Sleepy Hollow Hotels, Chicago

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Check prices for these dates

This weekend
5 June - 7 June
Next weekend
12 June - 14 June

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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, (2,521 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
United States
Deborah
The price is AU$444
includes taxes & fees
30 June - 1 July
Sable at Navy Pier Chicago, Curio Collection by Hilton
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, (3,494 reviews)
"Staff was great."
United States
Marianne
The price is AU$374
includes taxes & fees
2 July - 3 July
Hyatt Regency Chicago
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,851 reviews)
"great hotel and excellent to stay"
United States
Ruben
The price is AU$366
includes taxes & fees
2 July - 3 July
Hilton 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, (4,318 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is AU$354
includes taxes & fees
30 June - 1 July
Hotel Riu Plaza Chicago
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,653 reviews)
"Excellent location."
United States
Mirna
The price is AU$380
includes taxes & fees
2 July - 3 July
Sheraton Grand Chicago Riverwalk
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, (2,177 reviews)
"Great place"
United States
JOSE
The price is AU$362
includes taxes & fees
1 July - 2 July
Fairmont Chicago at Millennium Park
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, (10,152 reviews)
"Excellent stay"
United States
Jennifer
The price is AU$232
includes taxes & fees
29 June - 30 June
Congress Plaza Hotel
Indoor pool

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 13 km from Sleepy Hollow
9.2 out of 10, Wonderful, (3,097 reviews)
"Excellent staff and location"
United States
Sandra
The price is AU$401
includes taxes & fees
30 June - 1 July
InterContinental Chicago Magnificent Mile by IHG
Ballroom

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,451 reviews)
"Great location, nice property, helpful staff, and spacious, comfortable rooms."
United States
Sunil
The price is AU$334
includes taxes & fees
2 July - 3 July
The Royal Sonesta Chicago Downtown
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,223 reviews)
"Great location"
United States
Nashadia
The price is AU$253
includes taxes & fees
1 July - 2 July
River Hotel
2 restaurants; breakfast, lunch and dinner served

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, (3,731 reviews)
"Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again."
United States
Matson
The price is AU$407
includes taxes & fees
21 June - 22 June
LondonHouse Chicago, Curio Collection by Hilton
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, (2,255 reviews)
"Great location"
United States
Gabino
The price is AU$279
includes taxes & fees
28 June - 29 June
Silversmith Hotel Chicago Downtown
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, (2,471 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is AU$346
includes taxes & fees
2 July - 3 July
Palmer House a Hilton Hotel
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,367 reviews)
"Great location!"
United States
Maria
The price is AU$406
includes taxes & fees
1 July - 2 July
Swissotel - Chicago
Exterior

Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Theatre District, 12 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,003 reviews)
"Room was clean great location"
United States
Eric
The price is AU$318
includes taxes & fees
1 July - 2 July
Hampton Inn Majestic Chicago Theatre District
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, (1,856 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is AU$521
includes taxes & fees
14 June - 15 June
The Wade
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, (1,082 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
United States
Debby
The price is AU$272
includes taxes & fees
1 July - 2 July
Staypineapple, An Iconic Hotel, The Loop
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, (1,532 reviews)
"Clean room, helpful staff and breakfast was amazing."
United States
Scott
The price is AU$259
includes taxes & fees
29 June - 30 June
The Chicago Hotel Collection Ambassador Gold Coast
Studio, 2 Double Beds | Bathroom

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,396 reviews)
"Nice location nestled I'm the middle of it all. Great stay the staff was communicative."
United States
Erik
The price is AU$376
includes taxes & fees
28 June - 29 June
Sports Illustrated Resorts Chicago
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,119 reviews)
"Excellent location and welcoming staff."
United States
Tammy
The price is AU$373
includes taxes & fees
2 July - 3 July
Arlo 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.

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.

Panoramic view of Lincoln Park and the Chicago skyline.

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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

8/10 Good
"Great location and very busy on the weekends. You can do a lot better for parking on Spothero.com. Try it! The property is an aging up Hilton from the 1990’s. Comfortable, brown and beige and in need of an overhaul. But the pool is rather majestic. Sky high, glass enclosed, well heated and open very early. That goes a long way for me."
david 2-night trip
Posted less than an hour ago
Hilton Chicago/Magnificent Mile Suites

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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