Sleepy Hollow Hotels, Chicago

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Check prices for these dates

Tonight
3 Mar - 4 Mar
Tomorrow
4 Mar - 5 Mar
This weekend
6 Mar - 8 Mar
Next weekend
13 Mar - 15 Mar

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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, (2,385 reviews)
"Great stay"
United States
Blake
The price is AU$279
includes taxes & fees
24 Mar - 25 Mar
Sable at Navy Pier Chicago, Curio Collection by Hilton
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,070 reviews)
"Great place "
United States
Kamilah
The price is AU$328
includes taxes & fees
30 Mar - 31 Mar
Fairmont Chicago at Millennium Park
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, (3,446 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
The price is AU$226
includes taxes & fees
4 Mar - 5 Mar
Hotel Riu Plaza Chicago
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,660 reviews)
"Yes it was a great stay"
United States
Rita
The price is AU$257
includes taxes & fees
1 Apr - 2 Apr
Hilton Chicago
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, (9,907 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
The price is AU$266
includes taxes & fees
21 Mar - 22 Mar
Congress Plaza Hotel
Room service – dining

The Wade

The Wade
4.5 star property
Streeterville, 13.8 km from Sleepy Hollow
8.4 out of 10, Very good, (1,705 reviews)
"Thoroughly enjoyed my stay at The Wade"
United States
Danielle
The price is AU$180
includes taxes & fees
22 Mar - 23 Mar
The Wade
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, (3,123 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is AU$164
includes taxes & fees
5 Mar - 6 Mar
Aloft Chicago Mag Mile
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,016 reviews)
"Location was great, staff was very friendly, and the rooms were clean. "
United States
Lori
The price is AU$261
includes taxes & fees
18 Mar - 19 Mar
Staypineapple, An Iconic Hotel, The Loop
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,206 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
The price is AU$250
includes taxes & fees
30 Mar - 31 Mar
Swissotel - Chicago
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,002 reviews)
"Clean hotel, helpful staff, restaurant food was delicious, great atmosphere, fabulous location!"
United States
Jennifer
The price is AU$234
includes taxes & fees
25 Mar - 26 Mar
Arlo Chicago
View from property

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
The Loop, 11.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,001 reviews)
"Beautiful place to stay, nice staff 🙏"
United States
Yu Ching Dexter
The price is AU$272
includes taxes & fees
5 Mar - 6 Mar
The Blackstone, Autograph Collection
Lobby lounge

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,004 reviews)
"Great place to stay..awesome staff!"
United States
Veronica
The price is AU$180
includes taxes & fees
4 Mar - 5 Mar
Le Méridien Essex Chicago
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,873 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is AU$195
includes taxes & fees
18 Mar - 19 Mar
Hilton Garden Inn Chicago Downtown South Loop
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, (2,311 reviews)
"Excellent stay, we loved it "
United States
Melani
The price is AU$252
includes taxes & fees
1 Apr - 2 Apr
Palmer House a Hilton 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, (3,716 reviews)
"Great location and overall great hotel."
United States
Fernando
The price is AU$226
includes taxes & fees
17 Mar - 18 Mar
L7 Chicago by LOTTE
Restaurant

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 11.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,391 reviews)
"Super comfy beds, helpful staff, free coffee and snacks and an amazing location "
United States
Stephanie
The price is AU$204
includes taxes & fees
6 Mar - 7 Mar
Hyatt Centric The Loop Chicago
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, (3,468 reviews)
"Clean room, great staff, great location "
United States
Tiffany
The price is AU$322
includes taxes & fees
1 Apr - 2 Apr
Hyatt Regency Chicago
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, (1,297 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is AU$177
includes taxes & fees
4 Mar - 5 Mar
The Chicago Hotel Collection Ambassador Gold Coast
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,289 reviews)
"Great stay "
United States
Kylee
The price is AU$225
includes taxes & fees
15 Mar - 16 Mar
Eurostars Magnificent Mile
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,034 reviews)
"Great stay, good location, accommodating staff."
United States
Ian
The price is AU$153
includes taxes & fees
5 Mar - 6 Mar
River Hotel
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 featuring a city

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.

Water Tower Place

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

The Loop - Downtown which includes a river or creek

The Loop

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

River North showing railway items, street scenes and a city

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.

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.

Top Sleepy Hollow Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"We always stay at the Congress Plaza - it's fairly convenient, the rooms are quiet, the beds comfortable, the restaurants decent. It's about a 7-10 minute walk to the Blue line, but bus stops right at the hotel or across the street. The hotel decor is gorgeous and well-maintained, everything worked, but the water pressure wasn't great and it took a long time to get any hot water."
Sharon 3-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, Balzekas Museum of Lithuanian Culture and Wintrust Sports Complex are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing around the area, United Center and Bridgeport Art Center are a couple of other sights to visit.

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