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, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,519 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
Deborah
The price is ฿7,432
฿9,957 total
includes taxes & fees
2 Jul - 3 Jul
Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,491 reviews)
"Staff was great."
Marianne
The price is ฿6,338
฿8,695 total
includes taxes & fees
2 Jul - 3 Jul
Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,849 reviews)
"great hotel and excellent to stay"
Ruben
The price is ฿7,768
฿10,190 total
includes taxes & fees
30 Jun - 1 Jul
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,309 reviews)
"Great location & breakfast was amazing."
sierra
The price is ฿6,144
฿8,230 total
includes taxes & fees
30 Jun - 1 Jul
Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,652 reviews)
"I LOVED my stay , i WILL be back."
Latonia
The price is ฿6,475
฿8,857 total
includes taxes & fees
2 Jul - 3 Jul
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,174 reviews)
"Great place"
JOSE
The price is ฿6,793
฿9,236 total
includes taxes & fees
1 Jul - 2 Jul
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,142 reviews)
"Excellent stay"
Jennifer
The price is ฿4,534
฿5,391 total
includes taxes & fees
29 Jun - 30 Jun
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHGMagnificent Mile, 13 km from Sleepy Hollow
9.2 out of 10, Wonderful, (3,095 reviews)
"Excellent staff and location"
Sandra
The price is ฿7,443
฿9,987 total
includes taxes & fees
1 Jul - 2 Jul
The Royal Sonesta Chicago Downtown
The Royal Sonesta Chicago DowntownThe Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,446 reviews)
"Great location, nice property, helpful staff, and spacious, comfortable rooms."
Sunil
The price is ฿5,656
฿7,764 total
includes taxes & fees
2 Jul - 3 Jul
River Hotel
River HotelThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,217 reviews)
"Location is great and staff is very nice and helpful"
Deborah
The price is ฿4,117
฿4,894 total
includes taxes & fees
1 Jul - 2 Jul
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, (3,725 reviews)
"Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again."
Matson
The price is ฿7,211
฿9,528 total
includes taxes & fees
21 Jun - 22 Jun
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,250 reviews)
"Great location"
Gabino
The price is ฿5,197
฿7,171 total
includes taxes & fees
28 Jun - 29 Jun
Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,469 reviews)
"Beautiful place to stay."
Charles Otto
The price is ฿6,189
฿8,324 total
includes taxes & fees
2 Jul - 3 Jul
Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,362 reviews)
"Great location!"
Maria
The price is ฿7,869
฿10,501 total
includes taxes & fees
2 Jul - 3 Jul
Hampton Inn Majestic Chicago Theatre District
Hampton Inn Majestic Chicago Theatre DistrictTheatre District, 12 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,003 reviews)
"Room was clean great location"
Eric
The price is ฿5,774
฿6,865 total
includes taxes & fees
28 Jun - 29 Jun
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, (1,081 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
Debby
The price is ฿4,843
฿6,722 total
includes taxes & fees
1 Jul - 2 Jul
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, (1,530 reviews)
"Clean room, helpful staff and breakfast was amazing."
Scott
The price is ฿5,081
฿6,040 total
includes taxes & fees
22 Jun - 23 Jun
Sports Illustrated Resorts Chicago
Sports Illustrated Resorts ChicagoTheatre District, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,395 reviews)
"Nice location nestled I'm the middle of it all. Great stay the staff was communicative."
Erik
The price is ฿6,933
฿9,158 total
includes taxes & fees
28 Jun - 29 Jun
Arlo Chicago
Arlo ChicagoTheatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,118 reviews)
"Love our stay! Will def stay again!!"
Stephany
The price is ฿6,512
฿8,724 total
includes taxes & fees
14 Jun - 15 Jun
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.
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.
