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21 Oct - 22 Oct
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22 Oct - 23 Oct
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24 Oct - 26 Oct
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31 Oct - 2 Nov

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Top Trending Hotels Near Sleepy Hollow, Chicago

Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4759)
"Staff friendly and helpful..and accommodations just right..great location! "
United States
Adrienne
The price is ₹8,977
₹10,538 total
includes taxes & fees
11 Nov - 12 Nov
River Hotel
Outdoor pool, 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, (2099)
"Great stay "
United States
Melinda
The price is ₹12,240
₹14,369 total
includes taxes & fees
16 Nov - 17 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (3074)
"Excellent stay, close to everything and the staff was super nice "
United States
Kieata
The price is ₹10,552
₹12,387 total
includes taxes & fees
2 Nov - 3 Nov
Eurostars 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, (2210)
"Rooms were clean with a great view of the lake and the city "
United States
Nathan
The price is ₹13,999
₹19,427 total
includes taxes & fees
9 Nov - 10 Nov
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, (2877)
"Had a great stay!"
United States
Josh
The price is ₹10,816
₹12,697 total
includes taxes & fees
9 Nov - 10 Nov
Aloft Chicago Mag Mile
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2260)
"We loved this hotel it was beautiful and convenient . "
United States
Daniel
The price is ₹16,173
₹21,566 total
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9537)
"Excellent location very convenient parking nice staff clean rooms"
United States
Mike
The price is ₹10,031
₹11,775 total
includes taxes & fees
9 Nov - 10 Nov
Congress Plaza Hotel
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, (1616)
"Great location!"
United States
Catherine
The price is ₹10,376
₹12,180 total
includes taxes & fees
16 Nov - 17 Nov
Crowne Plaza Chicago West Loop by IHG
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (3980)
"Great place to stay. "
United States
sherry
The price is ₹11,510
₹13,511 total
includes taxes & fees
9 Nov - 10 Nov
citizenM Chicago Downtown
Rooftop terrace
Best Western River North Hotel
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1001)
"Great stay"
Australia
Bart
The price is ₹8,894
₹10,441 total
includes taxes & fees
9 Nov - 10 Nov
Best Western River North Hotel
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
9.0 out of 10, Wonderful, (3122)
"Our stay was great"
United States
Bruce E
The price is ₹10,240
₹12,020 total
includes taxes & fees
16 Nov - 17 Nov
Hilton Chicago/Magnificent Mile Suites
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very good, (2506)
"Super clean, very good staff services, very convenient location, quiet, easy checking in and out "
United States
Lixiao
The price is ₹6,763
₹9,487 total
includes taxes & fees
12 Nov - 13 Nov
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, (4114)
"This hotel had a great location to shopping and several enjoyable restaurants."
United States
laura
The price is ₹10,838
₹12,722 total
includes taxes & fees
11 Nov - 12 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Lobby
Regal Inn - Chicago O'Hare Airport
Regal Inn - Chicago O'Hare Airport
2.0 star property
8.0 out of 10, Very good, (1000)
"Inexpensive, close to the airport, clean"
United States
Jay
Regal Inn - Chicago O'Hare Airport
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2629)
"Great place to stay "
United States
Larry William
The price is ₹11,648
₹16,151 total
includes taxes & fees
22 Oct - 23 Oct
Hotel Riu Plaza Chicago
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, (1488)
"I liked that people where super helpful, had its own shuttle and indoor pool"
Canada
Valeria
The price is ₹6,727
₹7,600 total
includes taxes & fees
23 Oct - 24 Oct
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, (2691)
"Clean quiet and great location!"
United States
Cyrus
The price is ₹6,652
₹7,582 total
includes taxes & fees
9 Nov - 10 Nov
Comfort Suites Chicago O'Hare Airport
Exterior
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very good, (280)
"Perfect location! Tons of restaurants and shopping nearby! "
United States
MaryJane
The price is ₹7,138
₹8,379 total
includes taxes & fees
10 Nov - 11 Nov
FOUND Hotel Chicago River North
Egyptian cotton sheets, premium bedding, pillow-top 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, (3625)
"Great historical hotel. Friendly and excellent location."
United States
Evelyn A
The price is ₹7,865
₹9,232 total
includes taxes & fees
16 Nov - 17 Nov
The Whitehall Hotel, BW Premier Collection
Front of property – evening/night
Eaglewood Resort and Spa
Eaglewood Resort and Spa
4.0 star property
8.6 out of 10, Excellent, (1019)
"Beautiful property, reasonably priced for an end of season stay. "
United States
ANDREW
The price is ₹9,426
₹12,396 total
includes taxes & fees
22 Oct - 23 Oct
Eaglewood Resort and Spa
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 free breakfast

Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
  • Breakfast included
9.0 out of 10, Wonderful, (3122)
The price is ₹10,240
₹12,020 total
includes taxes & fees
16 Nov - 17 Nov
Hilton Chicago/Magnificent Mile Suites
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Hotels in Sleepy Hollow with a pool

1 bedroom, premium bedding, down duvets, pillow-top beds
The Wade
The Wade
4.5 star property
  • Pool
8.4 out of 10, Very good, (1377)
The price is ₹11,871
₹13,935 total
includes taxes & fees
18 Nov - 19 Nov
The Wade
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Top guest rated hotels in Sleepy Hollow

2 bars/lounges
Hyatt Regency Chicago
Hyatt Regency Chicago
4.0 star property
    9.4 out of 10, Exceptional, (3405)
    The price is ₹20,752
    ₹26,942 total
    includes taxes & fees
    10 Nov - 11 Nov
    Hyatt Regency Chicago
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    Where to stay in Sleepy Hollow

    Find the best Sleepy Hollow areas for the activities you enjoy most.
    Downtown Chicago featuring 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 featuring a city and modern architecture

    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

    The Allegro Royal Sonesta Hotel Chicago Loop

    The Allegro Royal Sonesta Hotel Chicago Loop

    10/10 Excellent
    "Hotel was so cute & Quirky! Loved our room-lots of space to spread out. Coffee in room would’ve been nice but free in the lobby was good too. "
    Mary 1-night trip
    Posted 8 hours ago
    The Allegro Royal Sonesta Hotel Chicago Loop

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    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.