Hotels in Sleepy Hollow, Chicago

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Check prices for these dates

Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

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Our top choices for Sleepy Hollow hotels

Cocktail bar
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1482)
"I really liked this location - we will stay here again. "
United States
Lynnsey
The price is RM265
RM431 total
includes taxes & fees
28 Dec - 29 Dec
Claridge House Chicago, Tapestry Collection by Hilton
Exterior
Moxy Chicago Downtown

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (854)
"Great place to stay"
United States
Mason
The price is RM460
RM540 total
includes taxes & fees
28 Dec - 29 Dec
Moxy Chicago Downtown
Executive lounge
Level Chicago Fulton Market

Level Chicago Fulton Market

Level Chicago Fulton Market
4.0 star property
West Loop, 11.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (359)
"Great hotel!"
United States
Giselle
Level Chicago Fulton Market
Terrace/patio
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1000)
"Good place to stay in."
United States
Joan
The price is RM533
RM625 total
includes taxes & fees
26 Dec - 27 Dec
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Restaurant
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Gold Coast, 13.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1297)
"Great hotel!"
United States
Julie
The price is RM552
RM768 total
includes taxes & fees
4 Jan - 5 Jan 2026
Thompson Chicago, by Hyatt
Exterior
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North
3.5 star property
River North, 12.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1000)
"Great location, great hotel, friendly staff "
United States
Eric
The price is RM451
RM530 total
includes taxes & fees
1 Jan - 2 Jan 2026
Springhill Suites by Marriott Chicago Downtown/ River North
3 bars/lounges, piano bar
The Hoxton Chicago

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Fulton Market, 11 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1008)
"Awesome hotel"
United States
Eligija
The Hoxton Chicago
Exterior
Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1000)
"Staff was so friendly Hotel was so clean and spacious!!! Loved the bed!! "
United States
Denise
The price is RM517
RM607 total
includes taxes & fees
26 Dec - 27 Dec
Hampton Inn Chicago West Loop Fulton Market Area
Meeting facility
Courtyard by Marriott Chicago Downtown River North

Courtyard by Marriott Chicago Downtown River North

Courtyard by Marriott Chicago Downtown River North
3.0 star property
River North, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (1001)
"Super customer service! We will definitely stay here again!"
United States
AMANDA S
The price is RM417
RM489 total
includes taxes & fees
9 Jan - 10 Jan 2026
Courtyard by Marriott Chicago Downtown River North
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers
Radisson Blu Aqua Hotel 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, (1788)
"Great hotel, close to shopping and restaurants, excellent customer service, highly recommend."
United States
Gina
The price is RM546
RM747 total
includes taxes & fees
21 Dec - 22 Dec
Radisson Blu Aqua Hotel Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2268)
"Great staff and restaurants!!"
United States
Abigale
The price is RM372
RM576 total
includes taxes & fees
15 Jan - 16 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio
The Chicago Hotel Collection Ambassador Gold Coast

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, (1259)
"Solid stay in a great part of town"
United States
Michael
The price is RM527
RM618 total
includes taxes & fees
19 Dec - 20 Dec
The Chicago Hotel Collection Ambassador Gold Coast
Pillow-top beds, desk, blackout curtains, iron/ironing board
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2.5 star property
Streeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1006)
"The room was huge, great stay, clean, convenient, comfortable and great staff. "
United States
Madeline
The price is RM327
RM384 total
includes taxes & fees
22 Dec - 23 Dec
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 12.6 km from Sleepy Hollow
8.4 out of 10, Very good, (377)
"Good place, good location, friendly staff and a great bar! "
United States
Georgi
The price is RM268
RM314 total
includes taxes & fees
5 Jan - 6 Jan 2026
FOUND Hotel Chicago River North
Exterior
AC Hotels by Marriott 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, (1003)
"Clean room, good staff. Overall excellent place to stay."
United States
Shameer Ahmed Zakir Ali
The price is RM412
RM483 total
includes taxes & fees
18 Jan - 19 Jan 2026
AC Hotels by Marriott Chicago Downtown
Exterior
The Emily Hotel

The Emily Hotel

The Emily Hotel
4.0 star property
Fulton Market, 11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1283)
"Very pleasant stay for my birthday! Will definitely come back and recommend to others! Top notch service and rooms were beautiful and comfortable!"
United States
Daniela
The Emily Hotel
City view from property
Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop
3.5 star property
Fulton Market, 10.6 km from Sleepy Hollow
8.8 out of 10, Excellent, (1132)
"I always come back to this Hotel everything is close the area is full of things to do really love staying here !!"
United States
Sandra
The price is RM552
RM647 total
includes taxes & fees
26 Dec - 27 Dec
Hyatt House Chicago West Loop
Terrace/patio
Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North
3.0 star property
River North, 12.9 km from Sleepy Hollow
8.4 out of 10, Very good, (2088)
"Huge room, very friendly and helpful front desk "
United States
Maneesha
The price is RM389
RM457 total
includes taxes & fees
4 Jan - 5 Jan 2026
Home2 Suites by Hilton Chicago River North
Exterior
Residence Inn by Marriott Chicago Downtown / River North

Residence Inn by Marriott Chicago Downtown / River North

Residence Inn by Marriott Chicago Downtown / River North
3.5 star property
River North, 12.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1000)
"Breakfast is pretty simple but good quality and spacious room :)"
United States
JIEUN
The price is RM490
RM576 total
includes taxes & fees
1 Jan - 2 Jan 2026
Residence Inn by Marriott Chicago Downtown / River North
Lobby sitting area
Homewood Suites by Hilton Chicago-Downtown

Homewood Suites by Hilton Chicago-Downtown

Homewood Suites by Hilton Chicago-Downtown
3.0 star property
River North, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (1041)
"Nice hotel, good breakfast, great locatiin, nice staff"
United States
Victoria
The price is RM415
RM488 total
includes taxes & fees
3 Jan - 4 Jan 2026
Homewood Suites by Hilton Chicago-Downtown
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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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.
Downtown Chicago which includes 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.

Magnificent Mile - River North

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 featuring a river or creek

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.

Chicago showing rides

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

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Good"
David 2-night trip
Posted 20 hours ago
InterContinental Chicago Magnificent Mile by IHG

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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