Sleepy Hollow Hotels near Chicago

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Our top choices for Sleepy Hollow hotels

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, (2,435 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 P11,157
P15,148 total
includes taxes & fees
Apr 6 - Apr 7
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (3,158 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is P7,288
P8,557 total
includes taxes & fees
Apr 12 - Apr 13
Aloft Chicago Mag Mile

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,055 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is P6,566
P7,707 total
includes taxes & fees
Apr 5 - Apr 6
River Hotel

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,717 reviews)
"We love staying here "
United States
Carrie
The price is P11,987
P15,839 total
includes taxes & fees
Apr 10 - Apr 11
Hilton Chicago

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, (2,235 reviews)
"Great stay!"
United States
Jessica
The price is P6,452
P9,412 total
includes taxes & fees
Apr 12 - Apr 13
Silversmith Hotel Chicago Downtown

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, (10,017 reviews)
"The stay is well worth the affordable price."
United States
Thomas
The price is P6,564
P7,706 total
includes taxes & fees
Apr 5 - Apr 6
Congress Plaza Hotel

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, (2,099 reviews)
"lovely hotel "
United States
alyvia
The price is P11,987
P16,192 total
includes taxes & fees
Apr 5 - Apr 6
Fairmont Chicago at Millennium Park

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, (3,715 reviews)
"Great hotel "
United States
Marina
The price is P7,770
P10,819 total
includes taxes & fees
Apr 28 - Apr 29
Hotel Riu Plaza Chicago

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,056 reviews)
"For the price, it was a very nice a room and location. "
United States
Anna
The price is P5,581
P6,551 total
includes taxes & fees
Apr 8 - Apr 9
Central Loop Hotel

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,475 reviews)
"Increíble hotel súper friendly staff! "
United States
Alejandra
The price is P12,890
P17,253 total
includes taxes & fees
Apr 6 - Apr 7
Hyatt Regency Chicago

Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,307 reviews)
"Everything was really nice!"
United States
Tristen
The price is P9,885
P11,605 total
includes taxes & fees
Apr 19 - Apr 20
Hilton Garden Inn Chicago Central Loop

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,237 reviews)
"Excellent stay."
United States
Fenton
The price is P12,956
P17,331 total
includes taxes & fees
Apr 10 - Apr 11
Swissotel - Chicago

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, (2,140 reviews)
"Great room, lovely staff and fantastic location "
United Kingdom
Jessica
The price is P6,566
P7,708 total
includes taxes & fees
Apr 5 - Apr 6
Club Quarters Hotel Wacker at Michigan, Chicago

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,044 reviews)
"Excellent stay overall"
United States
Emre
The price is P8,257
P9,693 total
includes taxes & fees
Apr 12 - Apr 13
Hilton Chicago/Magnificent Mile Suites

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, (1,345 reviews)
"Very beautiful place to stay"
United States
angie
The price is P6,852
P8,043 total
includes taxes & fees
Apr 19 - Apr 20
The Chicago Hotel Collection Ambassador Gold Coast

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,358 reviews)
"Fantastic location and a luxury hotel for a fair price."
United States
Cornelius
The price is P10,788
P14,432 total
includes taxes & fees
Apr 6 - Apr 7
Sofitel Chicago Magnificent Mile

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, (2,398 reviews)
"Loved this hotel!"
United States
Ellen
The price is P7,168
P8,415 total
includes taxes & fees
Apr 5 - Apr 6
DoubleTree by Hilton Chicago - Magnificent Mile

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Theatre District, 11.6 km from Sleepy Hollow
8.2 out of 10, Very Good, (1,005 reviews)
"Great hotel."
United States
Kristin
The price is P10,602
P12,445 total
includes taxes & fees
Apr 5 - Apr 6
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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, (3,416 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is P6,263
P7,352 total
includes taxes & fees
Apr 27 - Apr 28
Club Quarters Hotel, Central Loop, Chicago

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, (527 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is P5,096
P5,982 total
includes taxes & fees
Apr 5 - Apr 6
FOUND Hotel Chicago River North
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 and neighborhoods 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.

O'Hare

Consider a visit to Fashion Outlets of Chicago and take some time to enjoy the abundant dining options during your time in O'Hare. If you want to see more of the city, jump on the metro at Cumberland Station or Remote Parking Station.

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

Frequently asked questions

What's it like in Sleepy Hollow?
Sleepy Hollow is a neighborhood that travelers 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 room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to get the best deals available in Sleepy Hollow.
What can I see and do in this Chicago neighborhood?
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.