Chicago Hotel Guide. Hotels in Sleepy Hollow, Chicago, United States of America

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Our top choices for Sleepy Hollow hotels

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,529 reviews)
"Great place to stay"
United States
Anthony
The price is €118
includes taxes & fees
23 Mar - 24 Mar
Claridge House Chicago, Tapestry Collection by Hilton

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Gold Coast, 13.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,329 reviews)
"We loved are stay at the Thompson hotel. It's very clean, and is close to our favorite shops and restaurants. "
United States
Corry
The price is €165
includes taxes & fees
5 Apr - 6 Apr
Thompson Chicago, by Hyatt

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,396 reviews)
"Great location, friendly staff. "
United States
Brian
The price is €180
includes taxes & fees
24 Mar - 25 Mar
Sable at Navy Pier Chicago, Curio Collection by Hilton

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (912 reviews)
"Very nice place to stay!"
United States
Daniel
The price is €114
includes taxes & fees
22 Mar - 23 Mar
Moxy Chicago Downtown

Level Chicago Fulton Market

Level Chicago Fulton Market
4.0 star property
West Loop, 11.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (425 reviews)
"room was perfect "
United States
Shaquille
The price is €164
includes taxes & fees
22 Mar - 23 Mar
Level Chicago Fulton Market

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,002 reviews)
"Great location. "
United States
Paige
The price is €144
includes taxes & fees
29 Mar - 30 Mar
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
11 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,002 reviews)
"Room was very clean and comfortable. Food at the hotel is a bit pricey but good. Very well located close to restaurants, bars and shops "
United States
Kim Z.
The price is €182
includes taxes & fees
22 Mar - 23 Mar
The Hoxton Chicago

Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North
3.5 star property
River North, 12.6 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,104 reviews)
"Everything is nearby and loved the breakfast they serve each day."
United States
Vrenelyn
The price is €127
includes taxes & fees
22 Mar - 23 Mar
Springhill Suites by Marriott Chicago Downtown/ River North

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
11.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,003 reviews)
"We loved the hotel, staff was friendly and area was amazing for food and is walkable to a lot of places on the west loop!"
United States
Benjamin
The price is €146
includes taxes & fees
26 Mar - 27 Mar
Hampton Inn Chicago West Loop Fulton Market Area

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop
3.5 star property
10.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,191 reviews)
"Great location, friendly staff, spacious room"
United States
Mary
The price is €139
includes taxes & fees
22 Mar - 23 Mar
Hyatt House Chicago West Loop

ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 12.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,970 reviews)
"Excellent location for shops,restaurants and casino."
United States
Deborah
The price is €100
includes taxes & fees
22 Mar - 23 Mar
ACME Hotel Chicago, Outset Collection by Hilton

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,336 reviews)
"Clean room, nice staff"
United States
Geidy
The price is €226
includes taxes & fees
16 Mar - 17 Mar
Sofitel Chicago Magnificent Mile

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,869 reviews)
"Overall a great stay."
United States
Joshua
The price is €175
includes taxes & fees
29 Mar - 30 Mar
Radisson Blu Aqua Hotel Chicago

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,621 reviews)
"Beautiful rooms, friendly staff, great location"
United States
Heather
The price is €235
includes taxes & fees
29 Mar - 30 Mar
LondonHouse Chicago, Curio Collection by Hilton

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 13.9 km from Sleepy Hollow
8.2 out of 10, Very good, (1,309 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is €138
includes taxes & fees
16 Mar - 17 Mar
The Chicago Hotel Collection Ambassador Gold Coast

The Emily Hotel

The Emily Hotel
4.0 star property
11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,315 reviews)
"Clean rooms, great amenities and amazing location "
United States
melina
The Emily Hotel

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
River North, 11.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,204 reviews)
"Great stay"
United States
Joshua
The price is €126
includes taxes & fees
5 Apr - 6 Apr
Holiday Inn Chicago Dwtn - The Mart by IHG

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
River North, 12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (4,392 reviews)
"Room was clean.. staff was great. "
United States
Ricoya
The price is €105
includes taxes & fees
24 Mar - 25 Mar
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop
4.0 star property
The Loop, 11.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,478 reviews)
"Excellent, welcoming staff. Great value."
United States
John
The price is €165
includes taxes & fees
29 Mar - 30 Mar
Canopy by Hilton Chicago Central Loop

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,353 reviews)
"Loved this hotel!"
United States
Ellen
The price is €109
includes taxes & fees
22 Mar - 23 Mar
DoubleTree by Hilton Chicago - Magnificent Mile
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.

Top Sleepy Hollow Hotel Reviews

Frequently asked questions

What's it like in Sleepy Hollow?
Sleepy Hollow is a neighbourhood that travellers like for its restaurants.
If I need to cancel my hotel reservation in Sleepy Hollow, will I receive a refund?
Yes! The majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of your booking. Put your dates in and click on "Search", then filter by "fully refundable" to view the top deals on offer in Sleepy Hollow.
What can I see and do in this Chicago neighbourhood?
Hawthorne Works Museum, Jedlica Performing Arts Center and Balzekas Museum of Lithuanian Culture are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Wintrust Sports Complex and Firehouse Community Arts Center of Chicago are also worth a stop.