Sleepy Hollow Hotels near Chicago
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
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, (2,507 reviews)
"I loved it here and will definitely stay again."
Gina
The price is P12,186
P16,616 total
includes taxes & fees
May 26 - May 27
Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,524 reviews)
"Very good place to stay. I really liked the lobby — it’s very spacious. The lobby design is also very open and artistic."
Tong
The price is P14,445
P19,376 total
includes taxes & fees
May 25 - May 26
Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,623 reviews)
"It was very clean, beautiful place"
Grisel
The price is P13,837
P18,653 total
includes taxes & fees
May 26 - May 27
L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (4,059 reviews)
"Clean hotel great restaurant "
ELIZABETH
The price is P15,223
P18,099 total
includes taxes & fees
May 25 - May 26
Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,332 reviews)
"Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!"
Saleem
The price is P12,231
P16,716 total
includes taxes & fees
May 27 - May 28
Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,802 reviews)
"Great staff and location. "
Robert
The price is P10,076
P13,791 total
includes taxes & fees
May 26 - May 27
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,190 reviews)
"Great location & breakfast was amazing."
sierra
The price is P9,200
P12,698 total
includes taxes & fees
May 25 - May 26
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
8.2 out of 10, Very Good, (2,858 reviews)
"It is a clean room and breakfast and the drinks and it was so nice in the inside the hotel"
Sparkle
The price is P9,087
P12,615 total
includes taxes & fees
May 26 - May 27
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, (1,469 reviews)
"A nice stay and lovely location. "
Robin
The price is P9,651
P11,474 total
includes taxes & fees
Jun 3 - Jun 4
Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,251 reviews)
"Nice place to stay"
Jimmie
The price is P9,817
P11,673 total
includes taxes & fees
May 26 - May 27
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, (3,713 reviews)
"I had a great stay and would book again."
Brandi
The price is P12,098
P16,195 total
includes taxes & fees
May 26 - May 27
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,162 reviews)
"Great place"
JOSE
The price is P10,840
P15,090 total
includes taxes & fees
May 25 - May 26
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHGMagnificent Mile, 13 km from Sleepy Hollow
9.2 out of 10, Wonderful, (3,069 reviews)
"Great location ,service and staff "
Tamar
The price is P13,087
P17,720 total
includes taxes & fees
May 26 - May 27
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (10,166 reviews)
"The bar was very welcoming and the historic ambience and location was exceptional"
Patricia
The price is P8,245
P9,802 total
includes taxes & fees
May 26 - May 27
The Royal Sonesta Chicago Downtown
The Royal Sonesta Chicago DowntownThe Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,415 reviews)
"Lovely hotel
Great location
Very friendly and helpful staff"
PATRICK
The price is P10,741
P14,746 total
includes taxes & fees
May 26 - May 27
Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,459 reviews)
"My favorite place to stay!"
Teresa
The price is P11,339
P15,316 total
includes taxes & fees
May 26 - May 27
River Hotel
River HotelThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,197 reviews)
"excellent stay"
Jaeyoung
The price is P7,820
P9,298 total
includes taxes & fees
May 25 - May 26
Sports Illustrated Resorts Chicago
Sports Illustrated Resorts ChicagoTheatre District, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,405 reviews)
"Nice location nestled I'm the middle of it all. Great stay the staff was communicative."
Erik
The price is P12,231
P16,281 total
includes taxes & fees
May 27 - May 28
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,483 reviews)
"Great location and super nice hotel"
Karolina
The price is P13,279
P17,622 total
includes taxes & fees
May 25 - May 26
Arlo Chicago
Arlo ChicagoTheatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,113 reviews)
"Very beautiful hotel!"
Ingrid
The price is P10,043
P13,807 total
includes taxes & fees
May 26 - May 27
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 and neighborhoods 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.
Top Sleepy Hollow Hotel Reviews
Hilton Chicago/Magnificent Mile Suites
10/10 Excellent
