Sleepy Hollow Hotels, 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, (2,550 reviews)
"The location was very convenient"
Jeffrey
The price is NZ$496
includes taxes & fees
30 June - 1 July
Omni Chicago Hotel
Omni Chicago HotelStreeterville, 13.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,811 reviews)
"All around great property and a wonderful location"
Bruce
The price is NZ$318
includes taxes & fees
1 July - 2 July
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,277 reviews)
"Great stay!"
Daniel
The price is NZ$278
includes taxes & fees
29 June - 30 June
Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,508 reviews)
"Beautiful place to stay."
Charles Otto
The price is NZ$425
includes taxes & fees
1 July - 2 July
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,446 reviews)
"Clean room, great breakfast and close to everything we needed"
Kyle
The price is NZ$375
includes taxes & fees
6 July - 7 July
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown ChicagoThe Loop, 11.8 km from Sleepy Hollow
7.4 out of 10, Good, (2,644 reviews)
"Great location and helpful staff."
Ming
The price is NZ$275
includes taxes & fees
1 July - 2 July
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, (1,101 reviews)
"Good location, friendly staff"
Philip
The price is NZ$334
includes taxes & fees
6 July - 7 July
Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,389 reviews)
"Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
Sergio
The price is NZ$419
includes taxes & fees
1 July - 2 July
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,254 reviews)
"Awesome place"
Mellany
The price is NZ$317
includes taxes & fees
6 July - 7 July
The Blackstone, Autograph Collection
The Blackstone, Autograph CollectionThe Loop, 11.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,011 reviews)
"Great location, clean hotel, and very accommodating staff."
Neydee
The price is NZ$383
includes taxes & fees
1 July - 2 July
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonThe Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,742 reviews)
"Great location!"
William
The price is NZ$480
includes taxes & fees
1 July - 2 July
Eurostars Magnificent Mile
Eurostars Magnificent MileRiver North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,654 reviews)
"Had an amazing stay here!"
Audrey
The price is NZ$323
includes taxes & fees
2 July - 3 July
Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,733 reviews)
"Nice place to stay at"
Tammy
The price is NZ$243
includes taxes & fees
1 July - 2 July
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,426 reviews)
"Great stay!"
Avradita
The price is NZ$338
includes taxes & fees
2 July - 3 July
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, (1,607 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
Zhiwen
The price is NZ$319
includes taxes & fees
29 June - 30 June
Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,667 reviews)
"Location was great"
Pamela
The price is NZ$467
includes taxes & fees
2 July - 3 July
Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,517 reviews)
"Staff was great."
Marianne
The price is NZ$475
includes taxes & fees
2 July - 3 July
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, (2,046 reviews)
"Great room and view. Clean, near by Grant park, great staff."
Kimberly
The price is NZ$299
includes taxes & fees
6 July - 7 July
Hotel 55 Chicago Downtown
Hotel 55 Chicago DowntownRiver North, 13.1 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,597 reviews)
"Great stay"
Matt
The price is NZ$338
includes taxes & fees
1 July - 2 July
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,199 reviews)
"Location is excellent!"
Michele
The price is NZ$499
includes taxes & fees
7 July - 8 July
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.
Our guide on 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
An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.
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.
Top Sleepy Hollow Hotel Reviews
The Chicago Hotel Collection - Magnificent Mile
8/10 Good
