Find hotels in Sleepy Hollow, Chicago from AED 300

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
6 Jan - 7 Jan
Tomorrow
7 Jan - 8 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Sleepy Hollow hotels

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (2692)
"Quite area in a good location to walk to different locations."
United States
John steve
The price is AED 200
AED 300 total
includes taxes & fees
1 Feb - 2 Feb
Freehand Chicago
Lobby
River Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (4903)
"Would stay there again"
United States
Zach
The price is AED 300
AED 352 total
includes taxes & fees
19 Jan - 20 Jan
River Hotel
Lobby
Aloft Chicago Mag Mile

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, (3034)
"Great place to stay"
United States
Elisha
The price is AED 305
AED 358 total
includes taxes & fees
11 Jan - 12 Jan
Aloft Chicago Mag Mile
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3120)
"Second time to stay here, everything is great!"
United States
Wei
The price is AED 366
AED 533 total
includes taxes & fees
8 Jan - 9 Jan
Hotel Riu Plaza Chicago
Lobby
Congress Plaza Hotel

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, (9776)
"Wonderful stay!"
United States
Zach
Congress Plaza Hotel
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

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, (2812)
"Great hotel staff and location. "
United States
Jacqueline
The price is AED 320
AED 483 total
includes taxes & fees
25 Jan - 26 Jan
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Terrace/patio
DoubleTree by Hilton 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, (2221)
"Fantastic stay! Looking forward to staying here again!!"
United States
Amber
The price is AED 313
AED 368 total
includes taxes & fees
13 Jan - 14 Jan
DoubleTree by Hilton Chicago - Magnificent Mile
Property amenity
The Wade

The Wade

The Wade
4.5 star property
Streeterville, 13.8 km from Sleepy Hollow
8.4 out of 10, Very Good, (1576)
"Easy check in and out, excellent room service and dining menu."
United States
Kevin Bradford
The price is AED 371
AED 435 total
includes taxes & fees
11 Jan - 12 Jan
The Wade
View from room
Hilton Chicago/Magnificent Mile Suites

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, (3662)
"Great hotel!"
United States
William
The price is AED 328
AED 385 total
includes taxes & fees
12 Jan - 13 Jan
Hilton Chicago/Magnificent Mile Suites
Exterior
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, (1514)
"Very nice and quiet, excellent location"
United States
Anthony
The price is AED 223
AED 369 total
includes taxes & fees
1 Feb - 2 Feb
Claridge House Chicago, Tapestry Collection by Hilton
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4167)
"Stay was great and in a great location!! "
United States
Ashley
The price is AED 378
AED 444 total
includes taxes & fees
29 Jan - 30 Jan
citizenM Chicago Downtown
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, 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, (2045)
"Great stay"
United States
Kramer
The price is AED 300
AED 352 total
includes taxes & fees
19 Jan - 20 Jan
Club Quarters Hotel Wacker at Michigan, Chicago
Nightclub
Club Quarters Hotel, Central Loop, Chicago

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, (3366)
"Nice Hotel, convenient location fot shopping and walking around"
United States
Kerima
The price is AED 299
AED 352 total
includes taxes & fees
19 Jan - 20 Jan
Club Quarters Hotel, Central Loop, 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, (2324)
"Great stay!"
United States
Angela
The price is AED 372
AED 561 total
includes taxes & fees
20 Jan - 21 Jan
Sable at Navy Pier Chicago, Curio Collection by Hilton
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3448)
"The Hotel was amazing great location "
United States
Donnisha
The price is AED 529
AED 729 total
includes taxes & fees
20 Jan - 21 Jan
Hyatt Regency Chicago
Indoor pool
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
River North, 12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (4328)
"Amazing staff and perfect location "
United States
Brandi
The price is AED 286
AED 336 total
includes taxes & fees
13 Jan - 14 Jan
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3168)
"Clean, nicely priced, nice staff, and perfectly located to food and nightlife "
United States
Calvin
The price is AED 344
AED 404 total
includes taxes & fees
5 Feb - 6 Feb
Eurostars Magnificent Mile
Exterior
Arlo Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1931)
"Clean and comfy room, friendly staff, great location. "
United States
Agata
The price is AED 300
AED 462 total
includes taxes & fees
8 Jan - 9 Jan
Arlo Chicago
Bar (on property)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.5 km from Sleepy Hollow
8.2 out of 10, Very Good, (3848)
" Breakfast is good, location is excellent, service staff is courteous."
United States
Luis
The price is AED 261
AED 306 total
includes taxes & fees
11 Jan - 12 Jan
The Whitehall Hotel, BW Premier Collection
Exterior
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Magnificent Mile, 13.3 km from Sleepy Hollow
8.4 out of 10, Very Good, (3029)
"Every thing is perfect, the location, safe for solo travel. "
United States
Ken
The price is AED 234
AED 383 total
includes taxes & fees
21 Jan - 22 Jan
Warwick Allerton - 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.
View all properties

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most.
Downtown Chicago showing a city

Downtown Chicago

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile - River North

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

The Loop - Downtown which includes a river or creek

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

River North showing railway items, street scenes and a city

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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 the city at Washington Station or Monroe Station (Blue Line).

Top Sleepy Hollow Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"Very approachable staff especially the front desk. Fast transactions checking in and out. "
Harlene Jane 2-night trip
Posted 4 hours ago
River Hotel

Explore a world of travel with Expedia

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.
Where can I learn more about changing or cancelling my trip to Sleepy Hollow?
For more information about picking new dates or cancelling your trip to Sleepy Hollow, click here.
What can I see and do in this Chicago neighborhood?
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.