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Our top choices for Sleepy Hollow hotels

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,069 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is Rp1.651.790
Rp2.433.731 total
includes taxes & fees
25 Jan - 26 Jan
Hyatt Centric Chicago Magnificent Mile

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North
3.5 star property
River North, 12.6 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,190 reviews)
"Great stay!"
United States
Tea
The price is Rp1.790.844
Rp2.102.272 total
includes taxes & fees
25 Jan - 26 Jan
Aloft Chicago Downtown River North

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 12.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,976 reviews)
"The room was nice, the area was perfect for walking distance for food and activities. "
United States
Alexis
The price is Rp1.329.909
Rp1.956.935 total
includes taxes & fees
10 Feb - 11 Feb
The Godfrey Hotel 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, (3,709 reviews)
"Great stay!!!"
United States
Lorenzo Martrel
The price is Rp1.503.282
Rp1.764.703 total
includes taxes & fees
1 Feb - 2 Feb
Hilton Chicago/Magnificent Mile Suites

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, (3,529 reviews)
"Amazing place to stay and super accommodating "
United States
Carson
The price is Rp2.370.469
Rp2.782.693 total
includes taxes & fees
26 Jan - 27 Jan
L7 Chicago by LOTTE

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,436 reviews)
"The Hotel was amazing great location "
United States
Donnisha
The price is Rp2.573.307
Rp3.514.441 total
includes taxes & fees
26 Jan - 27 Jan
Hyatt Regency Chicago

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
River North, 12 km from Sleepy Hollow
8.8 out of 10, Excellent, (3,594 reviews)
"Great location and breakfast.. can be a bit pricey but worth it. "
Canada
Shaurya
The price is Rp2.102.375
Rp2.467.978 total
includes taxes & fees
18 Jan - 19 Jan
voco Chicago Downtown - Riverwalk by IHG

The Wade

The Wade
4.5 star property
Streeterville, 13.8 km from Sleepy Hollow
8.4 out of 10, Very good, (1,598 reviews)
"Easy check in and out, excellent room service and dining menu."
United States
Kevin Bradford
The price is Rp1.698.719
Rp1.994.126 total
includes taxes & fees
22 Jan - 23 Jan
The Wade

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, (3,535 reviews)
"Great hotel "
United States
Natalie
The price is Rp2.335.766
Rp2.741.956 total
includes taxes & fees
25 Jan - 26 Jan
LondonHouse Chicago, Curio Collection by Hilton

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
4.5 star property
Theatre District, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,415 reviews)
"The sweetest staff ever! Very welcoming. Had a great stay!"
United States
Angelina
The price is Rp2.220.949
Rp3.080.963 total
includes taxes & fees
26 Jan - 27 Jan
Sports Illustrated Resorts Chicago

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, (1,823 reviews)
"Great hotel"
United States
Yavuz
The price is Rp2.358.352
Rp3.206.700 total
includes taxes & fees
1 Feb - 2 Feb
Radisson Blu Aqua Hotel Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,938 reviews)
"Clean and comfy room, friendly staff, great location. "
United States
Agata
The price is Rp1.504.309
Rp2.269.030 total
includes taxes & fees
15 Jan - 16 Jan
Arlo Chicago

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,068 reviews)
"My favorite hotel for a staycation"
United States
SABRINA L
Ivy Boutique Hotel

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
River North, 12.8 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,391 reviews)
"Lovely staff, very clean hotel, convenient location."
United States
Tierra
The price is Rp2.275.425
Rp3.210.482 total
includes taxes & fees
10 Feb - 11 Feb
The Royal Sonesta Chicago River North

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
8.4 out of 10, Very good, (1,806 reviews)
"Very clean and comfortable hotel!"
United States
HYUNJI
Hotel Saint Clair- Magnificent Mile

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,322 reviews)
"Great hotel !"
United States
Dr. Mark
The price is Rp2.844.934
Rp3.833.386 total
includes taxes & fees
18 Jan - 19 Jan
Sofitel Chicago Magnificent Mile

Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
River North, 12.7 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,391 reviews)
"Very nice hotel"
United States
Kimberly
The price is Rp1.503.282
Rp1.764.703 total
includes taxes & fees
21 Jan - 22 Jan
Hampton Inn & Suites Chicago Downtown

AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown
4.0 star property
River North, 13.1 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,002 reviews)
"Very nice cozy hotel "
United States
CARLA
The price is Rp1.698.984
Rp1.994.438 total
includes taxes & fees
12 Feb - 13 Feb
AC Hotels by Marriott Chicago Downtown

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, (2,323 reviews)
"Great stay!"
United States
Angela
The price is Rp1.701.242
Rp2.569.774 total
includes taxes & fees
19 Jan - 20 Jan
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (3,365 reviews)
"Perfect with a pub next door!"
United States
Chad
The price is Rp1.371.430
Rp1.609.920 total
includes taxes & fees
26 Jan - 27 Jan
Club Quarters Hotel, Central Loop, 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.

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.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

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, 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.