Search 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, 8.9 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (2,389 reviews)
"Great stay"
Blake
The price is £146
includes taxes & fees
24 Mar - 25 Mar
Swissotel - Chicago
Swissotel - Chicago8.1 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (3,215 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
Jon
The price is £132
includes taxes & fees
24 Mar - 25 Mar
Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 7.5 mi from Sleepy Hollow
8.6 out of 10, Excellent, (2,313 reviews)
"Excellent stay, we loved it "
Melani
The price is £150
includes taxes & fees
6 Mar - 7 Mar
Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 8 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (3,488 reviews)
"Clean room, great staff, great location "
Tiffany
The price is £194
includes taxes & fees
24 Mar - 25 Mar
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 8.2 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (3,390 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
Brisa
The price is £107
includes taxes & fees
4 Mar - 5 Mar
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 7.4 mi from Sleepy Hollow
8.0 out of 10, Very good, (9,926 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
Jennifer
The price is £78
includes taxes & fees
24 Feb - 25 Feb
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastGold Coast, 8.7 mi from Sleepy Hollow
8.2 out of 10, Very good, (1,287 reviews)
"Great hotel with great location. Would definitely stay here again. "
Sheila
The price is £93
includes taxes & fees
24 Feb - 25 Feb
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopTheatre District, 7.6 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (1,010 reviews)
"Location was great, staff was very friendly, and the rooms were clean. "
Lori
The price is £128
includes taxes & fees
22 Mar - 23 Mar
Aloft Chicago Mag Mile
Aloft Chicago Mag MileStreeterville, 8.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (3,105 reviews)
"Great location and friendly staff. "
Pablo
The price is £75
includes taxes & fees
24 Feb - 25 Feb
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonThe Loop, 7.9 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (3,606 reviews)
"Staff was friendly and loved the decor at this hotel…will definitely be staying again"
Osama
The price is £171
includes taxes & fees
1 Mar - 2 Mar
The Blackstone, Autograph Collection
The Blackstone, Autograph CollectionThe Loop, 7.3 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,005 reviews)
"Beautiful place to stay, nice staff 🙏"
Yu Ching Dexter
The price is £143
includes taxes & fees
26 Feb - 27 Feb
L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 7.8 mi from Sleepy Hollow
9.6 out of 10, Exceptional, (3,684 reviews)
"Great location and overall great hotel."
Fernando
The price is £140
includes taxes & fees
26 Feb - 27 Feb
Hilton Chicago
Hilton ChicagoThe Loop, 7.3 mi from Sleepy Hollow
8.4 out of 10, Very good, (2,650 reviews)
"The room was clean and the staff was very friendly."
Andrea
The price is £142
includes taxes & fees
5 Mar - 6 Mar
Pendry Chicago
Pendry ChicagoTheatre District, 7.9 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (1,152 reviews)
"Excellent hotel and location."
Marcelo
The price is £187
includes taxes & fees
15 Mar - 16 Mar
Hyatt Centric The Loop Chicago
Hyatt Centric The Loop ChicagoTheatre District, 7.4 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (2,396 reviews)
"Super comfy beds, helpful staff, free coffee and snacks and an amazing location "
Stephanie
The price is £100
includes taxes & fees
27 Feb - 28 Feb
Le Méridien Essex Chicago
Le Méridien Essex ChicagoThe Loop, 7.2 mi from Sleepy Hollow
8.8 out of 10, Excellent, (1,010 reviews)
"Great place to stay..awesome staff!"
Veronica
The price is £93
includes taxes & fees
16 Mar - 17 Mar
Sports Illustrated Resorts Chicago
Sports Illustrated Resorts ChicagoTheatre District, 7.8 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (1,403 reviews)
"Staff was super friendly and rooms were clean. Definitely will come back "
Daisy
The price is £157
includes taxes & fees
26 Feb - 27 Feb
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago8 mi from Sleepy Hollow
8.6 out of 10, Excellent, (1,873 reviews)
"Room was very nice, views were fantastic and the restaurant was excellent "
Michael
The price is £167
includes taxes & fees
28 Feb - 1 Mar
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 7.6 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (2,235 reviews)
"Amazing hotel and staff!"
Corey
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
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
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.
O'Hare
Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.
Top Sleepy Hollow Hotel Reviews
Palmer House a Hilton Hotel
10/10 Excellent
Frequently asked questions
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