Find hotels in Sleepy Hollow, Chicago from ￥12,435

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Oct 26 - Oct 27
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Oct 27 - Oct 28
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Oct 31 - Nov 2
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Nov 7 - Nov 9

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Discover 4,789 Sleepy Hollow hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (3082)
"Excellent stay, close to everything and the staff was super nice "
United States
Kieata
The price is ￥16,509
￥19,379 total
includes taxes & fees
Nov 25 - Nov 26
Eurostars Magnificent Mile
Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4750)
"Nice location, everything is convenient."
United States
Lloyd
The price is ￥14,718
￥17,278 total
includes taxes & fees
Nov 23 - Nov 24
River Hotel
Outdoor pool, cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (2103)
"Great stay "
United States
Melinda
The price is ￥18,221
￥21,389 total
includes taxes & fees
Nov 23 - Nov 24
DoubleTree by Hilton Chicago - Magnificent Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4 out of 10, Exceptional, (2221)
"Rooms were clean with a great view of the lake and the city "
United States
Nathan
The price is ￥15,428
￥23,316 total
includes taxes & fees
Nov 25 - Nov 26
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2872)
"Had a great stay!"
United States
Josh
The price is ￥16,509
￥19,380 total
includes taxes & fees
Nov 23 - Nov 24
Aloft Chicago Mag Mile
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (4002)
"Great place to stay. "
United States
sherry
The price is ￥17,410
￥20,437 total
includes taxes & fees
Oct 30 - Oct 31
citizenM Chicago Downtown
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very Good, (2266)
"Staff was wonderful, property was clean and welcoming. Great amenities for families and great location."
United States
Stephen
The price is ￥17,353
￥24,858 total
includes taxes & fees
Nov 24 - Nov 25
Hilton Chicago
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very Good, (9592)
"Area is great and walkable distance to touring areas. "
United States
Alejandro
The price is ￥26,001
￥30,523 total
includes taxes & fees
Nov 2 - Nov 3
Congress Plaza Hotel
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
9.0 out of 10, Wonderful, (3155)
"Overall it was a great place to stay."
United States
Edward
The price is ￥16,761
￥19,676 total
includes taxes & fees
Nov 16 - Nov 17
Hilton Chicago/Magnificent Mile Suites
American cuisine
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 star property
9.0 out of 10, Wonderful, (1627)
"Great Hotel"
United States
Cesar
The price is ￥15,592
￥18,302 total
includes taxes & fees
Nov 26 - Nov 27
Crowne Plaza Chicago West Loop by IHG
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very Good, (2527)
"Very accessible location and amazing staff. "
United States
Fatima
The price is ￥10,285
￥14,765 total
includes taxes & fees
Nov 26 - Nov 27
Freehand Chicago
Exterior
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.4 out of 10, Very Good, (4112)
"This hotel had a great location to shopping and several enjoyable restaurants."
United States
laura
The price is ￥16,761
￥19,676 total
includes taxes & fees
Nov 16 - Nov 17
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Rooftop terrace
Best Western River North Hotel
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1005)
"Great stay"
Australia
Bart
The price is ￥15,462
￥18,150 total
includes taxes & fees
Nov 9 - Nov 10
Best Western River North Hotel
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2659)
"Great place to stay "
United States
Larry William
The price is ￥16,428
￥23,592 total
includes taxes & fees
Nov 25 - Nov 26
Hotel Riu Plaza Chicago
Exterior
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very Good, (287)
"Perfect location! Tons of restaurants and shopping nearby! "
United States
MaryJane
The price is ￥11,632
￥13,655 total
includes taxes & fees
Nov 10 - Nov 11
FOUND Hotel Chicago River North
Lobby
Regal Inn - Chicago O'Hare Airport
Regal Inn - Chicago O'Hare Airport
2.0 star property
8.0 out of 10, Very Good, (1005)
"Inexpensive, close to the airport, clean"
United States
Jay
Regal Inn - Chicago O'Hare Airport
Lobby
Super 8 by Wyndham Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
3.5 star property
7.6 out of 10, Good, (1475)
"I liked that people where super helpful, had its own shuttle and indoor pool"
Canada
Valeria
The price is ￥11,006
￥12,435 total
includes taxes & fees
Nov 26 - Nov 27
Super 8 by Wyndham Chicago O'Hare Airport
Exterior
Comfort Suites Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport
3.0 star property
8.2 out of 10, Very Good, (2706)
"Clean quiet and great location!"
United States
Cyrus
The price is ￥11,564
￥13,180 total
includes taxes & fees
Nov 9 - Nov 10
Comfort Suites Chicago O'Hare Airport
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 star property
8.2 out of 10, Very Good, (3648)
"Excellent location, old style hotel with an independent feel. "
United States
Jose
The price is ￥13,016
￥15,280 total
includes taxes & fees
Nov 24 - Nov 25
The Whitehall Hotel, BW Premier Collection
Lobby
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (2023)
"Great place to stay "
United States
Cheryl
Silversmith Hotel 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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Hotels in Sleepy Hollow with a pool

1 bedroom, premium bedding, down comforters, pillowtop beds
The Wade
The Wade
4.5 star property
  • Pool
8.4 out of 10, Very Good, (1390)
The price is ￥16,967
￥19,918 total
includes taxes & fees
Nov 23 - Nov 24
The Wade
See more properties

Top guest rated hotels in Sleepy Hollow

Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
    9.0 out of 10, Wonderful, (3155)
    The price is ￥16,761
    ￥19,676 total
    includes taxes & fees
    Nov 16 - Nov 17
    Hilton Chicago/Magnificent Mile Suites
    See more 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

    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

    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 which includes modern architecture and a city

    Lincoln Park

    Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

    Top Sleepy Hollow Hotel Reviews

    citizenM Chicago Downtown

    citizenM Chicago Downtown

    10/10 Excellent
    "A new lodging experience. The hotel has phenomenal vibes and decor with excellent location and a very modern, innovative room design with great features. I was blown away, particularly given the reasonable price "
    Gino 1-night trip
    Posted 8 hours ago
    citizenM Chicago Downtown

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    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.