Sleepy Hollow Hotels, Chicago

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Check prices for these dates

Tonight
17 Apr - 18 Apr
Tomorrow
18 Apr - 19 Apr
This weekend
17 Apr - 19 Apr
Next weekend
24 Apr - 26 Apr

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Our top choices for Sleepy Hollow hotels

Terrace/patio

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, (2,443 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. "
United States
Christopher
The price is AU$400
includes taxes & fees
26 Apr - 27 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reception

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,390 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is AU$331
includes taxes & fees
8 May - 9 May
Palmer House a Hilton Hotel
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,481 reviews)
"Increíble hotel súper friendly staff! "
United States
Alejandra
The price is AU$418
includes taxes & fees
9 May - 10 May
Hyatt Regency Chicago
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,874 reviews)
"Great hotel "
United States
Marina
The price is AU$233
includes taxes & fees
26 Apr - 27 Apr
Hotel Riu Plaza Chicago
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,088 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is AU$221
includes taxes & fees
28 Apr - 29 Apr
River Hotel
55-inch LCD TV with cable channels, TV, pay films

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (3,921 reviews)
"Loved the stay here !"
United States
Alisha
The price is AU$237
includes taxes & fees
26 Apr - 27 Apr
L7 Chicago by LOTTE
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,128 reviews)
"lovely hotel "
United States
alyvia
The price is AU$382
includes taxes & fees
8 May - 9 May
Fairmont Chicago at Millennium Park
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 13.5 km from Sleepy Hollow
7.6 out of 10, Good, (1,297 reviews)
"Amazing stay "
United States
Napoleon
The price is AU$189
includes taxes & fees
22 Apr - 23 Apr
The Chicago Hotel Collection - Magnificent Mile
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,134 reviews)
"The stay is well worth the affordable price."
United States
Thomas
The price is AU$213
includes taxes & fees
27 Apr - 28 Apr
Congress Plaza Hotel
Lobby

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, (1,371 reviews)
"Very beautiful place to stay"
United States
angie
The price is AU$219
includes taxes & fees
19 Apr - 20 Apr
The Chicago Hotel Collection Ambassador Gold Coast
2 restaurants, breakfast, lunch, dinner served; American cuisine

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, (3,652 reviews)
"One of the best hotels to stay. "
United States
Julamad
The price is AU$313
includes taxes & fees
26 Apr - 27 Apr
LondonHouse Chicago, Curio Collection by Hilton
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,731 reviews)
"We love staying here "
United States
Carrie
The price is AU$321
includes taxes & fees
26 Apr - 27 Apr
Hilton Chicago
Lobby

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,182 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is AU$187
includes taxes & fees
26 Apr - 27 Apr
Aloft Chicago Mag Mile
Exterior detail

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 12.6 km from Sleepy Hollow
8.6 out of 10, Excellent, (553 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is AU$142
includes taxes & fees
26 Apr - 27 Apr
FOUND Hotel Chicago River North
Lobby sitting area

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,186 reviews)
"Great stay!"
United States
Hannah
The price is AU$202
includes taxes & fees
26 Apr - 27 Apr
Club Quarters Hotel Wacker at Michigan, Chicago
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,081 reviews)
"Great location and very clean hotel with nice staff. "
United States
Carrie
The price is AU$261
includes taxes & fees
26 Apr - 27 Apr
Arlo Chicago
Lounge

Pendry Chicago

Pendry Chicago
4.5 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,137 reviews)
"Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back. "
United States
Pablo Ibarra
The price is AU$447
includes taxes & fees
10 May - 11 May
Pendry Chicago
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,233 reviews)
"Great stay!"
United States
Jessica
The price is AU$238
includes taxes & fees
19 Apr - 20 Apr
Silversmith Hotel Chicago Downtown
Nightclub

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (3,430 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is AU$207
includes taxes & fees
28 Apr - 29 Apr
Club Quarters Hotel, Central Loop, Chicago
View from property

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago
4.5 star property
Magnificent Mile, 13.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,120 reviews)
"Room was gorgeous and staff very kind. "
United States
Marilyn
The price is AU$276
includes taxes & fees
26 Apr - 27 Apr
The Westin Michigan Avenue Chicago
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.
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Our guide on 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

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

Underground passage in the Chicago O'Hare airport

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.

Top Sleepy Hollow Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"We were in room 500, great corner room! I love the old charm. Traffic noise is a bit much and it was a Thursday evening. I imagine a holiday weekend in that area would be pretty noisy. But the bed was comfy! Staff is very courteous. I would stay again, I'll try for floor 12 next time."
Larry 1-night trip
Posted 1 hour ago
Congress Plaza Hotel

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.

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