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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, (2,404 reviews)
"Great stay"
United States
Blake
The price is ₹12,986
₹18,388 total
includes taxes & fees
24 Mar - 25 Mar
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,485 reviews)
"Clean room, great staff, great location "
United States
Tiffany
The price is ₹14,126
₹19,835 total
includes taxes & fees
5 Apr - 6 Apr
Hyatt Regency Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,230 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
The price is ₹11,230
₹16,434 total
includes taxes & fees
29 Mar - 30 Mar
Swissotel - Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2,798 reviews)
"I enjoyed my stay"
United States
Emily
The price is ₹7,229
₹10,112 total
includes taxes & fees
24 Mar - 25 Mar
Freehand Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,676 reviews)
"Yes it was a great stay"
United States
Rita
The price is ₹12,038
₹16,841 total
includes taxes & fees
1 Apr - 2 Apr
Hilton Chicago

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,341 reviews)
"Staff was friendly and helpful! Great stay!"
United States
Kristin
The price is ₹17,972
₹23,808 total
includes taxes & fees
15 Mar - 16 Mar
Sofitel Chicago Magnificent Mile

Pendry Chicago

Pendry Chicago
4.5 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,141 reviews)
"Excellent hotel and location."
United States
Marcelo
The price is ₹18,928
₹26,013 total
includes taxes & fees
26 Mar - 27 Mar
Pendry Chicago

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, (2,866 reviews)
"Amazing place to stay"
United States
victor
The price is ₹16,435
₹22,247 total
includes taxes & fees
15 Mar - 16 Mar
InterContinental Chicago Magnificent Mile by IHG

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, (9,939 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
The price is ₹15,373
₹18,046 total
includes taxes & fees
21 Mar - 22 Mar
Congress Plaza Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,054 reviews)
"Great stay, good location, accommodating staff."
United States
Ian
The price is ₹9,653
₹11,332 total
includes taxes & fees
23 Mar - 24 Mar
River Hotel

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, (3,648 reviews)
"Staff was friendly and loved the decor at this hotel…will definitely be staying again"
Canada
Osama
The price is ₹21,123
₹24,797 total
includes taxes & fees
21 Mar - 22 Mar
LondonHouse Chicago, Curio Collection by Hilton

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
8.2 out of 10, Very good, (2,827 reviews)
"Great stay "
United States
Rudy
The price is ₹11,744
₹16,497 total
includes taxes & fees
6 Apr - 7 Apr
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

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, (1,875 reviews)
"Room was very nice, views were fantastic and the restaurant was excellent "
United States
Michael
The price is ₹14,544
₹19,474 total
includes taxes & fees
5 Apr - 6 Apr
Radisson Blu Aqua Hotel Chicago

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 13.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,421 reviews)
"Can't wait to go back love the hotel and the location was great."
United States
eyulonda
The price is ₹11,449
₹13,440 total
includes taxes & fees
30 Mar - 31 Mar
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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, (2,330 reviews)
"Excellent stay, we loved it "
United States
Melani
The price is ₹12,417
₹16,884 total
includes taxes & fees
5 Apr - 6 Apr
Palmer House a Hilton Hotel

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, (3,503 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
The price is ₹12,709
₹17,521 total
includes taxes & fees
18 Mar - 19 Mar
Hotel Riu Plaza Chicago

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, (1,896 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is ₹10,969
₹12,876 total
includes taxes & fees
5 Apr - 6 Apr
Hilton Garden Inn Chicago Downtown South Loop

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, (486 reviews)
"Amazing staff and very clean, modern rooms!"
United States
genevieve
The price is ₹7,295
₹8,563 total
includes taxes & fees
18 Mar - 19 Mar
FOUND Hotel Chicago River North

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,019 reviews)
"Clean hotel, helpful staff, restaurant food was delicious, great atmosphere, fabulous location!"
United States
Jennifer
The price is ₹13,212
₹18,267 total
includes taxes & fees
29 Mar - 30 Mar
Arlo 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, (2,115 reviews)
"Great place"
United States
Nicholas
The price is ₹9,653
₹11,332 total
includes taxes & fees
23 Mar - 24 Mar
Club Quarters Hotel Wacker at Michigan, 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

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.

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.

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

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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