Search Hotels in Sleepy Hollow, 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
Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,395 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
Tim
The price is Rp3.059.683
Rp4.066.320 total
includes taxes & fees
8 May - 9 May
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, (2,435 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
Christopher
The price is Rp3.932.090
Rp5.199.874 total
includes taxes & fees
27 Apr - 28 Apr
FOUND Hotel Chicago River North
FOUND Hotel Chicago River NorthRiver North, 12.6 km from Sleepy Hollow
8.6 out of 10, Excellent, (549 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
William
The price is Rp1.451.069
Rp1.703.410 total
includes taxes & fees
27 Apr - 28 Apr
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, (1,368 reviews)
"The staff is so amazing, and accommodating, Cristin and David are amazing when helping! The area is so fun and so close to so many shopping centers and great places to eat. In a very convenient spot for traveling in !! "
Sonovia
The price is Rp1.950.111
Rp2.289.372 total
includes taxes & fees
30 Apr - 1 May
The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection - Magnificent MileStreeterville, 13.5 km from Sleepy Hollow
7.6 out of 10, Good, (1,291 reviews)
"I loved this hotel so much! The amenities are great and it’s a prime location with a beautiful view "
Lacey
The price is Rp1.817.321
Rp2.133.480 total
includes taxes & fees
29 Apr - 30 Apr
River Hotel
River HotelThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,082 reviews)
"Great location and nice hotel! "
James
The price is Rp2.316.876
Rp2.719.943 total
includes taxes & fees
29 Apr - 30 Apr
L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (3,918 reviews)
"Beautiful hotel, well appointed rooms, friendly staff. "
Robert
The price is Rp2.754.023
Rp3.233.170 total
includes taxes & fees
26 Apr - 27 Apr
Warwick Allerton - Chicago
Warwick Allerton - ChicagoStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,040 reviews)
"Excellent service, clean, comfortable, and a great location. "
Lisa
The price is Rp1.967.159
Rp2.812.481 total
includes taxes & fees
30 Apr - 1 May
Freehand Chicago
Freehand ChicagoRiver North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2,875 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
MaryJane
The price is Rp1.501.727
Rp2.065.046 total
includes taxes & fees
28 Apr - 29 Apr
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,231 reviews)
"Clean and quiet, very attentive staff and a great location. Would absolutely return for another stay!"
Robyn
The price is Rp2.044.303
Rp2.923.224 total
includes taxes & fees
26 Apr - 27 Apr
Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,730 reviews)
"Super friendly staff and the room was incredible!"
James
The price is Rp3.411.457
Rp4.559.695 total
includes taxes & fees
8 May - 9 May
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, (3,647 reviews)
"What an amazing location! Central and walkable to everything. CTA was close by and the views were absolutely amazing! "
Nhouka
The price is Rp4.211.521
Rp5.510.789 total
includes taxes & fees
7 May - 8 May
Aloft Chicago Mag Mile
Aloft Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,170 reviews)
"Nice location and good hotel"
Taneshia
The price is Rp2.211.447
Rp2.596.479 total
includes taxes & fees
19 Apr - 20 Apr
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, (1,227 reviews)
"It is a great hotel in a very nice location"
Emmanuel
The price is Rp2.316.876
Rp2.719.781 total
includes taxes & fees
30 Apr - 1 May
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,858 reviews)
"The property was absolutely stunning and the staff was great."
Pamela
The price is Rp2.142.704
Rp2.998.311 total
includes taxes & fees
26 Apr - 27 Apr
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, (2,191 reviews)
"Great room, lovely staff and fantastic location "
Jessica
The price is Rp2.262.876
Rp2.656.549 total
includes taxes & fees
19 Apr - 20 Apr
Eurostars Magnificent Mile
Eurostars Magnificent MileRiver North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,415 reviews)
"Great room and staff"
Jose
The price is Rp2.194.304
Rp2.576.079 total
includes taxes & fees
26 Apr - 27 Apr
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,910 reviews)
"Clean room, Staff friendly & helpful"
Carol
The price is Rp4.055.177
Rp5.267.187 total
includes taxes & fees
9 May - 10 May
Arlo Chicago
Arlo ChicagoTheatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,079 reviews)
"Second time staying @ Arlo & will come again anytime I’m in Chicago. So much to do walking distance & the staff is always amazing!"
Estephanie
The price is Rp2.298.876
Rp3.210.370 total
includes taxes & fees
26 Apr - 27 Apr
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio HotelTheatre District, 11.6 km from Sleepy Hollow
8.2 out of 10, Very good, (1,002 reviews)
"Loved this place. The staff is super friendly "
Catina
The price is Rp2.554.307
Rp3.036.997 total
includes taxes & fees
8 May - 9 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
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.
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.
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.
