Chicago
Arlo ChicagoTheatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,100 reviews)
"Great location! Loved staying here"
Nicole
The price is RM601
RM834 total
includes taxes & fees
26 May - 27 May
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South LoopThe Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,968 reviews)
"Easy check in and clean rooms, comfortable beds and easy access to everything downtown."
Megan
The price is RM517
RM615 total
includes taxes & fees
26 May - 27 May
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopTheatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,053 reviews)
"Wonderful restaurant, amazing food."
Robert
The price is RM526
RM741 total
includes taxes & fees
25 May - 26 May
FOUND Hotel Chicago River North
FOUND Hotel Chicago River NorthRiver North, 12.6 km from Sleepy Hollow
8.4 out of 10, Very good, (577 reviews)
"Great location great staff great hotel!"
Refak
The price is RM428
RM502 total
includes taxes & fees
25 May - 26 May
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,117 reviews)
"Bed was super comfy and location was great. "
Kelly
The price is RM527
RM627 total
includes taxes & fees
8 May - 9 May
Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,683 reviews)
"Great location, right across the street from the park."
Jamison
The price is RM510
RM606 total
includes taxes & fees
26 May - 27 May
Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,765 reviews)
"Always a great stay! Love this hotel. Great area with great restaurants and fun things to do close by. "
Matt
The price is RM628
RM863 total
includes taxes & fees
26 May - 27 May
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastGold Coast, 13.9 km from Sleepy Hollow
8.2 out of 10, Very good, (1,394 reviews)
"This hotel is superb value and I will definitely return"
Andrew
The price is RM661
RM786 total
includes taxes & fees
11 May - 12 May
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio HotelTheatre District, 11.6 km from Sleepy Hollow
8.4 out of 10, Very good, (1,004 reviews)
"A fantastic hotel for solo travelers - perfect area, close to museums and restaurants, great bar"
Michelle Renee
The price is RM589
RM700 total
includes taxes & fees
8 May - 9 May
Club Quarters Hotel Wacker at Michigan, Chicago
Club Quarters Hotel Wacker at Michigan, ChicagoThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,233 reviews)
"Perfect location great room for the price "
Lisa
The price is RM625
RM743 total
includes taxes & fees
7 May - 8 May
Freehand Chicago
Freehand ChicagoRiver North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2,930 reviews)
"Clean place good location "
Milca
The price is RM387
RM530 total
includes taxes & fees
25 May - 26 May
Central Loop Hotel
Central Loop HotelTheatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,098 reviews)
"Nice hotel perfect location "
YOEL
The price is RM510
RM606 total
includes taxes & fees
26 May - 27 May
Hotel Saint Clair- Magnificent Mile
Hotel Saint Clair- Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
8.4 out of 10, Very good, (1,887 reviews)
"Nice, clean, and quiet hotel. Staff was super nice and the bed was comfortable. Will make reservations again!"
Natalie
The price is RM535
RM647 total
includes taxes & fees
11 May - 12 May
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe 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."
Nicole
The price is RM681
RM948 total
includes taxes & fees
8 May - 9 May
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection HotelThe Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,228 reviews)
"Very close to location, walkable, good staff."
Eric
The price is RM598
RM701 total
includes taxes & fees
25 May - 26 May
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.
Where to stay in Sleepy Hollow
Find the best Sleepy Hollow areas for the activities you enjoy most.
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
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
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
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
