Search Hotels in Sleepy Hollow, Chicago
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Top Trending Hotels Near Sleepy Hollow, Chicago
The Godfrey Hotel Chicago
River North, 12.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1910)
"Awesome staff and great location "
Luis C
The price is ₹7,884
₹11,369 total
includes taxes & fees
29 Dec - 30 Dec
Aloft Chicago Downtown River North
River North, 12.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1156)
"Modern vibes, a lot to see, eat and do at walking distance, spotless room and very comfy bed. Very friendly staff. Definitely would stay there again."
Cristina
The price is ₹9,449
₹11,092 total
includes taxes & fees
21 Dec - 22 Dec
The Wade
Streeterville, 13.8 km from Sleepy Hollow
8.4 out of 10, Very good, (1501)
"Great location, walkable to so many area attractions. Would definitely stay here again. "
Debbie
The price is ₹9,088
₹10,668 total
includes taxes & fees
6 Jan - 7 Jan 2026
Club Quarters Hotel Wacker at Michigan, Chicago
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (1950)
"A good place for stay "
Julio
The price is ₹7,484
₹8,785 total
includes taxes & fees
7 Dec - 8 Dec
The Royal Sonesta Chicago River North
River North, 12.8 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2297)
"Great place - stayed with extended family. Lounge areas and amenities met everyone’s needs "
Elizabeth
The price is ₹9,260
₹13,750 total
includes taxes & fees
7 Dec - 8 Dec
The Chicago Hotel Collection - Magnificent Mile
Streeterville, 13.5 km from Sleepy Hollow
7.6 out of 10, Good, (1176)
"The room was spacious and clean and it was a good value."
Dj
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
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.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).
Top Sleepy Hollow Hotel Reviews
Silversmith Hotel Chicago Downtown
10/10 Excellent
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